Elementary Problems in Organic Chemistry For JEE by M S Chouhan

For More Material Join: @JEEAdvanced_2024

Organic Chemistry: Some Basic Principles and Techniques 1
1
Organic Chemistry:
Some Basic Principles and Techniques
[A] Classification and Nomenclature of Organic Compounds

Functional Groups Degree of Unsaturation and Double Bond-equivalent
1. How many rings and/or pi bonds are present in a hydrocarbon with the formula C 6 H 10 ?
(a) 0 (b) 1 (c) 2 (d) 3
2. How many pi ( p) electrons are there in the following molecule?
(a) 4 (b) 6 (c) 8 (d) 10

3. Which of the following is condensed structural formula ?
H H H
(a) (b) H — C — C — C — H
H H H
(c) CH 3 — CH 2 — CH 3 (d)
4. Which of the following is homocyclic compound?

(a) (b) (c) O (d) Both (a) & (b)

2 Elementary Organic Chemistry
5. Which of the following is heterocyclic compound?

(a) (b) (c) N—H (d) All of these
S O
6. Which of the following is bicyclo compound?
(a) (b)
(c) (d) All of these
7. Which of the following is organometallic compound?

(a) CH 3 MgBr (b) CH 3 — Li
(c) (CH 3 ) 2 Cd (d) All of these
8. How many different functional groups are present in given compound?
OH
HO2C
O
O
(a) 3 (b) 4 (c) 1 (d) 5
9.
How many functional groups are present in above compound?

(a) 2 (b) 3 (c) 4 (d) 5
OH
10. O
NH2
HO
Functional groups present in above compound are:
(a) alcohol, aldehyde & carboxylic acid
(b) alcohol, amine & aldehyde
(c) amine, alcohol & carboxylic acid
(d) amine, amide & aldehyde

OH
O
N SO3H
11. O
NH—CH3
NH2
Which functional group is present in above compound?
(a) Carboxylic acid (b) Aldehyde (c) Thiol (d) Alcohol
12. Which of the following is pair of homologues?
(a) CH 3 OH , CH 3 — O — CH 3 (b) CH 3 OH , CH 3 SH
(c) CH 3 — O — CH 3 , CH 3 — CH 2 — OH (d) CH 3 OH , CH 3 CH 2 OH
13. What is the homologue of CH 3 — CH 2 — OH ?
(a) CH 3 — CH 2 — O — CH 3 (b) CH 3 — CH 2 — CH 2 — OH
(c) CH 3 OCH 3 (d) CH 3 — CH 2 — O — CH 2 — CH 3
14. In homologous series, the molecular mass of two consecutive members differ by:
(a) 12 (b) 13 (c) 14 (d) 15
15. All the members of homologous series has:
(a) same I.U.P.A.C. (b) same functional group
(c) same boiling point (d) same number of carbons
16. Which of the following is smallest homologus of ketone?
O O
(a) (b) O (c) H 2 C == O (d)
17. In homologous series, successive members differ by :

(a) CH 3 — (b) CH 3 — CH 2 — (c) — CH 2 — (d)—H
18. Degree of unsaturation for is:
(a) 6 (b) 7 (c) 8 (d) 9

19. Double bond equivalent or degree of unsaturation for the compound given below is:
CO2H
(a) 12 (b) 13 (c) 14 (d) 15

20. Double bond equivalent of C 4 H 6 is:
(a) 0 (b) 1 (c) 2 (d) 3

21. Double bond equivalent of C 5 H 12 O is:

(a) 0 (b) 1 (c) 2 (d) 3
22. Double bond equivalent of C 8 H 8 is:
(a) 4 (b) 5 (c) 6 (d) 7
23. Which of the following compounds has DBE equal to benzene?
CH3
(a) (b) (c) (d) All of these
24. Difference of DBE in and is:
(a) 0 (b) 1 (c) 2 (d) 3
O
CO2H
C—NH2
HN
25. ; Number of functional groups and degree of unsaturation
O O NH
C2H
(respectively) in the above compound is:
(a) 7,8 (b) 6,8 (c) 6,6 (d) 5,6
26. Number of s-bond and p-bond in anthracene are respectively:
(a) 7, 26 (b) 24, 8 (c) 26, 7 (d) 26, 6
27. Which functional group can be presented in compound having molecular formula C 4 H 10 O ?
(a) Aldehyde (b) Ketone (c) Acid (d) Alcohol
28. Which functional group is present in compound having molecular formula C 4 H 8 O?
(a) Aldehyde (b) Ketone
(c) Unsaturated alcohol (d) All of these
29. Which functional group is present in compound having molecular formula C 4 H 8 ?
(a) Alkane (b) Alkene (c) Alkyne (d) Alcohol
30. Which functional group is present in compound having molecular formula C 2 H 4 O 2 ?
(a) Carboxylic acid (b) Ester (c) Amine (d) Both (a) and (b)
31. How many nodal planes are there in 3d-orbital ?
+ –
– +
(a) 0 (b) 1 (c) 2 (d) 3

32. Double bond equivalent for tetrahedral molecule given below is:
H
|
C
or C C—H
H
C
H
(a) 2 (b) 3 (c) 4 (d) 5
33.
Prismane
Double bond equivalent for prismane is:
(a) 2 (b) 3 (c) 4 (d) 4
34. Double bond equivalent for Dewar benzene is:
(a) 2 (b) 3 (c) 4 (d) 5
Hybridization and Bonding in Organic Molecules

1. How many p and s bonds present in N ºº C — C ºº N ?
(a) p = 4 , s = 4 (b) p = 4 , s = 5 (c) p = 4 , s = 3 (d) p = 2 , s = 1
2 2
2. Number of sp - sp s-bonds present in given compound is:
(a) 1 (b) 2 (c) 3 (d) 4

3. How many s-bonds are present in the given compound ?
(a) 6 (b) 12 (c) 18 (d) 24

4. What is the hybridization of carbon in compound H — C ºº N ?
(a) sp 3 (b) sp 2 (c) sp (d) All of these
5. What is the hybridization of C 1 ,C 2 ,C 3 carbon in the following compound?
CH 3 — CH 2 — CH == CH — C ºº C —H
1 2 3
3 3 3 3 2 2
(a) sp , sp , sp (b) sp , sp , sp (c) sp 3 , sp 2 , sp (d) sp , sp 2 , sp 2
6. What is the hybridization of carbon in the following compounds ?
CH 3 — F, CH 3 — Cl
(a) sp 2 , sp 2 (b) sp , sp (c) sp 3 , sp 3 (d) sp 3 , sp 2

7. In which of the following carbon is sp 2 hybridized state ?

O
(a) CH 3 — Cl (b) NH2 — C — NH2 (c) H — C ºº N (d) CH 3 — NH 2
8. What type of bonding is most important in CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 ?
(a) ionic (b) hydrogen (c) covalent (d) polar
9. Which carbon(s) in the following molecule is(are) sp hybridized?
O
||
CH 3 — C — CH 2 — C ºº C —H
1 2 3 4 5
(a) carbon 1 (b) carbon 2 (c) carbons 1, 3 (d) carbon 4 (e) carbons 4, 5
10. Which of the following has the strongest van der Waals’ interaction between molecules of the
same kind?
(a) CH 3 —CH — CH 2 CH 3 (b) CH 3 CH 2 CH 2 CH 3
|
CH 3
CH 3
|
(c) CH 3 — C — CH 3 (d) CH 3 CH 2 CH 2 CH 2 CH 3 (e) CH 3 — CH — CH 3
| |
CH 3 CH 3
11. What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following
structure?
CH== CH—CººCH
1 2
3 2
(a) sp , sp (b) sp 2 , sp 2 (c) sp , sp (d) sp 2 , sp (e) sp , sp 2
12. The carbon-carbon triple bond of an alkyne is composed of ..........................
(a) three s bonds (b) two s bonds and one p bond
(c) one s bond and two p bonds (d) three p bonds
Bond (1) Bond (2)
Bond (3)
13. C ºº C
Rank the indicated bonds in each compounds in order of increasing bond strength :
(a)1<2<3 (b) 3<1<2 (c) 1<3<2 (d) 2<3<1
14.
How many p-electrons are contained in given molecule?

(a) 6p (b) 8p (c) 10p (d) 12p

IUPAC Nomenclature of Alkanes

1. How many carbons are present in longest chain of given compound?
C—C—C—C—C—C
C—C—C—C
(a) 6 (b) 7 (c) 8 (d) 9
2. How many carbons are present in longest carbon chain of given compound ?
C—C
C—C—C
C—C—C—C—C
(a) 4 (b) 5 (c) 6 (d) 7
3. How many carbons are present in nonane ?
(a) 7 (b) 8 (c) 9 (d) 10
4. What is the common name for the following structure?
CH 3 — CH — CH 3
|
CH 3
(a) isobutane (b) t-butane (c) n-butane (d) sec-butane
5. How many carbon atoms are present in parent carbon chain in the given following compound?
(a) 6C (b) 7C (c) 8C (d) 9C

6. Which of the following alphabet have a five membered chain as a longest chain?
A, E, F, H, I, K, M, T, V, W, X, Y, Z
(a) A, E, H (b) E, M, W (c) K, M, X (d) F, W, Z
7. Give the complete IUPAC name for the structure below. Be careful to identify longest carbon
chain:
CH3—CH—CH2—CH—CH3
CH3—CH2 CH—CH3
CH2—CH3
(a) 3,5,6-trimethyl octane (b) 3,4,6-trimethyl octane
(c) 1,2,3,6-tetramethyl heptane (d) none of these
8. Give the IUPAC name for the following structure:

(a) 2-methyl-3-ethylheptane (b) 3-ethyl-2-methylheptane

(c) 5-isopropyloctane (d) 4-isopropyloctane
(e) 2-methyl-3-propylheptane
9. Give the IUPAC name for the following compound:
(a) isoprene (b) 3-methyl-1,3-butadiene

(c) 2-methyl-1,3-butadiene (d) 2-methyl-2,3-butadiene (e) isobutadiene
10. ; How many methyl —CH 3 group are present in given alkane?
(a) 4 (b) 5 (c) 6 (d) 7
11. ; How many 2° carbon present in above compound?
(a) 4 (b) 5 (c) 6 (d) 7

CH3
12. The structure shown CH3CH2CHCHCH2CH2CHCH3
CH2CH3 CH2CH3
(a) 1° 2°, and 3° carbon atoms (b) 1° and 2° carbon atoms only
(c) 1° and 3° carbon atoms only (d) 2° and 3° carbon atoms only
13. How many 1° carbon atom will be present in a simplest hydrocarbon having two 3° and one 2°
carbon atom ?
(a) 3 (b) 4 (c) 5 (d) 6
14. 1°, 2°, 3° and 4° carbon atoms are present in :
(a) 2, 2, 3-trimethyl pentane (b) 2, 3, 4-trimethyl pentane
(c) both (a) and (b) (d) none of these
15. ; Correct IUPAC name of the following compound is:
(a) 4-(1,1-dimethylethyl)-5-ethyloctane (b) 5-ethyl-4-(1,1-dimethylethyl) octane

(c) 5-(1,1-dimethylethyl)-4-ethyloctane (d) 4-ethyl-5-(1,1-dimethylethyl) octane

IUPAC Nomenclature of Alkynes/Alkenes

1. Which of the following name will be incorrect ?
(a) 3, 6-Dimethyl cyclohexene (b) 1, 6-Dimethyl cyclohexene
(c) 6,6-Dimethyl cyclohexene (d) 1,5-Dimethyl cyclohexene
2. Which pair of names refers to the same compound ?

(a) Ethyne and Acetylene (b) Ethyne and Ethene
(c) Ethane and Acetylene (d) Ethane and Ethene
3. What is the IUPAC name for the following compound?
CH 2 == C — CH 3
|
CH 2
|
CH 3
(a) 2-methyl-1-butene (b) isopentene
(c) 2-methybutene (d) 2-ethylpropene (e) 3-methyl-3-butene
CH3
(a) 5-methylcyclohexene (b) 4-methylcyclohexene
(c) 1-methyl-3-cyclohexene (d) 1-methyl-4-cyclohexene (e) methylcyclohexene
5. What is the IUPAC name for the following alkyne?
Br
|
CH 3 — C ºº C — CH 2 — C — CH 3
|
CH 3
(a) 5-bromo-2-heptyne (b) 3-bromo-5-heptyne
(c) 2-bromo-2-methyl-4-hexyne (d) 5-bromo-5,5-dimethylhexyne
(e) 5-bromo-5-methyl-2-hexyne
6. What is the common name for the following alkyne?
CH 3
|
CH 3 — C — C ºº CH
|
CH 3

(a) neohexyne (b) trimethylpropyne

(c) trimethylacetylene (d) tert-butylacetylene (e) isopropylacetylene
7. The IUPAC name of is:

Br
(a) 2-bromo-3-methylbut-3-ene (b) 4-bromo-3-methylpent-2-ene

(c) 2-bromo-3-methylpent-3-ene (d) 4-bromo-2,3-dimethylbut-2-ene
8. The IUPAC name of the compound CH 3 CH == CHCH == CHC ºº CCH 3 is :
(a) Octa-4,6-dien-2-yne (b) Octa-2,4-dien-6-yne
(c) Oct-2-yne-4,6-diene (d) Oct-6-yne-2,4-diene
9. The molecular formula of the first member of the family of alkenynes and its name is given by
the set :
(a) C 3 H 2 , alkene (b) C 5 H 6 , pent-1-en-3-yne
(c) C 6 H 8 , hex-1-en-5-yne (d) C 4 H 4 , butenyne
10. The correct IUPAC name of H 2 C == CH — CH — CH 2 C ºº CH
|
CH 3
(a) 3-methyl-1-hexen-5-yne (b) 4-methyl-5-hexen-1-yne

(c) 4-(ethenyl)1-pentyne (d) 3-(2-propenyl) butene-1
IUPAC Nomenclature of Alcohols/Aldehydes/Ketones/Acids

1. Which of the following compounds does not have the molecular formula C 6 H 14 O ?
(a) 1-hexanol (b) 2-hexanol
(c) 3-methyl-2-pentanol (d) 3-methyl-3-pentanol (e) cyclohexanol
2. Which of the following compound have 4 carbon atom in the parent chain ?
OH
OH
(a) OH (b)
CHO
(c) (d) Br
O
3. What is the common name of the following compound ?
O
||
CH 3 CHCH 2 COH
|
Cl

(a) l-chlorobutanoic acid (b) b-chlorobutanoic acid
(c) b-chlorobutyric acid (d) l-chlorobutyric aicd (e) 3-chlorobutyric acid
4. What is the IUPAC name of the following compound ?
O
||
CH 3 CHCH 2 — C — H
|
Br
(a) 2-bromobutanal (b) a-bromobutanal
(c) 3-bromobutanal (d) b-bromobutyraldehyde (e) 3-bromobutanone
O
||
CH 3 CCHCH 2 CHCl
| |
CH 3 CH 3
(a) 5-chloro-3-methylhexanone (b) 1-chloro-1,3-dimethyl-4-pentanone
(c) 5-chloro-3,5-dimethyl-2-pentanone (d) 5-chloro-3-methyl-2-hexanone
(e) 2-chloro-4-methyl-5-hexanone
6. The correct IUPAC name of CH 3 — CH 2 —C — COOH is :
||
CH 2
(a) 2-Methyl butanoic acid (b) 2-Ethylprop-2-enoic acid

(c) 2-Carboxy-1-butene (d) None of these
OH CH2CH2OH
7. (i) and (ii)
True statement for the above compounds is :

(a) (i) is phenol while (ii) is alcohol (b) Both (i) and (ii) are primary alcohol
(c) (i) is primary and (ii) is secondary alcohol (d) (i) is secondary and (ii) is primary alcohol
8. Which of the following is cyclohexanone ?
O
O
CH O
I. O II. III. IV.
O
(a) I (b) II (c) III (d) IV

Cl
|
9. The IUPAC name of CH 3 — C — CH 2 CH == CHCH 3 is:
|
OH
(a) 5-chloro-2-hydroxyhexene (b) 2-chloro-5-hydroxyhexene

(c) 2-chloro-2-hydroxy-5-hexene (d) 2-chloro-4-hexenol-2
10. The IUPAC name of the t-butyl group is:
(a) 2-methylpropyl (b) trimethylmethyl (c) 1, 1-dimethylethyl(d) 2-methyl-2-propyl
11. The IUPAC name of CH—OH is:
CH3
(a) 1-hydroxy-1-cyclopropylethane (b) 1-hydroxyethylcyclopropane

(c) cyclopropylethanol (d) 1-cyclopropylethanol
12. Correct IUPAC name of the given compounds is:
Br
Cl OH
(a) 2-bromo-3-ethyl-4-chlorocyclobutanol
(b) 4-bromo-1-chloro-3-ethylcyclobutanol
(c) 2-bromo-4-chloro-3-ethyl cyclohydroxybutane
(d) 2-bromo-4-chloro-3-ethylcyclobutanol
IUPAC Nomenclature of Acid Halides, Esters, Nitriles, Amines, Amides, Anhydrides

1. The IUPAC name of the following compound is:
O
O
(a) n-propyl ethanoate (b) ethyl propanoate
(c) pentanoic anhydride (d) n-propyl propanoate
2. Which of the following compound is an amide ?
(a) CH 3 CH 2 NH 2 (b) CH 3 NHNH 2
NH2
(c) CH 3 CNH 2 (d) HO C CH 2 NH 2 (e)
|| ||
O O

3. Which of the following compounds is an acyl chloride ?

O
Cl CCl
(i) (ii)
CH2Cl OCH2Cl Cl
(iii) (iv) (v)
(a) i (b) ii (c) iii (d) iv (e) v
4. Which of the following compounds is an anhydride ?

O O
(i) CH3CO (ii) CH3C
O O O O
|| || || ||
(iii)CH 3 COH (iv) CH 3 COOH (v) CH 3 CO CCH 3

5. What is the IUPAC name for the following compound ?
O O
|| ||
HC — O —CH
(a) Propanoic anhydride (b) Methanoic anhydride
(c) Formyl formate (d) Ethanoic anhydride
6. The IUPAC name of CH 3 —C — O — CH 2 —C — OH is :
|| ||
O O
(a) 1-acetoxy acetic acid (b) 2-acetoxy ethanoic acid

(c) 2-ethanoyloxy acetic acid (d) 2-ethanoyloxyethanoic acid
O
O
(a) n-propyl ethanoate (b) ethyl propanoate
(c) pentanoic anhydride (d) n-propyl propanoate

IUPAC Nomenclature of Poly Functional Compounds

1. The correct IUPAC name of the following compound O==C—CH2—CH—CHO is :
OH H—C==O
(a) 3,3-Diformyl propanoic acid (b) 3-Formyl-4-oxo-butanoic acid
(c) 3,3-Dioxo propanoic acid (d) 3,3-Dicarbaldehyde propanoic acid
2. The correct IUPAC name of compound: CH3—CH2—C—CH—CHO is :

O CN
(a) 2-Cyano-3-oxopentanal (b) 2-Formyl-3-oxopentanenitrile

(c) 2-Cyano-1,3-pentanedione (d) 1,3-Dioxo-2-cyanopentane
HO—C==O CH3
3. The IUPAC name of compound CH3—C==C–—C—H is :

NH2 Cl
(a) 2-Amino-3-chloro-2-methylpent-2-enoic acid

(b) 3-Amino-4-chloro-2-methylpent-2-enoic acid
(c) 4-Amino-3-chloro-2-methylpent-2-enoic acid
(d) All of the above
4. Which of the following compound is wrongly named ?
(a) CH 3 CH 2 CH 2 CHCOOH ; 2-Chloro pentanoic acid

|
Cl
(b) CH 3 C ºº CCHCOOH ; 2-Methyl hex-3-enoic acid

|
CH 3
(c) CH 3 CH 2 CH == CHCOCH 3 ; Hex-3-en-2-one

(d) CH 3 — CHCH 2 CH 2 CHO ; 4-Methyl pentanal
|
CH 3
5. The suffix of the principal group, the prefixes for the other groups and the name of the parent
in the structure
HO—CH2—CH—CH == C—CH2—C—C—OH
CH3 Cl O O
(a) -oic acid, chloro, hydroxy, oxo, methyl, 4-heptene

(b) -oic acid, chloro, hydroxy, methyl, oxo, 4-heptene

(c) -one, carboxy, chloro, methyl, hydroxy, 4-heptene
(d) -one, carboxy, chloro, methyl, hydroxy, 4-heptene
OC2H5
O
O
(a) 3-methoxy ethylpropanoate (b) ethyl-4-methoxybutanoate
(c) 1,4-diethoxybutane (d) 4-methoxy-ethylbutanoate
OH
|
7. The IUPAC name of CH 3 — CH — COOH is:
(a) 2-hydroxypropanoic acid (b) 1-hydroxypropanoic acid
(c) 1-hydroxyethane carboxylic acid (d) 1-hydroxyethanoic acid
IUPAC Nomenclature of Aromatic Compounds & Bicyclic & Spiro Compounds

1. What is the structure of 3-phenylpentane ?
CH3CH2CHCH2CH3
|
CH3CHCH2CH2CH2CH3 O
(a) (b)
CH3CH2CHCH2CH3
CH3CH2CHCH2CH3
COOH
(c) (d) (e)
OH
COOH
CH3
NO2
Br
(a) o-nitro-m-bromotoluene (b) 3-bromo-6-nitrotoluene
(c) m-bromo-o-nitrotoluene (d) 5-bromo-2-nitrotoluene (e) 2-nitro-5-bromotoluene

3. What is the IUPAC name of the compound given below ?
OH
CH2CH2CH2CH3
(a) 1-phenoxyethane (b) ethyl phenyl ether
(c) m-butylhydroxybenzene (d) o-butylhydroxybenzene (e) m-butylphenol
4. Which of the following compounds is benzoyl chloride ?
CH2Cl Cl
(i) (ii)
OCH2Cl COCl COOCl

(iii) (iv) (v)
COOC2H5
5. The IUPAC name of is :
COCl
(a) 2-Chlorocarbonyl ethylbenzoate (b) 2-Carboxyethyl benzoyl chloride

(c) Ethyl-2-(chlorocarbonyl) benzoate (d) Ethyl-1-(chlorocarbonyl) benzoate
6. What is the IUPAC name for the following compound ?
CººN
(a) Benzenecarbonitrile (b) Benzenecyanide

(c) Phenylcyanide (d) Cyanophenyl
7. Write the IUPAC name of the following compound:
CO—O—C2H5
CO—Cl
(a) ethyl 2-(chlorocarbonyl) benzoate (b) ethyl-2-(chlorocarbonyl) hexanoate

(c) 2-(ethoxycarbonyl) benzoyl chloride (d) none of these

[B] Isomerism
Structural Isomerism
1. How many dibromobenzenes are possible?
(a) 1 (b) 2 (c) 3 (d) 4
2. The number of all the possible isomers of chlorobutane is:
(a) 2 (b) 4 (c) 6 (d) 5
O
||
3. CH 3 — CH 2 — CHO ; CH 3 — C — CH 3
( A) ( B)
Relation between (A) and (B) is :
(a) chain isomers (b) positional isomers
(c) functional isomers (d) metamers
4. Which of the following pairs of structures does not represent isomers?
(a) and (b) and

O O
O
OH
OH
and O O
(c) (d) and
O
5. How many distinct terminal alkynes are possible for a compound having molecular formula
C 6 H 10 ?
(a) 3 (b) 4 (c) 5 (d) 6
6. How many distinct terminal alkenes are possible for a compound having molecular formula
C 6 H 12 ?
(a) 3 (b) 4 (c) 5 (d) 6
7. How many distinct terminal alkynes are possible for a compound having molecular formula
C 5H 8 ?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
8. How many distinct internal alkynes may exist with a molecular formula of C 6 H 10 ?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
9. The molecular formula of diphenyl methane is C 13 H 12
CH2
How many structural isomers are possible when one of the hydrogen is replaced by a chlorine
atom ?
(a) 4 (b) 6 (c) 7 (d) 8
10. The number of ether metamers represented by the molecular formula C 4 H 10 O is:
(a) 1 (b) 2 (c) 3 (d) 4

Cl
Cl
11. How many positional isomers are possible for ?
(a) 2 (b) 3 (c) 4 (d) 5
(a) 2 (b) 3 (c) 4 (d) 5

CH3
NO2
13. ; Number of positional isomers for the compound given are :
NO2
(a) 4 (b) 5 (c) 6 (d) 7
14. ; ( A) and ( B ) are:

(A) (B)
(a) chain isomers (b) positional isomers (c) metamers (d) functional isomers
15. OH ; ( A) and ( B ) are:
OH OH OH
(A) (B)
Cl Cl
Cl
16. ; ( A) and ( B ) are:
Cl
(A) (B)
17. CH 3 — CH 2 — CH 2 — CO 2 H CH 3 — CH — CH 3 ; ( A) and ( B ) are:
(A) |
CO 2 H
(B)
(a) chain isomers (b) positional isomers (c) functional isomers (d) metamers
OH
OH
18. ; ( A) and ( B ) are:
(A) (B)
(a) chain isomers (b) functional isomers (c) metamers (d) positional isomers

19. O ; ( A) and ( B ) are:

O
(A) (B)
(a) chain isomers (b) functional isomers (c) metamers (d) positional isomers
OH
20. OH ; ( A) and ( B ) are:
(A) (B)
(a) chain isomers (b) functional isomers (c) metamers (d) homologues
21. Which of the following pairs represent isomers?
(a) CH 3 — CH 3 , CH 3 — CH 2 — CH 3
(b) H 2 C == CH — OH, CH 3 — O — CH 3
(c) CH 3 — CH 2 — CH 2 — CH 3 , CH 3 — CH — CH 3
|
CH 3
(d) All of these
22. Which of the following represent a pair of chain isomers?
(a) n-pentane, Iso-pentane (b) n-pentane, Neo-pentane
(c) Iso-pentane, Neo-pentane (d) All of these
23. Total number of stereoisomers for 2,3-dichlorobutane is:
(a) 3 (b) 4 (c) 5 (d) 6
24. CH 3 — CH 2 — CH 2 — C ºº N ; CH 3 — CH — CH 3
( A) |
CN
( B)
Relation between (A) and (B) is:
25. Total number of stereoisomers possible for 2-Bromo-3-chlorobutane is:
(a) 3 (b) 4 (c) 5 (d) 6
26. Molecule of C 13 H 28 with the shortest possible parent carbon chain will contains:
(a) 5 carbon atoms (b) 6 carbon atoms
(c) 7 carbon atoms (d) 8 carbon atoms
27. CH 3 — O — CH 2 — CH 2 — CH 3 ; CH 3 — CH 2 — O — CH 2 — CH 3
( A) ( B)
Relations between (A) and (B) is:
28. How many cyclic structural isomers are possible for C 5 H 10 ?
(a) 4 (b) 5 (c) 6 (d) 7
29. How many structural isomers of C 9 H 18 may have a six-membered ring and are tri-substituted?
(a) 5 (b) 6 (c) 7 (d) 8
30. How many structural isomers of C 6 H 12 may contain 3-membered ring?
(a) 4 (b) 5 (c) 6 (d) 7
31. How many structural isomer of C 6 H 12 may contain 4-membered ring ?
(a) 3 (b) 4 (c) 5 (d) 6

32. How many structural isomers are possible for molecular formula C 3 H 6 BrCl ?
(a) 4 (b) 5 (c) 6 (d) 7
33. How many structural isomers are possible for C 8 H 16 that have a six-member ring ?
(a) 4 (b) 5 (c) 6 (d) 7
34. How many structural isomers of C 4 H 8 contain one p-bond?
(a) 2 (b) 3 (c) 4 (d) 5
CH2—NH2
(a) 3 (b) 5 (c) 6 (d) 8

36. How many ketones are possible with molecular formula C 6 H 12 O ?
(a) 5 (b) 6 (c) 7 (d) 8
37. How many aldehydes are possible with molecular formula C 4 H 8 O ?
(a) 1 (b) 2 (c) 3 (d) 4
38. There are 8 isomers that have the molecular formula C 5 H 11 Br . Among these, how many are
tertiary alkyl bromides?
(a) 0 (b) 1 (c) 2 (d) 3 (e) 8
39. What type of isomers CH 3 CH 2 OCH 3 and CH 3 CH 2 CH 2 OH are?
(a) Constitutional (b) Symmetrical
(c) Configurational (d) Conformational (e) Stereochemical
Tautomerism and Applications of Tautomerism

O O
O
1.
O O
(A) (B)
Enol content of ( A) and ( B ) is:

(a) B > A (b) A > B (c) A = B (d) A >>> B
2. Which of the following compound will not show tautomerism ?
OH O O O
(a) (b) (c) (d)

3. Which of the following compound will show tautomerism ?

O
O O O O
C—H CH3
(a) (b) (c) (d)
O
4. Which of the following compound has negligible enol content?
O O
(a) O (b)
O
O
O O O O
|| ||
(c) (d) CH 3 — C — CH 2 — C — CH 3
O
KOH
5. (B) Tautomer ( B ) is:
N
H
(A)
OH OH
OH
(a) (b) (c) (d)
N N N N
H OH
6. Order of stability of enol forms of the following keto forms is:
O O O O O
|| || || || ||
CH 3 — C — CH 3 CH 3 — C — CH 2 — C — CH 3 CH 3 — C — CH 2 — C — O — Et
( a) (b) (c)
(a) a > b > c (b) b > a > c (c) b > c > a (d) a > b > c
O
D2O/DO s
7. ; Prolonged treatment of ( A) with D 2 O DO s gives :
(A)

O
O D D
O O
D D D D
(a) D D (b) D D (c) (d)
D D D D
D D D D
8. How many hydrogens are replaced by deuterium when given compound reacts with D 2 O for
long time
æ O ö
ç || ÷
ç ÷
ç CH 3 — CH 2 — C — CH 3 ÷ ?
çç ÷÷
è ø
(a) 3 (b) 5 (c) 8 (d) 10
O
D2O/DO s
9. CH2—C—CH—CH—CH2
H1 H2 H3 H4
Which hydrogen is not replaced by deuterium in the above process?
(a) H 1 (b) H 3 (c) H 4 (d) (b) and (c) both
O O O O O O
10.
¾¾® (i) ¾¾® (ii) ¾¾® (iii)
Stability order of enol forms is:
(a) i > ii > iii (b) ii > i > iii (c) iii > i > ii (d) i > iii > ii
11. Which of the following compound has highest enol content ?
O O
O O O O O O
(a) (b) Ph (c) Ph Ph (d)
12. Which of the following are enol forms of 2-butanone ?

O
||
CH 3 CCH 2 CH 3
(a) CH 3 C == CHCH 3 and CH 3 CHCH == CH 2
| |
OH OH
(b) CH 3 CHCH == CH 2 and CH 2 == CCH 2 CH 3
| |
OH OH

(c) CH 3 C == CHCH 3 , CH 3 CHCH == CH 2 and CH 2 == CCH 2 CH 3

| | |
OH OH OH
(d) CH 3 CHCH 2 CH 3 and CH 3 C == CHCH 3
| |
OH OH
(e) CH 3 C == CHCH 3 and CH 2 == CCH 2 CH 3
| |
OH OH
13. Which of the following is the most stable enol form of 1,3-cyclohexanedione ?
O O
HO OH HO OH
(i) (ii)
HO OH HO O HO O
(iii) (iv) (v)

14. Which of the following compounds forms the most stable enol tautomer ?
(a) CH 3 CH (b) CH 3 CCH 3
|| ||
O O
(c) CH 3 CCH 2 CCH 3 (d) CH 3 C — CCH 3 (e) CH 3 C — COH
|| || || || || ||
O O O O O O
15. How many Hydrogens in the compound given below are replaced by deuterium when it is
shaken in D 2 O containing traces of hydroxide ?
O
CH3 CH3
(a) 1 (b) 2 (c) 3 (d) 6 (e) 7
16. Which of the following is the enol form of 4-phenyl-2-butanone?
O OH
(a) (b)
OH
O
(c) (d)

17. When compared to the keto form, the enol form of which of the following compounds is most
stable ?
O O
CH3
(i) (ii)
O O O O
CH
(iii) (iv) (v)
O
D 2O/DOs
18. ¾ ¾¾¾ ¾®
(Prolonged)
O
How many hydrogens are replaced by ( D) in the above reaction?
(a) 2 (b) 3 (c) 4 (d) 5
19. Which of the following will not form an enolate?
O
O
O
(a) (b)
(c) (d) O
20. How many enolizable hydrogens are there in the following compound?
O
(a) 2 (b) 4 (c) 5 (d) 7

21. How many tautomers can you draw for the following diketone?
O O
(a) 1 (b) 2 (c) 3 (d) 4

22. Keto and enol forms of a compound are related to each other as:
(a) resonance structures (b) conformations
(c) configurational isomers (d) constitutional isomers

Conformational Analysis
1. Which Newman projection formula does not represent the following compound?
1
2 Cl
H
Cl
Me Me
Me
(a) (b)
Cl H H
H H
H Me
Cl
H
Me H Me
(c) H (d)
Me H
H Cl
Me H
2. What are the total number of conformers (staggered and eclipsed) that you can draw for the
following molecule?
(a) 4 (b) 5 (c) 6 (d) 7

3. A “gauche” interaction costs 3.8 kJ/mol, a hydrogen–hydrogen eclipsing interaction costs 4.0
kJ/mol, a hydrogen–methyl eclipsing interaction costs 6.0 kJ/mol, and a methyl–methyl
eclipsing interaction costs 11 kJ/mol. What is the relative energy cost of the most stable
conformer of 2,3-dimethylbutane?
(a) 0 kJ/mol (b) 7.6 kJ/mol (c) 8.6 kJ/mol (d) 11.4 kJ/mol
4. Choose the correct Newman projection for 2-methylpentane.
H CH3
H CH3 H H
(a) (b)
CH3 H CH3 H
CH2CH3 CH2CH3
CH3 H
H H H CH3
(c) (d)
H CH3 H CH2CH3
CH3 H

5. Place the following structures properly on the (abbreviated) energy surface for cyclohexane
ring reversal.
1 4
2 2
a= b= c= d=
Twist boat Half chair Half chair Boat
(a) 1 = b or c, 2 = a, 3 = d, 4 = b or c (b) 1 = d, 2 = b or c, 3 = d, 4 = a
(c) 1 = d, 2 = b or c, 3 = a (d) 1 = b or c, 2 = d, 3 = a, 4 = b or c
6. Has how many eclipsing H–H interactions are present in boat conformation?
(a) 1 (b) 2 (c) 4 (d) 6
7. Identify conformer of 2-methyl pentane:
CH3 H
H H H H
(a) (b)
H H CH3 Et
CH2CH3 CH3
CH3 CH3
H H Et
(c) (d)
H H H
CH3 H
H H H

OH
H Z
8.
H H
H
Above gauche form is stable when Z is:
(a) -F (b) —OH (c) —OCH 3 (d) All of these
r
NMe3
H Z
9.
H H
H
Above gauche form is stable when Z is:
O
||
(a) —CH 3 (b) —Et (c) — C — OEt (d) —Ph
10. The eclipsed and staggered forms of ethane are said to differ in:
(a) molecular formula (b) configuration
(c) conformation (d) constitution (e) structure
11. Which of the following is the staggered conformation for rotation about the C 1 — C 2 bond in
the following structure?
CH 3
|
CH 3 CHCH 2 CH 3
1 2 3 4
H CH3
CH3 CH2CH3 CH3 CH2CH3
(I) (II)
H H CH3 H
H H
H
H C2H5 H
CH3 CH3
(III) (IV)
H H H H
H H
H
H
(V)
CH3
H H C2H5
(a) I (b) II (c) III (d) IV (e) V

12. Among the butane conformers, which occur at energy minima on a graph of potential energy
versus dihedral angle?
(a) gauche only (b) eclipsed and totally eclipsed
(c) gauche and anti (d) eclipsed only (e) anti only
13. Which of the following best explains the reason for the relative stabilities of the conformers
shown?
CH3 CH3
H H H CH3
(I) (II)
H H H H
CH3 H
(a) I has more torsional strain. (b) I has more steric strain
(c) II has more torsional strain (d) II has more steric strain
14. Which of the following is the most stable conformation of bromocyclohexane?
Br Br
H H
I II
III Br IV H
H Br
Geometrical Isomerism
1. How many isomers are possible for dimethylcyclopentane (neglecting enantiomers)?
(a) 3 (b) 4 (c) 5 (d) 6
2. How many isomers are possible for dimethylcyclopropane (neglecting enantiomers)?
(a) 1 (b) 2 (c) 3 (d) 4

3. How many isomers are there of dimethylcyclohexane (neglecting enantiomers)?

(a) 4 (b) 6 (c) 7 (d) 9
4. What is the relationship between trans-2-butene and cis-2-butene?
(a) Unrelated compounds (b) Constitutional isomers
(c) Enantiomers (d) Diastereomers
5. Determine the double bond stereochemistry (E or Z) for the following molecules.
F CH3 F Br
H3C H H I
A B
(a) A: E; B: E (b) A: Z; B: Z (c) A: E; B: Z (d) A: Z; B: E
6. Which of the following alkenes is (1E,3S)-1,3-dimethylcyclodecene?
(a) (b) (c) (d)

H H
C==C H
CH3 C==C
CH2CH3
H
(a) cis, trans-2, 4-heptadiene (b) 2Z , 4E-2,4-heptadiene
(c) cis, cis-2,4-heptadiene (d) trans, trans-2,4-heptadiene
(e) 2E , 4E-2,4-heptadiene
8. Geometrical isomerism results because the molecule:
(a) rotates the plane of polarized light
(b) has a plane of symmetry
(c) has a centre of symmetry
(d) has two dissimilar groups attached to both ends of double bond
9. (i) CH 2 == CH — CH 2 — CH == CH 2 (ii) CH 2 == CH — CH == CH — CH 3
(iii) CH 3 — CH == CH — CH == CH — CH 3
The numbers of possible geometric isomers for the above compounds respectively are:
(a) 0, 2, 4 (b) 2, 2, 4 (c) 0, 3, 3 (d) 0, 2, 3
10. Which of following compound will not show geometrical isomerism ?
(a) (b)
O O
(c) (d)

11. Which of the following compound show cis and trans isomerism ?
Cl Br
(a) Cl — CH == CH — Cl (b) C == C
Cl Br
CH3
(c) (d) C
CH3
12. Which of the following compound not show geometrical isomerism ?

CH3 CH3
(a) C == C == C (b) CH 3 — C ºº C — CH 3
H H
CH3 H
(c) C == C (d) All of these
Cl H
13. How many geometrical isomer are possible for the given compound ?
(a) 0 (b) 1 (c) 2 (d) 3

14. How many geometrical isomers are possible for
(a) 0 (b) 1 (c) 2 (d) 3

Cl
?
Cl Cl
(a) 0 (b) 1 (c) 2 (d) 3
CH 3 — CH == C == CH — CH == CH — CH 3 ?
(a) 0 (b) 1 (c) 2 (d) 3
CH 3 — CH == C == C == C == CH — CH == CH — CH 3 ?
(a) 1 (b) 2 (c) 3 (d) 4
18. Which of the following compound will not show geometrical isomers ?
Cl Cl
(a) (b) (c) Cl (d) All of these
Cl

(a) 6 (b) 7 (c) 8 (d) 9
20. How many geometrical isomers are possible for ?
(a) 3 (b) 4 (c) 5 (d) 6
CH3 CH3
21. How many geometrical isomers are possible for H H ?
(a) 2 (b) 3 (c) 4 (d) 6

22. How many geometrical isomers are possible for CH 3 — CH == CH — CH == CH — Cl ?
(a) 2 (b) 3 (c) 4 (d) 5
23. How many geometrical isomers are possible for Ph — CH == CH — CH == CH — Ph ?
(a) 2 (b) 3 (c) 4 (d) 5
?
(a) 0 (b) 1 (c) 2 (d) 3

25. What is the relationship between the following compounds?
CH3 H H H
C==C and C==C
H Br CH3 Br
(a) Configurational isomers (b) Conformational isomers
(c) Constitutional isomers (d) Structural isomers (e) Positional isomers
Optical Isomerism
1. Determine the relationship between the two molecules shown.
O O
CH CH3
3
(a) constitutional isomers (b) enantiomers

(c) diastereomers (d) identical molecules
2. Which of the following diols exists as a pair of enantiomers?
(a) cis-1,3-cyclohexanediol (b) trans-1,3-cyclohexanediol

(c) cis-1,4-cyclohexanediol (d) trans-1,4-cyclohexanediol

3. Which of the 7 isomers of dichlorocyclohexane possess a plane of symmetry?
(a) cis-1,2; cis-1, 3 (b) 1, 1; cis-1,2; cis-1, 3
(c) cis-1,2; cis-1,3; cis-1,4 (d) 1,1; cis-1,2; cis-1,3; cis-1,4; trans-1,4
20
4. What is the specific rotation [a ]D of the following molecule?
a = 4.42°
C = 0.1g ml–1
l = 10cm
O
(a) + 4.42° (b) + 0.442° (c) + 44.2° (d) - 44.2°
5. If a sample of 2-butanol has an enantiomeric excess of 60% of l-2-butanol, then per cent of
each isomer in the mixture is:
(a) 60% levorotatory and 40% dextrorotatory (b) 80% levorotatory and 20% dextrorotatory
(c) 70% levorotatory and 30% dextrorotatory (d) 66% levorotatory and 34% dextrorotatory
6. How many stereocenters are there in the following molecule?
NH2
O
HO
(a) 0 (b) 2 (c) 3 (d) 1

7. Explain why the two stereoisomers of 1,4-dimethylcyclohexane are achiral?
(a) Because they are identical
(b) Because they are enantiomers
(c) Because they both have the plane of symmetry
(d) Because there are no stereocenters present in either molecule
8. Consider the following two stereoisomers. How are they different?
Cl Cl
O O
(a) They have different melting points
(b) They rotate plane-polarized light in opposite directions
(c) They have different solubilities in water
(d) They have different indices of refraction

9. Which of the following steroid derivatives has 9 stereocenters?

O
O Me
Me Me
Me
Me H H
(a) (b) Me H
Et
H OH
H H
HO
H HO
Digitoxigenin Stigmasterol
OH
Me CO2H Me Me
Me H O
Me
(c) (d) H
Me H O
H H H
HO
H H H
Cholic acid Diosgenin
10. Which of the following compound is chiral ?
O OH
(a) (b)
H
F CH3 F
(c) CH3 F (d) Cl C Br
H H
11. Identify meso compound:
CH3
CH3 H Cl
H Cl
(a) (b)
Cl H
Cl H CH3
CH3
Cl
Cl
(c) (d)
Cl
Cl
12. In which of the following compound have plane of symmetry ?

CH3 CH3
Cl Cl
(a) (b)
CH3 CH3
Cl Br
(c) (d) I C H
Cl Cl
13. ; Relation between (A) and (B) is:
(A) (B)
(a) Diastereomers (b) Enantiomer (c) Identical (d) Structural isomer
Cl
14. ; Number of plane of symmetry in above compound is:

Cl
Cl
(a) 0 (b) 1 (c) 2 (d) 3
15. Which of the following is chiral compound ?
(a) (b) (c) (d)
16. Which of the following compound is achiral although it contain chiral center ?
CH3
Cl
H OH
(a) Br F (b)
HO H
I
CH3
CH3
H OH O
(c) H OH (d)
CH3 O

17. Which of the following compound is achiral ?

O O O O
(a) (b) (c) (d)
O O O O
18. Which of the following compound is resolvable ?
NO2 SO3H NO2 SO3H
(a) (b)
NO2 SO3H SO3H NO2
(c) (d)
H H
19. How many planes of symmetry are present in H C == C H ?
(a) 1 (b) 2 (c) 3 (d) 4
20. How many planes of symmetry are present in (Benzene) ?
(a) 3 (b) 5 (c) 7 (d) 9

CO2H
H OH
21. ; Number of plane of symmetry in given compound is:
H OH
CO2H
(a) 1 (b) 2 (c) 3 (d) 4

OH
22. ¾¾® (a) (Number of chiral center)
O
¾¾® (b) (Number of chiral center)
CO2H
sum of ( a + b = ?) :
(a) 3 (b) 4 (c) 5 (d) 6

23. Which of the following are meso compound ?

CH2OH
H OH
Br Br
(a) H H (b) HO H
CH3 CH3 CH2OH
CH3
OH
OH
24. For the following compound number of chiral centers and stereoisomers are:
CH 2 — CO 2 H
|
CH — CO 2 H
|
HO — CH — CO 2 H
(a) 1, 2 (b) 2, 4 (c) 2, 3 (d) 3, 8
25. Relation between pair given below is:
Cl H H Cl
H OH OH H
(a) enantiomers (b) diastereomers (c) identical (d) structural isomer
26. Which of following compound has one of the stereoisomers as a meso compound ?
(a) (b) (c) (d)
H
27. H
Cl
Cl
How many plane of symmetry is present in above compound ?
(a) 0 (b) 1 (c) 2 (d) 3
28.
How many plane of symmetry is present in above compound ?

(a) 1 (b) 2 (c) 3 (d) 4

29. Which of the following compound has plane of symmetry and center of symmetry ?
F F F
F F F F F F

F F F F F F
F F F
CH3
CH3
30.
How many chiral center are present in above compound ?

(a) 1 (b) 2 (c) 3 (d) 4
31. Which compound has plane of symmetry and C 2 axis of symmetry ?
O
Cl H
(a) (b) C == C
H H Cl H
F
F
32. What is optical purity of 6 gm (d) and 4 gm (l) ?
(a) 40% (b) 20% (c) 10% (d) 60%
33. What is the optical rotation of ( A) ?
O Cl
Cl O
(A)
(a) +50° (b) -50° (c) 0° (d) 100°
CH3
34.
Number of chiral center present in above compounds are :

(a) 0, 1 (b) 0, 2 (c) 0, 3 (d) 1, 2
O O
N
35.
Number of chiral center present in above compounds are:

(a) 1, 2 (b) 2, 2 (c) 2, 1 (d) 2, 3

CH3 CH3
36.
O Or
H
Number of chiral center present in above compounds are:
(a) 1, 1 (b) 1, 2 (c) 2, 2 (d) 2, 1
Et H
37. CH3—C—H CH3—C—D
CH3CH2—CH3 T
Number of chiral center present are:
(a) 0, 0 (b) 1, 0 (c) 1, 1 (d) 2, 2
38. Number of stereo centre present are:
CH 3 — CH == CH — CH — CH 3
|
Cl
(a) 2 (b) 3 (c) 4 (d) 5
39. Br Cl
Number of stereocenters in the compound given are:

(a) 0 (b) 1 (c) 2 (d) 3
CO2H
H OH
40. Number of chiral centers present in tartaric acid is:
H OH
CO2H
(a) 1 (b) 2 (c) 3 (d) 4

CH3 CH3
H C Cl and C
H
H
CH3 CH2Cl
(a) Constitutional isomers (b) Enantiomers
(c) Diastereomers (d) Conformational isomers
(e) Superimposable without bond rotation

42. What is the relationship between the structures shown below?

CH2Br CH3
H Br
and
(a) Not isomers (b) Constitutional isomers

(c) Conformational isomers (d) Configurational isomers (e) Enantiomers
H H and H Br
Br Br H Br
(a) Diastereomers (b) Constitutional isomers
(c) Conformational isomers (d) Configurational isomers (e) Enantiomers
44. Which of the following compounds is never chiral?
(a) 2,3-dibromobutane (b) 1,3-dibromobutane
(c) 1,2-dichlorobutane (d) 1,4-dibromobutane (e) 1-bromo-2-chlorobutane
45. Which of the following compounds is chiral?
H H CH3 CH3
CH3 Cl CH3 Br CH3 Br CH3 Cl

(a) (b) (c) (d)
CH3 Cl CH3 Cl CH3 Cl CH3 Cl
H H CH3 CH3
46. How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?

(a) 0 (b) 1 (c) 2 (d) 3 (e) 4
47. How many asymmetric centers are present in the compound shown below?
H
CH(CH3)2
H3C
H3C H
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

48. A and B are stereoisomers. They are non-superimposable and are mirror images of each other.
Which of the following best describes the relationship between A and B?
(a) structural isomers (b) enantiomers
(c) conformational isomers (d) diastereomers (e) constitutional isomers
Cl Cl
H Br and Br CH3
CH3 H
(a) enantiomers (b) diastereomers
(c) configurational isomers (d) identical compounds (e) constitutional isomers
50. Which of the following compounds has an S configuration?
Cl CH2Cl
(a) H CH3 (b) H CH3
CH2Cl Cl
CH2Cl H CH2Cl
(c) CH3 H (d) CH3 Cl (e) Cl CH3
Cl CH2Cl H
51. Which of the following compounds has an R configuration?

H CH == CH2
(a) CH3CH2 Br (b) Br H
CH == CH2 CH2CH3
CH2CH3 CH2CH3 CH == CH2

(c) Br CH == CH2 (d) CH2 == CH H (e) CH CH Br
3 2
H Br H
52. Which of the following groups has the highest priority using the Cahn, Ingold, Prelog rules?
O O
|| ||
(a) — C— OH (b) — C— H
O
||
(c) —OH (d) —O—CH 3 (e) — C — O — CH 3
53. Which of the following is/are optically inactive?
(a) A 50-50 mixture of R and S enantiomers (b) A meso compound
(c) Every achiral compound (d) A racemic mixture (e) All of the above

54. If ( S)-glyceraldehyde has a specific rotation of –8.7º, what is the specific rotation of
( R )-glyceraldehyde?
(a) –8.7º (b) +8.7º
(c) 0.0º (d) cannot be determined from the information given
55. A mixture of equal amounts of two enantiomers.....................
(a) is called a racemic mixture (b) is optically inactive
(c) implies that the enantiomers are meso forms (d) both (a) and (b)
56. The specific rotation of a pure substance is 1.68º. What is the specific rotation of a mixture
containing 75% of this isomer and 25% of the (–) isomer?
(a) +1.68º (b) 0º (c) +1.26º (d) +0.84º (e) +0.42º
57. (–)-Mandelic acid has a specific rotation of –158º. What would be the specific rotation of a
solution which contains 40% (–)-mandelic acid and 60% (+)-mandelic acid?
(a) +95º (b) +63º (c) +32º (d) –32º (e) –63º
CH3 CH3
Cl H H Cl
and
H Cl Cl H
CH3 CH3
(a) Enantiomers (b) Diastereomers
(c) Constitutional isomers (d) Conformational isomers (e) Identical compounds
CH3 CH3
Cl H H Cl
and
Cl H Cl H
CH3 CH3
(a) Enantiomers (b) Diastereomers

(c) Constitutional isomers (d) Conformational isomers (e) Identical compounds
60. How many diastereomers exist for the compound below?
CO2H
H OH
H OH
HO H
CH2OH
(a) 2 (b) 4 (c) 6 (d) 7 (e) 8
61. Which of the following is a meso compound?

CH3 CH3
H Cl H Cl
(a) (b)
H Cl Cl H
CH3 CH3
CH3 CH3 CH3
H Cl H Cl Br Cl
(c) (d) (e)
H Cl Cl H Br Cl
CH2CH3 CH2CH3 CH2Cl
62. What is the configuration of the following compound?

CH3
H Cl
Cl H
CH2CH3
(a) 2 S ,3 R (b) 3 R ,3 S (c) 2 S ,3 S (d) 2 R ,3 R
(e) Can’t do R and S; the compound is achiral
63. In the Fischer projection below, what are the configurations of the two asymmetric centers?
CO2H
2
H CH3
3
H OH
CH2CH2OH
(a) 2 R ,3 R (b) 2 R ,3 S (c) 2 S ,3 R (d) 2 S ,3 S

(e) cannot be determined from structure
64. How many chiral carbon centers are in the following molecule ?
CH3
OH CH3
CH3
N
O H
(a) 0 (b) 1 (c) 2 (d) 3

Miscellaneous Problems on Stereomers

1. How many stereoisomers are there for the following structure?
(a) 1 (b) 2 (c) 3 (d) 4

2. Shikimic acid is an important natural product. How many stereoisomers are possible for
shikimic acid?
O
HO
OH
HO
OH
(a) 16 (b) 8 (c) 4 (d) 2
3. How many stereoisomers are there for 1-ethyl-3-methylcyclohexane?

(a) 2 (b) 3 (c) 4 (d) 6
4. Total number of stereoisomer
CH3 Br H
| |
CH—CH CH == CH—CH3
CH3
CH3 CH == C == CH—CH3
CH == CH2
(a) 2 3 (b) 2 4 (c) 2 5 (d) 2 6
NH2
5. ¾® ( a) ¾® ( b)
OH
Number of stereoisomer ( a + b = ?)
(a) 5 (b) 6 (c) 7 (d) 8
O
||
6. CH 3 — C — CH 2 — CH == CH — CH — CH 3
|
Cl
Total number of stereoisomers are:
(a) 4 (b) 6 (c) 8 (d) 12

7. ¾¾® a(stereoisomers)
¾¾® b (stereoisomers)
a and b are stereoisomers sum of ( a + b = ?) :

(a) 4 (b) 6 (c) 8 (d) 12
Br
8. ¾¾® a
Cl
Br
¾¾® b
Cl
sum of stereoisomer ( a + b = ?):
(a) 4 (b) 6 (c) 8 (d) 12
9. How many isomer of C 6 H 12 containing cyclobutane ring ? (Including stereoisomeris)
(a) 5 (b) 6 (c) 7 (d) 8
10. How many stereoisomers are possible for:
Cl CH == CH—Cl
Cl CH == CH—F
4 5
(a) 2 (b) 2 (c) 2 6 (d) 2 7
11. How many stereoisomers exist for the compound given below?
BrCH 2 CH(CH 3 )CH 2 CH 3
(a) 0 (b) 1 (c) 2 (d) 4 (e) 8
12. How many stereoisomers exist for the compound given below?
CH 3 CHClCH 2 CHClCH 3
(a) 0 (b) 1 (c) 2 (d) 3 (e) 4

[C] General Organic Chemistry

Inductive Effect & its Applications
1. Which of the following has strong +I effect ?
–
(a) O (b) —Et (c) —CH 3 (d) —NH — CH 3
2. In which of the following compounds inductive effect is not present ?
(a) CH 3 — CH 2 — Br (b) CH 3 — CH == CH 2
(c) CH 3 — C ºº CH (d) CH 3 — CH 2 — CH 3
3. In which of the following compounds + I effect of methyl group is not present ?
CH3 CH3
(a) (b)
(c) H 2 C == CH — CH 3 (d) CH 3 — CH ==O

4. In which of the following compounds – I effect of methyl group is operating?
(a) CH 3 — Cl (b) CH 3 — CH 3
(c) CH 3 MgBr (d) CH 3 — NO 2
5. In which of the following compounds ( +I ) effect of alkene will operate?
(a) CH 3 — CH == CH 2 (b) CH 3 — CH 2 — CH == CH 2
(c) HC ºº C — CH == CH 2 (d) H 2 C == CH — CH == CH 2
CH3 C ºº CH
6. ;
;
(a) (b)
In the compounds (a) and (b) inductive effect of phenyl group is:
(a) + I , + I (b) -I , + I (c) -I , - I (d) +I , – I
7. CH3 — CH2 — CH2 — CH2 — Cl

4 3 2 1
Inductive effect of chlorine is minimum on:
(a) C 1 (b) C 2 (c) C 3 (d) C 4
8. Which of the following substituent/group is an electron donating group overall ?
r
(a) —Br (b) — C CH 3 (c) —OCH 3 (d) — N(CH 3 ) 3 (e) —CCl 3
||
O

9. Rank the indicated bond in the given compound in order of decreasing bond strength:
a b
c
—Cºº C—
(a) a > b > c (b) b > a > c (c) b> c > a (d) a > c > b
10. In which of the following compounds — CH 3 shows -I effect ?
CH3 CH3
(a) (b)
(c) CH 3 — Mg — Br (d) CH 3 — CH 3
11. Which of the following compounds on heterolytic fission gives most stable carbocation ?
CH3 CH3
Br Br Br
(a) (b) (c) (d)
12. Which of the following represent methyl carbocation ?

r H
CH3 rC H
(a) H C (b)
H H
CH3 r CH3
C CH3 rC CH3
(c) (d)
H CH3
13. Which of the following is the most stable carbocation?

CH3
CH3 CH3 CH3 Å CH2
Å
(I) (II) (III) Å (IV) (V)
Å Å

14. Which of the following carbocations is the most stable?
Å Å
(a) CH 3 CH 2 (b) CH 3 CHCH 3
CH 3 CH 3
| |Å r
(c) CH 3 C Å (d) CH 3 CCH 2 (e) CH 3 CH 2 CH 2
| |
CH 3 CH 3

15. Stability order of given carbocation is:

r r r
CH2 ; CH ; C
(a) (b)
(c)
(a) b > a > c (b) a > b > c (c) c > b > a (d) c > a > b
Resonance
1. How many total resonance structures can be drawn for the following anion (including those
without separation of charge)?
: O:
s
(a) 1 (b) 2 (c) 3 (d) 4

2. How many resonance structures can be drawn for the following molecule?
r
H2N
(a) 1 (b) 4 (c) 3 (d) 2

3. How many other major contributing resonance structures are possible for the following
heterocycle?
O
(a) 2 (b) 4 (c) 6 (d) 8

4. How many energetically equivalent resonance structures exist for the oxalate dianion?
O O
C—C
O– O–
(a) 1 (b) 2 (c) 3 (d) 4
5. How many resonance structures can be drawn for the following carbocation?
r
O
(a) 0 (b) 1 (c) 3 (d) 4
6. Which of the following structures is not a resonance structure of the others?
+
OCH3 OCH3 OCH3 OCH3
+
(a) (b) (c) (d)
+ +

7. Which of the following resonating structures contributes maximum to the resonance hybrid?
+
OCH3 OCH3 OCH3 OCH3
+
(a) (b) (c) (d)
+ +
8. How many resonating structures are there for anthracene?
(a) 6 (b) 5 (c) 4 (d) 3

9. How many uncharged resonating structures are there for azulene?
(a) 1 (b) 2 (c) 3 (d) 4

10. How many resonating structures are there for phenanthrene?
(a) 6 (b) 5 (c) 4 (d) 2

11. Draw the given carbocation in orbital phase.
r
CH2
(a) CH2 (b) CH2
H
(c) C (d) CH2
H
12. Which of the following substrates is an electron withdrawing group ?

(i) —CH 3 (ii) —OH
(iii) (iv) —OCH 3 (v) —SO 3 H

13. Which of the following has two equivalent resonating structure ?

O O O O
|| || s || ||
(a) H — C — NH 2 (b) H — C — O (c) H — C — OH (d) H — C — CH 3
14. Which of the following has maximum number of resonating structure ?
r r r
r
(a) (b) (c) (d)
15. Which of the following compound is not resonance stabilized ?

s
O s
(a) (b) (c) (d)
O O s O
16. Which of the following is not a resonance structure of the others ?

O– O O O
–
–
(a) (b) (c) (d)
–
17. Stability order of the following resonating structure will be:

O Os Os Or
|| | | |
r r s
O O O O
(i) (ii) (iii) (iv)
(a) i > ii > iii > iv (b) ii > i > iii > iv (c) iii > ii > i > iv (d) i > iii > ii > iv
18. Select the molecule in which p bonds are conjugated ?
H H
(a) H 2 C == CH — CH — CH == CH 2 (b) H C == C == C H
(c) H C== C H (d) both (a) and (c)
H C== O
H
19. Which of the following is not a valid resonance structures ?
–2
s O
O O O
s r
(a) (b) (c) (d)
s
20. In which of the following compound resonance is not possible?
O
(a) (b) (c) (d)

21.
How many resonating structure are possible for Napthalene (lacking formal charges) ?
(a) 1 (b) 2 (c) 3 (d) 4
r
H—C—H
22. ( A). Most stable resonating structure for ( A) is :
O—H
CH2
CH2 CH2 CH2
r r
(a) (b) (c) (d)
r
O—H
OH OH r OH
r
23. (A). Number of resonating structure of ( A) is:
(a) 1 (b) 2 (c) 3 (d) 4

24. Which of the following is not resonance stabilized ?
O O
O O
(a) (b) (c) (d)
25. In which of the following compounds lone pair of oxygen is delocalized ?

O
(a) (b) (c) (d)
O O O O
r
26. Resonance hybrid of H 2 C == CH — CH 2 is :
dr dr ds ds ds
(a) H2C—CH—CH2 (b) H2C—CH—CH2
ds d ·
(c) H2C—CH—CH2 (d) H 2 C == CH — CH 2
27. In which of the following resonating structures, extra bond will be formed ?
s r
CH2
(a) H 2 C == CH — CH 2 (b)
r
(c) H 3 C — CH — O — CH 3 (d)
r
28. In which of the following compounds d-orbital resonance takes place ?

s s r s
(a) Cl — CH 2 (b) CH 3 — S — CH 3 (c) Me 3 P— CH 2 (d) All of these
s Cl
29. Cl—C ; In above carbanion electron is delocalized in :
Cl
(a) p-orbital (b) d-orbital (c) s-orbital (d) f-orbital
30. Which of the following carbanions is resonance stabilized ?
(a) O (b) H—N N—H (c) S S (d)

O s s s
s
31. Compare relative stability of following resonating structure:
s s
O O O
|| | r |
CH 3 — C — OH ¬
¾® CH 3 — C == O— H ¾® CH 3 — C — OH
¬
r
( a) ( b)
( c)
(a) a > b > c (b) a > c > b (c) b > a > c (d) c > a > b
32. Which of the following is not the resonating structure of each other?
O OH
r
(a) ¬
¾® (b) CH 3 — N == O ¬ ¾® CH 3 — O — N == O
|
Os
r s
(c) CH 3 — C ºº N ¬¾® CH 3 — N ºº C (d) All of these
33. Which of the following is not the resonating structure of given?

s
H 2 C == CH — CH 2
14
s s
(a) H 2 C — CH == CH 2 (b) H 2 C == CH— CH 2
14 14
s
(c) H 2 C == CH — CH 2 (d) both (b) and (c)
34. Most stable resonating structure of given cation is:
r
(a) r (b) (c) r (d)

O O O O
r r

35. Most stable resonating structure of given cation is:

r
CH2
NH2
CH2 CH2 CH2 CH2
r r
(a) (b) (c) (d)
r
NH2 NH2 NH2 NH2
r
36. Most stable resonating structure of formic acid is:
O s s r
O O O
|| r r s
(a) H — C — OH (b) H—C == O—H (c) H—C—OH (d) H—C—OH
s
O
37. Most stable resonating structure of is:
Cl
O O O O
s s
(a) (b) (c) (d)
s
Cl Cl Cls Cl
38. Most unstable resonating structure of phenol is:
r r
OH O—H O—H r
O—H
s s
(a) (b) (c) (d)
s
39. Most unstable resonating structure of given is:
r
(a) (b) r (c) (d) All of these

r
40. Compare leaving group tendency of following halide ion :
(a) Is > Br s > Cl s > F s (b) F s > Cl s > Br s > Is
(c) Cl s > Br s > Is > F s (d) Br s > Cl s > F s > Is

41. Compare relative stability of following resonating structures :

r s
CH 3 — O — CH == CH — C ºº N; CH 3 — O — CH == CH — C == N
(a) (b)
r s r s
CH 3 — O == CH — CH — C ºº N ; CH 3 — O == CH — CH == C == N
(c) (d)
(a) a > b > c > d (b) a > c > d > b (c) a > d > c > b (d) c > d > b > a
42. Compare relative stability of following resonating structures :
r s
CH 3 — NH == CH — CH — CH == CH 2 CH 3 — NH — CH == CH — CH == CH 2
( a) ( b)
s r
CH 3 — NH — CH — CH == CH — CH 2
( c)
(a) a > b > c (b) b > a > c (c) b > c > a (d) a > c > b
43. Most stable resonating structure is:
r
(a) CH 3 — O — CH == CH — CH == CH — CH 2
r
(b) CH 3 — O — CH == CH — CH — CH == CH 2
r
(c) CH 3 — O — CH — CH == CH — CH == CH 2
r
(d) CH 3 — O == CH — CH == CH — CH == CH 2
44. Most stable resonating structure is:
r CH3 r
(a) CH3—CH == CH—CH == N (b) CH3—CH == CH—CH—N
CH3
r s r r
(c) CH3—CH—CH == CH—N (d) CH3—CH—CH—CH == N
r
CH2
CH3
r r r
(a) (b) (c) (d)
r

r
CH2
NH2
CH2
r r
(a) (b) (c) (d)
NH2 NH2 NH2 NH2

r
r
O
47. Most unstable resonating structure of is :
s
s O O O
O
r r s
(a) (b) (c) (d)
r s r
D
C
B
48. E A
Formic acid
A , B ,C , D are resonating structure of formic acid. Structure of B is :
s s r
O O O O
r r
(a) H—C—OH (b) H—C == O—H (c) H—C—OH (d) H—C—OH
s
49.
E A&B
A and B are resonating structure of :

O O O
O s
(a) CH3—C—OH (b) (c) CH3—C—O (d) CH3 NH2
s r s r
50. O == C == O; O— C ºº O ; O— C == O
( A) ( B) (C )
A, B, C is represent by:
B C B
(a) (b) (c) B (d) C
E A, B, C E A&C E E
A A
51. Which of the following pairs are resonance structures?

CH3 CH3 CH3
I. and IV. and
CH2 CH3 CH2 CH3

Å
Å
II. and V. and
CH3 CH3
Å Å
III. and

52. Which of the following pairs are resonance structures?
s
I. CH2 == CHCH3 and IV. CH3—C—H and CH3—C—H
O .. O ..
..
CH2 == C—H and CH3—C—H Å

II.
..
..
.. OH .. O .. V. CH3—O—CH3 and CH3CH2OH

..
..
..
Å
III. CH3—C—H and CH3—C—H
.. O .. .. O ..
s
..

53. Which of the following is not a resonating structure of the species shown?
..
NH2
E
H
Å
Å
..
..
..
NH2 NH2 NH2 NH2
E E E E
Å
(I) H (II) H (III) H (IV) H
Å Å Å
s
54. In which of the following does resonance delocalization of electron density not play a role?
(a) allyl cation (b) benzyl anion
(c) CO 2-
3 (d) O3 (e) cyclohexyl radical
55. Due to electron delocalization, one would predict that the carbon-oxygen bond in acetamide,
CH 3 CONH 2 , ------------ .
(a) is nonpolar
(b) has more double bond character than the carbon-oxygen bond of acetone, (CH 3 ) 2 CO
(c) is longer than the carbon-oxygen bond of dimethyl ether, (CH 3 ) 2 O
(d) is longer than the carbon-oxygen bond of acetone, (CH 3 ) 2 CO
(e) is formed by overlapping sp 3 orbitals
56. Which of the following is the most stable resonance contributor to acetic acid ?
.. O ..
.. ..
CH3—C—O—H
OÅ Os
s Å
(a) CH3—C—OH (b) CH3—C == O—H
Å Å
s
..
..
Å
(e) CH3—C—O—H
.. ..
(c) CH3 == C—O—H (d) CH2 == C—O—H

..
.. OH
.. O ..
..
.. O ..
s
..
..
57. Which is the most important contributing resonating structure of the following ?
O s
CH2—N—O
.. O ..s O ..
..
..O ..s ..O ..s

..
..
..
s CH —N—O ..s
.. ..
s s
CH2—N—O .. (c) CH2 == N—O.. (d) s CH2—N == O..
Å
.. ..
.. ..
..
..
(a) (b) 2
..
Å
..
Å Å

58. Which of the following pairs are resonating structure?

s
O O
s s s r s
(a) H—O—C—O and H—O—C == O (b) N== C—O and C ºº N—O
O O
O
(c) and O (d) H—C—NH—CH3 and CH3—C—NH2
59. Rank the resonance structure in each group in order of increasing contribution to the
resonance hybrid :
CH 3 CH 3 CH 3
| | r | ··
CH 3 — C == N — NH 2 ¬® CH 3 — C— N == NH 2 ¬® CH 3 — C— N— NH 2
s r s
(i) (ii) (iii)
(a) i<ii<iii (b) ii<i<iii (c) iii<ii<i (d) iii<i<ii
60. In which of the compound lone pair of nitrogen is not involved in resonance?
(a) (b) (c) (d)
61. Which of the following compounds has localized lone pair of electrons?
s
NH2 CH2 — NH2 CH — CH3
(a) (b) (c) (d) N

H
62. Which of the following compounds has delocalized lone pair of electrons?
O
(a) (b) (c) (d)
N N N
N
H H H
63. Which of the following group shows (+M) effect ?
O
NH—CH3 CH3
C—H
(a) (b) (c) (d)

64. Which of the following group shows (–M) effect ?

O
OCH3 O—C—CH3
(a) (b)
NO2
NH2
(c) (d)
65. Which of the following carbanions is resonance stabilized?

s s s
(a) CH 3 — O (b) CH 3 — C == O (c) CH 2 — CH == O (d) All of these
66. Which of the following carbocations is resonance stabilized?
r r r r
(a) (b) (c) (d)
67. Which of the following carbocations has maximum number of resonating structures ?
r r r r
(a) (b) (c) (d)
68. Resonance hybrid of given carbocation is:

r
CH2
dr dr
CH2 CH2 CH2
H
dr dr dr s
(a) (b) (c) (d) H—B—H
dr
dr dr H
r
69. Resonance hybrid of H 2 C == CH — CH — CH 3 is :
dr dr dr dr dr
(a) H2C—CH—CH—CH3 (b) H2C—CH—CH—CH3
dr dr
(c) H2C—CH—CH2—CH3 (d) H2C—CH—CH—CH3
70. Which of the following is an allylic carbocation?

Å Å
(I) CH 3 CH == CH 2 (II) CH 3 CH == CH — CH 2
Å Å Å
(III) CH 3 CHCH 3 (IV) CH 3 CHCH 2 CH == CH 2 (V)

71. Which of the following is a benzylic cation?

Å
(I) (II) (III) (IV) (V)

Å
Å Å Å
CH2 CH2 CH2 CH3

72. Which of the following is the most stable carbocation?
Å Å
(I) CH 3 C == CH 2 (II) CH 3 CH == C
CH 3
| Å Å
(III) CH 3 — C (IV) CH 3 — C — CH 3 (V) CH — CH 3
Å |
CH 3
73. Which of the following carbocation is not resonance stabilized?
r r r r
CH2 CH—CH3 CH3— C—CH3 CH3— C—CH3
CH3 CH3
(a) (b) (c) (d)
74. Which of the given following stability order is correct ?

r
r O < O
(a) H2C
r r
>
(b) O
r
(c) r > H2N CH2
s s
CH2 < CH2
(d) Cl F
75. Which of the following carbocation is most stable ?

r r
(a) CH 2 — CH == CH — O — CH 3 (b) CH 2 — CH == CH — CH == CH 2
r r
(c) CH 3 — CH 2 — CH— O — CH 3 (d) CH 3 — CH— CH 2 — O — CH 3

76. Which of the following carbocation is most stable?
r r r r
CH2 CH2 CH2 CH2
(a) (b) (c) (d)
NH2 s CH3
OH O
77. Which of the following carbocation is highly unstable ?
r r
(a) H 2 C == CH — CH 2 (b) CH 3 — CH— CH 3
r r
(c) CH 3 — C == O (d) CH 2 — CH == O
78. Compare stability of the following carbocation?
r r r
CH2 CH2 CH2
(i) (ii) (iii)
CH3 CD3 CT3
(a) i>ii>iii (b) iii>ii>i (c) iii>i>ii (d) i>iii>ii

79. Which of the following is most stable carbocation ?
r
CH2
r r
(a) (b) (c) (d)
r
O O O
80. Which of the following carbocation is most stable?

r r
CH2 r r CH2
CH2 CH2
(a) (b) (c) (d)
81. Which of the following carbocation is most stable ?

r
CH2 r r r
CH2 CH2 CH2
(a) (b) (c) (d)

82. Compare relative stability of following carbocation :

r r
r
(i) (ii) (iii)
(a) i>ii>iii (b) iii>i>ii (c) i>iii>ii (d) iii>ii>i

83. Most stable resonating structure of the given anion is:
s
O == CH — CH == CH — CH 2
s s
(a) O == CH — CH — CH == CH 2 (b) O— CH == CH — CH == CH 2
r s s r s r
(c) O == CH — CH — CH — CH 2 (d) O— CH == CH — CH — CH 2
84. Which of the following carbanion is/are resonance stabilized ?
O
O
s
(a) (b) CH2
s
O
|| s s
(c) CH 3 — C — CH 2 — CH 2 (d)
85. Which of the carbanion is most stable?
s s s
s CH2 CH2 CH2
CH2
(a) (b) (c) (d)
CH3 OCH3 NO2

86. Which of the following is most stable carbanion ?
s
CH2 s
s O CH2
O s
(a) (b) CH3—C—O (c) (d)
CH3
87. Which of the following carbanion is most stable ?
s s s
CH2 CH2 s CH2
CH2
(a) (b) (c) (d)
F Cl CH3

88. Arrange the following radical in their decreasing order of stability :
(i) (ii) (iii)
(a) ii>i>iii (b) i>ii>iii (c) i>iii>ii (d) ii>iii>i

89. Which of the following is the most stable radical?
• •
CHCH3 CH2—CH2
(I) (II)
CH2CH3 CH2CH3 CH2CH3

•
(III) (IV) (V)
• •

90. Arrange the following radical in order of decreasing stability :
(i) CH2—CH3 (ii) CH—CH3 (iii) CH—CH2
(a) ii>i>iii (b) i>ii>iii (c) iii>ii>i (d) iii>i>ii

91. Which of the following carboanion is resonance stabilized ?
s s s
s
(a) (b) (c) (d)
92. Which of the following carboanion is not resonance stabilized ?

s
CH2
s s
s
(a) (b) (c) (d)
O
93. Resonance hybrid of s C s is:
O O
–1/3 –1 –2/3
– 2/3 O O
O O
(a) C (b) C –1/3 (c) C –1 (d) C –1/3
– 2/3 O O
O O O O O
O –1/3 –1 –1/3
– 2/3

94. In which of the following carbanions electron will be delocalized in d-orbital?

s s s
Os O O O
(a) (b) (c) (d)

Cl
Cl Cl
95. In which of the following compound Steric inhibition of resonance effect will operate?
CH3 NO2
CH3 CH3
(a) (b)
CH3 CH3
NO2 NO2
CH3 CH3 CH3
(c) (d)
96. In which of the following lone pair of nitrogen is not involved in resonance?
(a) (b) (c) (d)
97. Most unstable resonating structure amongst those given below is :

s
O O
|| s |
(a) H — O — C — O (b) H — O — C == O
s
O
r | s
(c) H — O == C — O (d) All are equally stable
r
O O r O
98. ¬¾® ¬¾®
r
(I) (II) (III)
The most stable canonical structure among the given structure is:
(a) I (b) II
(c) III (d) all are equally stable

99. The increasing order of stability of the following free radicals is:
· · · ·
(a) (C 6 H 5 ) 3 C <(C 6 H 5 ) 2 CH < (CH 3 ) 3 C <(CH 3 ) 2 CH
· · · ·
(b) (C 6 H 5 ) 2 CH <(C 6 H 5 ) 3 C < (CH 3 ) 3 C <(CH 3 ) 2 CH
· · · ·
(c) (CH 3 ) 2 CH <(CH 3 ) 3 C < (C 6 H 5 ) 3 C <(C 6 H 5 ) 2 CH
· · · ·
(d) (CH 3 ) 2 CH <(CH 3 ) 3 C < (C 6 H 5 ) 2 CH <(C 6 H 5 ) 3 C
100. Which of the following is a cumulated diene?
(I) (II) (III)
(IV) (V)

101. Which of the following is most stable?
(a) (b)
(c) (d)
102. Arrange the following in decreasing order of stability :

(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) ii>i>iii (d) iii>ii>i
103. Which of the following is most stable dienes?
(a) (b) (c) (d)
Hyper Conjugation
1. Which of the following is the most stable diene?
(a) (b) (c) (d)

2. Which of the following is the most stable, and which is the next most stable isomer?
O O O O
a b c d
(a) c > a (b) a > c (c) d > c (d) b > a

3. Which of the following compounds does not have an alpha hydrogen ?

O
O O CH 3 O
CH || | ||
(i) (ii) H — C — H (iii) (iv) CH 3 C — CH
|
CH 3
(a) i (b) ii
(c) iii (d) iv (e) all of the above
4. Which of the following has maximum number of a-hydrogen?
(a) (b) (c) (d)
5. ; Number of a-hydrogens in given compound is:
(a) 4 (b) 5 (c) 6 (d) 7

6. Sum of a-hydrogens in given alkene is:
(i) (ii) (iii) (iv)
(a) 30 (b) 31 (c) 32 (d) 33

7. Sum of a-hydrogens in :
(i) (ii)
(i) + (ii) = ?
(a) 13 (b) 14 (c) 15 (d) 16
8. Sum of a-hydrogen in :
(i) (ii)
(i) + (ii) = ?
(a) 8 (b) 9 (c) 10 (d) 11
9. Sum of a-hydrogen in :
(i) 1- hexene , (ii) 2 - hexene , (iii) 3 - hexene
(i) + (ii) + (iii) = ?
(a) 8 (b) 10 (c) 11 (d) 12

10. In which of the following alkene hyperconjugation does not take place?
(a) (b)
(c) (d) CH==CH
11. Which of the following represent hyperconjugation in carbocation?

E
E H r H
(a) H—C—C (b) H C—C
H H
H
H
r
(c) H2C—CH—CH2 (d)
12. Which carbocation is most stable ?
r
r
(a) r (b) (c) r (d)
13. Most stable structure of carbocation C 4 H+

9 is:
r
(a) r (b) (c) (d) r
r
14. Which of the following carbocations is least stable?
Å Å
(I) CH 3 CH 2 (II) CH 3 CHCH 3
CH 3 CH 3
|r |Å Å
(III) CH 3 — C (IV) CH 3 CCH 2 (V)
| |
CH 3 CH 3
15. Sum of a-hydrogens in given carbocation :
CH 3 Et
|r |r r
(i) CH 3 — C (ii) Et —C (iii) C
| |
CH 3 Et
(a) 15 (b) 16 (c) 17 (d) 18

16. Which of the following carbocation violates Bredt’s rule?
(a) (b)
r
r r
(c) (d)
17. Rank the free radicals (I-III) shown below in order of decreasing stability (i.e., from most
stable to least stable).
• •
•CH 2 CH 2 CH(CH 3 ) 2 CH 3 CH 2 C(CH 3 ) 2 CH 3 CHCH(CH 3 ) 2
I II III
(a) I > III > II (b) II > III > I
(c) I > II > III (d) II > I > III (e) III > II > I
18. Sum of a-hydrogens in given radical:
C CH
(i) (ii)
(i) + (ii) = ?
(a) 6 (b) 7 (c) 8 (d) 9
19. Arrange the following carbocation in order of stability :
r r
r r
(i) (ii) (iii) (iv)
(a) i>ii>iii>iv (b) i>ii>iv>iii (c) ii>i>iv>iii (d) ii>i>iii>iv

20. Arrange the following in decreasing order of number of alpha hydrogens:
(a) (b) (c) (d)

(a) a > b > c > d (b) b > a > c > d (c) c > a > b > d (d) d > a > b > c
21. Which of the following is a conjugated diene ?
(I) (II) (III)
(IV) (V)

22. Which of the following is most stable alkene ?

(a) (b) (c) (d)
23. Which of the following is most stable alkene ?

(a) (b) (c) (d)
24. Which of the following is least stable alkene ?
(a) (b) (c) (d)
25. Arrange the following in decreasing order of a-hydrogen :
(i) (ii) (iii)
(a) i>ii>iii (b) ii>i>iii (c) ii>iii>i (d) iii>ii>i

26. Which of the following is most stable?
(a) (b) (c) (d)
27. Arrange the following in decreasing order of stability :
(i) (ii) (iii)
(a) i>ii>iii (b) ii>i>iii (c) iii>i>ii (d) iii>ii>i

28. Which of the following is least stable alkene?
(a) (b) (c) (d)
29. Which of the following alkene is more stable than 1-butene?

(a) Cis- 2-butene (b) Trans-2-butene (c) Iso-butene (d) All of these
Heat of Hydrogenation, Heat of Combustion and Bond Length

1. Consider the bond dissociation energies listed below in kcal/mole.
CH 3 —Br 70
CH 3 CH 2 —Br 68
(CH 3 ) 2 CH—Br 68
(CH 3 ) 3 C—Br 65

These data show that the carbon-bromine bond is weakest when bromine is bound to a ........
(a) methyl carbon (b) primary carbon
(c) secondary carbon (d) tertiary carbon (e) quaternary carbon
2. On the basis of bond dissociation energies given below (in kcal/mole), estimate the DH º for
the propagation step
(CH 3 ) 2 CH + Cl 2 ¾®
¾ (CH 3 ) 2 CHCl + Cl
CH 3 CH 2 CH 2 —H 98
(CH 3 ) 2 CH—H 95
Cl—Cl 58
H—Cl 103
CH 3 CH 2 CH 2 —Cl 81
(CH 3 ) 2 CH—Cl 80
(a) –30 kcal/mole (b) +22 kcal/mole
(c) – 40 kcal/mole (d) +45 kcal/mole (e) – 45 kcal/mole
3. Compare bond length in the given compounds across (carbon-oxygen):
OH
OH O
; ;
CHO
(a) (b) (c)
(a) a > b > c (b) b > c > a (c) b > a > c (d) a > c > b
4. Compare bond length in the given compounds:
H 2 C == CH 2 H 3 C — CH 3
; ;
(a) (b) (c)

(a) a > b > c (b) c > a > b (c) c > b > a (d) a > c > b
5. Arrange the proton shown, in decreasing order of their bond energy ?
Hc
Hd
Hb
Ha
(a) Ha > Hb > Hc > Hd (b) Hb > Hc > Ha > Hd
(c) Hb > Hc > Hd > Ha (d) Hd > Ha > Hc > Hb

6. Arrange the following hydrogen in decreasing order of bond energy :

Ha Hb CH
3
H2C == CH—CH—CH—C—CH2— Hd
Hc
(a) Ha > Hc > Hb > Hd (b) Ha > Hd > Hb > Hc
(c) Hd>Hc>Hb>Ha (d) Hd>Hb>Hc>Ha
7. Arrange the following in decreasing order of bond energy :
Ha —CH—CH2— Hb
Hc
(a) Ha>Hb>Hc (b) Hb>Ha>Hc (c) Hc>Ha>Hb (d) Hc>Hb>Ha

8. Arrange the following in decreasing order of bond energy :
Ha
Hb
Hc
CH3
(a) Ha>Hc>Hb (b) Ha>Hb>Hc (c) Hb>Ha>Hc (d) Hb>Hc>Ha
9. Which of the following compounds contains the longest carbon-carbon single bond?
(a) allene (b) 1,3-butadiyne
(c) 1,3-butadiene (d) propyne (e) ethane
10. Compare heat of hydrogenation of the following :
(i) (ii) (iii)
(a) i>ii>iii (b) iii>ii>i (c) ii>i>iii (d) ii>iii>i

11. Rank the following in decreasing order of heat of hydrogenation :
(i) (ii) (iii) (iv)
(a) iii>i>ii>iv (b) i>iii>ii>iv (c) iv>ii>iii>i (d) iv>iii>ii>i

12. Rank the following in decreasing order of heat of hydrogenation :
(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) i>iii>ii (d) ii>i>iii

13. Rank the indicated bond in the given compound in order of decreasing bond strength:
a b
c
N
H
Cºº N
(a) a > b > c (b) c > b > a (c) b > c > a (d) c > a > b
14. Which of the following has minimum heat of hydrogenation?
(a) (b) (c) (d)
(B)
(A)
(C)
15. Energy H2/Ni H2/Ni H2/Ni
CH3—CH2—CH2—CH3 (n-butane)
Alkene (C) is:

(a) cis-2-butene (b) trans-2-butene (c) 1-butene (d) ethene
(A)
(B)
(C)
16. Energy H2/Ni H2/Ni H2/Ni
(1,2-Dimethyl cyclohexane)
Structure of (A) is:
(a) (b) (c) (d)
17. Which of the following has largest heat of combustion ?

(a) Ethyl cyclopentane (b) Ethyl cyclohexane
(c) Ethyl cyclobutane (d) Ethyl cycloheptane
18. Compare the heats of combustion for the compounds given:
(i) 2,3-dimethyl-2-butene (ii) 2-methyl-2-butene
(iii) 1,3-butadiene (iv) 1,2-butadiene
(a) iii>iv>ii>i (b) iii>iv>i>ii (c) i>ii>iv>iii (d) i>ii>iii>iv

Aromaticity
1. Which of the following is antiaromatic?
r
(a) (b) (c) (d)
2. Based upon your understanding of the basic principles of molecular orbitals it should be
possible to answer the following question. Consider the following molecular orbitals of
benzene. Which of these molecular orbitals has the lowest energy?
benzene =
I II III
IV V VI
(a) orbital II (b) orbital III (c) orbital IV (d) orbital V
possible to answer the following question. Consider the following molecular orbitals of
benzene. Which of these molecular orbitals has the highest energy?
benzene =
I II III
IV V VI
(a) orbital I (b) orbital II (c) orbital III (d) orbital IV

4. Which of the following structures are aromatic according to Hückel’s rule?
CH2
a b c d e
(a) a and c (b) a, c, and d (c) b and d (d) b, d, and e
5. Which of the following cations is aromatic?
+
r +
+
+
a c b d
(a) b, d (b) d (c) a, b, d (d) b, c, d
6. Benzene can be reduced to cyclohexane when it is treated with hydrogen in the presence of a
nickel catalyst under conditions of high temperature and pressure. Predict the signs of DH°
and DS° for this process.
(a) DH ° > 0 , DS°> 0 (b) DH ° > 0 , DS°< 0
(c) DH ° > 0 , DS° = 0 (d) DH ° < 0 , DS°> 0 (e) DH ° < 0 , DS°< 0
7. + –
Cyclononatetraenyl cation Cyclononatetraenide anion

(A) (B)
Number of p-electrons in (A) and (B) respectively are :
(a) 8, 8 (b) 8, 10 (c) 10, 8 (d) 10, 10
8. Compare the stability of carbocation which are formed when react with AgNO 3 ?
I I I
O
(A) (B) (C)
(a) A > B > C (b) A > C > B (c) B > C > A (d) B > A > C
9. The order of stability of the following carbanion is:
s s
s s
CH3CH2
(I) (II) (III) (IV)

(a) I > II > III > IV (b) I > III > II > IV (c) IV > III > II > I (d) III > IV > I > II

10. Decreasing order of stability of given carbocations is as:

r
r
(1) (2) CH 2 == CH — CH 2
r r
(3) C 6 H 5 — CH 2 (4) CH 3 — CH — CH 3
(a) 3 > 2 > 4 > 1 (b) 1 > 3 > 4 > 2 (c) 1 > 3 > 2 > 4 (d) 3 > 2 > 1 > 4
11. Which of the following is least stable dienes?
(a) (b) (c) (d)
12. Which of the following is aromatic compound ?

s s r r
(a) (b) (c) (d)
13. Which of the following is Aromatic ?

s
r s
(a) r (b) s (c) (d) All of these
14. Which of the following is non-Aromatic ?
2 Na
15. ¾® ; Product of the reaction is:
¾¾
r s s r
(a) r (b) s (c) (d)
2 Fe+3
16. ¾ ¾¾® ; Product of the reaction is:
s r s r
(a) s (b) r (c) (d)
Br Br
rs rs
Ag NO3 AgNO
17. ¾¾¾¾® r1; 3
¾¾¾¾® r2
Rate of reaction r1 and r2 is:

(a) r1 > r2 (b) r2 > r1 (c) r1 = r2 (d) r2 >> r1
18. Which of the following is aromatic ?
O O O
(a) (b) (c) (d) O

O

19. Which of the following is Anti-aromatic ?

20. Which of the following statements is incorrect about benzene?

(a) All of the carbon atoms are sp hybridized
(b) It has delocalized electrons
(c) The carbon-carbon bond lengths are all the same
(d) The carbon-hydrogen bond lengths are all the same
(e) All twelve atoms lie in the same plane
21. Aromatic molecules contain.............. p-electrons.
(a) no (b) 4n + 2 (with n an integer)
(c) 4n + 2 (where n = 0.5) (d) 4n (with n an integer) (e) unpaired
s
(i) (ii)
(iii) r (iv) (v)

23. Which of the structures below would be aromatic ?
+ + +
(i) (ii) (iii) (iv)
(a) i and iv (b) i, iii and iv (c) iii and iv (d) ii

(i) (ii)
(iii) (iv) (v)

O S
(i) (ii)
H H
S N O
(iii) (iv) r (v)
S

26. Which of the following is antiaromatic ?
(i) (ii)
O
r
(iii) (iv) (v) r
O
(a) iii (b) i (c) ii (d) v (e) iv
27. Which of the following aromatic compounds is the most stable ?
(i) (ii)
S O
s
..
(iii) (iv) (v)
N
H
28. Which of the following compound will undergo dimerization?
(a) (b) (c) (d)
29. Which of the following compound will not undergo dimerization ?

N
(a) (b) (c) (d)
N N N
30. Which of the following is non-planar compound ?

r
(a) (b) (c) (d)
31. Which of the following carbanion is aromatic ?

s s
s s
(a) (b) (c) (d)
32. Which of the following is anti-aromatic ?

N == N
(a) (b) O O (c) (d)
B B N N
H N
H H
33. Which of the following is non-aromatic ?
s
(a) (b) (c) (d)

34. To convert cyclononatetraene in aromatic ion, the process needed is :
(a) addition of one more p-bond

(b) addition of two more p-bond
r
(c) loss of H from sp 3 -hybridized carbon
r
(d) loss of H from sp 2 -hybridized carbon
35. To convert given compound into aromatic compound, best reagent is:
Cl
O
(a) AlCl 3 (b) HCl (c) H 2 SO 4 (d) Na
36. To convert given compound into aromatic best reagent is:
(a) H s (b) H r (c) NaOH (d) NaHCO 3

37. To convert given compound into aromatic best reagent is:
OH
(a) HCl (b) NaOH (c) NaH (d) NaHCO 3
Acidic and Basic Strength

1. Which of the following compounds can behave as an acid as well as a base?
H : O:
s ..
(a) H—B—H (b) (c) NH2 (d) :Br s
H H
H
2. What are the product(s) of the following acid–base reaction?
+ HBr ¾® ? Br
N
(a) + Br– (b)
N N
|+ |+
H H

H Br H H
(c) (d)
N N
| |
H Br
3. Using pK a values which is the strongest acid (HA is any acid).
pK a HA
3.7 HCOOH
4.2 C 6 H 5 COOH
4.75 CH 3 COOH
15.5 CH 3 OH
(a) Acetic acid (b) Benzoic acid (c) Methanol (d) Formic acid
4. Rank the following compounds in order from most basic to least basic.
OH OH OH OH
1 2 3 4
NO2
(a) 2 > 3 > 4 > 1 (b) 4 > 3 > 1 > 2 (c) 3 > 1 > 2 > 4 (d) 1 > 4 > 3 > 2
5. Rank the following compounds in order from most acidic to least acidic.
O O CH3 O CH3 O CH2
H H H H H C
O CH3 H2
(a) (b) (c) (d)
(a) c > d > a > b (b) d > a > b > c
(c) b > a > d > c (d) a > b > d > c
6. Which is the strongest base?
(a) LiOH (b) CH 3 Li (c) LiNH 2 (d) LiF
7. Consider ammonia (I) and water (II). Which of the following statements is true?
H 3 N: H 2 O:
I II
(a) I is more basic and more nucleophilic than II
(b) I is less basic and less nucleophilic than II
(c) I is more basic but less nucleophilic than II
(d) I is less basic but more nucleophilic than II
8. Which of the following is the most acidic?
(a) 1-butyne (b) 2-butyne
(c) 1-butene (d) butane

9. Which of the following aniline derivatives is the strongest base?

NH2 NH2
(a) (b) MeO
NH2 NH2
(c) O2N (d) Cl

10. Which of the following compounds is most basic?
(a) cyclohexylamine (b) aniline
(c) p-methoxyaniline (d) p-nitroaniline
11. Which of the following compounds has the most basic nitrogen?
O O
N N N N
H O H H
O
a b c d
(a) a (b) b (c) c (d) d
12. Which of the following is correct representation of curved arrow ?
(a) H+ Cls (b) H+ Cls
(c) Cl• Cl• (d) Cl• Br•

13. Which of the following would have the highest boiling point?
(a) CH 3 CH 2 — O — CH 2 CH 2 — O — CH 3 (b) CH 3 — O — CH 2 CH 2 CH 2 — O — CH 3
(c) HO — CH 2 CH 2 CH 2 CH 2 — OH (d) CH 3 CH 2 — O — CH 2 — O — CH 2 CH 3
(e) CH 3 — O — CH 2 CH — O — CH 3
|
CH 3
14. An alcohol, an aldehyde and a carboxylic acid of comparable mass will have their boiling
points in the order:
(a) alcohol < carboxylic acid < aldehyde (b) aldehyde < alcohol < carboxylic acid
(c) alcohol < aldehyde < carboxylic acid (d) carboxylic acid < aldehyde < alcohol
15. What is the conjugate acid of (A)?
OH
NH2

H s
O
rO—H OH
(a) (b) (c) (d) both (a) and (b)
NH2
NH2 NH3
r
16. Rank the following in decreasing order of acidity :
(i) (ii) (iii)
(a) iii>i>ii (b) i>ii>iii (c) ii>i>iii (d) iii>ii>i

17. Compare acidic strength :
(i) CHCl 3 (ii) CHF3 (iii) CH 3 — CH 3
(a) i>ii>iii (b) ii>i>iii (c) iii>i>ii (d) ii>iii>i
18. Which of the following is strongest base ?
O NH
(a) H—N N—H (b) H—N N—H
NH2 N
(c) (d)
19. Which of the following compound have highest K a value ?

OH OH
O2N NO2
(a) (b)
O2N NO2
NO2 NO2
OH OH
NO2 NO2
(c) (d)
NO2
NO2 NO2

20. The most acidic among the following compounds is:

OH
(a) Cl — CH 2 — CH 2 — OH (b)
OH OH
(c) (d)
NO2 CH3
21. The strongest bronsted base among the following compounds is:
(a) NaCH 3 (b) NaOH (c) NaF (d) NaNH 2
22. Which of the following is lowest pK a value ?
r
NH3 OH NH2 CººCH
(a) (b) (c) (d)
23. Which of following is lowest pK a value ?

(a) Cl — CH 2 — CO 2 H (b) Cl — CH — CO 2 H
|
Cl
(c) Cl 3 C — CO 2 H (d) CH 3 — CO 2 H
24. Conjugate base of HO s
(a) H 2 O (b) H 3 O r (c) O 2- (d) H 2
25. Conjugate base of CH 3 — CH 3 is:
r s •
(a) CH 3 — CH 2 (b) CH 3 — CH 2 (c) CH 4 (d) CH 3 — CH 2
26. Conjugate acid of H 2 O is:
(a) H 3 O r (b) HO s (c) O 2- (d) CH 4
27. Conjugate acid of H 2 C == CH 2 is:
s r •
(a) CH 3 — CH 2 (b) CH 3 — CH 2 (c) CH 3 — CH 2 (d) CH 4
O O
|| r || s r
28. CH 3 — C — OH + HO s N a º CH 3 — C — O N a + H 2 O
in the above reaction:
(a) Keq > 1 (b) Keq < 1 (c) Keq = 1 (d) Keq = 0

r s s r
29. H—CººC—H + NaOH º H—CººC Na + H2O
For the above reaction:

(a) Keq > 1 (b) Keq < 1 (c) Keq = 1 (d) Keq = 0
30.
N—H
N N
H
(a) (b) (c)
Compare basic strength:
(a) a > b > c (b) b > a > c (c) c > a > b (d) c > b > a
NH2 (b)
31. ; Correct order of basic strength is:

N
(a)
(a) a > b (b) b > a (c) a = b (d) b >> a
(a) NH2 O
NH (b)
32. ; Correct order of basic strength is:
CH2—NH2
(c)
(a) a > b > c (b) b > a > c (c) c > a > b (d) c > b > a
(b)
NH
33. C ; Correct order of basic strength is:

NH2 NH2
(a) (c)
(a) b > a > c (b) a = c > b (c) b > a = c (d) c > a > b
s s s
34. CH 3 — C H 2 HC ºº C CH 2 == C H
( a) ( b) ( c)
Compare basic strength:
(a) b > c > a (b) c > b > a (c) a > b > c (d) a > c > b

H
N O
35. ;
N N N
H H H
(a) (b) (c)
Compare basic strength
(a) a > b > c (b) c > a > b (c) b > a > c (d) c > b > a
H H H H H
N N N N N N N
(a) (b) (c) (d)
N
37. Correct order of basic strength is: CH 3 — C ºº N ( a)
CH 3 — CH == NH ( b)
CH 3 — CH 2 — NH 2 ( c)
(a) a > b > c (b) c > b > a (c) b > a > c (d) a = b > c
38. Compare acidic strength of H-atoms marked.
O O
OPh S—Ph
H1 H2
(a) H 1 > H 2 (b) H 2 > H 1 (c) H 1 = H 2 (d) H 1 >> H 2

O
OH 1
39.
OH 2
OH 3
Compare acidic strength of hydroxylic H-atoms marked.

(a) 1 > 2 > 3 (b) 2 > 1 > 3 (c) 3 > 2 > 1 (d) 3>1>2
40.
r r
NMe3 H1 PMe3 H2
Compare acidic strength of H-atoms marked.

(a) H 1 > H 2 (b) H 2 > H 1 (c) H 1 = H 2 (d) Cannot compare
41. CH 3 — CO 2 H ; CH 3 — OH ; CH 3 — C ºº CH ; CH 3 — NH 2
( a) (b) (c) ( d)
Compare acidic strength of compounds a - d :

(a) a > b > c > d (b) b > c > a > d (c) b > a > c > d (d) a > c > b > d

OH
CººCH NaNH
42. ¾ ¾¾2® ( A); Product ( A) is:
(1- mole)
SH
s r
OH O Na
CººCH CººCH
(a) (b)
r
SNa SH
s
OH OH r
sr Na
CººC Na s CººCH
(c) (d)
SH SH
OH CO2H OH
43.
(a) (b) (c)

Correct order of acidic strength of the compounds given is :
(a) a > b > c (b) b > c > a (c) b > a > c (d) a > c > b
OH OH CO2H CO2H
44.
(a) CH3 CH3 (d)

(b) (c)
Correct order of acidic strength of the compounds given is :
(a) a > c > d > b (b) d > a > c > b (c) d > c > a > b (d) d > c > b > a
45. Which of the following has highest pK a value ?
Cl
|
(a) Cl — CH 2 — CO 2 H (b) Cl — CH — CO 2 H
(c) Cl 3 C — CO 2 H (d) CH 3 — CO 2 H
46. Which of the following has lowest pK a value ?
(a) Ph — OH (b) Ph — CO 2 H (c) Ph — SO 3 H (d) Ph — NH 2

47. Which of the following contains least acidic hydrogen ?

r
(a) R — NH 3 (b) R — CO 2 H (c) R — OH (d) R — SO 3 H
48. Which of the following has highest pK a value ?
O
||
(a) CH 3 — SO 3 H (b) CH 3 — C — OH (c) CH 3 — OH (d) H 2 O
49. Which of the following ions is most acidic?
(a) C 6 H 5 NH +3 (b) C 6 H 5 CH 2 NH +3
(c) (CH 3 ) 2 CHNH +3 (d) CH 3 CH 2 NH +3 (e) CH 3 NH +3
50. Which of the following is the weakest base?
(a) Phenolate ion (C 6 H 5 O - ) (b) Ethoxide ion (CH 3 CH 2 O - )
(c) Hydroxide ion (HO - ) (d) Acetate ion (CH 3 CO -2 ) (e) Methoxide ion (CH 3 O - )
51. Which of the following is strongest acid?
(a) CH 3 NH (b) CH 3 OH (c) CH 3 SH (d) CH 3 OCH 3 (e) CH 3 Cl
52. Which of the following is strongest base?
(a) HOMgBr (b) H 2 O (c) CH 4 (d) CH 3 OH (e) CH 3 MgBr
53. Which of the labeled hydrogen atoms in the following structure is the most acidic ?
O
H CH2CH2COH
1 3 4 5
H
2
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
54. Which of the following underlined alpha hydrogen are the most acidic ?
O O O
|| || ||
(a) CH 3 — CH (b) CH 3 — C —CH 2 — CH
O O O O
|| || || ||
(c) CH 3 — C — CH 2 —C — OCH 3 (d) CH 3 — C — CH 3 (e) CH 3 — C — O — CH 3
55. Which of the labeled hydrogen atoms in the following structure is the most acidic ?
O
C—CH2CH2CH3
3 4 5
H H
1 2
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

56. Which of the labeled hydrogen atom in the following structure is the most acidic ?
O O
H CH2—C—CH2—C—CH3
1 3 4 5
H
2
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
57. Rank the following compound in order of increasing acidic strength :
r s
(i) H 3 O (ii) H 2 O (iii) HO
(a) i < ii < iii (b) ii < i < iii (c) iii < ii < i (d) iii < i <ii
(i) NH 3 (ii) H 2 O (iii) H 2 S
(a) i < ii < iii (b) ii < i < iii (c) i < iii < ii (d) iii < ii < i
(i) CH 3 — CH 2 — CH 2 — OH(ii) Cl — CH 2 — CH 2 — OH (iii) CH 3 — CH 2 — OH
(a) i < ii < iii (b) i < iii < ii (c) ii < i < iii (d) ii < iii < i
(i) CH 3 OH (ii) CH 3 — NH 2 (iii) CH 3 — CH 3
(a) i < ii < iii (b) iii < ii < i (c) i < iii < ii (d) ii < i < iii
61. Rank these protons in order of decreasing acidic strength :
(iii) (ii)
O NH2 OH O
NH2 OH (i)
(iv)
(a) iv > i > iii > ii (b) i > ii > iv > iii (c) i > iv > ii > iii (d) i > iv > iii > ii
62. Compare basic strength of the following:
CH3
CH3 CH3
(i) N (ii) N
CH3 CH3
CH3
(a) i > ii (b) i = ii (c) ii > i (d) i >> ii

63. Compare acidic strength of the following:
OH OH
OH
(i) (ii) (iii)
F Cl
(a) i > ii > iii (b) ii > iii > i (c) iii > ii > i (d) iii > i > ii

64. Which of the following has most acidic hydrogen?
(a) (b)
r
Ha H NMe3
(c) (d)
r
H PMe3 H CH3
65. Which of the following has least acidic hydrogen?
O O
(a) (b) O S
Ha
Ha
H
S S
(c) (d) CH3—S—C—S—CH3
Ha O CH3

(i) Ph — CO 2 H (ii) Ph — OH (iii) Ph — C ºº CH (iv) Ph — CH 2 — OH
(a) i > ii > iii > iv (b) i > ii > iv > iii (c) i > iv > iii > ii (d) ii > i > iv > iii
67. Which of the following is most acidic?
r
OH NH3 OH CH
3
(a) (b) (c) (d) CH 3 — CH 2 — OH

O OH
(i) (ii) OH (iii)
CH2—OH C ºº CH
(iv) (v)
(a) i > ii > iii > iv > v (b) i > iii > ii > iv > v
(c) iii > i > ii > iv > v (d) ii > i > iii > iv > v

69. Which of the following has highest pK a value?
F
F
CO2H CO2H
(a) (b)
F
CO2H CO2H
(c) (d)
F
70. Which of the following has highest K a value ?
Cl
|
(a) Cl — CH 2 — CO 2 H (b) Cl —CH — CO 2 H
Cl
|
(c) Cl — C — CO 2 H (d) CH 3 — CO 2 H
|
Cl
O OH(b)
71. H—O (a) SO3H(d) ; Order of acidic strength is:

NH3(c)
r
(a) d > c > b > a (b) d > a > b > c (c) d > a > c > b (d) a > d > c > b
72. Compare basic strength :
N
(i) (ii) (iii)
N N N
H
(a) i > ii > iii (b) i > iii > ii (c) iii > i > ii (d) iii > ii > i
73. Which of the following is strongest base?

NH2 NH2 CH2—NH2
NH2
CH3
(a) (b) (c) (d)
CH3
CH3
74. Which of the following is strong base?
NH O CH3 NH
(a) NH2—C (b) NH2—C (c) NH2—CH (d) NH2—C
CH3 NH2 CH3 NH2


NH
(a) (b) (c) H—N N—H (d)
76. Which of the following is weakest base?

O
(a) (b) (c) N (d)

H
77. Which of the following compound is virtually non-basic?
CF3
(a) (b) (c) (d) N CF3
CF3

NH
(a) CH3—C (b) CH 3 — CH == NH
NH2
NH2
O
(c) CH3—C—NH2 (d)

O O
s || || s
s s
(a) Ph — O (b) Ph —C — O (c) Ph — S — O (d) Ph — CH 2
||
O
SO3H
(x) NaHCO3
80. H—CººC COOH ;Total number of moles of NaHCO 3 consumed
during given reaction will be (x).
OH
So the value of x will be :
(a) 1 (b) 2 (c) 3 (d) 4

81. Which of the following carbon will be deprotonated first on treatment with base?
4 2
5 3 1
N O
(a) 4 (b) 5 (c) 2 (d) 3
82. When benzene sulfonic acid and p-nitrophenol are treated with NaHCO 3 , the gases released
respectively are:
(a) SO 2 ,NO 2 (b) SO 2 ,NO (c) SO 2 ,CO 2 (d) CO 2 ,CO 2
83. Correct order of acidic strength of given compounds will be:

CO2H OH OH CO2H
CH3 NO2
(I) (II) (III) (IV)
(a) IV > II > I > III (b) IV > III > I > II (c) IV > I > II > III (d) IV > I > III > II
84. Which of the following is the strongest base?
CH3 CH3 CH3 CH3
NH2 N NH2 N
NO2 NO2 NO2 NO2
(a) (b) (c) (d)
O OH(b) NO2 NO2
85. H—O
(a)
SO3H(d) ; Order of acidic strengths is:
NH3(c)
r
(a) d > c > b > a (b) d > a > b > c (c) d > a > c > b (d) a > d > c > b
86. The strongest Bronsted base among the following compounds is:
(a) NaCH 3 (b) NaOH (c) NaF (d) NaNH 2
87. Oxygen atom of the carbonyl group is most basic in:

(a) Amide (b) Ester (c) Acid chloride
88. In the following compounds:
OH OH OH OH
NO2
CH3 NO2
(I) (II) (III) (IV)
the order of acidity is:
(a) III > IV > I > II (b) I > IV > III > II (c) II > I > III > IV (d) IV > III > I > II
89. Most basic compound is:

O
NH ||
(a) CH3—C (b) CH 3 CH 2 NH 2 (c) (CH 3 ) 2 NH (d) CH 3 C NH 2
NH2
O O
|| ||
¾ ( A) gas; Ph — C — OH + NaHCO 3 ¾®
90. Ph — C — OH + NaHCO 3 ¾® ¾ ( B ) gas .
14 14
Difference between the molar mass of A and B gas is:
(a) 1 (b) 2 (c) 3 (d) 4
Na
¾¾¾® (A)
NaH
91. Ph—CO2H ¾¾¾¾® (B) ; Molar mass of gas A + B + C + D = E so the value of E is:
NaNH
2
¾¾¾® (C)
NaHCO
3
¾¾¾® (D)
(a) 19 (b) 63 (c) 64 (d) 65
92. Which one among the following is the least basic?
(a) CH 3 NH 2 (b) NH 3 (c) C 2 H 5 NH 2 (d) PhNH 2
Electrophile & Nucleophile and Type of Reaction & Solvent

1. C 6 H 13 Br + OH - ¾® C 6 H 13 OH + Br - . This reaction is an example of :
(a) nucleophilic addition (b) nucleophilic substitution
(c) electrophilic addition (d) electrophilic substitution
(e) Free radical substitution
2. Which of the following solvents is aprotic ?
(a) CH 3 CH 2 OH (b) CH 3 CH 2 CH 2 NH 2
(c) CH 3 CH 2 OCH 2 CH 3 (d) CH 3 CH 2 NHCH 3 (e) CH 3 COH
||
O
3. Which of the following solvents is protic ?
O O
|| ||
(a) CH 3 CH (b) CH 3 CCH 3
(c) CH 3 CH 2 OCH 3 (d) CH 3 CH 2 OH (e) CH 3 CH 2 CH 2 Cl
4. Protic and aprotic solvents are very similar as solvents except for their :
(a) polarity
(b) dielectric constant
(c) ability to stabilize anions by hydrogen bonding
(d) ability to stabilize cations by hydrogen bonding
(e) ability to stabilize cations with unshared pairs of electrons

5. CH 3 CHO + HCN ¾® CH 3 CH(OH) CN:

(e) free radical substitution
6. Which of the following is not normally considered to be a nucleophile?
-
(a) NH 3 (b) NH 2 CH 3 (c) HC ºº C•
• (d) CH 3 CH +2
7. Which of the following is the strongest nucleophile in an aqueous solution?
(a) HO - (b) F - (c) Cl - (d) Br - (e) I -
8. Which of the following is the best leaving group?
(a) HO - (b) F - (c) Cl - (d) Br - (e) I -
9. Which of the following species is the least nucleophilic?
(a) (CH 3 ) 3 CO - (b) H 2 O (c) (CH 3 ) 3 N (d) BF3 (e) CN -
10. Which of the following is the best nucleophile in water?
(a) I - (b) CH 3 SCH 3 (c) CH 3 OCH 3 (d) Cl -
11. Which of the following is not an electrophile?
(a) H + (b) BF3 (c) NO +2 (d) Fe 3+ (e) CH 2 == CH 2
12. Which of the following is not a nucleophile?
(a) FeBr 3 (b) Br - (c) NH 3 (d) (e) CH 3 OCH 3
13. Which of the following carbocations is likely to rearrange?

Å
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH2
(I) (II) Å (III) (IV)

Å
Å
(a) I (b) II (c) III (d) IV (e) II and IV
14. Which of the following carbocations do not rearrange?
Å Å
(a) CH 3 CH 2 (b) CH 3 CHCH 3
CH 3
| r
(c) CH 3 C Å (d) CH 3 CH 2 CHCH 3 (e) all of these
|
CH 3
15. Which of the following are the products obtained from the disproportionation of the propyl
radical?
·
CH 3 CH 2 CH 2

(a) CH 3 CHCH 3 + CH 2 == CHCH 3 (b) CH 3 CH 2 CH 3 +CH 3 CHCH 3

(c) CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 (d) CH 3 CH 2 CH 3 + CH 2 == CHCH 3
(e) CH 2 == C == CH 2 + CH 3 CH 2 CH 3
16. Which of the following is singlet carbene?
¼ r s
(a) ¼CH 2 (b) CH 3 (c) ¼¿CH 2 (d) CH 3
OH OH
Br Br
17. + 3Br2 ¾® + 3HBr This reaction is an example of :
Br

CH3 CH2Br
hn
18. + Br2 ¾® + HBr This reaction is an example of :

Br
Br
19. + Br2 ¾® This reaction is an example of :

Miscellaneous Problems
1. Which of the following compounds easily undergo homolytic bond fission ?
(a) CH 3 — Cl (b) CH 3 — CH == O
(c) H — O — O — H (d) NH 2 — CH 3
2. Which of the following cleavage is homolytic cleavage ?
r s hn
(a) H — O — O — H ¾® ¾ HO HO (b) H — O — O — H ¾¾® 2HO º
D
r s r s
(c) R — Br ¾®
¾ R Br (d) R — Cl ¾®
¾ R Cl

3. Which of the following cleavage is heterolytic cleavage?

r s hn •
(a) R — Br ¾¾® R Br (b) R — R ¾¾® 2 R
D
hn • hn •
(c) R — S — S — R ¾¾® R — S (d) Cl 2 ¾¾® 2Cl
4. Compare resonance energy of following :
O O O
(i) (ii) (iii)
(a) i>ii>iii (b) ii>i>iii (c) ii>iii>i (d) i>iii>ii

5. Which of the following has highest resonance energy?
O O O O
(a) (b) (c) (d)
6. Which of the following compound has highest dipole moment ?
(a) (b) (c) (d)
7. The most electron-rich carbon in the molecule below:

2
H3C OH
1
3
C C
H3C CH2CH2CH3
4
(a) 1 (b) 2 (c) 3 (d) 4
8. Which of the following has lowest resonance energy per ring ?
(a) (b)
(c) (d)

5H2/Ni
9. Energy
H2/Ni
DH=– 350 kJ /mol
(DH=– 120 kJ /mol)
Resonance energy of naphthalene is:

(a) –150 kJ mol (b) -250 kJ mol
(c) –350 kJ mol (d) – 450kJ mol
3H2/Ni
10. Energy H2/Ni DH=– 208 kJ/ mol
DH=– 120 kJ/mol
Resonance energy of benzene is:

(a) –152 kJ / mol (b) –252 kJ / mol (c) –92 kJ / mol (d) – 42 kJ / mol

Answers
[A] Classification and Nomenclature of Organic Compounds

Functional Groups Degree of Unsaturation and Double Bond-equivalent
1. (c) 2. (d) 3. (c) 4. (d) 5. (d) 6. (d) 7. (d) 8. (b) 9. (c) 10. (c)
11. (d) 12. (d) 13. (b) 14. (c) 15. (b) 16. (a) 17. (c) 18. (b) 19. (c) 20. (c)
21. (a) 22. (b) 23. (d) 24. (a) 25. (b) 26. (c) 27. (d) 28. (d) 29. (b) 30. (d)
31. (c) 32. (b) 33. (c) 34. (c)
Hybridization and Bonding in Organic Molecules

1. (c) 2. (c) 3. (c) 4. (c) 5. (c) 6. (c) 7. (b) 8. (c) 9. (e) 10. (d)
11. (d) 12. (c) 13. (c) 14. (c)
IUPAC Nomenclature of Alkanes

1. (c) 2. (c) 3. (c) 4. (a) 5. (c) 6. (b) 7. (b) 8. (d) 9. (c) 10. (b)
11. (b) 12. (a) 13. (b) 14. (a) 15. (a)
IUPAC Nomenclature of Alkynes/Alkenes

1. (c) 2. (a) 3. (a) 4. (b) 5. (e) 6. (d) 7. (b) 8. (a) 9. (d) 10. (a)
IUPAC Nomenclature of Alcohols/Aldehydes/Ketones/Acids

1. (e) 2. (a) 3. (c) 4. (c) 5. (d) 6. (b) 7. (d) 8. (d) 9. (d) 10. (c)
11. (d) 12. (d)
IUPAC Nomenclature of Acid Halides, Esters, Nitriles, Amines, Amides, Anhydrides

1. (d) 2. (c) 3. (b) 4. (e) 5. (b) 6. (d) 7. (d)
IUPAC Nomenclature of Poly Functional Compounds

1. (b) 2. (b) 3. (b) 4. (b) 5. (b) 6. (b) 7. (a)
IUPAC Nomenclature of Aromatic Compounds & Bicyclic & Spiro Compounds

1. (e) 2. (d) 3. (e) 4. (d) 5. (c) 6. (a) 7. (a)

[B] Isomerism
Structural Isomerism
1. (c) 2. (d) 3. (c) 4. (d) 5. (b) 6. (d) 7. (b) 8. (c) 9. (a) 10. (c)
11. (b) 12. (b) 13. (c) 14. (a) 15. (b) 16. (b) 17. (a) 18. (d) 19. (b) 20. (d)
21. (c) 22. (d) 23. (a) 24. (a) 25. (b) 26. (a) 27. (d) 28. (b) 29. (b) 30. (c)
31. (b) 32. (b) 33. (b) 34. (b) 35. (a) 36. (b) 37. (b) 38. (b) 39. (a)
Tautomerism and Applications of Tautomerism

1. (a) 2. (a) 3. (d) 4. (a) 5. (a) 6. (c) 7. (b) 8. (b) 9. (d) 10. (a)
11. (c) 12. (e) 13. (e) 14. (c) 15. (c) 16. (b) 17. (c) 18. (a) 19. (d) 20. (d)
21. (c) 22. (d)
Conformational Analysis
1. (d) 2. (c) 3. (b) 4. (b) 5. (a) 6. (c) 7. (d) 8. (d) 9. (c) 10. (c)
11. (a) 12. (c) 13. (d) 14. (c)
Geometrical Isomerism
1. (c) 2. (c) 3. (c) 4. (d) 5. (d) 6. (a) 7. (a) 8. (d) 9. (d) 10. (c)
11. (a) 12. (d) 13. (c) 14. (c) 15. (c) 16. (c) 17. (b) 18. (d) 19. (c) 20. (b)
21. (a) 22. (c) 23. (b) 24. (c) 25. (a)
Optical Isomerism
1. (c) 2. (b) 3. (d) 4. (c) 5. (b) 6. (b) 7. (c) 8. (b) 9. (d) 10. (d)
11. (b) 12. (a) 13. (a) 14. (b) 15. (d) 16. (c) 17. (b) 18. (b) 19. (c) 20. (c)
21. (a) 22. (c) 23. (d) 24. (b) 25. (a) 26. (b) 27. (b) 28. (d) 29. (c) 30. (c)
31. (d) 32. (b) 33. (c) 34. (c) 35. (c) 36. (b) 37. (c) 38. (b) 39. (c) 40. (b)
41. (a) 42. (b) 43. (b) 44. (d) 45. (b) 46. (a) 47. (c) 48. (b) 49. (b) 50. (b)
51. (a) 52. (d) 53. (e) 54. (b) 55. (d) 56. (d) 57. (c) 58. (a) 59. (b) 60. (c)
61. (a) 62. (c) 63. (a) 64. (c)
Miscellaneous Problems on Stereomers

1. (b) 2. (b) 3. (c) 4. (c) 5. (c) 6. (a) 7. (b) 8. (c) 9. (c) 10. (c)
11. (c) 12. (d)

[C] General Organic Chemistry

Inductive Effect & its Applications
1. (a) 2. (d) 3. (b) 4. (c) 5. (c) 6. (b) 7. (d) 8. (c) 9. (c) 10. (c)
11. (c) 12. (b) 13. (d) 14. (c) 15. (c)
Resonance
1. (d) 2. (d) 3. (c) 4. (d) 5. (c) 6. (d) 7. (d) 8. (c) 9. (b) 10. (b)
11. (b) 12. (e) 13. (b) 14. (b) 15. (c) 16. (d) 17. (a) 18. (c) 19. (d) 20. (d)
21. (c) 22. (c) 23. (c) 24. (c) 25. (c) 26. (a) 27. (c) 28. (d) 29. (b) 30. (c)
31. (a) 32. (d) 33. (d) 34. (b) 35. (c) 36. (a) 37. (c) 38. (c) 39. (c) 40. (a)
41. (c) 42. (b) 43. (d) 44. (a) 45. (b) 46. (b) 47. (c) 48. (b) 49. (c) 50. (c)
51. (c) 52. (c) 53. (d) 54. (e) 55. (d) 56. (b) 57. (c) 58. (a) 59. (c) 60. (a)
61. (b) 62. (c) 63. (c) 64. (d) 65. (c) 66. (c) 67. (a) 68. (c) 69. (b) 70. (b)
71. (d) 72. (c) 73. (d) 74. (a) 75. (a) 76. (c) 77. (d) 78. (a) 79. (a) 80. (d)
81. (d) 82. (c) 83. (b) 84. (b) 85. (d) 86. (b) 87. (b) 88. (b) 89. (a) 90. (d)
91. (a) 92. (d) 93. (a) 94. (b) 95. (c) 96. (b) 97. (c) 98. (c) 99. (d) 100. (c)
101. (c) 102. (c) 103. (c)
Hyper Conjugation
1. (c) 2. (a) 3. (e) 4. (a) 5. (c) 6. (d) 7. (c) 8. (c) 9. (c) 10. (d)
11. (b) 12. (c) 13. (c) 14. (a) 15. (d) 16. (a) 17. (b) 18. (c) 19. (b) 20. (b)
21. (a) 22. (c) 23. (a) 24. (b) 25. (a) 26. (d) 27. (b) 28. (c) 29. (d)
Heat of Hydrogenation, Heat of Combustion and Bond Length

1. (d) 2. (a) 3. (c) 4. (b) 5. (c) 6. (d) 7. (d) 8. (d) 9. (e) 10. (b)
11. (c) 12. (d) 13. (b) 14. (a) 15. (b) 16. (a) 17. (d) 18. (c)
Aromaticity
1. (a) 2. (d) 3. (a) 4. (a) 5. (c) 6. (e) 7. (b) 8. (a) 9. (d) 10. (c)
11. (c) 12. (b) 13. (d) 14. (d) 15. (b) 16. (b) 17. (a) 18. (c) 19. (c) 20. (a)
21. (b) 22. (c) 23. (c) 24. (b) 25. (a) 26. (e) 27. (d) 28. (b) 29. (d) 30. (c)
31. (b) 32. (a) 33. (b) 34. (c) 35. (a) 36. (b) 37. (a)

Acidic and Basic Strength
1. (c) 2. (a) 3. (d) 4. (c) 5. (c) 6. (b) 7. (c) 8. (a) 9. (b) 10. (a)
11. (a) 12. (b) 13. (c) 14. (b) 15. (d) 16. (d) 17. (a) 18. (b) 19. (b) 20. (c)
21. (a) 22. (a) 23. (c) 24. (c) 25. (b) 26. (a) 27. (b) 28. (a) 29. (b) 30. (c)
31. (a) 32. (c) 33. (c) 34. (d) 35. (b) 36. (b) 37. (b) 38. (b) 39. (b) 40. (b)
41. (a) 42. (a) 43. (c) 44. (c) 45. (d) 46. (c) 47. (c) 48. (c) 49. (a) 50. (d)
51. (c) 52. (e) 53. (e) 54. (b) 55. (c) 56. (d) 57. (c) 58. (a) 59. (b) 60. (b)
61. (c) 62. (c) 63. (c) 64. (c) 65. (a) 66. (b) 67. (b) 68. (a) 69. (c) 70. (c)
71. (c) 72. (c) 73. (d) 74. (d) 75. (c) 76. (b) 77. (d) 78. (c) 79. (c) 80. (b)
81. (a) 82. (d) 83. (d) 84. (d) 85. (c) 86. (a) 87. (a) 88. (d) 89. (a) 90. (b)
91. (d) 92. (d)
Electrophile & Nucleophile and Type of Reaction & Solvent

1. (b) 2. (c) 3. (d) 4. (c) 5. (a) 6. (d) 7. (e) 8. (e) 9. (d) 10. (a)
11. (e) 12. (a) 13. (e) 14. (e) 15. (d) 16. (c) 17. (d) 18. (e) 19. (c)
1. (c) 2. (b) 3. (a) 4. (b) 5. (d) 6. (c) 7. (a) 8. (c) 9. (b) 10. (a)

1. Which of the compound contains only 1° ,2° and 4° carbon atoms ?
(a) (b) (c) (d)
2. Which of the following compounds has maximum number of p-bonds?

(a) (b) N ºº C — C ºº C — C ºº CH
(c) (d)
3. Which of the following is isomer of benzene ?
(a) (b) (c) (d)
4. In which of the following compound +M of —OCH 3 will operate ?

s
(a) CH 2 == CH — O — CH 3 (b) CH 3 — CH — O — CH 3
CH2—OCH3 OCH3
(c) (d)
5. Which of the following carbocations is/are resonance stabilized?

r r r r
CH2
(a) (b) (c) (d)
6. In which of the following compounds inductive effect is absent ?

Cl
CH3
(a) (b) (c) (d) H 2 C == CH — CH 3

7. Which of the following pairs is/are resonating structure?

O s
O OH O
(a) ¬
¾® (b) s ¾®
O ¬ O
O OH
r
(c) ¬
¾® (d) ¬
¾®
r
8. In which of the following compounds lone pair of nitrogen is involved in resonance?
(a) (b) (c) (d)

O N N
N N
H H
H
9. In which of the following alkenes hyperconjugation is not possible?
CH2
(a) (b) (c) H 2 C == CH 2 (d)
10. Which of the following compound is chiral ?

CH3
O
Me ||
NH Cl
(a) (b) H (c) (d) Cl
Cl
Cl
11. Which of the following can exist in diastereomeric pair ?
F Cl CH3
Cl H Cl
(a) Cl Br (b) (c) (d)
H Cl
I CH3
12. Which of the following compound has one of the stereoisomer as a meso compound ?
|
(a) (b)
|
||
(c) (d) 2 ,3-Dimethyl butane

13. Which of the following has one of the isomer is meso?
(a) (b) (c) (d)
14. Which of the following is diastereomer of meso-2,3-dichloro butane?

CH3 CH3 Cl CH3
H Cl Cl H Cl Cl
(a) Cl H (b) H Cl (c) CH3—C—Et (d) H H
CH3 CH3 Cl CH3
15. Which of the following has/have P. O.S. (plane of symmetry)?
CH3 Cl
H Cl
(a) CH3 CH3 (b) (c) H Cl (d) F Br
C==C
H H CH3 I
16. Functional groups present in given compound are:

O
O
OH
O NH2
(a) alcohol (b) ketone (c) carboxylic acid (d) amide
17. Which of the following is aromatic?
(a) (b) (c) (d) O

O N O
18. Phenol is less acidic than:
(a) acetic acid (b) p-methoxy phenol (c) p-nitrophenol (d) ethanol
Answers
1. (a, b) 2. (b) 3. (a, b) 4. (a, d) 5. (a, b, d) 6. (a, b)
7. (b, c) 8. (a, c, d) 9. (b, c) 10. (a, b) 11. (b, c, d) 12. (a, b)
13. (a, b) 14. (a, b) 15. (a, b, c) 16. (a, b, d) 17. (b, c) 18. (a, c)

Passage-1:
CH3 CH3 Me Me
H Cl H Cl H Cl Cl H
(a) H Cl (b) Cl H (c) H Cl (d) Cl H
H Cl H Cl Cl H H Cl
CH3 CH3 Me Me
1. Pair of enantiomers:
(a) 0 (b) 1 (c) 2 (d) 3
2. Pair of Diastereomers are:
(a) 3 (b) 4 (c) 5 (d) 6
3. Number of meso isomers are:
(a) 1 (b) 2 (c) 3 (d) 4
4. Number of chiral isomers are:
(a) 1 (b) 2 (c) 3 (d) 4
Passage-2:
CH2—CH3 CH3
CH3—CH2—CH2—CH—CH2—CH—CH2—CH2—C—CH3
CH3—CH—CH3 CH3
1. Number of 1° carbon in above compounds are:

(a) 5 (b) 6 (c) 7 (d) 8
2. Number of 2° carbon in above compounds are:
(a) 5 (b) 6 (c) 7 (d) 8
3. Number of 3° carbon are:
(a) 1 (b) 2 (c) 3 (d) 4
4. Number of 4° carbon are:
(a) 1 (b) 2 (c) 3 (d) 4
Passage-3:
Keto-enol tautomerism is a dynamic equilibrium which is depends on the
stability of keto or enol tautomerism take place in dilute acidic or basic
medium.

OH
Prolonged treatment
1. ¾ ¾ ¾ ¾ ¾ ¾¾®
D 3Or
How many hydrogen atoms replaced by deuterium ?

(a) 1 (b) 3 (c) 4 (d) 5
2. Which of the % enol content order is wrong ?
O O O O
O
(a) > (b) >
O
O O O O
(c) (d) >
> O O
OEt
O O
Passage-4:
The theory of resonance was developed primarily by Pauling in the 1930s.
According to this theory, many molecules and ions are best described by
writing two or more lewis structures and considering the real molecule or ion
to be a composite of these structures. Individual lewis structure are called
contributing structures. They are also sometimes referred to as resonance
structures or resonance contributors. We show that the real molecule or ion is
a resonance hybrid of the various contributing structures by interconnecting
them with double headed arrows. Resonance structures are not in equilibrium
with each other.
s
O O
N N
O Os
(equivalent contributing structures)

1. More stable resonating structure of the given cation is:

r
CH2
:OMe
:
r
(a) (b)
r
OMe OMe
(c) (d)
r OMe OMe
2. Find out the stability order of intermediate:

OMe r OMe r
Me OMe H2C — OMe
r
r
Me
(I) (II) (III) (IV)
(a) I > II > III > IV (b) I > II > IV > III (c) IV > I > II > III (d) III > I > II > IV
3. Which of the following is not a valid resonating structure ?
r
NH2 NH2
||
s
(a) (b)
r
NH2 r
|| NH3
||
s
(c) (d)
s

Passage-5:
In any proton transfer reaction:
Acid + Base conjugate acid + conjugate base the reaction proceeds in
the direction that converts the stronger acid and the stronger base to the
weaker acid and the weaker base.
K>1
Stronger acid + Stronger base weaker acid + weaker base
The reaction will be favourable when the stronger acid is on the left and the
weaker acid is on the right. The equilibrium lies to the side of the acid that
holds the proton more tightly.
H H r s
O+H—Br O—H+ Br
H Hydrogen H Bromide
water Bromide Hydronium ion
pKa=–5.8 ion
strongeracid pKa=–1.8
weakeracid
O O
H H r s
O + H—O—C—CH3 O—H + O—C—CH3
H pKa =4.7 HpK
a =–1.8
weaker acid stronger acid
1. In the following compound;

O OH OH OH OH
O
N
O
N C
O O
N
(I) (II) (III) (IV)
the decreasing order of acidic strength:
(a) I > II > IV > III (b) II > I > IV > III (c) II > IV > I > III (d) II > IV > III > I
2. Which of the following compound is strongest base ?
NH2 Me NH
(a) (b) (c) HN NH2 (d) H N NH2

2
N
Me

Matching Type Problems

1. Match the following:
Column-I Column-II (Double bond equivalent value)
(a) (p) 11
(b) (q) 12
O
|
(c) (r) 13
O
|
(d) (s) 14
(t) 15

2. Match the column:

Column-I Column-II
(a) (p) Number of p-bonds is even
(b) (q) Number of p-bonds is odd
(c) (r) Number of s-bonds is odd
(d) (s) Number of s-bonds is even

Column-I Column-II
(a) C 4H 8 (p) Number of structural isomer=2
(b) C 5 H 12 (q) Number of structural isomer=3
(c) C 6 H 14 (r) Number of structural isomer=4
(d) C 4 H 10 O (alcohol only) (s) Number of structural isomer=5

Column-I Column-II
(a) Chain isomer (p) CH 3 — CH 2 — OH, CH 3 — CH 2 — CH 2 — OH
(b) Positional isomer (q) CH 3 — CH 2 — OH, CH 3 — O — CH 3
O
||
(c) Metamers (r)
CH 3 — C — O — CH 2 — CH 3 ,
O
||
CH 3 — CH 2 — C — O — CH 3
(d) Functional isomer (s) CH 3 — CH 2 — CH 2 — NH 2 , CH 3 — CH — CH 3

|
NH 2
(e) Homologous (t) CH 3 — CH 2 — CH 2 — CH 3 ,

CH3

O
5. With reference to compound A drawn below label each compound as an isomer
resonating structure or neither :
Column-I Column-II
(a) O (p) Isomers
(b) O (q) Resonating structure
s
(c) O (r) No relation
(d) O (s) Homologous

CH2
6. Relation between molecules or ions in each pairs related :

Column-I Column-II
CH 3
(a) | (p) Resonating structure
CH 3 — O — CH 2 — CH 3 , CH 3 — C — OH
|
H
s s (q) Isomers
(b) H 2 C == CH — CH— CH 3 , CH 2 — CH == CH — CH 3
(c) (r) No relation

, CH 3 — C == C — CH 3
| |
H H
s (s) Homologous
(d) CH 3 — CH 2 — CH 3 , CH 3 — CH 2 — CH 2


Column-I Column-II
OH
(a) (p) Resonance stabilization in the

compound
Cl
OH
(b) (q) IUPAC name is 2-chlorocyclobutenol
Cl
HO
(c) (r) IUPAC name is 3-chlorocyclobutenol
Cl
(d) HO (s) Hyperconjugation is possible

Cl
(t) Aromatic compound

Column-I (Various isoelectronic species) Column-II (Relative stability)
( a) r (b) s
(a) O == C == O ¬
¾® O ºº C — O (p) a> b
s r r s
(b) N == N == O ¬
¾® N ºº N— O (q) b> a
s2 –1 s
(c) ¾® NººN—O
N —N == O ® (r) a=b
s s
(d) O— C == O ¬
¾® O == C — O


Column-I Column-II
(a) R (p) R groups show +I effect
(b) R—Mg—Br (q) R groups show -I effect
(c) H2C == CH—R (r) (H 2 C == CH —) show +I effect
(d) H2C == CH—C ººCH (s) (H 2 C == CH —) show -I effect

Column-I Column-II
(a) 2,3-dichlorobutane (p) Number of stereoisomers are odd

numbers
(b) 2,4-dichloropentane (q) Number of stereoisomer are even

numbers
(c) 1,2-dichlorocyclohexane (r) Number of meso are odd numbers
(d) 1,3-dichlorocyclohexane (s) Number of meso are even numbers

Column-I Column-II
(a) Cl (p) Number of chiral center = 1

Me
Me
(b) Me Cl (q) Number of chiral center = 2
(c) Cl (r) Number of chiral center = 3
Me Me
(d) Cl Cl (s) Number of chiral center = 4
Me Me


Column-I Column-II
(a) CH 3 — CH == CH — CH 3 (p) Number of stereoisomer are=2
(b) CH 3 — CH == CH — CH — CH 3 (q) Number of stereoisomer are=3

|
OH
(c) CH 3 — CH — CH == CH — CH — CH 3 (r) Number of stereoisomer are=4

| |
OH OH
(d) OH (s) Number of stereoisomer are=6
OH

Column-I Column-II
(a) Br (p) C 2 axis of symmetry
Br
(b) Br (q) C 3 axis of symmetry
Br Br
(c) Br (r) Plane of symmetry
(d) (s) Center of symmetry

1. Find out the value of degree of unsaturation in the given compound.

O
O
2. How many 2° carbon in the following ?
C == C == C
3. Find out the double bond equivalent (D. B. E) value of the given following compound.
O O
|| ||
NH2
N
||
O
4. How many structural isomers are possible for C 4 H 10 O (only alcohol) ?
5. The total number of functional groups present in the given following compound:
O
O
6. How many 5 members parent chain alkane are possible for C 7 H 16 ?
7. Total number of possible structural isomers of C 5 H 11 Br.
8. Total number of structural isomers of C 9 H 18 containing cyclohexane ring:
9. Provide the structure of all distinct terminal alkynes with a molecular formula of C 6 H 10 .
10. How many compound reacts with NaHCO 3 ?
O OH
OH
O
||
(i) CH3 H (ii) (iii)
O

OH OH
OH
O2N NO2
(iv) (v) (vi)
O Me NO2
OH
O OH O == S == O
(vii) (viii)
11. Which of the given following compound will react with NaHCO 3 or soluble in NaHCO 3 ?
O OH
OH OH C—OH O == S == O
CH3—CººCH
(a) (b) (c) (d) (e)
12. In how many compound lone pair of nitrogen is involved in resonance ?

NH2 NH2 NH2
(a) (b) (c) (d)

N
O
||
(e) N (f) (g) CH 3 —C — NH 2
H N O
13. How many compound have odd number of a-hydrogens ?

Me
(a) (b) (c) (d)
(e) (f) (g)

14. How many compounds has odd number of a-hydrogens ?
(a) (b) (c) (d)
(e) (f) (g)
CH2–Cl
15. (a) ¾® (x) (Number of plane of symmetry)
CH2–Cl
(b) ¾® ( y) (Number of meso isomer of 1,2-dichlorocyclopentane).

Cl Cl
Sum of ( x + y) = ?
16. Find out the total number of stereocentre in the given compound:
CH 3 — CH == CH — CH — CH — CH 3
| |
Br Cl
17. Find the total number of isomers of C 7 H 14 (only 5-member ring):
18. Total number of plane of symmetry present in given compound is:
Cl Cl
Cl Cl
19. Total number of isomers for C 4 H 6 Br 2 containing cyclobutane ring are (including
stereoisomer).
20. How many structural isomers are possible for C 4 H 9 Cl ?
21. Total number of stereoisomer of 2, 3-dichlorobutane containing compound:
22. How many asymmetric centers are present in the compound below?
(CH3)2N
OH
CH3
C CCH3
H
H
O

23. Total number of a-hydrogen in the given following compound is:
24. How many carbon atom present in the parent chain in the given following compound ?
O
CH3
25. How many alkane will be formed by molecular formula C 6 H 14 ?

26. Total number of carbon in the parent chain of given compound is:
27. Total number of substituents present in following compound are:

O Br
Cl
28. Total number of a-hydrogen in the given compound is:
29. How many compounds are aromatic?

(1) (2)
r
(3) + (4) (5) (6)
N N
| |
H H
r
(7) (8)
r
r
30. x = Types of functional group
y = Double bond equivalent

Value of ( x + y) in given compound is:

O
OH
O H
O
31. Total number of carbon atoms present in parent chain is:
CH3
CH3—C—CH3
CH3—CH2—CH2—C—CH2—CH2—CH3
CH3—CH2—C—CH2—CH2—CH3
CH3
gas
(A)
¾¾®
KHCO3
O
KH 2 KNH
32. (D) Ph—S—O—H ¾¾¾® (C)
¾¾®
gas gas
O
®¾¾
(B)
gas
Sum of molecular weight of gaseous ( A + B + C + D) involved during given reactions will be:
33. Degree of unsaturation of the compound having molecular formula C 6 H 3 N 3 O 7 .
34. NH2 , , , —NH ,
NH— NH2
N , OH , , ,
OH OH OH
What is the sum of 3°-alcohols and 2°-amines from above compound?
35. IfNumber of 1°-C = a
Number of 2°-C = b
Number of 3°-C = c
Number of 4°-C = d
then what is the value of a + b + c + d in the given compound ( e. g., if
a + b + c + d = 2 + 3 + 1 + 2 = 7 then write your answer 07)?
O
||
36. (i) Ph — C — OH + NaHCO 3 ¾® ¾ A(gas)

(ii) Ph — OH + NaNH 2 ¾®
¾ B(gas)
Sum of mol. wt. of A + B = X , so the value of X -54 is.
37. Number of compounds undergo dimerization at room temperature?
N
(a) (b) (c) (d)
(e) (f)
38. X = Number of a-hydrogen.

CH3 CD3
C == C
CH3 CD3
39. Y = Number of resonating structure.
s
40. X = Number of R.S. (Resonating structure)

r
41. X = Number of R.S. (Resonating structure)

r
O
42. X = Number of a-Hydrogen,
43. X = Number of compound unstable at room temperature.

CH3
N
(a) (b) (c) (d)
N
O
(e) O (f)
s
O
44. x = No. of resonating structure.

1. Draw the important resonance contributing forms for the structure shown below.
+
2. Provide the structure of the major organic product(s) in the reaction below:
HCl
3. List the following compounds in order of decreasing basicity.

NH2 NH2 NH2
H3C O2N Br
4. List the following compounds in order of decreasing acidity .

OH OH OH
O
H3CO Cl HC
5. Draw the important resonance structures of:
CH3 –
6. Provide 1° , 2° , 3° and 4° carbons and hydrogens in each structure:
Structures 1° 2° 3° 4°
C H C H C H C

7.
S.No. Molecular Formula Number of Structural Isomers
1. C 4H 8
2. C 3H 6
3. C 6 H 12 (having cyclobutane ring)
4. C 4 H 6 (cyclic)
5. C 7 H 16
6. C 4 H 10 O
7. C 6 H 14
8. C 3H 9N
9. C 6 H 12 (cyclopropane ring only)
10. C 3 H 6 Cl 2
11. C 8 H 10 (only one benzene ring)
12. C 7 H 8 O (only one benzene ring)
13. C 5 H 12
14. C 7 H 14 (cyclobutane ring)
15. C 5 H 10 O (only aldehyde and ketone)
16. C 5 H 10 (cyclic)
17. C 5 H 11 Br
18. C 4 H 11 N
19. C 3 H 5 Br 3
20. C 7 H 7 Cl (only one benzene ring)
21. C 5 H 12 O (only ether)

8. Find the number of Stereocenter and Chiral center in all structural isomers of given molecular
formula:
S.No. Molecular Formula Stereocenter Chiral Center
(i) C 6 H 12 (open chain)
(ii) C 6 H 12 (excluding cyclopropane ring)
(iii) C 6 H 14
(iv) C 3 H 6 Cl 2
(v) C 5 H 12
(vi) C 5 H 10 (all cyclic isomers)
(vii) C 5 H 11 Br
(viii) C 4 H 6 (all cyclic isomers)
(ix) C 7 H 14 (cyclopentane ring)
(x) CH3
H CH3
C
H
(xi) CH3
CH3 CH3
C
H
(xii) CH3
CH3
C
CH3
CH3
(xiii) CH3
CH3
CH3 C
CH3
CH3
(xiv) CH3—CH—CH2
O
(xv) Br
CH3
r
C == N
H

(xvi) CH3
H D
H Et
C
H CH3
D
(xvii) 2,4-Hexadiene
(xviii) CH(OH)CH3
Cl
9. Rank the following groups of compounds in order of decreasing solubility in H 2 O:

(i) CH 3 — CH 2 — CH 2 — OH , Cl — CH 2 — CH 2 — CH 2 — Cl ,
CH 3 — CH 2 — CH 2 — CH 2 — OH , HO — CH 2 — CH 2 — OH
CH3 NH2 OH
(ii) , ,
(iii) CH 3 — F , CH 3 — Cl , CH 3 — Br
(iv) CH 3 — O — CH 3 , CH 3 — O — CH 2 — CH 3 , CH 3 — CH 2 — O — CH 2 — CH 3
(v) EtOH , CH 3 — CH 2 — CH 3
(vi) CH 3 — O — CH 3 , CH 3 — CH 2 — CH 3
(vii)H 3 C — CH 2 — CH 2 — CH 2 — OH , CH 3 — CH 2 — CH 2 — OH , CH 3 — CH 2 — OH
Os OH
OH OH OCH3
(viii) , , (ix) ,
OH OCH3 OCH3
O
O
(x) ,
CH 3
NH | ,
(xi) NH2, , CH 3 — N — CH 2 — CH 3 (xii)
10. Rank the following in decreasing order of boiling point :
(i) , ,
(ii) EtOH , Et — NH 2 , CH 3 — O — CH 3 , CH 3 — CH 2 — CH 3
(iii) CH 3 CO 2 H , CH 3 — CH 2 — OH , CH 3 — CH == O , CH 3 — CH 2 — CH 3

OH OH OH OH OH
OH OH
(iv) , (v) , ,
OH
OH
(vi) (vii) ,
, N N
O
CH3 H
CH 3
|
(viii) CH 3 — CH 2 — CH 2 — CH 2 — OH , CH 3 — CH — CH 2 — OH , CH 3 — C — OH
| |
CH 3 CH 3
(ix) cyclooctane, cycloheptane, cyclohexane
CH3 C ºº N CH3 H
(x) C == C C == C
H H , H C ºº N
11. Amongst the following, the total number of compound will show geometrical isomerism:
Cl Cl
Cl
(A) (B) (C) (D)
Cl
Cl Cl
C6H5 OH
(E) H — C ºº C — H (F) C == N (G)
H
O
||
NaNH
12. Ph — C — O — H ¾ ¾ ¾2® ( A) gas
O
||
NaH
¾® ( B ) gas
Ph — C — O — H ¾ ¾
( A) and ( B ) are molecular mass of gas so the value of A + B -10 is:

13. Amongst the following, the total number of compounds which will show aromatic character
will be:
+ r
(i) (ii) (iii) (iv) s
+
s
(v) (vi) (vii) (viii)
O
s
(ix)
s
14. How many stereoisomers of given compound are possible when alkenyl substituent have a
cis-configuration.
O
O
||
15. CH 3 — CH 2 — C — CH — CH 2 — CH 3
|
CH 3
(Racemic)
Total number of enol (including stereoisomer) possible of given compound is ( x).
So the value of ( x) is:

16. Identify which of the following compounds may show geometrical isomerism?
Cl Cl
CH 3 CH2CH 3 H H
1. 2. 3.
Cl Cl
Cl
Cl
4. 5. 6.
Cl Br
CH3 CH3
Br
7. 8. 9.
CH3
H
10. 11. 12.
H OH CH 3 H CH3 + H
13. C N 14. O+ 15. N C
Br H H CH3
..
..
H H
H H C C C C CH 3 CH3
16. C C C 17. CH 3 Br 18.
Br Br
CH3
H O
19. CH2 C C C 20. 21.
CH3
O
CH3
Cl Br
22. 23. C ==C 24. CH 3 — C ºº C — CH 3
F I

17. Identify which of the compound is cis or trans or none of these?
CH3 CH 3 CH3
Cl
1. CH3 2. 3.
CH 3
CH3 CH3
Cl Cl
4. 5. 6.
7. 8. 9.
10. 11. 12.
CH3 CH3
CH3
13. 14. CH3 15. H
CH3
CH3 CH3
H CH3 H H CH3 ..
O..
16. Br Ph 17. Br Cl 18. H
H + H
19. N 20. 21.
CH 3 CH3

18.
Total number of Geometrical Isomers
Compound
possible
1. CH 3 — CH — CH — CH 2 CH 3
2. CH 3 — CH — CH — CH — CH 2
3. CH 3 — CH — CH — CH — CH — CH 3
4. CH 3 — CH — CH — CH — CH — Br
CH 3 — CH — CH — CH — CH — CH — CH 2
5.
6. CH 3 —( CH — CH —
) 3 Ph
7. CH 3—
( CH — CH—
) 3 CH 3
O CH3
8.
CH3
Br
9.
Br Br
Br
10.
Br Cl
11.
12.
13. CH 3 — CH — CH 2

19. Count the total number of chiral center.
CH 3
O
CH3 CH
CH2 CH2 CH 2 CH2
1. CH CH2 2. 3. CH2 CH
O CH CH C
CH3
CH3 CH3 H
CH3
CH2 CH2
H 2C O CH CH
NH 2 – CH – COOH
H 2C CH OH CH2 CH2 |
4. CH2 CH2 5. CH 6. CH3
CH
CH2 CH2
CHO CHO CH3

H OH H OH H Me
H OH
7. H OH 8. 9. H Et
H OH
CH2OH CH2OH C2H5
O
O
10. NH 11. 12.
Ph – S – CH3
H
.. 16 O
+ As C 2H 5 ||
CH3 N Ph CH3 — S — Ph
13. D 14. CH 3 H 15. ||
18 O
16. 17.
HO HO
Cholesterol Estrone

20. R-S System
Cl OH CH2CH3
H CH3 Br
1. F 2. CH3CH2 3. CH3 H
Br CHO
D Br Cl Br Cl
Cl
4. H CH3 5. 6.
Br Br
CH3
F Cl
7. 8. 9.
H
Cl Cl
CH3 CH3 CH3

H Br H Br
HO CHO
10. 11. H Br 12. Br H
CH2CH3 CH3 CH3
CH3 CMe3
13. H D 14. CH3 CH3

14
CD3 CD3

21. Relationship between enantiomer, diastereomer and other :
Identify the relation Enantiomer Diastereomer Other
H T
1. T H
Cl Cl
D D
F I
2. I F
Cl Cl
Br Br
H F
3. T D H D
F T
CH==CH2 D
4. D F Cl F
Cl CH==CH2
H H
HO F F OH
5.
Cl OH HO Cl
D D
Me Et
H OH H OH
6.
HO H HO H
Et Me
Cl Cl
7.
Br Br

Cl Cl
8.
Br Br
D D
9.
T T
OH
10.
OH
Et Me
H OH H OH
11.
Cl H Cl H
Me Et
12.
OH CH3
H OH
13. H
A B
O O
14.
O O
C D

22. Identify the plane of symmetry (POS) in the given molecule.
POS POS
CH3
Cl
1. 7.
Cl CH3
CH3
H
H3C H
CH3
2. C==C 8.
H H D D
D D
OH
CH3
H H
H Br
3. 9.
Br H
H H
CH3
OH
CH3
H Br H H
4. 10. C==C==C
H Br
Cl H
CH3
CH3
H H
5. 11. C==C==C
Br Br
CH3 H H
CH3
6. 12. H–C C–H
H H

POS POS
Cl
O
13. 15.
O
Cl
H H
H H
14.
Cl
Cl
23. Identify the molecules having centre of symmetry
Ci Ci
F H D T
D
1. 4.
D
F H D
T
Cl
H D H D
2. 5.
T T
Cl
Cl
H D T
3. 6.
T D H
Cl

Ci Ci
Cl
Br O
7. 12.
Br O
Cl
H
T D
8. 13.
D T
H
H D
H
D
9. 14.
T
T
Cl
Br
10. 15.
Br
Cl
O
11.
O

24. S. Compound Chiral Chiral compound Optically active Optically Geometrical
POS COS
NO. carbon isomerism isomerism
1. H H
C==C==C
H H
CH3 CH3
2. C==C==C
H H
3. Cl CH3
C==C==C
Cl H
CH 3 CH3
4. C==C==C==C
H H
Cl CH 3
5. C==C==C==C
Cl H
Organic Chemistry: Some Basic Principles and Techniques
6. H CH3
C
CH3 H
7. CH3
H C

H
CH3
8. CH3
H C
H
CH3
135
S. Chiral Optically Geometrical
136
Compound POS COS Chiral compound Optically active
25. NO. carbon isomerism isomerism
1.
2. H H
CH3 CH3
3. H CH3
CH3 CH3
4. H H
CH3 CH3
5. CH3
H3C C
CH3
CH3
SO3H
NO2
6.

SO3H NO2
Br I
7.
I Br
Elementary Organic Chemistry
26. Calculate the number of isomeric molecules as per direction.
Number of
S. Total no. of Number of
Compound optically active
No. stereoisomers meso compd.
isomers
1.
2.
3. CH 3 — CH — C — CH — CH 3
F
4. Cl Br
CH3
H Cl
5. H Br
CH3
CH3
H Cl
6.
Cl H
CH3
7. 2,4-dichloropentane
10.
11.

Number of
S. Total no. of Number of
Compound optically active
No. stereoisomers meso compd.
isomers
12.
Cl
13.
Cl
Cl
14. CH–CH==CH–Cl
Br
Cl
15.
Br
Cl Cl
16.
Cl Cl
CH 3 — CH — C — CH — CH —
17.
CH — CH 3
Cl
18.
CH3
19. Tartaric acid

27. State different types of gases evolved in the following given blocks :
S.No. Compound Na NaH NaNH2 NaHCO 3 CH3 — Li
a. EtOH
b. H — C ºº C — H
c.
d. Ph—OH
e. Ph — CO 2 H
f. Ph — SO 3 H
g.
h.
28. gas (B) sum of molecular weight of ( A + B )?
29. Find sum of x + y + z ?

30. Draw the resonating structure and resonance hybrid of following species?
S. Resonating S. Resonating
Compounds Compounds
No. Hybrid No. Hybrid
CH CH
1. 2.
CH
3. 4.
HC
H 2C CH
5. CH3
O
H2C
CH3
6. 7.
O
H 2C O +
CH
8. O 9.
H HO
N + +
10. CH 11. CH
H3C
S +
CH
12. 13. +
C
OH
O
14.
+
CH

31.
S.No. Resonating Structure Relative Stability

Å
OCH3 O – CH3
1. Q
;
Å
O O
2. Å
;
O OQ OQ
3. || Å Å
CH3 – C – OH , CH3 – C – OH , CH3– C == O – H
Å
Å NH2
NH2 NH2
4.
Q
; ;
Q
Å Q
O == C == O ; O º C – O
5. Å Q +2 Q
O == C – OQ ; O – C – O
O OQ
|| Å |
H – O – C – NH 2 ; H—O==C – NH2 ;
6.
OQ OQ
| Å |
Å
H – O – C==NH2 ; H – O – C – NH 2
Å
7. ;
Å
Q Q
O O O
Å
8.
; ;
Å

32.
Huckel Rule Complete
S.No. Compound Planarity Cyclic Nature
( 4n + 2) pe - delocalisation
1.
2.
3.
4.
5.
6.
7.
8.


S.No. Compound Planarity Cyclic Nature
9.
10.
33.
S.N. Compounds Planarity Cyclic Nature
1.
Q
2.
Å
3.
+
4.
+
Q
5.
Q
6.
Q
7.
8.
9.
10.
O

11.
12.
34. Write the IUPAC name of the compounds given in the blank box.
S. No. Compounds S. No. Compounds
O O
OH Cl
1. 2.
O NH2 O CH3
O
3. 4.
O
N
CH3
O
5. 6.
O
7.
OH

S.No. Compounds S.No. Compounds
O
O
OH
NH2
O
1. 2. O
O
CH3 OH
O
CH3
O
3. 4. O
O CH3
O O
CH3
5. 6.
7.

O
O
1. 2.
H3C O
3. 4.
HO
Cl Cl
Cl
Cl
5. Cl 6.
Cl Br
7. 7.
Cl Cl Cl Cl
Cl
Cl
9. 10.
Cl Br
Br

S. No. Compound S. No. Compound
Br Br
Br Cl
1. 2.
+ +
- N - N
O O O O
Cl
Br OH
Br
3. 4.
+ Cl
- N
O O
Br
CH3
5. 6.
Br
NH2
Br
7. Cl
NH2

38. Draw Resonance hybrid of following ?
+
CH
1. 2. +
CH
+
CH2
+
3. 4. H 2C CH2
+
+
CH
CH
5. H 2C CH3 6.
+
CH
+
CH
7. 8.
CH3
+
CH2
+
CH
9. +
10.
CH
H2C
11.
+
CH
CH3

39. Draw the resonating structure and resonance hybrid of following species?
Compounds Compounds
No. Structure No. Structure
1. O
- H3C
H 2C CH2 2.
-
O
3. NH2 -
CH
4.
5.
-
NH2 C
6.
O
-
CH O
7. 8. -
O -
O
CH3
Cl
O
9. 10.
- CH3
11. H 2C
O -
CH
12. H3C 13.
NH2

Compounds Compounds
No. Structure No. Structure
H3C
O
-
CH
14. 15.
O
-
O O
CH3
16. H3C 17.
O
O
18. H3C
OH
S. S.
Compounds Compounds
No. No.
O O
1. Cl NH Br
2. Br NH Cl
O
O
H3C NH
3. 4. H2N CH3
CH3

S. S.
Compounds Compounds
No. No.
O
O
H 3C CH3 H2N
5. NH 6.
CH2
O
O
H3C CH3
NH
7. 8. H 3C NH CH3
Cl
Br
O O
H3C
NH O
9. 10.
H3C O
CH
H3C NH2
11. O 12.
H 3C CH2 Br
H3C CH3
13. NH2 14.
H2N

S. S.
Compounds Compounds
No. No.
Cl
H3C CH3
H3C CH3
NH2 NH2
1. 2.
HO O O
HO
HO H2C
O S O
H3C
H3C HO CH3
3. CH3 4.
O S O
O
HO O OH
HO
O S O CH3
H 3C
5. H3C CH3 6. NH2 CH3

NH2
CH3
CH3
H3C
7. O 8.
O Cl O
O H3C
HO

O
H3C CH3
H3C
CH3
9. 10.
O Cl O
Cl O
HO O
S
H3C CH3 O CH3
CH2
O S O O
11. CH3 12.
OH
O
H3C
H3C
NH2
O O CH3
H3C
13. H3C CH3 14. Cl Cl

HO O
Cl
O

S. S.
Compounds Compounds
No. No.
HO
H3C CH3
O S O
H3C CH3
O O O
1. 2.
CH3
H2N O
CH3
CH3
O
CH3
O
3. 4. NH2
O
CH3
CH3
CH3
O OH O O
H3C
H3C
CH3 CH3
5. NH2 6. H2N
O S O O O
OH
CH3

S. S.
Compounds Compounds
No. No.
CH3
H3C NH
H3C CH3
O O
O O
7. 8.
H3C N
O
CH3
O
HO H3C
NH2
9. O 10. CH3
F F
F
CH3 CH2
H3C CH3 O
O CH3 H3C
HO S NH CH3
11. 12.
O CH3
H3C CH3
HC

S. S.
Compounds Compounds
No. No.
HO O OH
O S O
CH3 CH3
1. O O 2.
O O
CH2 CH3 CH3
O OH
HO CH3
O O
3. 4. O
O
O CH3
O OH
O H3C CH3
HO
5. S 6. N
O N
H3C
CH3
O HO
H3C
CH3 CH
7. O 8.
H2N O

F CH3 Cl NH2
F
O
O
F CH3
9. 10. O
O
Cl O CH3
H2C
O OH HC HO
O S O
CH2
CH2
11. 12.
CH Cl O
HO
HO H2C
O S O
O
S
O O CH3
13. 14.
H3C Cl HO
Cl CH2
Cl O
H3C
H3C CH3
CH3
15. 16.
CH3
O S O
H3C CH3
H2N O
OH

Cl
O
Br
17.
+
- N
O O
S. S.
Compounds Compounds
No. No.
O OH F
HC
F F
O
1. HO 2.
S
HO O
O HO O
H2C Cl SH
CH3
3. 4. O S O
OH
HO O OH
O OH
HO H2C
O H2N
CH3
HO 6.
5. OH
O CH3 O S O
OH

O OH
O
– O OH
O +
H3C N
Cl
CH3
7. 8. Cl
HC O S O
CH3 CH2
CH3 OH
NH2
O OH
HO
O
H3C CH3
O CH3
9. 10.
O O H3C
CH3
CH3
OH
OH O
O
11. 12. HO
O CH3
HO O
O
+
O OH N -
H2C H3C O
CH2
13. 14. O S O
H3C SH H2C OH
HO O

HC
HO
Cl
O OH
15. Br
O CH2
CH3
S. S.
Compounds Compounds
No. No.
H2N H2N NH2 OH

O
H3C
H3C CH3
1. 2. OH
CH3 OH HO O
N
O NH2
O
O
H3C
3. H3C 4.
OH
OH
O O
Cl
Br Cl
O Cl Cl
H3C O
OH H3C
5. O 6. OH
O NH O
CH3
CH3 CH3

S. S.
Compounds Compounds
No. No.
O OH
NH2
O O S O
O
7. H3C 8. H3C
OH
Cl O
OH
H3C
H3C
CH3 O O
O H2C
OH
9. N S 10. CH3
O
H3C
HO O
N
O
H3C
11. Cl O 12.
O CH3
H3C
O O
H3C
O S O OH
13. 14.
HO O
15.

S. S.
Compounds Compounds
No. No.
H3C
O
O
H 3C
1. 2. H3C
CH3
CH3
O H 2C O
3. 4.
H2C CH3 H 2C CH3
O O
HC
5. 6.
CH3 CH3
O O
H2C
7. 8.
CH2 CH3
Br
H 3C O Br
O
H3C
9. CH3 10.
CH3

S. S.
Compounds Compounds
No. No.
CH3 CH3
H3C H3C
1. 2.
O O
Cl Cl
H3C
CH3
H3C
H3C
CH3
3. 4.
CH3 O CH2
Cl
Cl O
Cl H3C CH3
H3C CH3
5. Cl 6.
Cl O Cl O
H2C
H3C CH3
H3C CH3
7. Cl O 8.
Cl O
S. S.
Compounds Compounds
No. No.
H3C H3C CH3

CH3
1. 2.
N N

H3C CH3
H3C
CH3
3. 4.
N
CH
CH3
H3C
CH3
5. 6.
N
CH
CH3
7.
N
S. S.
Compounds Compounds
No. No.
H2C
O
H3C CH3
1. 2.
OH
HO O

S. S.
Compounds Compounds
No. No.
H3C OH
CH3 O
3. HO O 4. H3C
CH3
CH2 Br
HC
CH3
H3C CH3 H3C
5. 6.
HO O
HO O
O OH
H3C
H3C CH3 H3C

CH3
7. 8.
CH3
HO O
O OH
H3C CH3
H3C CH3
9. Br 10.
Br HO O
CH

S. S.
Compounds Compounds
No. No.
H3C
H3C
H3C CH3 CH3
11. 12. HO O CH2

CH3
HO O
O OH
CH3
H3C
CH3 CH3
13. 14.
O
HO
CH3
15.
O
HO
S. S.
Compounds Compounds
No. No.
H3C CH3
O
H3C
1. 2. O O
O CH3
CH3

S. S.
Compounds Compounds
No. No.
Br CH3
H3C CH3
O
3. O O 4.
O
CH3 CH3
Cl
H3C CH3
H3C CH3
Cl
5. 6. CH2 O O
O O
CH3
CH3
H3C
H3C CH3
O O
O O
7. CH3 8.
H3C
CH3
Br
H3C CH3
H3C
O O
O O
9. Br 10.
H3C CH3
CH3
Br

S. S.
Compounds Compounds
No. No.
H3C
CH3
O O
O O H3C
11. CH2 12. CH3
CH3
13. 14. O O
H3C
O
H3C
CH3
CH3 Cl
H3C
H3C
Br CH3
Br
O O O
O
15. 16.

S. S.
Compounds Compounds
No. No.
H3C CH3
O CH3
1. HN O 2.
H2N
CH3
Br CH3 Br CH3
O O
3. 4.
H2N Cl H2N Cl
O O
H2N H2N CH3

5. 6.
CH2
CH
O O
CH3
CH3
H2N H2N
7. 8.
CH2
HC
Br
O
O H3C
CH3
9. 10.
H 2N O
Cl

S. S.
Compounds Compounds
No. No.
Cl
O O
H3C
11. 12. H3C CH3
O O
Br
O
O O
H2C CH3
13. 14. H3C CH3
O
O O
O
CH3
H3C O O
15. 16. O
CH3
O O
CH3 O
H3C
17. 18.
NH2 O O CH3
O
O
19. 20.
H 3C CH3
H 3C O CH3
O
NH2
H3C CH3
21. 22 H3C CH3
NH2
Br

52. Count the number of primary, secondary, tertiary, quarternary carbon as well as hydrogen in
given compound :
S.
Compounds 1°C 2°C 3°C 4°C 1°H 2°H 3°CH
No.
CH3
1. CH3CH2CHCHCH2CH2CHCH3
CH2CH3 CH2CH3
CH2 - CH - CH2
2. | | |
OH OH OH
3. CH3
HO CH3
CO2H
4.
Cl
OH
5.
CH3
CH==CH—CHCH2CH3
6. |
CH3
7.
8.
9.

10.
CH2CH2CH2CH3
11.
53. Circle the functional groups and give the name in the following structures ?
1. 2
3. 4.
5. 6.
7. 8.
9. 10.
11. 12.
13. HCOOCH3 14. CH3COOH
15.

54. Circle the functional groups in the following compounds & find out the DBE value of each
compound ?
1. 2
3. 4.
5. 6.
7. 8.
9. 10.
11. 12.

55.
Name of
S. DBE
Compounds Functional
No. Value
Group
O
OH
1. S
O CH3
2.
3.
4.
O
HO CH2– OH
5.
HO CH==CH–CH==CH–CH2–CH2–CH3
COOH
COOH OCH3
6.
COOH

S. S.
Compounds Compounds
No. No.
CH3
H2C
H 3C CH2
1. 2.
H3C
H3C
CH3
CH3
3. 4. H3C
H3C CH2
Cl CH2
5. 6.
H3C CH2
Cl
CH2
7. H3C CH2 8. Br
CH3
CH3
H3C Br
9. CH3 10.
CH3
H3C CH2

S. S.
Compounds Compounds
No. No.
H3C
H 2C
CH2
1. 2.
CH2
CH2
H2C
3. 4.
CH
H3C CH2
H3C
CH3
HC
5. 6.
CH
H2C
H 3C
CH3
7. 8. Cl CH2
HC
Cl
9. 10.
H3C CH3
11.

CH3 CH3
1. CH3 2.
H3C
Br
Br
3. H3C CH3 4
Br
Cl
Br
5. 6.
Cl
Cl
CH3
7. 8.
CH2
CH2
H3C
9. 10.
CH2

H3C CH3 H 3C HO
H 3C CH3
1. OH 2.
HO OH
H3C CH3
CH3 H3C
3. 4.
CH3 CH3
H3C
CH2
5. 6. HO
OH
CH2
OH
H 2C
H3C OH
7. 8.
Br
HO H3C
CH3 Br
H3C
CH2
H3C
9. 10.
HO CH3

CH3
HO Br
1. 2.
OH
OH
HO OH
OH CH3
3. 4.
CH3
OH HO
5. 6.
OH OH
7. 8.
HO
Br
9.
Cl

S. S.
Compounds Compounds
No. No.
O
H3C
CH3
1. 2. H3C CH3
O CH2
CH3 Br
CH3
H3C H3C CH3
3. 4. CH3
O CH3
CH2 O
HC
O
CH3
H3C O
5. CH3 6. H3C CH3

CH3 Br
CH3
O
CH3 Cl
H3C
H3C
CH3
7. 8.
O CH2 Br

H3C O
O
1. 2.
H3C O
O
H2C
H3C
3. 4.
O
CH
O H3C
CH3
5. H3C 6.
O O
Cl
H3C CH3 H3C
Br CH3
7. 8.
O Br
O
9. H3C CH3

Answers
Comprehension Based Problems:
Passage-1: 1. (b) 2. (c) 3. (b) 4. (b)
Passage-2: 1. (c) 2. (b) 3. (c) 4. (a)
Passage-3: 1. (c) 2. (d)
Passage-4: 1. (c) 2. (b) 3. (d)
Passage-5: 1. (a) 2. (d)
Matching Type Problems:

1. a ® r; b ® t; c ® t; d ® s
2. (a) ® q, s; (b) ® q, r; (c) ® q, r; (d) ® q, r
3. (a) ® s; (b) ® q; (c) ® s; (d) ® r
4. (a) ® t; (b) ® s; (c) ® r; (d) ® q; (e) ® p
5. (a)® p; (b)® r; (c) ® q; (d) ® p
6. (a)® q; (b)® p; (c)® q; (d)® r
7. (a) ® p,q,s; (b) ® p,r,s; (c) ® s; (d) ® s
8. (a) ® p, (b) ® q, (c) ® q, (d) ® r
9. (a) ® p, (b) ® q, (c) ® s, (d) ® r
10. (a) ® p, r; (b) ® p, r; (c) ® p, r; (d)®p,r
11. (a) ® p; (b) ® q; (c) ® r; (d)®s
12. (a) ® p; (b) ® r; (c) ® s; (d) ® q
13. (a) ® p, r, s; (b) ® p, q, r; (c) ® p, r; (d) ® p, q, r, s
Multi Concept Subjective Problems
1. 7 2. 21 3. 11 4. 4 5. 3 6. 5 7. 8 8. 12 9. 5 10. 5
11. 2 12. 4 13. 3 14. 2 15. 4 16. 4 17. 8 18. 3 19. 6 20. 4
21. 3 22. 5 23. 6 24. 4 25. 5 26. 8 27. 4 28. 6 29. 5 30. 9
31. 8 32. 65 33. 7 34. 4 35. 17 36. 7 37. 2 38. 6 39. 5 40. 7
41. 3 42. 6 43. 3 44. 6

Unified Conceptual Problems

1.
+ +
+
Å Å
+ +
Cl
2. + enantiomer
NH2 NH2 NH2

3. > >
H3C Br O2N
OH
OH OH
O > >
4. H3CO
HC Cl
CH3 – CH3 CH3 –

5.
–
6. Provide 1° , 2° , 3° and 4° carbons and hydrogens in each structure:
Structures 1° 2° 3° 4°
C H C H C H C
2° 2° 1°
1° 2° 2°
2 6 4 8 0 0 0
1°
2°
1° 3° 1° 3 9 2 4 1 1 0
2°
2° 2°
3°
1° 1° 3 9 2 4 1 1 0
1°
1°
4° 1° 4 12 1 2 0 0 1
2°
1° 1°
1° 1°
3° 3° 4 12 0 0 2 2 0
1° 1°

7.
S.No. Molecular Formula Number of Structural Isomers
1. C 4H 8 5
2. C 3H 6 2
3. C 6 H 12 (having cyclobutane ring) 4
4. C 4 H 6 (cyclic) 5
5. C 7 H 16 9
6. C 4 H 10 O 7
7. C 6 H 14 5
8. C 3H 9N 4
9. C 6 H 12 (cyclopropane ring only) 6
10. C 3 H 6 Cl 2 4
11. C 8 H 10 (only one benzene ring) 4
12. C 7 H 8 O (only one benzene ring) 5
13. C 5 H 12 3
14. C 7 H 14 (cyclobutane ring) 8
15. C 5 H 10 O (only aldehyde and ketone) 7
16. C 5 H 10 (cyclic) 5
17. C 5 H 11 Br 8
18. C 4 H 11 N 8
19. C 3 H 5 Br 3 5
20. C 7 H 7 Cl (only one benzene ring) 4
21. C 5 H 12 O (only ether) 6

8. Short abbreviations * Þ (S.C. = Stereocenter) (C.C. = Chiral center)

(i)
, * , *
* *
, * ,
, , [S.C .Þ 5; C.C. Þ 1]
* *
, , , , ,
(ii) [S.C. Þ 4; C.C. Þ2]
*
*
, , ,
(iii) [S.C. = zero ; C.C. = zero]
Cl Cl
(iv) Cl Cl Cl [S.C. = 1; C.C. = 1]
*
Cl
Cl Cl
(v) [S.C. = zero; C.C. = zero]
*
(vi) [S.C. = 2; C.C. = 2]
*
Br
Br *
(vii) * Br
Br Br
Br
Br
* Br [S.C. = 3; C.C. = 3]
CH2
(viii) [S.C. = zero; C.C. = zero]
* *
*
(ix) [S.C. = 4; C.C. = 4]
*

CH3
*
H * CH3
*
(x) C [S.C. = 3; C.C. = 1]
H
CH3
CH3 * CH3
(xi) * C [S.C. = 2 ; C.C. = zero]
H
CH3 *
CH3
(xii) C [S.C. = 2 ; C.C. = 2]
CH3
CH3 *
CH3
*
CH3
(xiii) CH3 C [S.C. = 1 ; C.C. = 1]
CH3
CH3
*
(xiv) CH3— C H—CH2 [S.C. = 1 ; C.C. = 1]
O
Br
CH3 *
(xv) r [S.C. = 3 ; C.C. = 1]
C == N*
H *
CH3
H D
(xvi) H Et [S.C. = 3 ; C.C. = 3]

C
H CH3
D
(xvii) * * [S.C. = 4 ; C.C. = zero]
* *
*
* CH(OH)CH3
(xviii) * [S.C. = 3 ; C.C. = 3]
Cl

9.
(i) 4 > 1 > 3 > 2 (ii) 2 > 3 > 1 (iii) 1 > 2 > 3 (iv) 1 > 2 > 3 (v) 1 > 2
(vi) 1 > 2 (vii) 3 > 2 > 1 (viii) 1 > 2 > 3 (ix) 1 > 2 (x) 1 > 2
(xi) 1 > 2 > 3 (xii) 2 > 1
10.
(i) 1 > 2 > 3 (ii) 1 > 2 > 3 > 4 (iii) 1 > 2 > 3 > 4 (iv) 2 > 1 (v) 2 > 1 > 3
(vi) 2 > 1 (vii) 2 > 1 (viii) 1 > 2 > 3 (ix) 1 > 2 > 3 (x) 2 > 1
11. (3)
Strategy
(1) Restricted rotation
(2) l1 ¹ l 2
G.I.
Cl
(A) 3
Cl
Cl
H
(B) (l1 = l 2 ) 7
H
Cl
Same atom
CH3 Same gp.

(C) (l1 = l 2 ) 7
CH3
(D) 3
cis trans
(E) H — C ºº C — H (l1 = l 2 ) 7
C6H5 C6H5 OH
(F) C == N C == N 3
H OH H
(syn) (Anti)
CH3
(G) (l1 = l 2 ) 7
H

12. (9)
Strategy ® Acid-Base reaction always favour the formation of weaker acid and weaker
base.
O O
|| r s || s r
Ph — C — OH + NaNH 2 Ph — C — ONa + NH 3
Strong Acid Strong Base C.B. (Weak) C.A. (Weak)
(A) ® NH 3 gas
O O
|| sr r s || s r
Ph — C — OH + NaH Ph — C — ONa + H2
Acid Base C.B. (Weak) C.A. (Weak)
(B) ® H 2 gas
Mol. mass
(A) ® NH 3 17
(B) ® H 2 2
A + B ® 19 \ A + B - 10 Þ 9
13.
No. of
Compound Value of ‘ n’ Nature
pe -
r
2 0 A
r
4 1 N.A.
6 1 A
Tropolium ion
s 12 3 AA
s
6 1 A

A
14 3
Perimeter Reso. Present
8 2 N.A.
(Tub shaped molecule)
N.A.
5 1 (Hybrid state of one of
O the carbon is sp 3 )
s
6 1 A
s
*
14. (4) *
Total stereoisomers of given compound = 2 3 = 8

but when alkenyl substituent have cis then number of S.I. = 4.
15. (4 or 6)
OH No. of stereoisomers
* (1) cis– R
CH3—CH == C—CH—CH2CH3
(2) cis– S
O CH3 (3) trans– R
(4) trans– S
CH3—CH2—C—CH—CH2CH3
CH3
OH
(1) cis– –
CH3—CH2—C == C—CH2CH3 (2) trans– –
CH3 total- 6
Total enols possible are 6.
16. Compounds that show geometrical isomerism are:

1, 2, 4 5, 6, 8, 11, 12, 13, 14, 15, 17, 20, 21, 22, 23
17.
1. cis 2. trans 3. trans 4. none 5. cis
6. cis 7. trans 8. trans 9. cis 10. trans

11. cis 12. none 13. none 14. cis 15. cis
16. none 17. cis 18. none 19. cis 20. trans
21. trans
18.
1. 2 2. 2 3. 3 4. 4 5. 4 6. 8 7. 6 8. 2 9. 2 10. 3
11. 2 12. 2 13. 0
19.
1. 1 2. 2 3. 3 4. 1 5. 4 6. 1 7. 2 8. 3 9. 0 10. 1
11. 3 12. 1 13. 1 14. 1 15. 1 16. 8 17. 4
20.
1. S 2. R 3. R 4. R 5. 2-R, 3S
6. 2-S, 3-S 7. 2-R, 3-R 8. 2-S, 3-R 9. R 10. R
11. 2-S, 3R 12. 3-S, 3-S 13. S 14. R
21.
1. Enantiomer 2. Enantiomer 3. Identical
4. Identical 5. Enantiomer 6. Identical
7. Diastereomer 8. Diastereomer 9. Diastereomers
10. Enantiomer 11. Positional isomers 12. Diastereomers
13. Diastereomers 14. A, B diastereomers
A, C diastereomers
A, D enantiomers
B, C diastereomers
22.
Cl H3C CH3
C==C
1. P.O.S. 2.
H H
Cl
Vertical + molecular P.O.S.
CH3
H Br
3. No. P.O.S. 4.
H Br
CH3

CH3
CH3
CH3
5. 6.
Molecular + vertical
s
CH3 s H
H
H H
7. 8.
CH3 CH3 s D D D D D D
D D
+ molecular P.O.S.
OH
H H
H H
9. 10. C==C==C
H H Cl H
OH
Cl
H H O
11. C==C==C 12. H H 13. O
Br Br
H H
No. P.O.S. Cl
No. P.O.S.
H H H H
14. 15.
Cl Cl
+ molecular P.O.S.

23. The molecules having centre of symmetry are

1, 3, 6, 7, 8, 12, 15
24.
Chiral Chiral Optically Optical

Compound POS COS G.I.
carbon compound active isomerism
1. ✕ ✓ ✕ ✕ ✕ ✕ ✕
2. ✕ ✕ ✕ ✓ ✓ ✓ ✕
3. ✕ ✓ ✕ ✕ ✕ ✕ ✕
4. ✕ ✓ ✕ ✕ ✕ ✕ ✓
5. ✕ ✓ ✕ ✕ ✕ ✕ ✕
6. ✕ ✕ ✕ ✓ ✓ ✓ ✕
7. ✓ ✕ ✕ ✓ ✓ ✓ ✓
8. ✓ ✕ ✕ ✓ ✓ ✓ ✓
25.
Chiral Chiral Optically Optical

Compound POS COS G.I.
carbon compound active isomerism
1. ✕ ✓ ✕ ✕ ✕ ✕ ✕
2. ✕ ✕ ✕ ✓ ✓ ✓ ✕
3. ✕ ✓ ✕ ✕ ✕ ✕ ✕
4. ✕ ✓ ✕ ✕ ✕ ✕ ✓
5. ✕ ✓ ✕ ✕ ✕ ✕ ✕
6. ✕ ✕ ✕ ✓ ✓ ✓ ✕
7. ✕ ✕ ✕ ✓ ✓ ✓ ✕
26.
Total number of Number of meso Number of optically
Compound
stereoisomers compound active isomers
1. 2 0 0
2. 4 0 4
3. 2 0 2
4. 2 0 2


28. A + B = 90
29. 3
30.
d
d d d d
d d
d d
1. 2. d 3. d
4.
d d d d
d d
d–
O
d
d
d d d d d d
5. 6. 7.
d
d Od–
d H
d– O d
d d O d N
8. 9. 10. d
d d d
OH S d d d O
d
11. d 12. 13. 14.
d d
d
OH
31.
1. I > II 2. II > I 3. I > III > II 4. I > II > III
5. I > II > III > IV 6. I > III > II > IV 7. I > II 8. I > II > III
32.
1. 6p ✓ ✓ ✓ Aromatic 2. 6p ✓ ✓ ✓ Aromatic
3. 6p ✓ ✓ ✓ Aromatic 4. ´ ´ ✓ ´ Non-Aromatic
5. ´ ´ ✓ ´ Non-Aromatic 6. ´ ´ ✓ ´ Non-Aromatic

7. ´ ✓ ✓ ✓ Anti-Aromatic 8. 6p ✓ ✓ ✓ Aromatic
9. ´ ´ ✓ ´ Not-Aromatic 10. ´ ´ ✓ ´ Non-Aromatic
33.
1. ´ ´ ✓ ´ Non-Aromatic 2. ´ ✓ ✓ ✓ Anti-Aromatic
2p
3. ✓ ✓ ✓ Aromatic 4. 2p ✓ ✓ ✓ Aromatic
6p
5. ✓ ✓ ✓ Aromatic 6. ´ ´ ✓ ´ Non-Aromatic
6p
7. ✓ ✓ ✓ Aromatic 8. ´ ✓ ✓ ✓ Anti-Aromatic
9. ´ ✓ ✓ ✓ Anti-Aromatic 10. 6p ✓ ✓ ✓ Aromatic
11. ´ ✓ ´ ✓ Non-Aromatic 12. 6p ✓ ✓ ✓ Aromatic
34.
1. benzenecarboxylic acid or benzoic acid
2. benzenecarbonyl chloride or benzoyl chloride
3. benzenecarboxamide or benzamide
4. ethyl benzene carboxylate or ethyl benzoate
5. methyl benzene carboxylate or methyl benzoate
6. benzenecarbonitrile
7. 2-cyano benzenecarboxylic acid or 2-cyanobenzoic acid
35. 1. 2-(methoxycarbonyl)benzenecarboxylic acid

2. 2-carbamoyl benzenecarboxylic acid
3. cyclopropylbenzene
4. ethyl methyl benzene-1,2-dicarboxylate
5. benzene carbaldehyde or benzaldehyde
6. 1-phenylethanone
7. 2-cyclopropyl-1-phenylethanone
36. 1. 1-phenylbutane-1,3-dione 2. 1,2-diphenylethanone

3. diphenylmethanol 4. diphenylmethanone
5. (trichloromethyl)benzene 6. 1,2-dichlorobenzene
7. 1,2,4-trichlorobenzene 8. 1-bromo-2,4-dichlorobenzene
9. 2-bromo-1,4-dichlorobenzene 10. 1-bromo-4-chlorobenzene

37. 1. 1,2-dibromo-4-nitrobenzene 2. 1-bromo-2-chloro-4-nitrobenzene

3. 2-bromo-1-chloro-4-nitrobenzene 4. 2-bromo-5-chlorophenol
5. toulene or methylbenzene 6. 2,4-dibromo aniline
7. 5-bromo-2-chloro aniline
38.
d+ d+ d+ d+
1. 2. 3.
d+ d+ d+ d+ d+
+
CH
d+ d+ d+ d+
H 2C CH CH 2 H2C CH
4. 5. d+ 6.
CH 3
d+
CH d+ d+
+1/2 +1/2
7. d+ 8. 9.
d+ d+ +1/2 +1/2
d+
CH3
d+
H2C
d+
d+ d+ d+
d+ d+
10. 11.
d+ d+ d+
CH
CH3
39.
d
NH2
d
O d d
1. d d 2. CH3–C 3.
d
O
d
d d
d NH2 d d
4. d d 5. 6.
Od
d d d
d d d

d
OCH3
d d
O
d d
C
7. 8. dO 9.
d d Od
d
d
Cl
d d
d d d O
10. 11. d 12.
d
d NH2
d
OCH3
d d d
d d
13. 14. 15.
d d d
d
Od
d
O
d d
O OH
d d
16. 17. 18.
Od Od
d
40.
1. 2-bromo-N-chloroacetamide 2. N-bromo-2-chloro ethanamide
3. N-propylbutanamide 4. acetamide
5. N-[but-2-enyl]pent-2-enamide 6. 3-cyclopropylbut-3-enamide
7. N-(2-bromopropyl)-3-chloropentanamide 8. N-butylacetamide
9. N-[penta-1,3-dienyl]but-3-ynamide
10. ethonoic cyclohexanecarboxylic anhydride
11. cyclobutylethanoic cyclohexanecarboxylic anhydride
12. hepta-3,5-dien-1-amine
13. hexa-1,4-dien-3-amine
14. 3-bromo-7-cyclobutylnon-5-en-4-amine

41.
1. 4-amino-2-methylpentanoic acid
2. 2-amino-3-chloro-2-methylbutanoic acid
3. 2-methyl-5-sulfohexanoic acid
4. 2-cyclopropyl-2,7-dimethyl-6-sulfo non-8-enoic acid
5. 7-aminooctane-2-sulfonic acid
6. 6-methylheptan-2-amine
7. 8-cyclohexyl-4-methyl-9-oxodec-2-enoic acid
8. 2,6dimethyl-7-oxo octanoyl chloride
9. 2,4-dimethyl-5-oxopentanoyl chloride
10. 2,3-dimethyl-4-oxobutanoyl chloride
11. 6-methoxy-6-methyloct-7-ene-2-sulfonic acid
12. 5-cyclopropyl-6-oxoheptane-2-sulfonic acid
13. 4-Formyl-1-methylpentylethanoate
14. 5-amino-7,7,7-trichloro-2, 6-dimethylheptanoic acid
42.
1. 2-carbamoylpentane-3- sulphonic acid
2. methyl 2-ethyl-6-methyl-7-oxoheptanoate
3. 6-cyclohexyl-3-methylheptan-2-one
4. ethyl-4-amino-4-cyclohexyl-2-methyl butanoate
5. 3-amino-2-methyl-7-sulfo octanoic acid
6. 6-ethyl 1-methyl 3-amino-2,5-dimethylhexanedioate
7. ethyl 4-cyano-3-methoxy-2-methylbutanoate
8. phenyl-5-(N-ethylamino)-2-methylhexanoate
9. 5-ethenyl-4,4-diphenylhept-5-enoic acid
10. 4-amino-6,6,6-trifluoro-4-methylhexan-3-one
11. 2,4-dimethyl-3-(1-methylethyl)pentane-3-sulfonic acid
12. N-(2-methylbut-3-ynyl)acetamide
43.
1. 4-(1-ethenylprop-1-enoxycarbonyl) pentane-1-sulfonic acid
2. 5-ethoxycarbonylhexanoic acid
3. 4-methoxycarbonylbutanoic acid
4. 3-pentoxycarbonylpropanoic acid
5. 4-cyano-2-cyclopropylbutane-1-sulfonic acid
6. 3-(N,N-dipropylamino)-2-methylhexanoic acid
7. ethyl 3-aminobutanoate
8. prop-2-ynoic acid
9. ethyl 5-(chlorocarbonyl)-6,6,6-trifluoro-4-methylhexanoate

10. ethyl 2-amino-3-chloro-4-cyclohexylhex-5-enoate

11. 3-ethynyldec-9-enoic acid
12. 4-(chlorocarbonyl)undec-1-en-10-yne-3-sulfonic acid
13. 6,6-dichloro-5-sulfo nonanoic acid
14. 7-(chlorocarbonyl)-3-methyldeca-1,9-diene-4-sulfonic acid
15. 9-carbamoyl-7-methylnona-1,8-diyne-1-sulfonic acid
16. 2,4-dimethyl-3-(1-methylethyl)pentane
17. 6-bromo-4-chloro-6-cyclopropyl-5-nitrohexanal
44.
1. 2-phenylnonanedioic acid
2. 7-sulfo-3-(trifluoromethyl)non-8-ynoic acid
3. 6-hydroxy non-8-enoic acid
4. 6-chloro-2-merceptohexane-3-sulfonic acid
5. 6-cyclohexyl-5-hydroxy-6-methoxyhexanoic acid
6. 6-amino-3-hydroxy-2-methyl-7-sulfodec-9-enoic acid
7. 6-amino-3,5-dimethyl-4-(1-methylethyl)oct-7-ynoic acid
8. 6,7-dichloro-8-nitro-3-sulfodec-9-enoic acid
9. 5-(ethoxyformyl)-2-methylhexanoic acid
10. 5,5-dimethyl-4-oxohexanoic acid
11. 4-(Phenoxycarbonyl)butanoic acid
12. 3,7-dihydroxy-6-methylheptanoic acid
13. 2-ethenyl-6-methyl-5-mercepto oct-7-enoic acid
14. 8-methyl-4-nitro-6-sulfodeca-2,9-dienoic acid
15. 2-bromo-6-chloro-3-ethynyl-4-hydroxy-7-methoxyoct-7-enoic acid
45.
1. 2,4-diamino-5-methylhexan-3-ol
2. 3-amino-7-hydroxy-2-methyloctanedioic acid
3. 3-(chlorocarbonyl)-4-cyanopentanoic acid
4. 6-carbamoyl-5-formyloct-3-enoic acid
5. 4-bromo-5-(ethoxycarbonyl)-3-ethylheptanoic acid
6. 5-(acetylamino)-4-(trichloromethyl)heptanoic acid
7. 6-carbamoyl-5-(chlorocarbonyl)nona-4,7-dienoic acid
8. 4-sulfohexanoic acid
9. 3-cyano-4-ethylhex-4-ene-2-sulfonic acid
10. 2-(1-ethoxycarbonylpropyl) non-8-enoic acid
11. 2-cyano-4-propyloct-5-enoyl chloride
12. 2-oxopropanal
13. 5,10-dioxodec-6-ene-3-sulfonic acid

14. cyclohexanecarboxylic acid

15. cyclohexanecarbaldehyde
46.
1. pentan-2-one 2. 3-methylbutan-2-one
3. but-3-en-2-one 4. 3-ethenylpent-4-en-2-one
5. 1-(cyclopenta-2,4-dien-1-yl)ethanone 6. but-3-yn-2-one
7. ethenone 8. hexa-3,5-dien-2-one
9. 5-bromo-6-cyclopropylhept-3-en-2-one 10. 5-bromohepta-3,5-dien-2-one
47.
1. 2-methylpropanoyl chloride 2. 2-methylpentanoyl chloride
3. 4-methyl-2-(methylethyl)pentanoyl chloride 4. 2,6-dimethyloct-7-enoyl chloride
5. 4,7-dichloro-2-ethylnonanoyl chloride
6. 6-cyclopropyl-2-methylheptanoyl chloride 7. 6-cyclobutyl-2-ethylnonanoyl chloride
8. 7-ethyl-2-methylnon-8-enoyl chloride
48.
1. 2-methylbutanenitrile 2. 2-methylpentanenitrile
3. 2-propylpentanenitrile 4. 2,5-dimethylhept-6-ynenitrile
5. 2-cyclobutylpropanenitrile 6. 2,7-dimethylnon-8-ynenitrile
7. 4-cyclohexyl-2-ethylbutanenitrile
49.
1. acetic acid 2. 2-methylhex-5-enoic acid
3. 2-ethyl-4-methylhept-6-enoic acid 4. 3-bromo-2-ethylpentanoic acid
5. 3-ethyl-2-methylpent-4-ynoic acid 6. 5-cyclopropyl-2-methylheptanoic acid
7. 3-(cyclopenta-2,4-dien-1-yl)-2-methylhexanoic acid
8. 4-methyl-2-(methylethyl)pentanoic acid
9. 5-bromo-2-(1-bromoethyl)-3-cyclopropylhexanoic acid
10. 2,4-dimethylhex-5-ynoic acid 11. 2,3,6-trimethylheptanoic acid
12. 8-butyl-2-methyl dec-9-enoic acid 13. 2-ethylheptanoic acid
14. 3-cyclohexyl-2-methylhexanoic acid 15. 4-cyclobutyl-2-methylbutanoic acid
50.
1. methyl acetate or methyl ethanoate 2. methyl 2-methylpentanoate
3. methyl 3-bromo-2-ethylpentanoate 4. methyl 2-cyclohexylbutanoate
5. methyl 3,6-dichloro-2-methyloctanoate 6. methyl 2,6-dimethyloct-7-enoate
7. ethyl 5-bromo-2-ethylhexanoate 8. ethyl 6-cyclobutyl-2-methyloctanoate
9. ethyl 5,6-dibromo-2-methylheptanoate 10. ethyl 2-methylpropanoate

11. ethyl 2-methyloct-7-enoate

12. ethyl 3-(cyclopenta-2,4-dienyl)-2-methylhexanoate
13. phenyl ethanoate 14. phenyl 2-methylhexanoate
15. phenyl 2-bromo-2-methylpropanoate
16. phenyl 6-bromo-5-chloro-2-ethylheptanoate
51.
1. N-(1-methyl ethyl) ethanamide 2. hexanamide
3. 4-bromo-5-chlorohexanamide 4. 4-bromo-5-chlorohexanamide
5. but-3-enamide 6. 2-methylbut-3-ynamide
7. 3-cyclobutyl-5-methylhept-6-enamide 8. 2-ethylbut-3-ynamide
9. butanamide 10. chloromethyl 2-bromobutanoate
11. bromomethyl 2-chlorobutanoate 12. but-2-enyl propanoate
13. butyl prop-2-enoate 14. diethyl ethanedioate
15. ethyl methyl ethanedioate
16. 1-cyclopropylethyl 3-cyclopropylpropanoate 17. ethanamine
18. ethanoic anhydride 19. ethyl ethanoate
20. methyl propanoate 21. hexan-3-amine
22. 5-bromooctan-2-amine
52.
S. No. 1°C 2°C 3°C 4°C 1°H 2°H 3°H
1. 5 5 3 0 15 10 3
2. 2 1 0 0 4 1 0
3. 2 5 0 1 6 9 0
4. 3 3 1 0 6 5 1
5. 1 3 1 0 3 3 1
6. 2 8 2 0 6 14 2
7. 3 6 1 0 9 12 1
8. 3 4 1 0 7 4 1
9. 5 1 3 0 15 2 3
10. 0 4 0 0 0 4 0
11. 1 8 1 0 3 16 1

53.
1. 1° amine, alcohol 2. 3° amine, carboxylic acid
3. alcohol, ketone, carboxylic acid 4. Ketone, Aldehyde
5. Thio alcohol, 2°amine, 3° amine 6. Alkene, Acid halide
7. ester, carboxylic acid 8. Ketone, alkene
9. Ether 10. Anhydride
11. 1° amine, ketone, amide 12. cyanide, isocyanide, ether
13. Ester 14. Carboxylic Acid
15. Thio ether, alkene
54.
Functional Groups DBE
1. Alkene, ketone, Aldehyde 4
2. Alkene, 1° amine 2
3. Alkene, Carboxylic acid 3
4. Alkene, cyanide, aldehyde 6
5. Alkene, isocyanide 6
6. Thioalcohol, ester 3
7. Aldehyde, Acid halide 3
8. Alkene, Alkyne, Sulphonic acid 5
9. Ketone, alcohol, Thio alcohol 3
10. Anhydride 4
11. Alkene, alcohol (enol) 1
12. Ketone, Thio ketone 2
55.
Name of functional Groups DBE Value
1. Alcohol, ether, Thio ester 2
2. Alkene 4
3. Amide 3
4. Ether, anhydride 5
5. Alkene, Alcohol, Ketone 4
6. Ether, Carboxylic acid, alkene 10
56.
1. prop-1-ene 2. 3-methylhex-1-ene
3. 2-methylbut-1-ene 4. 5-methylhept-2-ene
5. 2-cyclopropyl propene 6. chloroethene
7. 4-chloropent-1-ene 8. 3-bromoprop-1-ene
9. 3-ethyl-6-methylhept-2-ene 10. 4-bromo-2-methylpent-1-ene

57.
1. hexa-1,4-diene 2. hexa-1,5-diene
3. 2-methylpenta-1,4-diene 4. but-1-en-3-yne
5. pent-3-en-1-yne 6. oct-5-en-1-yne
7. 3-ethylhex-1-en-5-yne 8. 7-chlorodec-1-en-4-yne
9. 5-chlorocyclopenta-1,3-diene 10. cyclopenta-1,3-diene
11. 5-(methyl ethyl)cyclopenta-1,3-diene
58.
1. 1,2-dimethylcyclobutene 2. 1,3-dimethylcyclobutene
3. 1,4-dimethylcyclobutene 4. 1,6-dibromocyclohexene
5. 1,6-dibromo-3-chlorocyclohexene 6. 1,3-dichlorocyclohexene
7. cyclohexa-1,4-diene 8. 1-ethyl-2-(prop-2-enyl)cyclohexene
9. 1-ethenyl-3-(prop-2-enyl)cyclohexene 10. 3-methylcyclopropene
59.
1. hexan-3-ol 2. 4-methylhexan-2-ol
3. 4-ethylhexan-3-ol 4. 4-methylhexan-3-ol
5. prop-2-en-1-ol 6. hexa-1,4-dien-3-ol
7. 6-bromohex-2-en-2-ol 8. hexa-1,5-dien-1-ol
9. 6-cyclopropylhept-4-en-3-ol
10. 3-(1-bromoethyl)-4-methylpent-4-en-2-ol
60.
1. cyclopropane-1,2-diol 2. 2-(2-bromopropyl)cyclopentanol
3. cyclohex-2-ene-1,1-diol 4. 3-ethyl-2-propylcyclohexanol
5. cyclopent-2-en-1-ol 6. cyclopenta-2,4-dien-1-ol
7. cyclopenta-1,3-dien-1-ol 8. 1-cyclopropylcyclopenta-2,4-dien-1-ol
9. 6-bromo-4-chlorocyclohex-2-en-1-ol
61.
1. 4-ethyl-2-methylhex-5-enal 2. 3-bromo-2,5-dimethyloctanal
3. 2,6-dimethyloct-7-enal 4. 4-methyl-2-(2-methylpropyl)hexanal
5. 4-bromo-2,2,6-trimethylheptanal 6. 4-ethyl-2,3-dimethylhex-5-ynal
7. 2,4-dimethylhex-5-enal
8. 2-(1-bromopropyl)-4-chloro-3-cyclopropylhexanal
62.
1. 2-methylpropanal 2. ethanedial
3. 2-ethynylpenta-2,4-dienal 4. but-2-enal
5. methylpropanedial 6. 2-propylpentanal
7. 4-bromo-2-ethylpentanal 8. 4-bromo-5-chloro-2-ethylheptanal
9. 2-ethylbutanal

2
Hydrocarbons
(Aliphatic and Aromatic Hydrocarbons)
[A] Aliphatic Hydrocarbons
Alkanes
Br Na
1. ¾¾2®( A) ¾ ¾¾
¾®( B ). Product B is:
hv Dry ether
(a) (b) (c) (d)
O
s r electrolysis
2. C—O K ¾¾¾¾® (A) ; Major-product ( A) is :
(Major)
(a) (b)

Hydrocarbon (Aliphatic and Aromatic Hydrocarbons) 205
O
C—O
(c) (d)
3. CH 3 MgBr + D 2 O ¾®
¾ (A); Product (A) of the reaction is:
(a) CH 4 (b) CH 3 D (c) CH 2 D 2 (d) CHD 3
4. Which of the following alkane will be formed in high yield by Wurtz reaction ?
(a) (b) (c) (d)
Br
Br 2Na
5. ¾¾¾®
dry ether
(A) ; Product A is:
Br
Br
Br Br
(a) (b) (c) (d)

Br Br
6. Which of the following has the lowest boiling point?
CH 3
|
(a) CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 (b) CH 3 CH 2 CH 2 CHCH 3 (c) CH 3 CHCHCH 3
| |
CH 3 CH 3
(d) CH 3 CH 2 CHCH 2 CH 3 (e) CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

|
CH 3
7. Which of the following has highest solubility in CH 3 CH 2 CH 2 CH 3 ?

(a) CH 3 OH (b) CH 3 O - Na +
(c) CH 3 NH 2 (d) CH 3 OCH 3 (e) (CH 3 ) 3 CH
8. Which of the following is most soluble in H 2 O?
(a) CH 3 OCH 3 (b) CH 3 CH 2 OH
(c) CH 3 CH 2 Cl (d) CH 3 CH 2 CH 3 (e) CH 3 CHO
9. During the free radical chlorination of methane, which of the following reactions has lowest
collision frequency?
(a) Cl•+•CH 3 ¾®
¾ CH 3 Cl (b) Cl•+Cl 2 ¾®
¾ Cl 2 + Cl•
(c) •CH 3 + CH 4 ¾®
¾ CH 4 + •CH 3 (d) •CH 3 + Cl 2 ¾®
¾ CH 3 Cl + Cl•

hn
10. In the reaction Br 2 + CH 3 Br ¾¾® CH 2 Br 2 + HBr which of the following mechanism steps is
productive, but relatively unlikely to occur?
(a) Br•+CH 3 Br ¾®
¾ HBr+•CH 2 Br (b) Br•+•CH 2 Br ¾®
¾ CH 2 Br 2
(c) Br• + Br 2 ¾®
¾ Br 2 + Br• (d) Br• + • CH 3 ¾®
¾ CH 3 Br
11 Which of the following reactions is a termination step in the free radical chlorination of
methane?
(a) Cl 2 + Cl• ¾®
¾ Cl• + Cl 2 (b) Cl 2 ¾®
¾ 2Cl•
(c) •CH 3 + Cl• ¾®
¾ CH 3 Cl (d) CH 4 + Cl• ¾®
¾ HCl + •CH 3
12. Which of the following is a chain propagation step in the free radical chlorination of methane?
(a) CH 4 + Cl• ¾®
¾ •CH 3 + HCl (b) Cl 2 ¾®
¾ 2Cl•
(c) Cl• + •CH 3 ¾®
¾ CH 3 Cl (d) •CH 3 + CH 4 ¾®
¾ CH 4 + •CH 3
Br
Mg
13. 2 ¾¾® (A); Product ( A) is:
ether
OH
(a) (b) (c) (d)
14. What is the major product of the following reaction?

Cl2
+ ?
hv
Cl Cl
Cl Cl
(I) CH2CH2CH2CH2CH2CH2 (II) (III)
Cl
Cl
Cl
(IV) (V)
Cl
Cl
15. Compare the heats of combustion of the following compounds:
(i) (ii) (iii)
(a) i>ii>iii (b) ii>i>iii (c) iii>i>ii (d) ii>iii>i

16. Compare heats of combustion of the following compounds:

CH3 CH3 CH3
CH3
(i) (ii) (iii)
CH3 CH3
CH3
(a) i>ii>iii (b) ii>i>iii (c) iii>i>ii (d) iii>ii>i
Cl
17. Na ( x) Dimeric product ( x) is :

¾¾¾®
dry ether
(a) 1 (b) 2 (c) 3 (d) 4

Na
18. Cl ¾¾¾® (x) . Products x is :
dry ether
(a) 1 (b) 2 (c) 3 (d) 4

CO2H
2NaOH electrolysis
19. ¾¾¾¾® (A) ¾¾¾¾® (B); Product ( B ) is:
CO2H
O
(a) HC ºº CH (b) H 2 C == CH (c) O (d)

O
CO2H
2KOH electrolysis
20. ¾¾¾¾® (A) ¾¾¾¾® (B) + (C) ; Products ( B ) and (C ) are:
CO2H
(a) geometrical isomers (b) enantiomer
(c) positional isomer (d) structural isomer
21. How many products will formed in the given reaction ?
Cl
Na
¾¾¾®
dry ether
(a) 1 (b) 2 (c) 3 (d) 4

22. How many products will formed in the following reaction ?
Na
CH 3 — Cl + CH 3 — CH 2 — Cl ¾ ¾¾®
dry ether
(a) 1 (b) 2 (c) 3 (d) 4

23. Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per
methylene?
(a) cyclopropane < cyclobutane < cyclohexane < cycloheptane

(b) cyclohexane < cyclopentane < cyclobutane < cyclopropane

(c) cyclopentane < cyclobutane < cyclopentane < cyclopropane
(d) cyclopentane < cyclopropane < cyclobutane < cyclohexane
(e) cyclopropane < cyclopentane < cyclobutane < cyclohexane
24. Cl—C—Cl bond angle in 1,1,2,2-tetrachloro ethene and tetrachloromethane is:
(a) 120° and 109.5° (b) 90° and 109.5° (c) 109.5° and 90° (d) 109.5° and 120°
Cl
25. ¾¾2®( X ) mono chloro product: (including stereoisomer)
hv
(a) 2 (b) 3 (c) 4 (d) 5
26. How many products are formed from the monochlorination of ethylcyclohexane? Ignore
stereoisomers ?
CH2CH3
(a) 6 (b) 8 (c) 5 (d) 9 (e) 11

27. How many distinct dichlorination products can result when isobutane is subjected to free
radical chlorination?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 6
28. How many distinct monochlorinated products, including stereoisomers, can result when the
alkane below is heated in the presence of Cl 2 ?
(a) 2 (b) 4 (c) 5 (d) 6 (e) 8

29. A sample of (R)-2-chlorobutane,
H
CH3 Cl
CH2CH3
reacts with Br 2 in the presence of light, and all the products having the formula C 4 H 8 BrCl were
isolated. Two possible isomers are shown below:
CH3 CH3
Br Cl and Cl Br
CH2CH3 CH2CH3
I II
of these:
(a) only I was formed
(b) both I and II were formed in equal amounts

(c) both I and II were formed in unequal amounts

(d) only II was formed
(e) neither I nor II was formed
30. How many dichlorinated products, including stereoisomers, can be isolated when ( S)-2-
chlorobutane reacts with Cl 2 hv ?
CH2CH3
Cl H
CH3
(S)-2-chlorobutane
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
Alkenes
1. In which of the following alkenes will a hydrogen shift occur upon addition of HCl?
(a) (b) (c) (d)
2. Predict the major product of the reaction of 1,4-pentadiene with excess HCl.
(a) 1,4-dichloropentane (b) 1,5-dichloropentane
(c) 2,4-dichloropentane (d) 4-chloro-1-pentene
3. Indicate the product resulting from the hydrogenation (excess H 2 /Pd) of 2-hexyne.
(a) ( Z )-2-hexene (b) (E)-2-hexene (c) hexane (d) 1-hexene
4. Consider the following carbocations and their resonance hybrids. Which is the MOST stable
carbocation?
+
(a) (b)
+
+ +
(c) (d)
5. Which of the following is the MOST stable carbocation?

r r
(a) (b) (c) (d) r
r
6. In the addition of HBr to 1,3-butadiene, one product is called the kinetic product and the other
is called the thermodynamic product. Which of the following descriptors applies to the kinetic
product?
(a) 1,2 product (b) 1,4 product
(c) most stable (d) least stable
(e) formed slowest (f) formed fastest
(g) formed at low temperature (h) formed at high temperature

(i) most substituted alkene (j) least substituted alkene

(k) bromide attack at more substituted site (l) bromide attack at least substituted site
(a) a, c, e, g, j, l (b) b, c, f, g, i, l
(c) a, d, f, g, j, k (d) b, d, f, h, i, k
7. Which of the following statements regarding 1,2- or 1,4-conjugate addition of HBr to
1,3-butadiene is false?
(a) The kinetic product, 3-bromo-1-butene, arises from the more stable carbocation
intermediate.
(b) The thermodynamic product, 1-bromo-2-butene, is the more stable product.
(c) The kinetic product is favored by carrying out the reaction at high temperature.
(d) Formation of the two products arises from a common resonance stabilized carbocation
intermediate.
8. What is the product of the following reaction?
O
HO 31. O
¾¾¾¾¾®
2. (Me) S
?
2
O O O
+ O +
(a) O
O
O + O
(b) HO
O
O O O O
+ +
(c) HO
OH OH OH OH
O
O O
(d) HO O + O +
9. The molecular formula of compound A is C 15 H 24 . Ozonolysis gives the following compound

and formaldehyde. Which could be compound A?
O O
O and HCHO
(a) (b) (c) (d)

10. What is the product of the following synthesis?
1. O3
H 2. Zn, HCl
¾¾¾¾®
3. KOH
?
H H
O
O
H
H
(a) H H (b)
O O H H
O
O
O
H
H
H H
(c) (d) O
O H H
11. Decreasing order of heat of hydrogenation ?

||
(I) (II) (III)

|
(a) I > III > II (b) II > I > III (c) III > I > II (d) II > III > I
12. Which of the following is the most stable diene?
(I) (II) (III) (IV) (V)
O OH
KMnO 4
13. Alkene ( X ) ¾ ¾¾
¾® + ; X is:
D O

(a) (b)
(c) (d)
CH3 H Br
14. C == C ¾¾2®( X ) products. Value of X is:
CCl 4
H CH3
(a) 0 (b) 1 (c) 2 (d) 3

O
O
15. ¾¾3® ( A); Product ( A) is:
Zn
CHO CO2H CO2H

(a) (CH2)4 (b) (CH2)4 (c) (CH2)4 (d) All of these
CHO CHO CO2H
CH3
H2O
+ ?
H+
OH
CH2OH CH3 CH3
(I) (II) (III) OH
CH3
CH3
(IV) (V)
OH HO

17. Which of the following alkenes yield(s) 3-bromo-3-methylpentane as the major product upon
addition of HBr?
I II III IV
(a) I and II only (b) III only (c) I, II, and III only
(d) all of them (e) none of them

18. Which of the following alkenes reacts with HCl at the slowest rate?
(a) CH 3 CHCH == CH 2 (b) CH 3 CH 2 C == CH 2 (c) CH 3 C == CH 2
| | |
CH 3 CH 3 CH 3
H CH3 CH3CH2 CH3
(d) C == C (e) C == C
CH3 CH3 CH3 CH3
19. What is/are the product(s) from the following reaction?

CH3 CH3 Cl CH3
+ HCl ? Cl
(I) (II)
(a) I only (b) II only (c) I is minor, II is major
(d) I is major, II is minor (e) equal amounts of I and II
NBS
+ heat
?
Br
NBS NBS Br Br
(I) (II) NBS (III) (IV) Br (V)

CH3
HBr
?
Br
CH3 CH2Br
(I) (II)
CH3 CH3
CH3
(III) (IV) Br (V)
Br Br
CH3
HBr
?
Peroxide
Br
CH3 CH2Br
(I) (II)

CH3 CH3
CH3
(III) (IV) (V)
Br Br Br

23. Which of the following is a step in the mechanism of the reaction shown?
Peroxide
CH 2 == CHCH 3 + HBr ¾ ¾¾¾® CH 2 CH 2 CH 3
|
Br
• ·
(a) CH 2 CHCH 3 + HBr (b) CH 2 CH 2 CH 3 + HBr
|
Br
Å
r ·
(c) CH 2 CHCH 3 + HBr (d) CH 2 CH 2 CH 3 + HBr (e) CH 2 CHCH 3 + H ·
| |
Br Br
24. What is the major organic product of the following reaction ?

CH == CH2
H2
¾¾®
Pt
?
CH == CH2 CH2CH3
(i) (ii)
CH2CH3 CH == CH2 CH == CH2

(iii) (iv) (v)

25. What are the major organic products when the following molecule is treated with ozone, and
then with Zn H 2 O ?
CH2
O
O || O
(i) ,H — C — H (ii) , CO 2 ,H 2 O
O O
COOH O || O ||
(iii) , CH 2 O (iv) , H — C — OH (v) , HO — C — OH

3H + /CH OH
26. ¾ ¾¾¾ ¾®( A); Product (A) is :
H H OH H
(a) (b) (c) (d)
OH H OH OCH3
Dr
27. ¾¾®( A) ; Product (A) is:
D 2O
D OD OD H
(a) (b) (c) (d)
D D OD OD
28. Which of the following product is not formed in the following reaction ?
+ HBr ¾®
¾
Br
Br Br
Br
(a) (b) (c) (d)
29. Product ( B ) of the reaction is:
H—Br KSH
¾¾¾®
Peroxide
(A) ¾¾¾® (B)
O
SH
SH
SH
(a) (b) (c) (d)
30. What is/are the product(s) from the following reaction?
+ Br2/CCl4 ?
Br
(I) (II) (III) (IV)

Br Br Br Br Br Br
Br
(a) I and II (b) I and III (c) I and IV (d) II and III (e) II and IV

31. Most acidic hydrogen is present in:
(a) (b) (c) (d)
D rs
(1) NaH
32. ¾ ¾¾ ¾® P , Product formed in this reaction is:
D ( 2) - H 2O
D D
(a) D (b) (c) (d) All of these
MgBr
D O
33. 2
¾¾® (A); Product ( A) is:
D
D
(a) (b) (c) D (d)
D
34. Which of the following reactant is more reactive towards electrophilic addition reaction with
HBr.
Ph Ph
(a) (b) (c) Ph (d)
OCH3 Ph OCH3
H+
35. ¾¾® Product ; Product of the reaction is:
D
(a) (b) (c) (d)
3CH COCl PCl 2 NaNH

36. (A) ¾ ¾¾ ¾5® (C) ¾ ¾¾¾2® (D), If (A) is C 6 H 6 ,then:
¾® (B) ¾ ¾
AlCl 3
(a) D is a terminal alkyne (b) (A) is an aromatic compound

(c) D has 8 carbon (d) All the statements are true.

37. How many different products are obtained upon the ozonolysis of the following C 20 -tetraene?
(a) 2 (b) 3 (c) 4 (d) 5

38. Major product obtained in the following reaction r1 , r 2 and r 3 in respectively is:
HBr
r1
H2O
CH3
HBr r2
CH3OH
HBr
r3
D2O
OH OD OCH3 OH OCH3 OD
CH3 CH3 CH3 CH3 CH3 CH3
(a) , , (b) , ,
Br OH
CH3 CH3
(c) in all reaction (d) in all reaction
39. Which of the following is/are the major product(s) of the following reaction?
CH3
CH == C HBr
?
CH3
CH3 CH3
CH—CH CH2—C CH == C
Br Br
Br
(I) (II) (III)
(a) I (b) I and III (c) II (d) II and III (e) III
40. Which of the following is/are the major product(s) of the following reaction?
HI
+ ?

I I
I
(I) (II) (III)
(a) I (b) I and II (c) I and III (d) II (e) III
41. What compound results from the 1,4-addition of one equivalent of HBr to 1,3-butadiene?
(a) 1-bromo-1-butene (b) 2-bromo-2-butene
(c) 4-bromo-1-butene (d) 3-bromo-1-butene (e) 1-bromo-2-butene
42. Which energy diagram best describes the electrophilic addition of hydrogen halides to
alkenes?
(a) (b)
(c) (d)

H /Pd
2
¾¾¾¾¾¾®
EtOH, 25°C, 1atm.
?
(a) (b) (c) (d)
44. Which alkene will give only optically active product upon catalytic hydrogenation (H 2 /Pd)?
(a) (b) (c) (d)

45. What are the products formed in the following reaction?
4 eq. H , Pd
2
¾¾¾¾¾® ?
(a)
+
(b)
+
(c)
+
(d)
+
46. Which of the following product(s) is(are) formed when 1,2,4-trimethylcyclopentene is

hydrogenated?
I II III IV
(a) I (b) I and III (c) II (d) I and IV

47. The major product of the following reaction is:

OH
(i) H PO ,150°C
3 4
¾ ¾¾¾¾¾¾®
(ii) C 6 H 5COOOH
O OH
CHO
(a) O (b) (c) (d)
CHO
48. What is the major product of the following E 2 reaction?
heat
CH 3 CHCH 2 CH 3 + HO - ¾ ¾
¾® Product(s)
|
Br
H
H
(a) CH3CH2C == C (b) CH 3 — CH 2 — CH 2 — CH 3
H
CH3 H CH3 CH3
(c) C == C (d) C == C (e) CH 3 C == CH 2
H CH3 H H |
CH 3
49. Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a
strong base to give 2-pentene as the only alkene product?
(a) 1-chloropentane (b) 2-chloropentane
(c) 3-chloropentane (d) 1-chloro-2-methylbutane (e) 1-chloro-3-methylbutane
50. Give the major product of the following reaction :
rs
3CH S Cl
¾ ¾¾ ¾®
Cl Cl
(a) (b)
CH3S H CH3S H
(c) (d)
CH3S Cl SCH3
Cl H H

51. Which of the following species is an intermediate in the reaction shown below ?
Br
Br /H O
2 2
¾¾¾®
OH
(a) (b) (c) (d)
Br+ O +O Br–
H
CH3
Br2
+ ?
H2O
CH3 CH3 CH3 CH3 CH3

(I) Br (II) OH (III) (IV) (V) Br
Br OH
OH Br Br
53. Which reaction intermediate is formed when Br 2 CCl 4 reacts with cyclohexene?
Br Å Br Br
(I) (II) (III) (IV) Å (IV)
Br
Å Br Br
–
1. KMnO4, OH. Cold
¾¾¾¾¾¾¾® ?
2. H2O
O
OH OH H CH
(i) (ii) (iii) (iv) CH
OH OH
O
(a) i (b) ii (c) iii (d) iv (e) all of these

H
Br
55. ¾¾2®
H CCl 4
Product of above reaction is:

(a) meso (b) racemic (c) diastereomer (d) structural isomer

Br
56. ¾¾2®
H 2O
Product of above reaction is:

(a) meso (b) racemic (c) diastereomer (d) structural isomer
57. What is the kinetic product for the following reaction?
CH3
+ HCl ?
Cl Cl
CH3 CH3 CH3 Cl
CH3
(I) (II) (III) (IV) (V) CH3
Cl
Cl
Cl
58. How many Grignard reacts with alcohol to give n-butane?
(Excluding stereoisomer)
(a) 1 (b) 2 (c) 3 (d) 4
59. Addition of Br 2 on cis-2 butene gives:
(a) A racemic mixture of 2,3-dibromobutene (b) Meso form of 2,3-dibromobutane
(c) Dextro form of 2,3-dibromobutane (d) Laevo form of 2,3-dibromobutane
60. Classify the reaction below as an oxidation, a reduction, or neither.
cis-2-pentene ® pentane
(a) oxidation (b) reduction (c) redox reaction
Br
61. A ¾¾2® Meso 2,3-dibromobutane, identify reactant ( A) :
CCl 4
(a) (b) (c) (d)
ColdKMnO
62. 4
¾¾¾¾¾® (A)
2 4 Br /CCl
¾¾¾¾¾® (B)
Relation between ( A) and ( B ) :

(a) Diastereomers (b) Enantiomers
(c) Structural isomer (d)Different compound

Alkynes
1. Which of the following will produce 4-methyl-1-pentyne?
(a) ethyne + 1) NaNH 2 2) 1-iodobutane
(b) propyne + 1) NaNH 2 2) 1-iodopropane
(c) ethyne + 1) NaNH 2 2) 1-iodo-2-methylpropane
(d) propyne + 1) NaNH 2 2) 2-iodopropane
2. Predict the product of the following reaction sequence.
ethyne + 1) excess NaNH 2 2) excess I— CH 2 — (CH 2 ) 2 — CH 3 ®
(a) 6-iodo-1-hexyne (b) 1-hexyne
(c) 5-decyne (d) 1-iodo-1-hexene
3. Which of the following anions is the strongest base?
– – – –
:OCH3 :OH : H :NH2
i ii iii iv
(a) i (b) ii (c) iii (d) iv
3 eq. Cl
2
¾¾¾¾®
CCl
?
4
Cl Cl Cl
Cl Cl
(a) (b) Cl
Cl Cl Cl Cl
Cl Cl
(c) (d) Cl
Cl Cl Cl
5. Predict the product of the reaction of 1-pentyne and excess HCl in the presence of hydrogen
peroxide.
(a) 1,1-dichloropentane (b) 1,2-dichloropentane
(c) 2,2-dichloropentane (d) 2-chloro-1-pentene
6. Identify the product of the following reaction.
Excess HBr
¾¾¾¾¾®
Br
Br
(a) (b)
Br Br Br
Br
(c) (d)

1. O3
¾¾¾¾®
2. Zn, HOAc
?
OH
O
O + O
(a) O + O (b)
O OH
OH O
COOH
(c) + O (d)
O
8. How many compounds are formed upon the ozonolysis of the following triyne?
(a) 2 (b) 3 (c) 4 (d) 5

1.KMnO 4,NaOH
H2O,Heat
¾¾¾¾¾¾¾®
+
?
2.H 3O ,H 2O
O
O O O
(a) 3 + (b) + H OH
H OH H H OH
O O
+ O == C == O O +
(c) (d) H H
OH
2 (1) H /Pd/CaCO
10. CH 3 — C ºº C — CH 3 ¾ ¾¾¾¾¾¾3® X :
(2) Br2
(a) (d)-2,3-Dibromobutane (b) (l)-2,3-Dibromobutane

(c) (dl)-2,3-Dibromobutane (d) meso-2, 3-Dibromobutane
Hg 2+
CH ¾H¾¾®
SO 2 4
O H
(a) (b) OH
H
H
H
(c) (d)
H
O HO

12. The reagent needed to convert 2-butyne to cis-2-butene is:

(a) H 2 Pt (b) H 2 Lindlar’s catalyst
(c) Li NH 3 (d) Na NH 3 (e) H + zinc dust
13. The reagent needed to convert 2-butyne to trans-2-butene is:
(a) H 2 Pt (b) H 2 Lindlar’s catalyst
(c) Li NH 3 (d) Na NH 3 (e) (c) or (d)
14. What organic compound is produced when 3-hexyne undergoes ozonolysis followed by
hydrolysis ?
(a) 3,4-hexanedione (b) cis-3,4-hexanediol
(c) trans-3,4-hexanediol (d) propanal (e) propanoic acid
15. What compound results when 1-heptyne undergoes ozonolysis ?
(a) heptanal (b) 2-heptanone
(c) heptanoic acid (d) hexanoic acid (e) 1-heptanol
16. The major product of the following reaction is:
(i) NaNH (ii)CH CH Br
2 3 2
CH 3 — CH 2 — C ºº CH ¾ ¾¾¾¾¾¾¾¾®
(a) H 3 C — CH 2 — C ºº C — CH 2 — CH 3 (b) H 3 C — CH — C ºº CH
|
CH 2 CH 3
(c) H 3 C — CH 2 — CH — CH 3 (d) H 3 C — CH 2 — C ºº C — NH 2
|
NH 2
20% D SO in D O / Hg ++
2 4 2
17. Ph — C ºº C — Me ¾ ¾¾¾¾¾¾¾¾ ® ( P ) Principle organic product is:
O O
|| ||
(a) Ph — C — CD 2 — Me (b) Ph — CD 2 — C — Me
O O H
|| || |
(c) Ph — C — CH 2 — CHD 2 (d) Ph — C — C — CH 2 D
|
D
18. How many compounds are formed upon ozonolysis of the following triyne?
(a) 2 (b) 3 (c) 4 (d) 5

19. When iodoform is heated with silver powder, it forms:
(a) acetylene (b) ethylene (c) methane (d) ethane

[B] Aromatic Hydrocarbons
Preparation & Properties

1. Identify the site where electrophilic aromatic substitution takes place ?
H—N O
a d
b c
(a) a (b) b (c) c (d) d
O
a d
b c
(a) a (b) b (c) c (d) d
c O
b O
a
H—N
O
(a) a , b (b) b, c (c) a , c (d) b
O
c a
O O
O
d b
(a) a (b) b (c) c (d) d
5.
O
O O O
(a) (b) (c) O
Compare rate of EAS:
(a) a > b > c (b) b > c > a (c) a > c > b (d) b > a > c
H
O N
6.
O H—N
(a) (b) (c)
Compare rate of EAS

(a) a > b > c (b) a > c > b (c) b > a > c (d) c > a > b
CH3 CH 3
H O
2
7. ¾¾¾®
1
SN
Cl
Total number of plane of symmetry present in carbocation formed (of given compound) in rate
determining step will be:
(a) 1 (b) 2 (c) 3 (d) 4
possible to answer the following question. Consider the following six molecular orbitals of
benzene. How many of these orbitals will contain electrons?
benzene =
I II III
IV V VI
(a) 1 (b) 3 (c) 4 (d) 6
9. How would you synthesize the following compound?
?
¾¾®
(a) 1. MeCOCl, AlCl 3 (b) 1. CH 3 COOH , AlCl 3 2. H 2 , Pd

2. Zn (Hg) HCl 3. H 2 SO 4 ,H 2 O , heat
(c) 1. CH 3 CH 2 Br , FeBr 3 (d) 1. CH 3 CHO , Mg in ether
2. Br 2 , light 2. NaBH 4 , MeOH
3. tBuONa , tBuOH , heat 3. EtONa, EtOH

10. Which of the following represents the best reagent(s) for the electrophilic nitration of
benzene?
? NO2
¾¾¾®
(a) NO 2 (b) HNO 2 (c) HNO 3 (d) H 2 SO 4 , HNO 3

11. Predict the major product of the following reaction.
NO2
FeBr
3
¾¾¾®
Br 2
(a) o-bromonitrobenzene and p-bromonitrobenzene

(b) m-bromonitrobenzene
(c) o-bromoaniline and p-bromoaniline
(d) m-bromoaniline
12. Predict the major product of the following reaction.
OH
HNO 3
¾¾¾®
H SO
2 4
NO2
(a) 2,4-dinitrophenol (b) 3,4-dinitrophenol

(c) 2,4,6-trinitrophenol (d) 3,4,5-trinitrophenol
13. Cumene ( )is prepared by:
Cl
AlCl
3 AlCl
3
(a) + ¾¾® (b) + Cl ¾¾®
H+
(c) + ¾¾® (d) All of these
Br
Mg D—O—D
14. ¾¾® ¾¾¾¾® (B) ; Product ( B ) is:
ether (A)
OD D D
(a) (b) (c) (d) none of these
D

Br
Na
15. ¾¾¾® (A); product ( A) is:
dry ether
Br
(a) (b) (c) (d)
Br
Br 4Na
16. ¾¾¾®
dry ether (A). Product ( A) of the reaction:
Br
Br
(a) (b) (c) (d)
Br
Mg 2 DO
17. ¾¾®( A) ¾ ¾
¾ ®( B ) ; Product (B) is:
ether
(a) Ph — D (b) Ph — O — D (c) Ph — H (d) Ph — OH
1
O
2
Br
18. ¾¾2® Substitution takes place at the position:
3 Fe
4
(a) 1 (b) 2 (c) 3 (d) both (a) and (c)

19. Which of the following compounds is more reactive than benzene toward ring bromination ?
O O
OH NHCCH3 C—CH3 CH3
(a) (b) (c) (d)
20. Compare rate of EAS

sr
O Na OH NH2
(a) (b) (c) (d)

(a) a > b > c > d (b) a > c > b > d (c) c > a > b > d (d) c > b > a > d

21. Which of the compound will not undergo Friedel Craft reaction ?
O
OCH3 NH2 NH—C—CH3
(a) (b) (c) (d)
CH3 CH3
E r Er
22. ¾¾® ortho-complex ( r1 ) ; ¾¾® meta-complex ( r2 ).
Rate of reaction is:

(a) r1 > r2 (b) r2 > r1 (c) r2 = r1 (d) r2 >> r1
NO2
E r
23. ¾¾® Ortho-complex (r1)
r
¾
E
¾¾¾¾® Meta-complex (r2)
Rate of reaction is:
(a) r1 > r2 (b) r2 > r1 (c) r2 = r1 (d) r1 >> r2
24. Which of the following is the electrophile that attacks the aromatic ring during Friedel-Crafts
acylation ?
O
|| r
(a) R — C — Cl (b) R — C == O
O O
|| r || ds dr
(c) R — C — AlCl 3 (d) R — C — Cl — Cl (e) AlCl 3
25. Which of the following substituents acts as a moderate activator and o p director in
electrophilic aromatic substitution reactions ?
(a) —Br (b) —SO 3 H (c) —CO 2 H (d) —NHCOR (e) —CHO
26. In electrophilic aromatic substitution reactions a chlorine substituent :
(a) is a deactivator and a m-director
(b) is a deactivator and an o, p-director
(c) is an activator and a m-director
(d) is an activator and an o, p-director
(e) none of the above
27. Which of the following structures is the most important contributor to the resonance hybrid
formed when toluene undergoes para-nitration ?

CH3 CH3
r
(i) (ii) r
H NO2 H NO2
CH3 CH3 CH3

r
(iii) (iv) r (v) r
H NO2 H NO2 H NO2

28. Which of the following structure is the most important contributor to the resonance hybrid
formed when anisole undergoes o-bromination ?
OCH3 OCH3
r Br Br
(i) H (ii) H
r
OCH3 r
OCH3 OCH3
Br Br Br
r
(iii) H (iv) H (v) H
r

29. What is/are the product(s) from the following reaction ?
NO2
3 CH Cl
+ ¾¾®
AlCl
?
3
NO2 NO2
NO2
CH3
(i) (ii)
CH3
CH3
Cl NO2 NO2
CH3
(iii) + CH 3 NO 2 (iv)
CH3
(a) i (b) ii (c) iii (d) iv (e) no reaction

30. Which of the following is benzenoid aromatic compound?
31. Which of the following is most stable alkene?
(a) (b)
(c) (d)
32. Which of the following is least stable alkene ?
(a) (b)
(c) (d)
AlCl
33. + O ¾ ¾¾3®( A), Product ( A) is:
O
O
O OH
OH
(a) Ph (b) O
O
O O
(c) (d) O
||
O O
O
34. Cl—C Cl ¾¾¾®
AlCl ( A), product ( A) is:
3

C == O O
||
C == O
(a) (b) (c) (d) Ph — C — Ph
C == O
Cl Cl Cl
35. Compound A (C 6 H 8 ) which is optically active, react with excess H 2 in Pd to give C 6 H 14 which
is resolvable compound. How many moles of H 2 molecules are required for the hydrogenation
of compound A ?
(a) 1.5 (b) 2 (c) 3 (d) 4
CH3
3 AlCl
36. + CH3—C—CH2—Cl ¾¾®
CH3
Major product of the reaction is:
(a) (b) (c) (d)
37.
Number of benzylic hydrogens in given compound is:

(a) 7 (b) 8 (c) 9 (d) 10
38. What is the major organic product of the reaction between benzene and isobutyl chloride in
the presence of AlCl 3 ?
(a) tert-butylbenzene (b) isobutylbenzene
(c) n-butylbenzene (d) chlorobenzene (e) sec-butylbenzene
39. What is the major organic product that results when benzene is treated with 1-chlorobutane
and AlCl 3 ?
(a) Ethylbenzene (b) Isobutylbenzene
(c) Butylbenzene (d) Sec-butylbenzene (e) Terbutylbenzene
40. Which of the following aromatic rings is alkylated most rapidly by CH 3 CH 2 Cl AlCl 3 ?
(a) Benzene (b) Ethylbenzene
(c) Chlorobenzene (d) Benzenesulfonic acid (e) Nitrobenzene

41. What is the major product of the following reaction ?

CH3
HNO
3
+ ¾¾¾®
H SO
?
2 4
CH3 NO2 CH3 CH3
(i) (ii) (iii)
NO2 NO2
(a) i (b) ii
(c) iii (d) a and b equally (e) a and c equally
42. What reagents can best be used to accomplish the following transformation?
OH
(a) 1. BH 3 ,THF 2. HO - ,H 2 O 2 (b) H + ,H 2 O

(c) 1. Hg(OAc) 2 ,H 2 O THF 2. NaBH 4 (d) 1. Hg(O 2 CCF3 ) 2 ,CH 3 OH 2. NaBH 4
(e) NaOH, H 2 O
43. The compound X in the reaction,
3anhydrous AlCl
+ ICl ¾¾¾¾¾® X is:
I
Cl I Cl
(a) (b) (c) (d)

Cl
I
CH3
KMnO 4
¾¾¾®
H+, heat
?
CH3CH2
COOH CH3
(i) (ii)
CH3CH2 HOOC

CH3 COOH
(iii) (iv)
HOOCCH2 HOOC
COOH
(v)
CH3OOC

KMnO 4
¾¾¾®
H+, heat
?
COOH
COOH
(a) (b) COOH
COOH
COOH COOH COOH

(c) (d) COOH (e)
46. The product A in the reaction

Br
2 dry ether
+ 2Na ¾ ¾¾¾® A + 2NaBr , is:
Br
(a) (b) (c) 2 (d)
47. Which one of the following compounds undergoes bromination of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?
(a) (b)
N
H
(c) (d)
NH NH
O

48. The compound P ,Q were separately subjected to halogenation using Br 2 Fe. The major
product formed in each case respectively is:
O O
O CH3
NH—C—CH3
(P) (Q)
O O O O
O CH3 O CH3
NH—C—CH3 NH—C—CH3
(a) (b)
Br
Br Br Br
O O O O
O CH3 O CH3
(c) (d)
Br
Br Br Br
1
2
O
2 Br
49. ¾¾® substitution take place at the position.
3 Fe
4
(a) 1 (b) 2 (c) 3 (d) both (a) and (b)

NHCOCH3
O
||
AlCl
50. + Cl — C — CH 2 — Cl ¾ ¾¾3® ( A) (79 - 83%). Product ( A) is:
O O
(a) (b) O
C—CH2—Cl
CH2—C—Cl
O

O O
(c) (d) O
CH2—C—Cl
C—CH2—Cl
O
51. Give the major product of the following reaction:
O
NHPh ¾CH 3Cl,AlCl 3

¾¾¾ ¾®
O O
NHPh NHPh
(a) (b)
H3C
CH3
NHCOPh NHCOPh
(c) (d)
H3C
CH3

Answers
[A] Aliphatic Hydrocarbons

Alkanes
1. (a) 2. (b) 3. (b) 4. (a) 5. (b) 6. (c) 7. (e) 8. (b) 9. (a) 10. (b)
11. (c) 12. (a) 13. (b) 14. (b) 15. (a) 16. (c) 17. (c) 18. (c) 19. (a) 20. (a)
21. (a) 22. (c) 23. (b) 24. (a) 25. (b) 26. (a) 27. (b) 28. (e) 29. (b) 30. (e)
Alkenes
1. (d) 2. (c) 3. (c) 4. (a) 5. (d) 6. (c) 7. (c) 8. (c) 9. (a) 10. (b)
11. (a) 12. (c) 13. (a) 14. (b) 15. (b) 16. (c) 17. (d) 18. (a) 19. (d) 20. (e)
21. (d) 22. (c) 23. (a) 24. (c) 25. (a) 26. (d) 27. (b) 28. (d) 29. (b) 30. (a)
31. (a) 32. (d) 33. (c) 34. (b) 35. (d) 36. (d) 37. (b) 38. (b) 39. (c) 40. (a)
41. (e) 42. (d) 43. (b) 44. (b) 45. (d) 46. (b) 47. (a) 48. (c) 49. (c) 50. (a)
51. (a) 52. (b) 53. (d) 54. (b) 55. (b) 56. (b) 57. (e) 58. (b) 59. (a) 60. (b)
61. (a) 62. (d)
Alkynes
1. (c) 2. (c) 3. (d) 4. (d) 5. (c) 6. (c) 7. (b) 8. (c) 9. (b) 10. (c)
11. (a) 12. (b) 13. (e) 14. (e) 15. (d) 16. (a) 17. (a) 18. (c) 19. (a)
[B] Aromatic Hydrocarbons

Preparation & Properties
1. (b) 2. (c) 3. (c) 4. (a) 5. (a) 6. (d) 7. (b) 8. (b) 9. (c) 10. (d)
11. (b) 12. (a) 13. (d) 14. (b) 15. (b) 16. (c) 17. (a) 18. (d) 19. (a) 20. (b)
21. (c) 22. (a) 23. (b) 24. (b) 25. (d) 26. (b) 27. (a) 28. (d) 29. (e) 30. (d)
31. (d) 32. (b) 33. (a) 34. (c) 35. (c) 36. (b) 37. (c) 38. (a) 39. (d) 40. (b)
41. (c) 42. (a) 43. (b) 44. (d) 45. (a) 46. (d) 47. (b) 48. (c) 49. (d) 50. (c)
51. (d)

cold KMnO (dil)

4
1. ¾ ¾¾¾¾¾¾® Identify products:
HO OH
(a) (b)
OH OH
OH OH
(c) (d)
OH OH
O O
O
2. ¾¾3® Identify all possible product:
Zn
(a) CH 3 COOH (b) CH 3 CH 2 COCHO (c) CH 3 COCHO (d) CH 3 CH 2 COOH

3. Which of the following compounds are aromatic ?
O
(a) (b) (c) (d)
N O
4. In which of the following electron density on phenyl ring is more than benzene?
CH3 OH Cl NO2
(a) (b) (c) (d)
Br
5. ¾¾2® Identify the products.
CCl 4
Br
Br
(a) Et (b) Et
Br Br

Et
Br
Br
(c) (d) Br
6. Heat of hydrogenation of is less than:
(a) (b) (c) (d)
7. Which of the following is/are aromatic ?

s r s r
(a) (b) (c) (d)
8. Which of the following compounds when react with AlCl 3 aromatic compound will form ?
Cl Cl Cl Cl
(a) (b) (c) (d)

O
9. In which of the following reaction formation of racemic mixture ?
Br Cold. KMnO
(a) ¾¾2® (b) ¾ ¾¾¾¾4®
CCl 4
CH3
H
H
CH3
H+ Hr
(c) ¾¾® (d) ¾¾®
D D
OH
OH
10. Which of the following is most reactive toward bromination ?
(a) (b) (c) (d)
Answers
1. (a, b) 2. (a, b, c, d) 3. (b, c) 4. (a, b) 5. (b, d) 6. (a, b, c, d)
7. (a, d) 8. (a, c) 9. (c) 10. (a)

Passage-1:
We've now learned that benzene is unusually stable, and that this stability
seems to be correlated with the overlap of its carbon 2p orbitals to form p
molecular orbitals. In 1931, Erich Huckel (1896-1980), a German chemist
physicist, elucidated with molecular orbital arguments the criteria for this
sort of stability, which has come to be called aromaticity.
Criteria for aromaticity:
● Aromatic compounds contain one or more rings that have a cyclic
arrangement of p-orbitals. Thus, aromaticity is a property of certain
cyclic compounds.
● Every atom of an aromatic ring has a p-orbital.
● Aromatic rings are planar.
● The cyclic arrangements of p-orbitals in an aromatic compound must
contain 4 n + 2 p electrons, where n is any positive integer (0, 1, 2, ...). In
other words, an aromatic ring must contain 2, 6, 10, ...p electrons.
1. Which of the following compound is not anti-aromatic ?
(a) s (b)
(c) (d)
N
2. Which of the following compound is non-aromatic ?
(a) (b) (c) (d)

3. Compare rate of reaction with AgNO 3

I I I
(I) (II) (III)

O
(a) I > II > III (b) I > III > II (c) II > III > I (d) II > I > III
Passage-2:
In electrophilic addition reaction, alkene behave as a nucleophile or base.
During reaction electrophile react with alkene in rate determining step to
form carbocation according to advance markownikoff rule. In second step
carbocation react with nucleophile to give product so overall addition
reaction take place.
Br
1. ¾¾2® Possible product:
Br Br Br Br Br Br
(a) Br (b) (c) (d)
Br
CCl
2. ¾4® Number of product formed in the reaction:
+Br 2 ¾ ¾
(a) 1 (b) 2 (c) 3 (d) 4
3. Correct order of rate of Bromination:
(I) (II) (III)

(a) I > II > III (b) II > I > III (c) III> II > I (d) II > III > I

Passage-3:
The most characteristic reactions of benzenoid arenes are the substitution
reaction that occur when they react with electrophilic reagents. These
reactions are of the general type shown below.
Ar — H + E — A ¾
¾® Ar — E + H — A
E
or Free Energy
+ E—A¾¾® +H— A
++ +
DG(1) DG(2)
+
H–A
E–A
E
Reaction co-ordinate
CH3
N O
1.
a d
b c
Identify the position where EAS (Electrophilic Aromatic Substitution) reaction takes place:
(a) a (b) b (c) c (d) d
2. Compare rate of EAS (Electrophilic Aromatic Substitution):
O O
|| ||
Cl C—O—CH3 O—C—CH3
(a) (b) (c) (d)
(a) a > b > c > d (b) b > a > c > d (c) d > b > c > a (d) d > b > a > c

3. Which of the following is o p director for EAS (Electrophilic Aromatic Substitution) ?

O O
|| ||
NH—C—CH3 C—NH—CH3
(a) (b)
O
NO2
CH3
(c) (d)
Passage-4:
O OH
|| |
Mg
( A) ¾¾®( B) + CH 3 — C — O — Et ¾®
¾ CH 3 — C — Ph
ether r |
2H
Ph
1. Compound (A) is:

Br
Br
(a) (b)
Br CH2—Br
(c) (d)
2. Compound (B) is:

(a) Ph — MgBr (b) Ph — CH 2 — MgBr
MgBr
(c) Ph — OMgBr (d)


Column-I Column-II
(a) (p) Electrophilic-addition reaction

HBr
¾ ¾¾®
Peroxide
(b) (q) Free-radical-addition reaction

HCl
¾ ¾¾®
Peroxide
(c) CH3 (r) Free-radical-substitution reaction
NBS
¾¾
¾®
(d) Cl (s) Formation of free-radical as a intermediate in

major product formation
aq. KOH
¾ ¾¾
¾®
(t) One-step reaction

Column-I Column-II
(a) HBr (p)

¾ ¾¾®
Peroxide
Br
(b) HBr (q)

¾ ¾¾® Br
No Peroxide
(c) HCl (r)

¾ ¾¾® Cl
Peroxide
(d) HCl (s)

¾ ¾¾®
CCl 4
Cl
Br
NBS
(e) ¾¾
¾® (t)


Column-I Column-II (Reagent used is)
CH3 CH2—Br
(a) (p) NBS

¾¾®
CH3 CH2—Cl
(b) (q) Br 2 hv
¾¾®
Br
(c) (r) SO 2 Cl 2 hv
¾¾®
Cl
(d) (s) Cl 2 hv
¾¾®

Column-I Column-II
O
O—C—CH3
(a) (p) o p-directive
O
C—O—CH3
(b) (q) meta directive
O
NH—C—CH3 rate of EAS is less than
(c) (r)
benzene

O
C—NH—Me rate of EAS is more than
(d) (s)
benzene.

Column-I
Column-II
(Groups are attached with phenyl ring)
r
(a) — NR 3 (p) shows +I effect
O
(b) || (q) shows +H effect
— C— H
..
(c) — O—
.. Me (r) shows +M effect
(d) —CH 3 (s) shows -I effect
(t) shows -M effect

Column-I Column-II
OH
(p) Group attached with benzene ring is +M
(a) group.
NO2
(q) Group attached with benzene ring is -M
(b) group.
(r) Group attached with benzene ring is -I.

N
(c)

SO3H
(s) Group attached with benzene ring is +I.
(d)

Column-II
Column-I
(Group attached with phenyl ring is)
OH
(a) (p) +M
NO2
(b) (q) -M
O
C—CH3 (r) -I
(c)
O
O—C—CH3 (s) +I
(d)

1. How many groups are o p director in the electrophilic aromatic substitution ?

(i) —NH 2 (ii) —CHO (iii) —N == O (iv) —COOH
O
||
(v) –OMe (vi) —O — C — Me (vii)-Et
O
||
(viii) — C — NH — Me (ix) —N == NH 2 (x) —SO 3 H
2. How many isomer of C 8 H 10 when reacts with hot alkaline KMnO 4 give di-carboxylic acid as a
product ?
O
||
PCl 5 x NaNH2 CH 3 I
3. Reaction-1: Ph — C — CH 3 ¾ ¾ ¾® ¾¾¾® ¾¾ ¾® Ph — C ºº C — CH 3
Br
y NaNH
2
Reaction-2: ¾¾¾® CH 3 — C ºº C — CH 3
Br
z NaNH2 Et— I
Reaction-3: Ph —CH — CH 2 ¾¾¾® ¾ ¾¾® Ph — C ºº C — Et
| |
Cl Cl
x , y , z are moles used.
Sum of [ x + y + z =]
4. Amongst the following, the total number of compounds which will undergo addition reaction
will be:
O
(A) CH 3 — CH == CH 2 (B) (C) CH 3 — C ºº N
O
||
(D) CH 3 — C — H (E) CH 4 (F) CH 3 C ºº CCH 3

1. Predict the major monobromination product in the following reaction.

hv
CH2CH2CH3+Br 2
2. Provide the major organic product(s) of the reaction below.

O
Br2 (1eq)
H3CO ¾¾¾¾®
CH3 FeBr3
3. This questions gives you an idea about mono and dihalogenated products of an reactant.
Number of monochloro
Number of monochloro
S.No. Compound product (excluding
product
stereoisomer)
1.
2.
3.
4.
5.
6.
7.
8.
9. CH2

4. Identify product including stereo chemistry

CH3
CH 3 CH3
Ni / D 2 Ni / D 2
1. ¾¾ ¾
¾® 2. ¾¾ ¾
¾®
CH3
CH3
CH 3 CH2CH3
Ni / D 2 Ni / D 2
3. ¾¾ ¾
¾® 4. ¾¾ ¾
¾®
CH2CH3
CH3
Ni / D 2 Ni / D 2
5. ¾¾ ¾
¾® 6. ¾¾ ¾
¾®
CH3
Ni / D 2 Ni / D 2
7. CH 3 — CH — CH 2 ¾ ¾ ¾
¾® 8. CH 3 — C ºº C — CH 3 ¾ ¾ ¾
¾®
Ni / D 2
¾¾ ¾
¾® Ni / D 2
9. 10. ¾¾ ¾
¾®
5. Identify product including stereo chemistry

CH3
CH 3 CH3
Br2 , CCl4 Br2 , CCl4
1. ¾¾ ¾¾ ¾® 2. ¾¾ ¾¾ ¾®
CH3
CH3
CH 3 CH2CH3
3. ¾¾ ¾¾ ¾® 4. ¾¾ ¾¾ ¾®
CH2CH3
CH3
5. ¾¾ ¾¾ ¾® 6. ¾¾ ¾¾ ¾®
CH3
COOH
7. CH 3 — CH — CH 2 ¾ ¾ ¾¾ ¾® 8. ¾¾ ¾¾ ¾®
COOH
Br2 , CCl4
HOOC COOH
CH 3 — CH ºº C — CH 3 ¾ ¾ ¾ ¾ ¾®
9. 10. Br2 , CCl4
¾¾ ¾¾ ¾®

Br2 , CCl 4
11. CH 2 — CH — CH 2 — C ºº CH ¾ ¾ ¾¾ ¾®
CH3
Br2 , CCl4
H Br ¾ ¾ ¾¾ ¾®
H2O
¾¾¾®
12. 13.
CH
+ Br 2 (cis)
CH
CH3
CH3
Br2 , CCl4
H Br ¾¾ ¾¾ ¾®
14.
CH
(trans)
CH
CH3
6. Identify monochlorination products (including stereo)
Cl2 / h n Cl 2 / h n
CH 3 CH 2 CH 2 CH 3 ¾ ¾
1. CH 3 CH 2 CH 3 ¾¾ ¾¾® 2 ¾¾®
Cl 2 / h n
¾¾ ¾¾® Cl 2 / h n
¾¾ ¾¾®
3. 4.
5. Cl 2 / h n 6. Cl 2 / h n
¾¾ ¾¾® ¾¾ ¾¾®
Cl 2 / h n
7. Cl 2 / h n
8. ¾¾ ¾¾®
¾¾ ¾¾®
Cl 2 / h n
9. ¾¾ ¾¾® 10. Cl 2 / h n
¾¾ ¾¾®

7. Identify product including stereo chemistry:
1. CH 3 CH3 Cold KMnO 4

¾¾ ¾¾¾ ¾® 2 CH3
Cold KMnO 4
¾¾ ¾¾¾ ¾®
CH3
3. CH 3 CH2CH3 4. CH3
Cold KMnO 4
¾¾ ¾¾¾ ¾® Cold KMnO 4
¾¾ ¾¾¾ ¾®
CH2CH3
5. 6. CH3
Cold KMnO 4
¾¾ ¾ ¾ ¾
¾® Cold KMnO 4
¾¾ ¾¾¾ ¾®
CH3
7. Cold KMnO 4
CH 3 — CH — CH 2 ¾ ¾ ¾¾¾ ¾® 8. COOH
Cold KMnO 4
¾¾ ¾¾¾ ¾®
COOH
9. CH 3 — C ºº C — CH 3 10. HOOC COOH Cold KMnO 4

¾¾ ¾¾¾ ¾®
Cold KMnO 4
¾¾ ¾ ¾ ¾
¾®
11. CH 2 — CH — CH 2 — C ºº CH 12. CH3

Cold KMnO 4
¾¾ ¾ ¾ ¾
¾® Cold KMnO 4
H Br ¾ ¾ ¾¾¾ ¾®
CH
(cis)
CH
CH3
13. CH3
Cold KMnO 4
H Br ¾¾ ¾¾¾ ¾®
CH
(trans)
CH
CH3

8.
S.No. Compare Rate of EAS
1.
2.
3.
4.
5.
, ,
6.
, ,
7.
, ,

9. Prepare the following by Friedal Craft reaction.
S. S.
Compounds Compounds
No. No.
1. 2.
O
CH3
3. 4.
Ph
5. 6. O
7. O 8.
O
9. 10.
Cl
11. 12.
O

Answers
Passage-1: 1. (c) 2. (d) 3. (b)
Passage-2: 1. (a) 2. (b) 3. (a)
Passage-3: 1. (b) 2. (d) 3. (a)
Passage-4: 1. (a) 2. (a)

1. (a) ® q,s; (b) ® p; (c) ® r,s; (d) ® t
2. (a)® q; (b)® p; (c)® s; (d)® s; (e)® t
3. (a)®p, q; (b)®r, s; (c)®p, q; (d)®r, s
4. (a)®p, s; (b)®q, r; (c)®p, s; (d)®q, r
5. (a) ® s; (b) ® s,t; (c) ® r,s; (d) ® p,q
6. (a)® p, r; (b)® q, r; (c)® p, r; (d)® q, r
7. (a) ® p,r (b) ® q,r (c) ® q,r (d) ® p,r
Multi Concept Subjective Problems
1. 6 2. 3 3. 8 4. 5
Br
1. CHCH2CH3
O
2. H3CO
CH3
Br
3.
1. 4, 3 2. 3, 2 3. 6, 4 4. 10, 6
5. 6, 4 6. 1, 1 7. 1, 1 8. 1, 1
9. 2, 2

4. Ni / D 2 performs syn addition

1. Meso 2. Racemic mixture 3. Racemic mixture
4. Racemic mixture 5. Meso 6. Meso
7. Racemic mixture 8. Single product 9. Racemic mixture
10. Racemic mixture
5.
1. 2-racemic 2. 1-meso 3. 2-racemic 4. 2-racemic 5. 2-racemic
6. 2-racemic 7. 2-racemic 8. 1-meso 9. 2-diastereomers
10. 2-racemic 11. 2-diastereomers 12. 2-racemic
13. 2-diastereomers 14. 2-diastereomers
6.
1. 2 2. 3 3. 4 4. 8 5.
6. 2 7. 5 8. 3 9. 1 10. 5
7.
1. 1-Meso 2. 2-Racemic 3. 2-Racemic 4. 2-Racemic
5. 1-Meso 6. 1-Meso 7. 2-Racemic 8. 2-Racemic
9. Left 10. 1-Meso 11. 1-Meso
12. 2-(Diastereomers) 13. 2-(Diastereomers)
8.
1. 4 > 3 > 1 > 2 2. 1> 2 > 3 3. a>b>d>c
4. 3 > 1 > 2 5. 2>3>1 6. a>b>c
7. c > b > a
9.
Cl
AlCl3 AlCl3
1. + Cl 2. +
O
AlCl3 AlCl3
3. + CH3 – Cl 4. + CH3 – CH2 – C – Cl
O O
+ Ph – C – Cl AlCl3 + C – Cl AlCl3
5. 6.

AlCl3 AlCl3
7. O 8.
Cl Cl–C
||
O
Cl Cl
9. + 10.
O
AlCl3
11. + Cl2 12. + AlCl
3

Haloalkanes and Haloarenes 259
3
Haloalkanes and
Haloarenes
[A] Haloalkanes : Preparation and Properties

Bimolecular Nucleophilic Substitution (SN 2 ) Reactions
1. What is the K eq of the following reaction?

NaCN, r.t.
¾¾¾® DG° = –0.010 kJ mol –1
Cl CN
(a) 1.7 (b) 0.17 (c) 17 (d) 0.017
2. Which halide ion is the best nucleophile in dimethyl sulfoxide solution?
(a) F - (b) Cl - (c) Br - (d) I -
3. Which is the best leaving group in a substitution reaction of an alkyl halide?
(a) Cl - (b) Br - (c) I - (d) F -
4. Which statement is true with respect to an S N 2 reaction?
(a) A good leaving group is a strong base
(b) A good leaving group is a weak base
(c) A leaving group must be negatively charged
(d) A leaving group must be a halide
5. Which of the following nucleophiles is going to promote an S N 2 reaction?
r Nu ?
O ¾¾® Nu + OH
|
H
(a) NaI (b) Water (c) NH 4 Cl (d) MeONa

6. What is the major product of the following synthesis?
1. NaS
Br ¾¾¾¾¾¾¾® ?
2. H2, Pd
(a) S (b) S (c) S (d) S
7. Give the major product of the following reaction.

Br –
Br HO
¾¾¾¾¾®
CH3 1 equivalent
H3C
HO Br OH
Br
(a) (b)
H3C CH3 H3C CH3
H H
Br Br
(c) CH2 (d)
H3C CH3 CH3
CH3
CH3
H Br NaI acetone
8. ¾¾¾¾ ¾® Product, product of the reaction is :
H Cl (S 2 ) condition
N
CH3
CH3 CH3 CH3

H I H I I H
(a) (b) (c) (d)
H Cl Cl H H Cl
CH3 CH3 CH3
9. Among the following which is most reactive in S N 2 reactions?
Cl
(a) CH 3 — Cl (b) H 2 C == CH — Cl (c) (d) CH 3 — F
10. Which of the following species is most reactive in S N 2 reaction?

(a) CH 3 CH 2 — Cl (b) CH 3 CH 2 — Br
(c) CH 3 CH 2 — I (d) CH 3 CH 2 — F (e) CH 3 CH 2 — OH

K
11. CH 3 — CH 2 — Br + NaOH ¾¾1® CH 3 — CH 2 — OH + NaBr ¾® reaction ...(1)
CH 3
|
K
CH 3 — C — CH 2 — Br + NaOH ¾¾2®(CH 3 ) 3 C — CH 2 — OH + NaBr ¾® reaction ...(2)
|
CH 3
K 1 and K 2 are rate constant for above reactions. Correct relation is:
(a) K 1 = K 2 (b) K 1 > K 2 (c) K 1 < K 2 (d) K 1 << K 2
12. Free energy profile for given reaction is
HO s + CH — Br ¾® HO — CH + Br s
3 3
Free Free
(a) Energy (b) Energy
Reaction co-ordinate Reaction co-ordinate
Free Free
Energy Energy
(c) (d)
Reaction co-ordinate Reaction co-ordinate
CH3
H Cl
H D NaI
13. ¾¾®( A), Major product ( A) is:
H Br acetone
H D
CH3
CH3 CH3 CH3 CH3
H I H Cl H Cl Cl H
H D H D H D H D
(a) (b) (c) (d)
H Br H I I H I H
H D H D H D H D
CH3 CH3 CH3 CH3
LiBr
14. Cl ¾ ¾ ¾¾® ( A), Product A is :
S 2 condition
N
Cl
Cl Br
(a) (b) (c) (d) Cl
Cl
Br
Br Cl
s
15. CH 3 — I + OH ¾® CH 3 — OH + Is
Which of the following solvents is most suitable for this reaction ?
(a) H 2 O (b) EtOH (c) Et 2 O (d) None of these
16. Which of the following reactions is not possible ?
(a) R — OH + NaBr ¾® R — Br + NaOH (b) R — OH + HBr ¾® R — Br + H 2 O
(c) Both reactions are possible (d) Both reactions are not possible
17. Which of the following nucleophilic substitutions is practically not possible ?
s s
OH s OH
¾¾®
(a) ¾¾®
H2O + Br (b) H2O
Br OH Br OH
(c) Both (a) and (b) (d) none of these
18. From each of the following pairs select the compound that will react faster with sodium iodide
in acetone:
(A) 2-Chloropropane or 2-bromopropane (B) 1-Bromobutane or 2-bromobutane
I II I II
(a) (A)-I, (B)-I (b) (A)-I, (B)-II (c) (A)-II, (B)-I (d) (A)-II, (B)-II
Br CH3 S 2
19. + OH - ¾ ¾
N
® A; A is:
H H
HO H CH3 HO CH3
H
(a) (b) (c) Both (a) and (b) (d)
H CH3 HO H H H
20. Correct order of nucleophilicity in polar protic solvent is:
(c) Is > Cl s > Br s > F s (d) F s > Is > Br s > Cl s
21. Correct order of nucleophilicity in polar aprotic solvent is:
(c) Is > Cl s > Br s > F s (d) F s > Is > Br s > Cl s

22. Which of the reactions shown below will be faster ?

Br OH Br OH
KOH KOH
Reaction-1: ¾¾¾® ; Reaction-2: ¾¾¾¾®
H2O Crown ether
(a) Reaction 1 (b) Reaction 2

(c) Both have equal rates of reaction (d) Cannot be predicted
PhSNa
23. Cl ¾¾¾® (X)
PhSNa
¾¾¾® (Y)
Cl
Relationship between ( X ) and (Y ) is:
(a) constitutional isomer (b) enantiomer
(c) identical (d) none of these
24. Without exception, S N 2 reaction at chiral carbon gives:
(a) enantiomer of substrate (b) product of opposite polarity
(c) diastereomeric mixture (d) only one stereoisomer
25. The order of reactivities of the following alkyl halides for a S N 2 reaction is:
(a) RF > RCl > RBr > RI (b) RF > RBr > RCl > RI
(c) RCl > RBr > RF > RI (d) RI> RBr > RCl > RF
26. (CH 3 ) 3 C × MgCl on reaction with D 2 O produces:
(a) (CH 3 ) 3 CD (b) (CH 3 ) 3 OD (c) (CD 3 ) 3 CD (d) (CD 3 ) 3 OD
27. When chloroform is hydrolysed with KOH, then the final product is:
(a) HCOOH (b) HCOOK (c) CH 3 OH (d) None of these
28. Which of the following alkyl halides gives the slowest S N 2 reaction?
(a) CH 3 CH 2 Cl (b) CH 3 CHCH 2 Cl
|
CH 3
Cl Cl
| |
(c) CH 3 CCH 2 CH 3 (d) CH 3 CHCHCH 3 (e) CH 3 CHCH 2 CH 3
| | |
CH 3 CH 3 CH 2
|
Cl
29. Assuming no other changes, what is the effect on rate of reaction if the concentration of the
alkyl halide doubled in a S N 2 reaction?

CH 3 Br + HO s ¾® CH 3 OH + Br s
(a) No change (b) Doubles the rate
(c) Triples the rate (d) Quadruples the rate (e) Rate is halved
30. Assuming no other changes, what is the effect on rate of reaction if the concentrations of both
alkyl halide and the nucleophile are doubled ?
CH 3 Br + HO s ¾® CH 3 OH + Br s
31. Which of the following S N 2 reactions is the fastest ?
(a) CH 3 CHCH 3 + HO - ¾® CH 3 CHCH 3 + Br -
| |
Br OH
(b) CH 3 CH 2 CH 2 I + HO - ¾® CH 3 CH 2 CH 2 OH + I –
(c) CH 3 CHCH 3 + HO - ¾® CH 3 CHCH 3 + I -
| |
I OH
(d) CH 3 CH 2 CH 3 Br + HO - ¾® CH 3 CH 2 CH 3 OH + Br -
(e) CH 3 CH 2 CH 2 I + H 2 O ¾® CH 3 CH 2 CH 2 OH + HI
32. Which of the following S N 2 reactions is the slowest ?
(a) CH 3 CH 2 CH 3 Br + HO - ¾® CH 3 CH 2 CH 3 OH + Br –
(b) CH 3 CH 2 CH 2 Cl + HO - ¾® CH 3 CH 2 CH 2 OH + Cl -
(c) CH 3 CH 2 CH 2 I + HO - ¾® CH 3 CH 2 CH 2 OH + I -
(d) CH 3 CH 2 CH 3 F + HO - ¾® CH 3 CH 2 CH 2 OH + F -
(e) CH 3 CHCH 3 + HO - ¾® CH 3 CHCH 3 + F -
| |
F OH
33. Which halide reacts most rapidly via an S N 2 mechanism?
(a) (CH 3 )CCH 2 CH 2 F (b) (CH 3 )CCH 2 CH 2 Cl
(c) (CH 3 )CCH 2 CH 2 Br (d) (CH 3 )CCH 2 CH 2 I
(e) all primary halides react at the same rate in S N 2
34. Which halide reacts most rapidily via an S N 2 mechanism ?
I
(a) I (b) Cl (c) (d) (e)
Br
Cl

35. Assuming no other changes, what is the effect of doubling only the concentration of the alkyl
halide in the following S N1 reaction?
(CH ) CBr + Is ¾® (CH ) CI + Br s
3 3 3 3

CH3 Br
rs
36. K SH ( P ) ; Major product ( P ) is:
¾¾®
Br
SH SH
CH2
(a) (b) (c) (d)
Br Br
37. Arrange the following in order of their nucleophilicity in protic solvent

–
O
O
||
CH 3 O - CH 3 — C — O -
(i) (ii) (iii)
(a) i>ii>ii (b) iii>ii>i (c) ii>i>iii (d) None
38. In which of the following protic solvents, S N 2 reaction will occur most rapidly?
(a) CH 3 O - (1m) (b) CH 3 O - (2m)
(c) CH 3 O - (3m) (d) all have equal rate.
39. Rate of S N 2 reaction will be maximum in which of the following solvents?
OH
(a) H 2 O (b) CH 3 OH (c) (d) DMF
40. For the following groups, the order of leaving group ability is:
(a) — OAc (b) — OMe (c) — O — SO 2 Me (d) — OSO 2 CF3
(I) (II) (III) (IV)
(a) I>II>III>IV (b) IV>III>I>II (c) III>II>I>IV (d) II>III>IV>I

41. Consider the following two anionic molecules. Which of the following statements is TRUE?
– –
O S
(I) (II)
(a) I is more basic and more nucleophilic than II
(b) I is less basic and less nucleophilic than II
(c) I is more basic but less nucleophilic than II
(d) I is less basic but more nucleophilic than II
42. Which of the following is a secondary alkyl halide?
(a) CH 3 Br (b) (CH 3 ) 3 CBr (c) (CH 3 ) 2 CHBr (d) (CH 3 ) 2 CHCH 2 Br
43. Which of the following compounds will undergo an S N 2 reaction most readily?
(a) (CH 3 ) 3 CCH 2 I (b) (CH 3 ) 3 CCl
(c) (CH 3 ) 2 CHI (d) (CH 3 ) 2 CHCH 2 CH 2 CH 2 Cl
(e) (CH 3 ) 2 CHCH 2 CH 2 CH 2 I
44. Which of the following S N 2 reactions is the fastest ?
(a) CH 3 CH 2 CH 2 CH 2 Br + OH - ¾® CH 3 CH 2 CH 2 CH 2 OH + Br -
(b) CH 3 CH 2 CH 2 CH 2 Br + H 2 O ¾® CH 3 CH 2 CH 2 CH 2 OH + HBr
(c) CH 3 CH 2 CHBrCH 3 + OH - ¾® CH 3 CH 2 CHOHCH 3 + Br –
(d) CH 3 CH 2 CHBrCH 3 + H 2 O ¾® CH 3 CH 2 CHOHCH 3 + HBr
45. Which of the following S N 2 reactions is the slowest ?
(a) CH 3 CH 2 CHBrCH 3 + OH - ¾® CH 3 CH 2 CHOHCH 3 + Br -
(b) CH 3 CH 2 CHBrCH 3 + H 2 O ¾® CH 3 CH 2 CHOHCH 3 + HBr
(c) CH 3 CH 2 CH 2 CH 2 Br + OH - ¾® CH 3 CH 2 CH 2 CH 2 OH + Br -
(d) CH 3 CH 2 CH 2 CH 2 Br + H 2 O ¾® CH 3 CH 2 CH 2 CH 2 OH + HBr
46. Which of the following bromides reacts readily via an S N 2 reaction with NaN 3 ?
(a) C 6 H 5 Br (b) CH 3 CH 2 CH == CHBr
(c) (C 6 H 5 ) 3 CBr (d) (CH 3 ) 3 CCH 2 CH 2 CH 2 Br
(e) 1-bromo-1-methylcyclohexane
Cl
LiBr acetone
47. ¾ ¾ ¾ ¾¾®( A), Product ( A) is:
Cl S condition
N2
Br Br
(a) (b)
Cl Br
Cl Cl
(c) (d)
Br

CH2Br
48. The major product in the given reaction: + NH 3 ¾®
Br
CH2NH2 CH2NH2 CH2Br

Br NH2 NH2
CH2—Cl
sr
Ph—S Na
49. ¾¾¾® (A), Structure of product ( A) is:
Br
Cl SPh SPh
(a) (b) (c) (d) None
SPh Br SPh
50. The substances used for the preparation of ether by Williamson's synthesis are:
(a) (CH 3 ) 3 C Br and CH 3 O Na (b) (CH 3 ) 3 C Br and CH 3 OH
(c) CH 3 Br and (CH 3 ) 3 CONa (d) CH 3 Br and (CH 3 ) 3 COH
51. The best method for synthesis of given ether by Williamson’s ether synthesis is:
—O—CH == CH2
s s
(a) —O + H2C == CH—Br (b) —O + H2C == CH—Br
s s
(c) —B r + H2C == CH—O (d) +H2C == CH—O
Br
Unimolecular Nucleophilic Substitution (SN 1 ) Reactions

1. What is the most reactive alkyl halide for the following reaction?
RX + H 2 O ¾® R — OH + X -
Br Br
Br Br
(a) (b) (c) (d)

2. Give all of the expected products of the following reaction.

MeOH
I ¾¾¾¾®
OMe H
a b c d
(a) a (b) a and c (c) a, b, c and d (d) a, c, and d
3. Order of rate of reaction with AgNO 3 or rate of S N1 :
Cl
Cl Cl
(I) (II) (III)

(a) I > III > II (b) II > III > I (c) I > II > III (d) III > I > II
4. Which of following is least reactive toward S N1 ?
I I I I
(a) (b) (c) (d)
5. S N1 reactivity of the following halides,

(i) (CH 3 ) 3 CBr (ii) (C 6 H 5 ) 2 CHBr
(iii) (C 6 H 5 ) 2 C(CH 3 ) Br (iv) (CH 3 ) 2 CHBr will be in the order:
(a) iv > i > ii > iii (b) ii > i > iii > iv (c) i > iii > ii > iv (d) iii > ii > i > iv
6. The compound which would undergo S N 2 reaction fastest is:
Cl
Cl
(a) (b)
Br
(c) Br (d)
CH 3
|
7. CH 3 — C — Br CH 3 — CH — Br CH 3 — CH 2 — CH 2 Br
| | (c)
CH 3 CH 3
( a) (b)
Reactivity toward S N1 :
(a) a > b > c (b) b > a > c (c) b > c > a (d) c > b > a

8. Which of the following compound give same S N1 and S N 2 product ?

Cl
(a) (b) (c) (d)

Cl Cl Cl
CH CO H
9. Ph — CH — Cl ¾ ¾3 ¾¾
2
®, This reaction is known as:
|
CH 3
(a) methanolysis (b) ethanolysis (c) acetolysis (d) formalysis
10. The rate of solvolysis of tert-butyl bromide will be maximum in which of the following
solvents?
(a) Et 2 O (b) CCl 4 (c) EtOH (d) H 2 O
11. Which one of the following compounds will be most reactive for S N1 reactions ?
I Cl Br Cl
O O O
(a) (b) (c) (d)
O
12. In the given reaction:
Cl
Cl
CH OH
¾ ¾3 ¾®[ X ], X is:
O Cl
Cl OCH3 Cl OCH3
Cl Cl OCH3 Cl
(a) (b) (c) (d)
O OCH3 O OCH3 O Cl O Cl
13. Among the bromides I-III given below, the order of reactivity S N1 reaction is:
O
(I) (II) (III)
Br Br Br
(a) III > I > II (b) III > II > I (c) II > III > I (d) II > I > III
14. When ethyl bromide is treated with moist Ag 2 O , main product is:
(a) Ether (b) Ethanol (c) Aldehyde (d) All of these
Cl OEt
15. ¾¾¾®
EtOH
Rate = R1

CH3 CH3
EtOH
Cl ¾¾¾® OEt
Rate= R 2
Cl OEt
EtOH
¾¾¾® Rate = R3
Which of the following is correct order?

(a) R 1 > R 2 > R 3 (b) R 3 > R 2 > R 1 (c) R 2 > R 1 > R 3 (d) R 2 > R 3 > R 1
16. Which of the following compounds has the largest dipole moment?
(a) CH 3 Cl (b) CH 2 Cl 2 (c) CHCl 3 (d) CCl 4
17. Which of the following will react with water?
(a) CHCl 3 (b) Cl 3 CCHO (c) CCl 4 (d) ClCH 2 CH 2 Cl
18. The reaction is described as:
H H
CH 3 ¾ (CH 2 )5 ½ - ½ (CH 2 )5 CH 3
OH
C ¾ Br ¾® H¾O¾ C
H 3C CH 3
(a) S E 2 (b) S E1 (c) S N 2 (d) S N1
19. Assuming no other changes, what is the effect of doubling only the concentration of the
nucleophile in the following reaction?
3 3 3 3
20. Assuming no other changes, what is the effect of doubling both the concentration of the alkyl
halide and the nucleophile in the following reaction?
3 3 3 3
21. Which of the following alkyl halides gives the fastest S N1 reaction?
(a) CH 3 CH 2 CH 2 Br (b) CH 3 CHCH 3
|
Br
(c) CH 3 CHCH 3 (d) CH 3 CH 2 CH 2 I (e) CH 3 CH 2 CH 2 Cl

|
I

22. Which of the following alkyl halides gives the fastest S N1 reaction?
Br
|
(a) CH 3 CHCHCH 3 (b) CH 3 CHCH 2 CH 2 Br
| |
CH 3 CH 3
Br
|
(c) CH 3 CCH 2 CH 3 (d) ClCH 2 CHCH 2 CH 3 (e) CH 3 CHCH 2 CH 3
| | |
CH 3 CH 3 CH 2 Cl
23. Which of the following factors has no effect on the rate of S N1 reactions ?
(a) Nature of the alkyl halide (b) Nature of the leaving group
(c) Concentration of the alkyl halide (d) Concentration of the nucleophile
(e) Value of the rate constant
24. Which of the following is the rate law for S N 1 mechanisms?
(a) Rate = k [Alkyl Halide] [Nucleophile]
(b) Rate = k [Nucleophile]
(c) Rate = k [Alkyl Halide]
(d) Rate = k[Alkyl Halide] [Nucleophile] + k 2 [Alkyl Halide]
(e) Rate = k1 [Alkyl Halide] + k 2 [Nucleophile]
25. In the S N1 hydrolysis mechanism of (CH 3 ) 3 CBr , there are -------------- elementary steps, ----------
distinct transition states, and ---------------- distinct intermediates.
(a) 2, 2, 2 (b) 2, 2, 3 (c) 2, 3, 2 (d) 3, 2, 3 (e) 3, 3, 2
r s
26. Compare rate of reaction with Ag NO3 or rate of S N1 reaction :
I I I
(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) ii>i>iii (d) i>iii>ii

r s
Br Br Br
(i) (ii) (iii)
(a) i>iii>ii (b) i>ii>iii (c) iii>ii>i (d) ii>i>iii

r
28. Compare rate of reaction with Ag NOs3 or rate of S N1 reaction :
Br Br Br
(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) iii>i>ii (d) ii>i>iii

r s
I I I
(i) (ii) (iii)

O
(a) i>ii>iii (b) ii>i>iii (c) iii>ii>i (d) ii>iii>i
r s
I I I
(i) (ii) (iii)

O
(a) i>ii>iii (b) ii>iii>i (c) ii>i>iii (d) iii>ii>i
r s
Br Br CH2—Br
(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) iii>ii>i (d) iii>i>ii

r s
CH 3
|
(i) CH 3 — C — Br (ii) CH 3 — CH — Br (iii) CH 3 — CH 2 — Br
| |
CH 3 CH 3
(a) i>ii>iii (b) ii>iii>i (c) iii>ii>i (d) ii>i>iii

r
33. Compare rate of reaction with Ag NOs3 or rate of S N1 reaction :
Br Br
CH2—Br
(i) (ii) (iii)
(a) i>ii>iii (b) ii>iii>i (c) ii>i>iii (d) iii>i>ii

r s
(i) (ii) (iii)

Br Br Br
(a) i>ii>iii (b) iii>ii>i (c) ii>iii>i (d) iii>i>ii
r s
Br Br Br
(i) (ii) (iii)
(a) i>iii>ii (b) ii>iii>i (c) i>ii>iii (d) iii>i>ii

r
36. Which of the following is most reactive toward Ag NOs3 or rate of S N1 reaction ?
Br Br
(a) (b)
Br Br
(c) (d)
r s
37. Which of the following is most reactive toward Ag NO 3 or rate of S N1 reaction ?
Br Br
(a) (b)
CH3
Br
(c) (d)

38. Which of the following is least likely to be found in the product mixture which results when the
alkyl iodide below is heated in water?
OH OH
I II III IV V
I I I
39. Compare the reactively of these halide in S N1 reactions
(I) (II) (III)

(a) II > III > I (b) II > I > III (c) I > II > III (d) III > II > I
40. Arrange in order of increasing S N1 reaction rate (protic solvent).
(i) Ph Br , (ii) , (iii) Br , (iv)
Br Cl
(a) iv < ii < iii < i (b) i < ii < iii < iv (c) iv < i < iii < ii (d) iv < i < ii < iii
41. CHCl 3 + aq.KOH ¾®
¾ (A) + H 2 O
(Exces) D
¾® (B) + H 2 O
CCl 4 + aq. KOH ¾
D
(Exces)
(a) A is acid, B is aldehyde (b) (A) is acid , B is alcohol

(c) A is acid, B is CO 2 (d) A is aldehyde, B is acid.
42. Rank the following in order of decreasing reactivity with methanol.
Br
I Br I
I II III IV
(a) III > II > IV > I (b) IV > I > II > III (c) I > IV > II > III (d) I > IV > III > II
43. Under identical conditions, solvolysis of which of the following substrates would lead to
maximum recemization ?
Et CH3 CD3
(a) H Br (b) H Cl (c) H Cl (d) H Cl
CH3 D CH3 D

44. Which one of the following compounds will give enantiomeric pair on treatment with HOH ?
C 2H 5 CH 3
| |
(a) C 6 H 5 — C — I (b) CH 3 — C — Br
| |
C 2H 5 C 2H 5
H C 2H 5
| |
(c) C 6 H 5 — C — Br (d) C 2 H 5 — C — Br
| |
D CH 3
R1 R1
| |
HOH
45. For the given reaction; R — C — X ¾ ¾
¾® R — C — OH
| |
R2 R2
Which substrate will give maximum racemisation ?
CH 3 CH 3
| |
(a) C 6 H 5 — C — Br (b) CH 2 == CH — C — Br
| |
C 2H 5 C 2H 5
Br Br
(c) C6H5—C OCH3 (d) C6H5—C NO2
CH3 NH3
r
46. Which of the following compounds is most rapidly hydrolysed by S N1 mechanism ?

(a) C 6 H 5 Cl (b) Cl — CH 2 — CH == CH 2
(c) (C 6 H 5 ) 3 CCl (d) C 6 H 5 CH 2 Cl
47. Which will give white ppt. with AgNO 3 ?
(a) Cl (b) Cl
(c) CH2Cl (d) Both (a) and (c)

CH2—OH
( X ) HBr
48. ¾®; Value of ( X ) is:
¾¾¾
OH
(a) 1 (b) 2 (c) 3 (d) 4
49. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl
halides due to:
(a) The formation of less stable carbonium ion
(b) Resonance stabilization
(c) Longer carbon-halogen bond
(d) The inductive effect
D
50. The reaction products of: C 6 H 5 OCH 3 + HI ¾® is :
(a) C 6 H 5 OH + CH 3 I (b) C 6 H 5 I + CH 3 OH (c) C 6 H 5 CH 3 + HOI (d) C 6 H 6 + CH 3 OI
O
3 CH CH OH
2
S ¾¾¾¾¾®
O
O
OCH2CH3
(a) OCH2CH3
OCH2CH3
(b) (c) (d)

OCH2CH3
Neighbouring Group Participation and SNi
NBS HBr Mg
1. CH 3 — CH == CH 2 ¾ ¾
¾® (A) ¾ ¾® (B) ¾¾®(C )
ROOR
Product (C) is:
CH3
(a) (b) (c) (d) CH 3 CH 2 CH 2 MgBr
2. In the given reaction

OH
H
H NaOH
¾ ¾¾®[ X ], Product [ X ] is:
Cl 25°C

OH OH
OH H
(a) H (b) H
H OH
O
(c) Mixture of (a) and (b) (d) H

H
CH3
3. H OH ¾SOCl
¾¾2®( A). Product ( A) in:
Et
CH3 Et CH3
(a) H Cl (b) H Cl (c) Cl H (d)
Et CH3 Et
4. The reaction of SOCl 2 on alkanols to form alkyl chlorides gives good yields because:
(a) alkyl chlorides are immiscible with SOCl 2
(b) the other products of the reaction are gaseous and escape out
(c) alcohol and SOCl 2 are soluble in water
(d) the reaction does not occurs via intermediate formation of an alkyl chloro sulphite
5. In the given reaction:
.. * HOH
CH 3 — CH 2 — S— CH 2 — CH 2 — Br ¾ ¾ ¾®[ X ],[ X ] will be:
..
* *
(a) CH 3 — CH 2 — S — CH 2 — CH 2 — OH (b) CH 3 — CH 2 — S — CH 2 — CH 2 — OH
(c) 1 : 1 mixture of (a) and (b) (d) 2 : 1 mixture of (a) and (b)
CH2CH3
TsCl Cl–
CH3 OH
H
CH2CH3 CH2CH3
(a) CH3 Cl (b) CH3 OTs
H H

(c) Cl CH3 (d) TsO CH3 (e) CH3 OCl
H H H


CH2CH3
CH3 OH + TsCl ?
H
CH2CH3 CH2CH3
(a) CH3 Cl (b) CH3 OTs
H H

(c) Cl CH3 (d) TsO CH3 (e) CH3 OCl
H H H
Unimolecular Elimination Reactions ( E 1 )

1. How many alkenes are formed by E 2 elimination of HBr from 2-bromo-2,3-dimethylhexane
using a strong base such as sodium methoxide?
(a) 1 (b) 2 (c) 3 (d) 4
2. How many alkenes are formed by E 2 elimination of HBr from 3-bromo-3,4-dimethylhexane
using a strong base such as sodium methoxide?
(a) 2 (b) 3 (c) 4 (d) 5
3. How many alkenes are formed by E 1 elimination of HCl from 3-chloro-3,4-dimethylheptane in
methanol?
(a) 2 (b) 3 (c) 4 (d) 5
4. Which of the following is not reasonable for an elimination reaction?
NaOH
(a) Br ¾¾¾¾® (b) Br ¾¾¾¾®NaOEt
H2O EtOH
NaOH
(c) Br ¾¾¾¾® (d) Br NaI
¾¾¾¾®
H2O/EtOH

Cl
tBuOK, tBuOH
¾¾¾¾¾® ?
Heat
(a) (b) (c) (d) OtBu


tBuOK
¾¾¾® ?
tBuOH
Cl
(a) (b) (c) (d)

O
7. What is the major product formed in the following reaction?

CH2D
EtOH, NaOH
¾¾¾¾¾® ?
H O, Heat
2
Cl
CH2D
CH2D
CH2D CH2D
(a) (b) (c) (d)
OEt
8. The major product of the reaction of 1,2-dibromobutane and excess NaNH 2 is
(a) 2-bromo-1-butene (b) 1-bromo-1-butene
(c) 1-butyne (d) 1,2-butadiene
9. Which of the following dibromides would yield 2-butyne upon elimination?
Br
Br
Br
Br Br Br Br
Br
I II III IV
(a) III (b) II and III (c) II and IV (d) I
10. Identify the rate of dehydrohalogenation in the following compound when allowed to reacts
with alc. KOH:
Br
Br
(i) (ii) (iii) Br
(a) i > ii > iii (b) ii > i > iii (c) ii > iii > i (d) iii > ii > i


CH3
alcohol
CH2—C—CH3 + KOH ?
heat
Br
CH3 CH3 CH3
CH2—C—CH3 CH2—C == CH2 CH2—CH—CH2OH

I. II. III.
OH
CH3 CH3
CH—C—CH3 CH == C—CH3
IV. V.
OH H
12. What is/are the product(s) of the following reaction?

CH 3
|
CH 3 CH 2 O s + CH 3 CBr ¾®
¾ ?
|
CH 3
CH 3
|
(a) CH 3 CH 2 OC — CH 3 (b) CH 2 == CH 2
|
CH 3
(c) CH 3 C == CH 2 (d) (a) and (b) (e) (a) and (c)

|
CH 3
alcohol
CH 2 == CHCH 2 CHCH 3 + KOH ¾ ¾¾® ?
heat
|
Br
(a) H 2 C == CH — CH 2 — CH == CH 2 (b) CH 3 CH 2 CH 2 CHCH 3

|
OH

(c) H 2 C == CH — CH == CH — CH 3 (d) CH 2 == CHCHCH 2 CH 3

|
OH
(e) CH 2 — CHCH 2 CH 2 CH 2 OH
alc. KOH
14. CH 3 — CH 2 — CH — CH 3 ¾ ¾ ¾¾® X (major)
D
|
Br
(a) (b) (c) (d) None of these
Br
|
15. CH 3 — CH 2 — CH 2 — C — CH 3
|
CH 3
Identify all possible product obtained by E 2 reaction :
CH3
(a) CH 3 — CH 2 — CH 2 — C == CH 2 (b) CH 3 — CH 2 — CH == C
| CH3
CH 3
(c) Both (a) and (b) (d) None of these
Br
Zn
16. ¾¾® + ZnBr2
Br
This reaction is an example of :
(a) a-elimination (b) b-elimination (c) g-elimination (d) None of these
17. The major product obtained when following substrate is subjected to E 2 reaction will be:
Br
(a) (b) (c) Both (a) and (b) (d) None of these
18. The major product obtained when following substrate is subjected to E 2 reaction under the
treatment of potassium tert-butoxide will be:
CH3
Br
CH3
CH2 CH3
(a) (b)
CH3 CH3
(c) Both in equal proportions (d) None of these

CH3 CH3 CH3

19. (I) (II) (III)
Br Br Br
CH3
Ease of b-dehydrobromination among these substrates under the treatment of strong base will
be in the order as:
(a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I
Br
|
Alc. KOH
20. Major product of the reaction is CH 3 — C — CH 2 — CH 3 ¾ ¾ ¾¾® :
|
H
(a) Butene-1 (b) Butene-2 (c) Butane (d) Butyne-1
21. Which alkyl bromide will yield only one alkene upon E 2 elimination ?
Br
(a) (b) Br (c) (d)
Br
Br
22. Which alkyl bromide will yield 3-methyl-1-hexene as the major product upon treatment with
potassium t-butoxide in t-butyl alcohol (solvent) ?
Br
(a) (b) (c) (d)
Br
Br Br
23. In order to accomplish the following conversion, what reagent and conditions would be
required ?
?
¾¾®
Cl
(a) Cold sodium hydroxide (b) Hot conc. sodium hydroxide
(c) Potassium t-butoxide and heat (d) Hot water
Cl Cl Cl
24. , Among these which is most easily dehydrohalogenated ?
(I) (II) (III)
(a) I (b) II (c) III (d) All with same ease

25. In dehydrohalogenations, the base (alcoholic KOH) abstracts:
(a) The halides ion
(b) The proton present on the carbon next to the carbon to which the halogen is attached
(c) The proton present on the carbon to which the halogen is attached
(d) The proton on the a-carbon

26. The major product obtained when this substrate is subjected to E 2 reaction will be:
CH3
Cl
CH3 CH2 CH3
(a) (b) (c) (d) Both (a) and (c)
Br
|
27. CH 3 — CH 2 — CH 2 — C — CH 3
|
CH 3
Major product obtained when this alkyl halide is subjected to E 2 reaction under the treatment
of potassium tert-butoxide will be:
CH3
(a) CH 3 — CH 2 — CH == C (b) CH 3 — CH 2 — CH 2 — C == CH 2
CH3 |
CH 3
(c) Both (a)and (b) (d) Trans isomer
28. The major product obtained when following substrate is subjected to E 2 reaction will be:
CH3
Br
CH3
CH3 CH3
CH3 CH3 CH2
29. Which of the following isomeric hexachlorocyclohexanes is least reactive in
b-dehydrochlorination on treatment with strong base ?
Cl Cl
Cl Cl Cl Cl
(a) (b)
Cl Cl Cl Cl
Cl Cl
Cl
Cl Cl
(c) (d) All three are equally reactive

Cl Cl
Cl

30. Correct order of yield of Hofmann alkene in following reaction will be:
CH 3 CH 2 CHCH 3 X may be F, Cl, Br or I
|
X
(a) F > Cl >Br > I (b) I > Br> Cl > F (c) Cl > F > Br > I (d) I > Br > F > Cl
Br
H3C H
31. ¾® ? Product is:

¾
H CH3 -Br2
Br
H3C H H3C H
(a) (b)
H CH3 H3C H
(c) Both (a)and (b) (d) None of these

C6H5
CH3 H
alcoholic KOH
32. ¾ ¾ ¾ ¾¾® A
Br H E2
C6H5
CH3 C6H5 CH3 C6H5 H CH3

C C C
(a) (b) (c) (d) None is correct
C C C
H C6H5 C6H5 H C6H5 C6H5
Cl
H H alc. KOH
33. ¾ ¾ ¾¾®A. The structure of ‘ A’ is:
D D
H D H D H H H D
(a) D (b) D (c) D (d) D
alc. KOH EtONa

34. CH 3 — CH 2 — CH — CH 3 ¾ ¾ ¾¾® X ; CH 3 — CH 2 — CH — CH 3 ¾ ¾¾® Y
Major D Major
| |
Br NMe 3
r

Product ( X ) and (Y ) respectively is:

(a) 1-butene, trans-2-butene (b) 1-butene, cis-2-butene
(c) cis-2-butene, 1-butene (d) trans-2-butene, 1-butene
35. Debromination of meso-dibromobutane gives mainly:
(a) n-butane (b) 1-butene
(c) cis-2-butene (d) trans-2-butene
36. Identify the set of reagents/reaction-conditions ‘ X ’ and ‘ Y ’ in the following set of
transformation:
X Y
CH 3 ¾ CH 2 ¾ CH 2 Br ¾® Product ¾® CH 3 ¾ CH ¾ CH 3
½
Br
(a) X = dilute aqueous NaOH, 20°C; Y = HBr / CH 3 COOH, 20°C
(b) X = conc. alcoholic NaOH, 80°C; Y = HBr / CH 3 COOH
(c) X = dilute aqueous NaOH, 20°C; Y = Br 2 / CHCl 3 , 20°C
(d) X = conc. alcoholic NaOH, 80°C; Y = Br 2 / CHCl 3
37. Under certain conditions alkyl halides reacts with base to give an alkene and HCl (elimination
reaction). For example, RCH 2 ¾ CH 2 Cl ¾® R ¾ CH == CH 2 +HCl
The extent of these reaction depends on the structure of alkyl halides (e. g., primary, secondary
and tertiary). The relative extent to which such reactions take place is in the order (of halo
alkanes):
(a) p < s < t (b) p > s > t (c) p > s < t (d) p < s > t
HOs s
38. ¾¾® D (A) ; HO
¾¾® (B)
D
NMe3 Br
r
Relation between ( A) and ( B ) is:
(a) positional isomer (b) functional isomer
(c) chain isomer (d) mesomers
39. Correct order of yield of Hofmann alkene in following reaction will be:
CH 3 CH 2 CHCH 3 X may be, F,Cl ,Br or I
|
X
(a) F > Cl > Br > I (b) I > Br > Cl > F (c) Cl > F > Br > I (d) I > Br > F > Cl
Ph KOH
40. ¾¾¾® (A), A is:
EtOH
F
CH2 CH3 CH3
(a) Ph (b) Ph (c) Ph (d) Ph
OEt

CH 3
|
| | (c)
CH 3 CH 3
( a) (b)
Reactivity toward E 1 :
42. Cl ¾CH ONa

¾3 ¾
¾®( A)
D (50°C)
(a) S N1 (b) S N 2 (c) E 2 (d) E 1

NaNH 2
43. Ph — CH 2 — CH — CH 2 — CH 3 ¾ ¾ ¾®( A)
|
Br
Total number of elimination product are (includes stereoisomer):
(a) 2 (b) 4 (c) 6 (d) 8
Br
|
x NaNH CH 3 I
44. Ph — C — CH 3 ¾ ¾ ¾¾2®( A) ¾ ¾ ¾® Ph — C ºº C — CH 3
|
Br
Br y NaNH
2
¾¾¾¾®
Br
Sum of ( x + y = ?)
(a) 2 (b) 4 (c) 5 (d) 6
45. How many distinct alkene products are possible when the alkyl iodide below undergoes E 2
elimination? (Including stereoisomers)
CH3
CH3
I CH3
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5
46. Which of the following halides is most reactive in an E 2 reaction with sodium methoxide?
(a) (CH 3 ) 3 CCH 2 I (b) (CH 3 ) 2 CHCHICH 3
(c) (CH 3 ) 2 CHCH 2 Br (d) (CH 3 ) 2 CHCH 2 Cl (e) (CH 3 ) 2 CHCH 2 CH 2 Cl
47. Which of the following alkyl halides undergoes E 1 reactions with the fastest rate?
(a) CH 3 CHCH 3 (b) CH 3 CHCH 3
| |
F Cl

(c) CH 3 CHCH 3 (d) CH 3 CHCH 3 (e) CH 3 I

| |
Br I
48. Which of the following alkyl halides forms the most stable carbocation when it undergoes an
E 1 reaction?
Br
Br Br Br Br
(I) (II) (III) (IV) (V)

49. Why is the alkyl halide below not capable of undergoing an E 2 reaction upon treatment with
sodium ethoxide?
CH3
Br
CH3
(a)Br - is too poor a leaving group
(b)the substrate is too hindered
(c)too much angle strain would be present in the alkene product
(d)sodium ethoxide is a poor base to use in E 2 reactions
(e)the C—H and C—Br bonds which need to break cannot achieve an anti-periplanar
orientation
50. Which of the following compounds is/are the products of the reaction:
heat
H H + HO– ?
CH3 Br
(I) CH3 (II) CH3
(a) I only (b) II only

(c) I and II are of equal yield (d) I is major, II is minor (e) I is minor, II is major
51. Which of the following statements correctly describe(s) E 1 reactions of alkyl halides ( RX )?
I. Rate = k [base]
II. Rate = k [base][RX]
III. Rate = k [RX]
IV. The reactions occur in two distinct steps
V. Rearrangements are sometimes seen
(a) II and IV (b) III and V
(c) I, IV and V (d) I only (e) III, IV and V
CH3
–
52. r
OH
¾¾¾® Olefinic product.
NMe3 D
Olefinic product formed in the reaction is:

Et Et
53. alc. KOH

Cl HO ¾¾¾® (A), Product (A) is:
H H
OH O
(a) (b) O (c) (d)

Cl
D HCl
54. Br Cl ¾¾®
–OH
(A) ¾¾® (B), B is:
NMe3
+
Cl
(a) Br Cl (b) Br Cl
Cl
Cl
(c) Br Cl (d) Br Cl
OCl
55. Which of the following undergo fastest dehydrobromination?

Br Br
(a) (b)
Br Br
(c) (d)
Br
56. H ¾alc.
¾¾
KOH
¾® (A) ; Product (A) is:
D

(a) (b) No-reaction (c) (d) None
Cl
Cl
( X ) alc. KOH
57. ¾ ¾ ¾ ¾¾®
Cl
Cl
Moles of alc. KOH consumed are:
(a) 0 (b) 1 (c) 2 (d) 3
58. Ph — Br + Mg ¾® solvent used in the above reaction is:
(a) ethane (b) ethanol (c) diethyl ether (d) acid
Br
(X) NaNH2 s r
59. Ph—CH—CH2 ¾¾¾¾® Ph—CººC Na
(X = No. of moles of NaNH2)
Br
Value of X is:
(a) 1 (b) 2 (c) 3 (d) 4
CH2—CH2—Br CD2—CH2—Br
60. (I) (II) (III) CD 3 — CH 2 Br
Ease of b-dehydrobromination among these halides under the treatment of strong base will be
in the order as:
(a) I > II > III (b) III > II > I (c) III > I > II (d) II > III > I
Elimination Reaction E 2 /Hoffmann Exhaustive Methylation and Elimination

1. What is the major alkene formed in the following Hofmann elimination ?
CH3 CH3
r
Heat
CH3CH2CH2N CCH3 ¾¾® ?
CH3 CH3
(a) CH 3 CH == CH 2 (b) CH 3 — C — CH 3
||
CH 2
(c) CH 3 CH 2 CH == CH 2 (d) CH 3 CHCH == CH 2 (e) CH 3 CH 2 C == CH 2
| |
CH 3 CH 3

2. What is the major alkene formed in the following Hofmann elimination ?

CH3
s heat
r OH ¾¾® ?
N
CH3 CH3
CH3 CH3
(i) (ii)
N N
CH3 CH3 CH3 CH3
CH3 CH3
H OH
(iii) (iv) r (v) C == N
N N H
CH3 CH3 CH3 CH3

3. What is the product of the following reaction ?
CH3 OH
C == N
H
I
H OH
(i) CH C == N (ii)
3 N CH3
CH3 CH3
I
r r r
(iii) N (iv) N (v) N Is
CH3 I CH3 CH3 CH3 CH3
CH3 CH3 CH3

4. What is the major alkene formed in the following reaction ?
2 Ag O heat
r + ¾¾® ¾¾® ?
H2O
N
CH3 CH3 Is
CH3
(i) (ii)
(iii) (iv) (v)

KSH
5. R-2-chloro butane ¾ ¾
¾®
acetone
(a) S N1 (b) S N 2 (c) E 2 (d) E 1
6. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium
ethoxide.
(a) S N 2 and S N1 (b) E 1 and E 2
(c) S N 2 and E 2 (d) E 1 and S N1 (e) E 2 and S N1
7. What mechanism predominates in the reaction below?
NaCN
CH2CH3
Cl
(a) S N 2 (b) S N1 without rearrangement
(c) S N1 with rearrangement (d) E 2 (e) E 1
CH3OH, D
CH2CH3
Cl
NaOCH3, CH3OH
CH2CH3
Cl
CH 3
|
| | (c)
CH 3 CH 3
( a) (b)
Reactivity toward E 2 :

[B] Haloarenes
1. Which of the following is used as refrigerant?
(a) CO 2 (b) CHCl 3 (c) SiC (d) CF2 Cl 2
2. CCl 4 is used as fire extinguisher because:
(a) high melting point (b) due to covalent bond
(c) low boiling point (d) gives incombustable vapour
3. CCl 2 F2 destroy ozone by liberating:
(a) Cl 2 (b) F2 (c) NO 2 (d) All of these
4. Freons are:
(a) fluoro derivatives of ethylene (b) CCl 4 +CS 2
(c) chloro-fluoro derivatives of alkanes (d) chloro derivative of alkanes
5. Dipole moment is highest in:
(a) CHCl 3 (b) CH 4 (c) CHF3 (d) CCl 4
6. Boiling point of alkyl iodide, bromide, chloride and methane are in this order:
(a) Iodide > Bromide > Chloride > CH 4 (b) CH 4 > Chloride > Bromide > Iodide
(c) CH 4 > Iodide > Bromide > Chloride (d) Chloride > Bromide > Iodide > CH 4
7. What compound is obtained when ethanol is distilled with potassium bromide and
concentrated sulphuric acid?
(a) Ethyl hydrogen sulphate (b) Ethyl bromide
(c) Ethylene bromide (d) Acetylene dibromide
8. Which one of the following compounds does not react with bromine?
(a) Ethylamine (b) Propane (c) Phenol (d) Chloroform
9. In the given reaction :
Br
Br
C H ONa
2 5
¾¾ ¾¾®( P ),( P ) is:
C 2H 5OH
NO2
OC2H5 Br OC2H5 Br
Br OC2H5 OC2H5 Br
(a) (b) (c) (d)
NO2 NO2 NO2 OC2H5

10. Which of the following correctly ranks the aryl halides in decreasing order of reactivity toward
sodium methoxide in methanol ?
Slowest rate Fastest rate
Br F Br F
NO2
(a)
NO2 NO2 NO2 NO2
NO2 NO2
F Br F Br
NO2
(b)
NO2 NO2 O2N NO2
NO2 NO2
Br Br F F
NO2
(c)
NO2 O2N NO2 NO2
NO2 NO2
F Br Br F
NO2
(d)
O2N NO2 NO2 NO2
NO2 NO2
11. The reduction of benzoyl chloride with H 2 / Pd - BaSO 4 gives:
(a) C 6 H 5 CHO (b) C 6 H 5 CH 2 OH (c) C 6 H 5 COOH (d) C 6 H 5 CH 2 CN
12. In chlorobenzene, the —Cl group:
(a) Activates the benzene ring more via resonance effect than deactivating it via inductive
effect
(b) Deactivates the benzene ring more via inductive effect than activating in via resonance
effect
(c) Activates the benzene ring via resonance effect and deactivates it via inductive effect. Both
these effects are more evenly matched
(d) None of these

13. The chemical name of DDT is:

(a) Dichlorodinitrotoluene
(b) Dichlorodimethyltoluene
(c) p , p¢-dichlorodiphenyltrichloroethane
(d) None of these
14. Replacement of Cl of chlorobenzene to give phenol requires drastic conditions but chlorine of
2,4-dinitrochlorobenzene is readily replaced because:
(a) NO 2 makes the electron rich ring at ortho and para positions
(b) NO 2 withdraws electrons at metaposition
(c) NO 2 donate electrons at m-position
(d) NO 2 withdraws electrons at ortho and para positions
NO2
(1) –OH (1 equivalent)

15. ¾¾¾¾¾¾¾¾® (A)
(2) K3FeCN6
NO2
Organic product ( A) is:

NO2
NO2
(a) (b) NO2

HO NO2 OH
OH NO2
(c) (d) NO2
NO2 OH

Answers
[A] Haloalkanes
30. Biomolecular Nucleophilc Substitution (SN2 ) Reactions
1. (a) 2. (a) 3. (c) 4. (b) 5. (a) 6. (c) 7. (b) 8. (c) 9. (a) 10. (c)
11. (b) 12. (b) 13. (c) 14. (b) 15. (c) 16. (a) 17. (a) 18. (c) 19. (c) 20. (a)
21. (b) 22. (b) 23. (d) 24. (a) 25. (d) 26. (a) 27. (b) 28. (c) 29. (b) 30. (d)
31. (b) 32. (e) 33. (d) 34. (e) 35. (b) 36. (d) 37. (c) 38. (c) 39. (d) 40. (b)
41. (c) 42. (c) 43. (e) 44. (a) 45. (b) 46. (d) 47. (c) 48. (a) 49. (b) 50. (c)
51. (c)
Unimolecular Nucleophilic Substitution (SN1 ) Reactions

1. (c) 2. (d) 3. (c) 4. (a) 5. (d) 6. (c) 7. (a) 8. (c) 9. (c) 10. (d)
11. (a) 12. (a) 13. (a) 14. (b) 15. (c) 16. (a) 17. (b) 18. (c) 19. (a) 20. (b)
21. (c) 22. (c) 23. (d) 24. (c) 25. (e) 26. (b) 27. (b) 28. (a) 29. (c) 30. (a)
31. (c) 32. (a) 33. (a) 34. (b) 35. (c) 36. (a) 37. (d) 38. (d) 39. (b) 40. (a)
41. (c) 42. (c) 43. (c) 44. (c) 45. (c) 46. (c) 47. (d) 48. (a) 49. (b) 50. (a)
51. (a)
Neighbouring Group Participation and SNi

1. (b) 2. (d) 3. (a) 4. (b) 5. (c) 6. (c) 7. (b)
Unimolecular Elimination Reactions (E 1 )

1. (b) 2. (d) 3. (d) 4. (d) 5. (a) 6. (b) 7. (a) 8. (c) 9. (b) 10. (a)
11. (e) 12. (c) 13. (c) 14. (a) 15. (c) 16. (b) 17. (b) 18. (a) 19. (d) 20. (b)
21. (b) 22. (d) 23. (c) 24. (a) 25. (b) 26. (a) 27. (b) 28. (a) 29. (b) 30. (a)
31. (a) 32. (a) 33. (c) 34. (d) 35. (d) 36. (b) 37. (a) 38. (a) 39. (a) 40. (c)
41. (a) 42. (b) 43. (b) 44. (c) 45. (e) 46. (b) 47. (d) 48. (d) 49. (e) 50. (e)
51. (e) 52. (a) 53. (c) 54. (c) 55. (c) 56. (a) 57. (c) 58. (c) 59. (c) 60. (a)
Elimination Reaction E 2 / Hoffmann Exhaustive Methylation and Elimination

1. (b) 2. (c) 3. (e) 4. (c) 5. (b) 6. (c) 7. (a) 8. (e) 9. (d) 10. (a)
[B] Haloarenes
1. (d) 2. (d) 3. (b) 4. (c) 5. (c) 6. (a) 7. (b) 8. (d) 9. (a) 10. (c)
11. (a) 12. (c) 13. (c) 14. (d) 15. (b)

1. Which of the following compounds will not undergo S N 2 reaction?

Cl Cl
(a) (b) (c) H 2 C == CH — Cl (d)
Cl
2. In which of the following reactions S N1 reaction takes place?
CH3
H2O H2O
(a) CH 3
I ¾® (b) Ph—CH—Br ¾®
CH3 CH3
2 H O 2 H O
(c) Ph — Br ¾ ¾
¾ ® (d) CH 3 — Br ¾ ¾
¾ ®
3. In which of the following reaction neither S N1 nor S N 2 take place ?
Cl
(a) (b) H 2 C == CH — Cl (c) (d) CH 3 — Cl

Cl
4. Which of the following compounds will not undergo nucleophilic substitution reaction?
Cl Cl Br
(a) (b) Cl (c) (d)
Br
rs
KSH
5. ¾¾¾® Correct statement regarding given reaction will be:
(a) above reaction is S N 2

(b) inversion of configuration takes place during given reaction
(c) bimolecular reaction
(d) second order reaction
6. Rate of S N 2 will be negligible in:
Br Br Br Br
(a) (b) (c) (d)

7. S N1 and S N 2 product are same in (excluding stereoisomer):

Cl
H
(a) (b)
Cl
(c) (d) Ph — CH — CH — CH 3
| |
Cl CH 3 Cl
PCl
¾5®
8. CH 3 — CH 2 — O — CH 3 ¾ ¾
Products are:
Cl
(a) CH 3 — Cl (b) Et — Cl (c) Cl (d)
Cl
moist Ag O
2
9. ¾ ¾¾¾
¾ ® Product; product of the reaction is:
S
N1
OH OH
(a) (b) (c) OH (d)

OH
10. Which of the following will give yellow precipitate with I 2 / NaOH ?
(a) ICH 2 COCH 2 CH 3 (b) CH 3 COOCOCH 3
(c) CH 3 CONH 2 (d) CH 3 CH(OH)CH 2 CH 3
CH 3
|
11. Given rate of reaction is observed CH 3 — C — Br > CH 3 — CH — Br > CH 3 — CH 2 — Br , for:
| |
CH 3 CH 3
(a) E 1 reaction (b) E 2 reaction (c) S N 2 reaction (d) S N1 reaction
12. In which of the following reaction Diastereomer isomer will formed ?
Cl Cl
KOH t- BuOs K r
(a) ¾¾
¾® (b) ¾ ¾¾¾
¾®
D D
Cl
NaNH alc. KOH

(c) ¾2®
¾ ¾¾ (d) ¾ ¾¾¾®
D Cl D

CH 3
|
13. CH 3 — C — Br CH 3 — CH — Br CH 3 — CH 3 — Br
| |
CH 3 CH 3
( a) ( b) ( c)
Correct statement is:
(a) rate of S N1 a > b > c (b) rate of S N 2 a > b > c
(c) rate of E 2 a > b > c (d) rate of E 1 a > b > c
14. Which of the following is/are polar aprotic solvent?
O
O
S
(a) (b) CH3 CH3 (c) CH 3 — O — Et (d) CH 4
CH3 CH3
15. In which of the following reactions inversion of configuration will take place?
I H
CH3
sr rs
(a) H O K + CH3 — I ¾® (b) KSH + ¾®
Et
(c) KSH + R - 2 - chlorobutane ¾®

¾ (d) KCN + CH 3 — Cl ¾®
¾
16. Which of the following is/are bimolecular reaction?
(a) S N1 (b) S N 2 (c) E 1 (d) E 2
Answers
1. (a, c, d) 2. (a, b) 3. (a, b, c) 4. (a, b, d) 5. (a, b, c, d) 6. (a, b, c)

7. (b, c) 8. (a, b) 9. (a) 10. (a, d) 11. (a, b, d) 12. (a,d)
13. (a, c, d) 14. (a, b, c) 15. (a, c) 16. (b, d)

Passage-1:
Nucleophilic aromatic substitution:
LG LG Y
: Ys
¾¾¾® Y ¾¾¾® + :L.Gs
slow fast
s
X X X
Step-1 Step-2
The species that adds to the aromatic ring in step-1 needs to be a nucleophile
such as methoxide (CH 3 O s ) instead of an electrophile such as nitronium ion
(NO 2+ ).
Step-1 will be facilitated by electron withdrawing rather than electron
donating substituents. Substituents that are deactivating in electrophilic
aromatic substitution are activating in nucleophilic aromatic substitution.
The effect is most pronounced for strongly electron-withdrawing group ortho
and/or para to the leaving group.
-In order of step-2 to occur, the pair of electrons bonding the leaving group to
the ring are lost with the leaving group, rather than becoming part of the ring's
p system.
F OMe
e.g. + NaOME ¾¾® + NaF
NO2 NO2
X OCH3
s r
CH ONa
1. 3
¾¾¾®
NO2 NO2
Above reaction has maximum rate when:
(a) X = -I (b) X = -Br (c) X = -Cl (d) X = -F

M.A. CH ONa
2. ¾®( A) ¾ ¾3 ¾
¾¾ ¾®( B ), Product ( B ) is:
D
F
F OCH3 F OCH3
NO2 NO2 OCH3 F
(a) (b) (c) (d)
OCH3 F F F
3. Which of the following compounds is most reactive towards ArS N 2 reaction ?
Cl Cl
Cl Cl
NO2 NO2
(a) (b) (c) (d)
NO2
NO2 NO2
Passage-2:
The halogens, Br2 and Cl 2 , add to alkanes. When the p electrons of the alkene
approach a molecule of Br2 or Cl 2 , one of the halogen atoms accepts them and
releases the shared electrons to the other halogen atom. Therefore, in an
electrophilic addition reaction, Br2 behaves as if it were Br + and Br - , and Cl 2
behaves as if it were Cl + and Cl - .
+
Br
H2C == CH2 + Br—Br ¾® H2C — CH2 + Br ¾® BrCH2CH2Br
1,2-dibromoethane
a vicinal dibromide
a bromonium ion
Br
1. cis-2-butene ¾¾2®
CCl 4
How many products will obtained in this reaction ?

(a) 1 (b) 2 (c) 3 (d) 4
I- Br
2. CH 3 — CH == CH 2 ¾ ¾¾® Product (A) is :
Br I I Br
(a) (b) (c) (d)
I Z Br Br
Br2
3. ( x) ¾¾®( y) products (including stereoisomer) sum of x + y = :
isomer of CCl 4
butene
(a) 8 (b) 9 (c) 10 (d) 11
Passage-3:
E 2 reaction ® Elimination bimolecular
In the general mechanism of the E 2 reaction a strong base abstract a proton
on a carbon atom adjacent to the one of the leaving group. As the base
abstracts a proton, a double bond forms and the leaving group leaves.
H CH3
CH3ONa
CH3—CH2—CH—CH3 ¾¾¾¾® CH3OH
+ +
CH3 H
Br (major)
Mechanism:
+
+
ds
H CH3O H
s
CH3ONa + CH3—CH—CH—CH3 ¾® CH3—CH—CH—CH3 ¾®
(trans-2-butene)
Br Br
anti-coplanar transition state
(staggered conformation
-lower energy)
1. Give the order of reaction rate with alc. KOH:

(i) Br (ii) Br (iii) Br
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii) (c) (iii) > (ii) > (i) (d) (iii) > (i) > (ii)
2. How many isomer of C 4 H 9 Br when reacts with NaNH 2 , diastereomers will form? (excluding
stereoisomer)
(a) 0 (b) 1 (c) 2 (d) 3
O Cl
x PCl
5 2 y NaNH
3 CH I
3. ¾¾® ¾¾¾® ¾¾®
O
CººC—CH3
Sum of x + y :
(a) 4 (b) 6 (c) 3 (d) 2
Passage-4:
These problems differ from those in earlier chapters in that they directly test
your knowledge of core material rather than using a descriptive passage to
extend the material or introduce new ideas. The number of factors that
contribute to nucleophilic substitution can be daunting. The really major
ones, though, are few and readily applied to specific by using the S N1 and S N 2
mechanisms to guide your analysis.

1. Which compound undergoes substitution by the S N1 mechanism at the fastest rate ?

Br
Br
(a) (b)
Br
(c) (d)
Br
2. Which compound undergoes substitution by the S N 2 mechanism at the fastest rate ?
Br
Br
(a) (b)
Br
(c) (d)
Br
3. Which reaction takes place at the fastest rate ?
Ethanol, 25°C
(a) CH 3 CH 2 CH 2 CH 2 Cl + NaSH ¾ ¾ ¾ ¾¾® CH 3 CH 2 CH 2 CH 2 SH + NaCl
Ethanol, 25°C
(b) CH 3 CH 2 CH 2 CH 2 Cl + NaSH ¾ ¾ ¾ ¾¾® CH 3 CH 2 CH == CH 2 +NaCl+H 2 S
Ethanol, 25°C
(c) CH 3 CH 2 CH 2 CH 2 Br + NaSH ¾ ¾ ¾ ¾¾® CH 3 CH 2 CH 2 CH 2 SH + NaBr
Ethanol, 25°C
(d) CH 3 CH 2 CH 2 CH 2 Br + NaSH ¾ ¾ ¾ ¾¾® CH 3 CH 2 CH == CH 2 + NaBr + H 2 S
4. Identify the mechanism most responsible for the major product in the following reaction.
Br
NaOCH CH
2 3
¾¾¾¾ ¾
¾ ®
Ethanol, 50°C
(a) S N1 (b) S N 2 (c) E 1 (d) E 2
CH3
H Br NaCN
5. ¾ ¾ ¾ ¾®; Which is the major product of the reaction shown ?
H3C H DMSO, 25°C
CH2CH3
CH3 CH3 CH3 CH3
H CN NC H H CN NC H
(a) (b) (c) H CH3 (d)
H3C H H3C H H CH3
CH2CH3 CH2CH3 CH2CH3 CH2CH3


1. Match the Column:
Column-I Column-II
CH2—Cl
(a) (p) Nucleophilic-aromatic substitution reaction
Cl
(b) (q) Elimination reaction
F
(c) (r) S N1 reaction
NO2
Cl
(d) (s) S N 2 reaction

Column-I (Primary alkyl bromide) Column-II (S relative rate)
N2
(a) CH 3 — CH 2 — Br (p) 10 -5
(b) Me — CH 2 — CH 2 — Br (q) 10 -2
(c) Me — CH — CH 2 — Br (r) 0.8

|
Me
Me
|
Me — C — CH 2 — Br (s) 1
(d)
|
Me


Substrate E 2 elimination SN2 -substitution
(a) CH 3 — CH 2 — Br (p) 1 (w) »0

(b) (CH 3 ) 2 CH — Br (q) 80 (x) 20
(c) (CH 3 ) 3 CBr (r) 100 (y) 90

Column-I (Compound) Column-II (Relative solvalysis rate in aqueous acetone)
Cl
(a) (p) 172
Cl
(q) 157
(b)
Cl
(c) (r) 178
Cl
(d) (s) 1
CH3

Column-I (Reaction) Column-II (Relative rate of reaction)
(a) HO r + R — CH 2 — I ¾® (p) 1
(b) HO s + R — CH 2 — Br ¾® (q) 200
(c) HO s + R — CH 2 — Cl ¾® (r) 10,000
(d) HO s + R — CH 2 — F ¾® (s) 30,000

6. Match the column-I with column-II for given S N 2 reaction and select the correct answer from
the codes given below:
Z — CH Br + CH O s ¾® Z — CH — OCH + Br s
2 3 2 3
Column-I Column-II (Relative reactivity)
(a) H— (p) 0.1
(b) CH 3 — (q) 3
(c) C 2H 5 — (r) 1
CH3 (s) 100
(d) CH—
CH3
7. Match the column-I with column-II (no. of structural isomers produced in b-E 2 elimination)
and select the correct answer:
Column-I Column-II
H3C Br
H3C CH3
(a) CH3 (p) Three
Br
(b) H3C CH3 (q) Zero

CH3
Br
H3C
(c) H3C (r) One

CH3 CH3
CH3
(d) H3C (s) Two

Br
CH3


Column-I Column-II
Cl (p) Undergo S N Ar (Nucleophilic aromatic
s
(a) substitution) with CH 3 O
Cl (q) Undergo S N1 reaction with H 2 O
(b)
NO2
F (r) Undergo S N 2 reaction with aq. KOH

NO2
(c)
NO2
Cl (s) Undergo E 2 reaction with alc. KOH

Cl
(d)
NO2
(t) Undergo E 1 reaction with EtOH on strong

heating
Column-I Column-II No. of possible products
E 2 reaction (elimination bimolecules) (including stereoisomerism)
(a) Br (p) 0
alc. KOH
¾ ¾ ¾¾®
D
(b) alc. KOH (q) 1

¾ ¾ ¾¾®
Br
(c) alc. KOH (r) 2
Br ¾ ¾ ¾¾®
D
(d) Br alc. KOH (s) 3

¾ ¾ ¾¾®
D


Column-I Column-II
(a) aq. KOH

¾¾¾® (p) Hard base (strong base)
Br
(b) alc. KOH

¾ ¾ ¾¾® (q) Soft base (weak base)
Br
(c) Br (r) S N 2 reaction
aq. KOH
¾¾¾
¾®
(d) alc. KOH (s) E 2 reaction

¾ ¾ ¾¾®
Br

Column-I Column-II
HNO3
NO2
(a) ¾¾¾¾® (p) Substitution reaction
H2SO4
Cl2
Cl
(b) ¾¾¾® (q) Addition reaction
AlCl3
F OCH3
r
CH3O
(c) ¾¾¾® (r) Carbocation is intermediate
D
NO2 NO2
Br
HBr
(d) ¾¾¾®
CCl (s) Carbanion is intermediate
4
H

12. Match the Column:

Column-I Column-II
H2O
(a) Cl ¾¾¾® OH (p) Substitution reaction
Br OH
(b) Moist Ag O
2
(q) Elimination reaction
¾¾¾¾®
Br
(c) NaNH
2 (r) Carbocation is intermediate
¾¾¾¾®
D
Br SH
(d) KSH (s) Carbanion is intermediate

¾¾¾®

1.
A to Z (Learning Chart)
MgBr
CH3
r
Haloalkanes and Haloarenes
Cl Cu H3O NaOH
S T 300°C
U V D
W CaO, D
OH s Et) 2
CO 2
D3Or CH( SOCl2
H+ HBr Na NH3 KOBr

D
A B C X Y Z
CCl4 dry Ether D
O
2
/H Br2/CCl4 Mg O
Br 2
D+E Cl—C—O—Et (1) PhMgBr (excess)
Na H I J
O Ether
G (2) H+
Mg Ether
CO2
CH3MgBr
F
H+
CH3—Li(excess)
O CH3 O
+
(1) Al(Mg) H (1) CH3MgBr
C—CH3 K C— C — CH3 L

(2) H2O D (2) NH4Cl
D
H+
(1) CH3MgBr
(2) H+
M
O+ P N Q+R
(2) H+
309
2. Determine whether a substitution reaction will take place by an S N1 or an S N 2 pathway.
S.No. SN1 SN2 No reaction
CH 3
|
H 2O
1. CH 3 — C — Br ¾ ¾
¾®
|
CH 3
Br
2. HO -
¾¾
¾®
Br
3. I-
¾
¾®
HO -
4. CH 3 — Br ¾ ¾
¾®
3 H O+
5. Ph — O — CH 3 ¾ ¾¾®
6. 3H O+
Ph — O ¾¾¾®
O 3 H O+
7. ¾¾¾®
+
8. Ph—O CH3 ¾H¾
3O
¾®
HI
9. O—CH3 ¾¾®
HI
10. Ph — O — CH 3 ¾¾®
CH 3
|
H— I
11. CH 3 — C — OH ¾ ¾
¾®
|
CH 3
OEt
H O+
3
12. ¾¾¾®
OEt

13. 3 H O+
Ph — O — Ph ¾ ¾¾®
H O+
3
¾¾¾®
14.
Br
I OH -
15. ¾¾
¾®
I
16. ¾¾
¾®
H 2O
CH2CH3
17. C + CH3O–
CH3 H high concentration
Br
CH2CH3
18. C + CH3OH
CH3 H
Br
Br
19. 2
¾¾¾¾
¾
Moist Ag O
®
CH 3 CH 2 CHCH 3 + HO -
high concentration
20. |
Cl
CH 3 CH 2 CHCH 3 + H 2 O
21. |
I
CH2CH3
22. C + CH3CH2CH2Os
CH3 H high concentration
Br
CH2CH2CH3
23. C + EtOH
CH3 H
Cl

H
CH3
24. + CH3O–
Cl high concentration
H
H
CH3
25. + CH3OH
Cl
H
3.
S.No. Compound SN1 + E1 (Total products) (including Stereoisomer)
EtOH
(i) ¾¾
¾®
Br
(ii) Cl
EtOH
¾¾
¾®
(iii) Br
(iv)
Br
(v) H
CH3 Br
(vi) Br
(vii) Cl
(viii) Br
(ix) Br

1. X = The number of compounds do not show S N 2 .
CH2–Br Br Cl
Cl
1. 2. 3. 4.
Cl F
5. 6. 7. 8.
Cl Cl
Cl Cl
9. 10.
CH2–CH2–CH2Br
11.
NH2
2. X = number of compound which are more basic than
NH2
O
||
(a) (b) R — C — NH 2 (c) R — C — NH (d) NH 2 — C — NH
| |
NH 2 NH 2
NH2 NH2
CH2–NH2
(e) (f) (g)
NO2 CH3

3.
Compare rate Compare rate

S.No. Compound
of S 2 of S 1
N N
1.
2.
3.
4.
5.
6.
7.
8.
9.
10. CH3 – O – CH2 – Br CH3 – CH2 – CH2 – Br
11.
12.

4. Type of mechanism & more reactive reactant is:

NaI
(1) Br or Cl acetone
C
NaCN
(2) C—C—C—C or C—C—C—C—C—Cl
DMSO
Cl
Cl
NaN3
(3) or C—C —C—C—C—C—Cl
ethanol
C C
or EtOH
(4) C—C —C—Br C—C—Br
C C
H 2O
(5) Iso-butyl bromide or sec-butyl bromide
sr
CH2–Cl Ph–SNa
(6) or
Cl
aq.KOH
(7) CH3 – I or CH3 – Br
EtOH
(8) or
Br Br
KSH
or Br acetone
(9) Br
Ph CH3
(10) Ph – C – Br or CH 3 – C – Br EtOH
Ph CH3

5. Identify the missing structure in each reaction ?
S.No.
Cl
15%NaOH
1. 160ºC
NO2
Cl
O 2N NO2
H2O
2. (A) acid
NO2
Br
NO2 s
CH3O
3.
NO2
Br
NO2
s
4. CHO
3
Br
Br
NO2 s
CH3—CH2—NH2 HO
5. (A) (B)
NO2
F OH
s s
HO HO
6. (A)
Stable
intermediate
NO2 NO2
F
KOH/ D
7.
NO2

NO2
KOH/ D
8.
Br
Br
CH3
KNH2
9. (A)
liq.NH3
(major)
Cl
OCH3
Cl
10. KNH2
(B)
liq.NH3 (major)
Br
sr
CH3ONa
6. (A)
NO2
Energy profile diagram of given reaction is:
7. Identify major product and type of reaction (S N1 S N 2 E 1 E 2 ).
S.No. Reaction S.No. Reaction

Cl
NaNH2
Alc.KOH
1. 2. Br
sr CH2–Cl
t-BuOK s
CHO3
3. 4.
Br

CH3 Cl
H D KSH
NaI
H Cl
5. acetone
6. H D
Et CH3
Br
Cl s
Ph–S
KCN
7. D 8.
Br
r
NMe3 F
s s
9. EtO 10. EtO
D D
Br
H2 O
11. Br 12. H2 O
Br EtOH
13. EtOH 14. D
D
EtOH Br
D
NaI
Br acetone
15. s 16.
EtO Br
D

Br Br
NaI aq.KOH
17. acetone 18.
Br Ph
H2O
alc.KOH Ph – C – Et
19. 20.
Br
H2SO4 H2SO4
21. OH D 22. OH
D
CH2–OH
PBr3
Pyridine
23.

Answers

Passage-1: 1. (d) 2. (b) 3. (c)
Passage-2: 1. (b) 2. (a) 3. (c)
Passage-3: 1. (a) 2. (b) 3. (b)
Passage-4: 1. (d) 2. (a) 3. (c) 4. (d) 5. (b)

1. (a)® r, s; (b)® q, r,s; (c)® p; (d)® q,r
2. (a) ® s; (b) ® r; (c) ® q; (d) ® p
3. (a) ® p , y ; (b) ® q , x; (c) ® r , w
4. (a) ® s; (b) ® q; (c) ® p; (d) ® r
5. (a) ® s; (b) ® r; (c) ® q; (d) ® p
6. (a) ® s; (b) ® q; (c) ® r; (d) ® p
7. (a) ® s; (b) ® r; (c) ® p; (d) ® q
8. (a) ® q, r, s, t ; (b) ® p ; (c) ® p ; (d) ® p, q, r, s, t
9. (a) ® s; (b) ® r; (c) ® q; (d) ® p
10. (a) ® q, r; (b) ® p, s; (c) ® q, r; (d) ® p, s
11. (a)® p, r; (b)® p, r; (c)® p, s; (d)® q, r
12. (a)® p, r; (b)® p, r; (c)® q; (d)® p
Multi Concept Subjective Problems:

1.
Br Br
Br
(A) (B) (C) (D)
Br OH MgBr
Br Br
(E) (F) (G) (H)

O OH
OH OH
(I) —C—OEt (J) —C—Ph (K)
Ph
CH3 OH CH3 OH O
(L) (M) (N) (O)
(P) MgBr (Q) (R) 2MeMgBr

O—Me
D
OD
(S) (T) D Cl (U) D D
O
COOEt
(V) (W) CH2—C—OH
COOEt
O O
(X) CH2—C—Cl (Y) CH2—C—NH2
(Z) CH2—NH2+CO2

2.
S.No. SN1 SN2 No reaction S.No. SN1 SN2 No reaction
1. ✓ 2. ✓
3. ✓ 4. ✓
5. ✓ 6. ✓
7. ✓ 8. ✓
9. ✓ 10. ✓
11. ✓ 12. ✓
13. ✓ 14. ✓
15. ✓ 16. ✓
17. ✓ 18. ✓
19. ✓ 20. ✓
21. ✓ 22. ✓
23. ✓ 24. ✓
25. ✓
3.
(i) S N1 ® 3; E1 ® 2 + 1 (ii) S N1 ® 1; E 1 ® 2
(iii) S N1 ® 3; E1 ® 3 (iv) S N1 ® 2; E1 ® 3
(v) S N1 ® 4; E1 ® 3 (vi) S N1 ® 4; E1 ® 7
(vii) S N1 ® 2; E1 ® 4 (viii) S N1 ® 1; E 1 ® 2
(ix) S N1 ® 2; E1 ® 5
Unified Conceptual Problems:

1. x = 5(2 , 3 , 6 , 8 , 9)
2. x = 5( a , c , d , f , g)
3.
1. a > b; a > b 2. a > b; b > a 3. b > a; b > a
4. a > b; b > a 5. a > b; a > b 6. a > b; a > b

7. a > b; a > b 8. b > a; b > a 9. a > b; b > a

10. a > b; a > b 11. b > a; b > a 12. b > a; b > a
4.
1. SN2, Br 2. S N 2 ,C — C — C — C — C — Cl
Cl
C
|
3. SN1, 4. S N1 , C — C — Br 5. S N1 , C — C — C — Br
| |
C C
SN2, CH2—Cl
6. 7. S N 2 , CH 3 I
Ph
Br |
8. SN1, 9. SN2, Br 10. S N1 , Ph — C — Br
|
Ph
5.
OH
OH OCH3
O2N NO2
NO2
1. 2. 3.
NO2
NO2 NO2
(picric acid)
OCH3 NH2–CH2–CH3 NH–CH2–CH3

NO2 NO2 NO2
4. 5. A= ,B=
Br NO2 NO2

NO2 CH3
F OH
OH
6. 7. 8. 9.
NO2 Br NH2
N OH
O O
OCH3
10.
NH2
Energy
Br OCH3
intermediate
6. DH=–ve R intermediate is
P NO2
Reaction coordinate
7.
, (E2) , (E2) , (E2)

1. 2. 3.
Me
OCH3
4. , (SN2) 5. I H ,(S 2 )
N
Et
SH S–Ph
D H
6. 7. ,S N
2
H D ,(S N
2 )
CH3

CN
, (E2) , (E2)
8. , (SN2) 9. 10.
Br
HO
OH
11. , (SN1) 12. , (SN1) 13. (E1)
,
14. 15.
(E1) (E1) (E2 )
I OH
, (E2) , (SN ) 2 , (SN2)
16. 17. 18.
Ph OH
, (E2)
19. 20. 21. , (E1)
Ph , (SN1)
, (E 1) Br
22. 23. , (SN2)

4
Alcohols, Phenols
and Ethers
[A] Alcohols
1. Which of the following is a secondary alcohol?
OH
H
(a) OH (b) CH3 (c) OH (d) CH 3 OH
CH3

OH
SOCl2
¾¾¾¾® ?
Pyridine
Cl Cl
(a) + enantiomer (b) Cl
Cl
(c) + (d) optically active
3. What is the major product formed in the following synthesis?

OH 1.PBr 3
2.CH 3COONa
¾¾¾¾¾® ?
CH3COOH

Alcohols, Phenols and Ethers 327
OCOCH3
(a) O (b)
Br
(c) (d) +
4. Which is not a likely product formed when the following alcohol is treated with sulfuric acid?
OH
(a) (b) (c) (d)
5. What are the products of the following reaction?

KMnO
4
¾¾¾¾® Product + Enantiomer
Cold
NaOH, H2O
OH H HO
(a) (b) (c) (d)
OH HO OH OH

OH
CrO , HCl, pyridine
OH 3
¾¾¾¾¾¾¾¾® ?
O O
OH
(a) (b) OH
O
O
OH
(c) (d)
OH O
7. How many compounds with molecular formula C 5 H 10 O may be reduced with NaBH 4 to a
primary alcohol?
(a) 2 (b) 3 (c) 4 (d) 5
8. Which of the following compounds gives 3-methyl-2-butanol upon reduction with LiAlH 4 ?
H O
O O O O
a b c d
(a) a (b) b (c) c (d) d

9. Which of the following products is formed in good yield by the reduction of methyl
4-oxo-hexanoate (M) with LiAlH 4 in ether?
O
O
O M
(a) 6-Methoxy-3-hexanone (b) 1,4-Hexanediol
(c) Methyl 4-hydroxyhexanoate (d) 4-Hydroxyhexanal
4 2 NaBH , H O
O ¾¾¾¾¾¾® ?
(a) O (b) OH
+ enantiomer
(c) OH (d) None of these
11. What are the major products of the following reaction?

O
OH
1.LiAlH 4,Et 2O
¾¾¾¾¾¾® ?
2. H2O, H2SO4
O
O OH OH
OH
(a) +enantiomer (b) OH + OH
OH OH OH OH
OH OH OH OH
(c) + (d) +
O O
12. Predict the product of the following reaction. CH 3 COOH + NaBH 4 ¾®
(a) CH 3 CHO (b) CH 3 CH 2 OH (c) CH 3 CH 3 (d) no reaction
13. Which of the following compounds does not give a tertiary alcohol upon reaction with
methylmagnesium bromide?
(a) 3-methylpentanal (b) ethyl benzoate
(c) 4,4-dimethylcyclohexanone (d) 4-heptanone
14. Which of the following compounds gives a secondary alcohol upon reaction with
methylmagnesium bromide? Assume the usual acid workup.
(a) butyl formate (b) 3-pentanone (c) pentanal (d) methyl butanoate

15. Which of the following compounds is not oxidized by pyridinium chlorochromate (PCC)?
(a) 2-methyl-2-butanol (b) 1-pentanol
(c) 2-pentanol (d) 1,3-propanediol
O
1. NaBH4, MeOH
2. Dilute acid, heat
O OH ¾¾¾¾¾¾¾® ?
O
O
O O
(a) OH (b) (c) (d)
17. Which of the following is an allylic alcohol?

(a) CH 2 == CHCH 2 OCH 3 (b) CH 2 == CHCH 2 CH 3
(c) HOCH == CHCH 2 CH 3 (d) CH 3 CH == CHCH 2 OH (e) CH 2 == CHCH 2 CH 2 OH
OH CrO 3 /H 2SO 4 NaCN /HCl
¾ ¾¾¾¾® ¾ ¾¾¾ ¾® Major product
O O O CN OH
Cl
(a) NC (b) (c) (d)
CN
OH
19. Identify which of the compound having 2° alcohol ?
(a) OH (b) OH (c) (d)

OH
OH
20. Identify 2° alcohol in the given following alcohols:

OH OH
(a) HO (b) (c) (d) None of these
21. Which of the following is /are 1º alcohol?

OH
OH
OH
(a) (b) (c) (d) OH
22. Which of the following is sec-butyl alcohol?

(a) CH 3 CH 2 CH 2 CH 2 OH (b) CH 3 CH(OH)CH 2 CH 3
(c) (CH 3 ) 2 CHCH 2 OH (d) (CH 3 ) 2 CHOH

23. The isomeric alcohol which has a chiral carbon atom is:
(a) n-butyl alcohol (b) iso-butyl alcohol (c) sec-butyl alcohol (d) tert-butyl alcohol
OH
2H SO
4 cold. KMnO
24. ¾ ¾¾ ®( A) ¾ ¾¾¾¾4®( B ). Product ( B ) is:
D
(a) diastereomer (b) meso

(c) racemic (d) geometrical isomer
r
H
25. (A) ¾¾®
D
Structure of (A) is:
(a) (b) (c) OH (d) all of these

OH OH
r
H
26. (A) ¾¾®
D ; Structure of (A) is:
(a) (b) (c) (d) all of these

OH OH OH
CH2—OH H
r
27. ¾¾® (A) ; Product (A) is:
D
(a) (b) (c) (d)
CH2—OH
H+
28. ¾® (A) ; Product ( A) is:
¾¾
D
CH3
(a) (b) (c) (d)
29. Best method to convert alcohol to halide is:

(a) ROH + SOCl 2 ¾® R — Cl + SO 2 + HCl (b) R — OH + PCl 3 ¾® R — Cl
(c) R — OH + PCl 5 ¾® R — Cl (d) R — OH + HCl ¾® R — Cl + H 2 O
CH3
Conc. H SO
2 4
30. In the given reaction ¾ ¾¾¾¾ ® A. The product A is:
OH
CH3 CH3
(a) (b)
O CH3 CH3
CH3
CH3
(c) (d) CH3
COOCH3
O
31. Which of the following is most reactive towards the acid-catalysed dehydration?
OH OH
OH OH
(a) (b) (c) (d)
32. Which of the following alcohols is least reactive towards acid-catalysed dehydration?
OH OH OH
OH
(a) (b) (c) (d)
OH
Hr
33. ¾ ¾®( A) ; Product (A) is:
D
(a) (b) (c) (d)
Hr
34. ¾¾®( A); Product (A) is:
D
HO
(a) (b) (c) (d)
35. In which of the following reaction pair of diastereomers will form ?

OH +
(a) (b) ¾¾®H
D
+
H
(c) ¾¾®
D (d) All of these
OH

CH 3
|
heat
36. CH 3 — C —— CHCH 3 + HBr ¾ ¾
¾® ?; Major product of the reaction is :
| |
CH 3 OH
CH 3 Br CH 3
| | |
(a) CH 3 — C — CHCH 3 (b) CH 3 — C — CH 2 CH 2
| | |
CH 3 CH 3 Br
CH 3 CH 3 CH 3
| | |
(c) CH 3 — C — CHCH 3 (d) CH 3 — C — CH 2 CH 3 (e) CH 3 — C — CH 2 CH 2 CH 3
| | | |
Br CH 3 CH 2 Br Br
CH3
37. CH3 + HBr ?, Major product of the reaction is :
OH
CH3 CH3
CH3 Br
(I) (II)
Br CH3
CH3 CH3 CH3
(III) CH2Br (IV) CH3 (V)
CH2Br
Br
38. Which of the following alcohols dehydrates most readily ?
OH
(I) CH3 OH (II)
OH
(III) OH (IV) (V) OH

39. Which of the following alcohols gives a rearranged carbocation when dehydrated?
CH3
CH 3
OH OH |
CH 3 CHCH 3 CH 3 CHCH 2 CH 3 H 3 C — C — OH
| | |
OH OH CH 3
(I) (II) (III) (IV) (V)
CH3 OH
H2SO4
40. ? , Major product of the reaction is :
heat
CH3 CH3 CH2 CH3 CH3
(a) (b) (c) (d) (e)
41. Which of the following reagents can be used to oxidize 1° alcohols to aldehydes ?
(a) KMnO 4 (b) MnO 2 (c) K 2 Cr 2 O 7 (d) H 2 O 2 (e) PCC
42. In the chromic acid oxidation of alcohols, the chromium is:
(a) reduced from Cr +6 to Cr +3 (b) oxidized from Cr +6 to Cr +3
(c) reduced from Cr +3 to Cr +6 (d) oxidized from Cr +3 to Cr +6
43. When the optically active alcohol given below is oxidized by H 2 CrO 4 , the major product is
............. .
OH
CH3
(a) a ketone which is meso and optically inactive
(b) an optically active ketone
(c) a racemic mixture of ketones which is optically inactive
(d) an aldehyde which is meso and optically active
(e) an acyclic carboxylic acid
44. Which of the following compound contains most acidic hydrogen ?
(a) HC ºº CH (b) CH 3 OH (c) NH 3 (d) H 2 C == CH 2
45. Which of the following compound will evolve H 2 gas with Na ?
(a) H 2 C == CH 2 (b) R — O — R (c) R — CH 3 (d) R — O — H

s
Nr
CrO3Cl
|
OH H
46. Br ¾¾¾¾¾® (A) ; ( A) is:
(a) Br COOH (b) Br CHO
H N—CrO3Cl–
Br
(c) (d)
O
CH3 ||
( i ) H 2O, Hg (O C CH 3 )2
47. ¾® ; Product of the reaction is:
¾ ¾¾¾¾¾¾¾
CH2 ( ii ) NaBD 4
H
| OD OH OH
(a) CH 3 — C — OD (b) (c) (d)
CH2D CH2D CH3
|
CH 3
48. The alcohol, which would not generate a carbonyl compound on oxidation with acidified
KMnO 4 , is:
OH
OH CH3 CH3 OH
(a) (b) OH (c) (d)
OH
CH3 OH
OH
H SO
2 4 NBS LiAlD
49. ¾ ¾¾ ¾® (B) ¾ ¾¾4® (C); Product (C) is:
® (A) ¾ ¾
D OH
(a) (b) (c) (d)
OH
H+
50. ¾¾® A, major product A is:
D
(a) (b) (c) (d)

OH
H+
51. ¾¾® Major product of the reaction is:
CH2
O

CH2 CH2
CH3
PBr Alc. KOH HBr NH

¾3® (A) ¾ ¾¾¾® (B) ¾ ¾
52. CH 3 CH 2 CH 2 OH ¾ ¾ ¾3® (D), (D) is:
¾® (C) ¾ ¾
(a) CH 3 — CH 2 — CH — NH 2 (b) CH 3 — CH — CH 3
|
NH 2
H CH 3
| |
(c) CH 3 — C — NH 2 (d) CH 3 — C — NH 2
| |
CH 3 CH 3

1. B H , THF
2 6
¾¾¾¾¾¾® ?
2. NaOH, H O
2 2
O
OH
(a) (b)
OH
(c) (d)
CH3
Na 3 CH I
54. H O—H ¾¾®( A) ¾ ¾
¾ ® ( B ), Product ( B ) is:
SN 2
Ph
CH3 CH3
(a) H Ph (b) H O—CH3
OCH3 Ph
Ph Ph
(c) H O—CH3 (d) CH3O H
CH3 CH3

Ph CH3
+
H
55. Ph—C—C—CH3 ¾¾® (A); Product (A) is :
D
OH OH
Ph O CH3 O O CH3
(a) Ph—C—C—CH (b) CH3—C—C—Ph (c) Ph—C—C—CH3 (d)
3
CH3 Ph
CH3
56. Which of the following alcohols is oxidized to a ketone by chromic acid ?
OH OH
(i) (ii)
CH3
CH2OH CH2OH C— CH3
(iii) (iv) (v)
OH
HO O
+
57. O H
¾¾® ? , Product of the reaction is:
D
O HO O HO OH OH
(a) O (b) (c) (d)
58. Which of the following products is formed in good yields by the reduction of methyl
4-oxo-hexanoate (M) with NaBH 4 ?
O
O
Me
O
(a) Methyl 4-hydroxyhexanoate (b) 6-Hydroxy-3-hexanone

(c) 1,4-Hexanediol (d) 4-Hydroxyhexanal
OH 1.PCC
O 2.NH 3,pH=4
59. ¾¾¾¾¾¾¾® ? , Product of the reaction is:
O NH H2N NH
(a) (b)
O OH O O
(b) O (d)
NH2 H2N
60. What is the product formed when the following lactone is treated with aqueous sodium
hydroxide solution?
O
HO OH OH
(a) O (b) O
O
O
– OH
O –
(c) H (d) O
O OH
O O
61. || ||
H
O O
In the above given compound how many functional groups are reduced by LAH (Lithium
aluminium hydride) and SBH (Sodium borohydride) respectively ?
(a) 4, 4 (b) 4, 3 (c) 3, 4 (d) 4, 2
62. Which of the following alcohol will give turbidity of alkyl chloride immediately at room
temperature when reacts with Lucas reagent?
OH
OH
OH
OH
(a) (b) (c) (d)
63. In which of the reaction rearrangement take place with change in carbon skeleton ?
CH3
+
H
(a) CH3—C—CH—CH3 ¾¾® (b) +
H
D OH ¾¾®
D
CH3 OH
+
H
(c) OH ¾¾® (d) All of these
D
OH
+ + +
64. H H ; H
OH ¾¾®
¾¾®
D
(A) ; OH ¾¾®
D
(B) D
(C)
Sum of a-hydrogen in (A+B+C=?)

(a) 17 (b) 18 (c) 19 (d) 20

OH
OH
+ +
65. H H (B) ;
¾¾® (A) Major ; ¾¾®
D
D
Sum of a-hydrogen in ( A + B = ?)
(a) 18 (b) 19 (c) 20 (d) 21
OH
OH
+ +
66. H H
¾¾®
D
(A) ; ¾¾®
D
(B) ;
Sum of a-hydrogen in ( A + B = ?)
(a) 15 (b) 16 (c) 17 (d) 18
+
H
67. OH H+ ¾¾®
D
(B)
¾¾®
D
(A) ; OH
Sum of a-hydrogen in (A+B =?)

(a) 12 (b) 13 (c) 14 (d) 15
+
+ H (B)
H (A) ; ¾¾®
68. ¾¾®
D
D
OH OH
OH OH
+ Al2O3
H (C) ; (D)
¾¾®
D
¾¾®
D
Sum of a-hydrogen in A+B+C+D is :

(a) 34 (b) 35 (c) 36 (d) 37
OH
(A)
69. ¾¾® ; Reagent (A) is :
r s s
(a) H 3 O (b) H + D (c) HO (d) NH 2

[B] Phenols
OH
FeBr3
+Br2 ¾¾¾® ?
CH3
OH
OH
(a) CH3 (b)

ClCH2
Br
OCl Br
OH
(c) (d) (e)
CH3 CH3
CH3 Br
2. Compare the rate of acid catalyst dehydration:

OH OH
OH
I II III
(a) I > II > III (b) II > III > I (c) III > II > I (d) II > I > III
3. Most reactive towards (acid catalysed dehydration) is:
OH OH
(a) (b)
OH
(c) (d)
OH
4. Which of the following is the best method for preparing aspirin,
COOH
O
OCCH3
Aspirin

O
COOH
(i) + HO—C—CH3 ¾¾®
OCCH3
(ii) + HCOOH ¾¾®
O
COOH
O + CH3Cl ¾¾®
(iii)
OCCl
O
COOH
Hr
+ CH3—C—NH2 ¾¾®
(iv)
OH
O O
COOH
Hr
+ CH3C—O—CCH3 ¾¾®
(v)
OH
OH
OMe
(i) KOH, CHCl
5. ¾ ¾¾¾¾¾3® ‘ P ’, Major product ( P ) of the reaction is:
(ii) H 3Or
OH
O OH OMe
||
OMe
(a) H (b) H
||
O
OH
OH O
OMe ||
H
(c) (d)
H O OMe

OH
O O
|| ||
(1) CO ,NaOH
2 CH 3 — C —O— C —CH 3
6. ¾ ¾¾¾¾ ¾®(B Aspirin) Product ( B ) is:
¾®( A) ¾ ¾¾¾¾¾¾¾
(2) Hr
O
||
OH O—C— Me
CHO COOH
(a) (b)
OMe OH O
||
COOH C—OCH3
(c) (d)
7. Which of the following compound gives Reimer-Teimann reaction ?

NO2 OH NO2
OMe
(a) (b) (c) (d)
OH NO2
8. ¾ (A); Product (A) is:

+ CHCl 3 + NaOH ¾®
OH OH
OH OH
CHO CO2H
(a) (b) (c) (d)
CHO
CO2H
9. Which of the following compound will not undergo Reimer-Tiemann reaction?
NO2 CHO

10. Electrophile in Reimer-Tiemann reaction is:

s
(a) CCl 3 (b) CH 2 Cl 2 (c) CHCl 3 (d) :CCl 2
OH HI
11. ¾¾® ‘ P ’ ; Major product ‘ P ’ is:
¾excess
OH
I
OH I I I
(a) (b) (c) (d)
I I OH OH
12. In Reimer-Tiemann reaction molecular weight of phenol increases by:

(a) 28 (b) 29 (c) 30 (d) 31
OH
13. ¾ ( A) ; Product (A) is:

+ CHCl 3 + NaOH ¾®
2Hr
CH3
OH OH
OH OH OH
(a) O (b) O (c) O (d)

CO2H
CH3 CH3
CH3 CH3
OH
O O
|| ||
NaOH CH 3 —C — O —C — CH 3
14. + CO 2 ¾ ¾¾®( A) ¾ ¾¾¾¾¾¾¾¾®( B); Products (A) and (B) respectively are:
2Hr
OH
OH O O
CO2H
(a) ; C—O—C—CH3
OH OH O
CO2H
H
(b) ;

O
OH
O—C—CH3
CO2H
(c) ; CO2H
OH
OH O
CHO
(d) ; O—C—CH3
NH2
NaNO , 2HCl
2 4 HBF
15. ¾¾¾¾¾®
0-5°C
(A) ¾¾® (B) ;Compound ( B ) is:
(a) Phenol (b) Chlorobenzene (c) Flurobenzene (d) Aniline
16. ¾®( A) ; Product ( A) is:

+ CHCl 3 + KOH ¾
OH
Cl O
(a) (b) (c) (d)
[C] Ethers
1. O Ph ¾ ¾¾® A+B, So A and B would be:
dil. HI
(a) MeOH and Ph—I (b) Me I and Ph — CH 2 — OH

(c) MeOH and Ph — CH 2 — I (d) MeI and Ph — OH
O
HBr, H2O
2. ¾¾¾¾® Major products of the following reaction are:
heat
OH
(a) recovered starting material (no reaction) (b) Br
Br Br
(c) Br (d) HO

+
MeOH,H
3. O ¾¾¾¾¾® ? Major product of the following reaction is:
Opticallyactive
OH
(S) OMe (S) OMe (R)
(R) (S) (R) (R) (R) (S)
(a) (b) (c) (d) None
OH OMe OMe
4. What starting material is needed to synthesize the following compounds?
1. KMnO4, cold HO HO
H2O, NaOH
? ¾¾¾¾¾¾®
2. NaH, DMF O + O
Br Br
(a) (b) Br (c) Br (d)
5. What reagents are needed to accomplish the following transformation?

O O
OH ? O
¾¾¾®
O O
(a) KMnO 4 , NaOH , H 2 O , heat (b) 1. LiAlH 4 , Et 2 O ; 2. 2H 2 O , H 2 SO 4
(c) CrO 3 , HCl, pyridine (d) H 2 CrO 4 , acetone, 35°C
1.HNO 3,H 2SO4
2. Fe, HCl
3. NaOH
¾¾¾¾¾¾¾® ?
4. HONO, ice bath
5. CuCl
O
Cl Cl
(a) (b)
HO O
Cl
Cl
(c) (d)
O O
O
heat
CH3 + CH3S– ¾¾¾® ?
alcohol
CH3

CH3 O
(i) OCH2CH (ii) CH3 SCH3
CH3
SCH3 CH3 H
SCH3
CH3
CH3
O
(iii) CH3 (iv) CH2—C—OH (v) HOCH2CSCH3
CH3
CH3 SCH3 CH3
H 3Or
8. O ¾ ¾¾ ® ; Product of this reaction is:
O OH O
(a) , (b) , CH 3 CHO
O O
O O
(c) (d) ,
H, H
O—CH3
Conc. HI
9. ¾ ¾¾¾® x mole of HI is consumed
O—CH3
Conc. HI
¾ ¾¾¾® y mole of HI is consumed
sum of ( x + y = ?):
(a) 2 (b) 3 (c) 4 (d) 5
O—CH3
Conc. HI
10. ¾¾¾® Products ; Products of this reaction are:
(excess)
O—CH3
I CH
(a) + 2CH3I (b) + 2CH3OH
I OH

OH OH
(c) + 2CH3I (d) +2CH 3I
OH I
Conc. HI
11. CH 3 — CH 2 — O — CH 2 — CH 3 ¾ ¾¾
¾® ?; Major product of the reaction is:
(excess)
(a) 2EtOH (b) 2EtI
(c) EtOH, EtI (d) 2H 2 C == CH 2
O—CH2 HI
12. ? ; Major products of this reaction are:
heat
I CH2OH OH CH2I
(I) + (II) +
OCH2OH I OCH2I OH
(III) + (IV) +
CH2OI OH
(V) +
O O
H Or
13. 3
¾¾® Product of the reaction is:
OH
OH
O
(a) (b) (c) Both (a) and (b) (d) No reaction
14. The reagent which will be suitable to distinguish 1-methoxy-3-methyl-2-butene from isomeric
4-methyl-3-penten-1-ol is:
(a) bromine in chloroform (b) alkaline potassium permanganate
(c) ammoniacal silver nitrate (d) sodium metal suspended in hexane

18
O—Ph
3 H Or
15. ¾¾ ¾® Products are:
18
OH OH
(a) (b) Ph — OH
18
(c) Ph — OH (d) No reaction
16. Compare the reactivities of ethers given in two pairs, towards hydrolysis :
(1) Ph — O — Ph Ph — O — CH 3
( a) ( b)
(2) O O
(c) (d)
(a) 1 - a , 2 - c (b) 1 - b, 2 - c (c) 1 - b, 2 - d (d) 1 - a , 2 - d
CH 3
|
Conc. H I
17. CH 3 — C — O — CH 3 ¾ ¾¾¾®; This mechanism followed by the reaction is:
|
CH 3
(a) S N1 (b) S N 2 (c) SN - AR (d) NGP
O r
H O
3
18. ¾¾¾® Product ; Product of the reaction is:
O O
(a) 2CH 3 CHO (b) 3HCHO (c) 3HCO 2 H (d) 3CH 3 OH
O O H O
r
3
19. ¾¾¾® ; Major product of the reaction is:
(a) HO HO OH (b) HO O OH
(c) O O O (d) HO O O

r
O—Et 3 H O
20. ¾¾¾® ; Products obtained in this reaction are:
OH O
(a) EtOH, (b) , CH 3 — CHO
O O
(c) CH 3 CO 2 H, (d) EtOH,
21. Which of the following is most reactive towards hydrolysis ?
(a) (b) (c) (d) O

O O O
HOs
22. CH 3 — O — CH 3 ¾ ¾¾® ; Product of the reaction is:
H 2O
(a) No reaction (b) 2CH 3 OH (c) 2CH 4 (d) Et—H
r
3 H O
23. ¾¾¾® ; Product of the reaction is:
O OEt
, EtOH ,EtOH
(a) HO OH (b) HO O
,CH 3OH +EtOH

(c) HO O (d) O O
18
Conc. HI
24. Ph — O— CH 3 ¾ ¾¾
¾® ; Products of the reaction is:
18 18
(a) Ph — O H, CH 3 — I (b) Ph — I, CH 3 OH
(c) Ph — I, CH 3 — I (d) Ph — OH, CH 3 I
CH3
25. O—C—CH3 , This ether is best prepared by:
CH3
s
(a) O + Br (b) Br + Os
(c) Os + OH (d) Os + Os

26. CH3O O O OCH3
How many moles of HI consumed in above reaction ?

(a) 1 (b) 2 (c) 3 (d) 4
-
27. Compare rate of reaction with OH :
(i) O (ii) O (iii)

O
(a) i>ii>iii (b) i>iii>ii (c) iii>ii>i (d) ii>i>iii
28. PhMgBr + Et — O — Et ¾®
¾ ; Product is:
(diethyl ether)
(a)Ph — OEt (b) Ph — OH (c) Ph — Et (d) no reaction
Answers
[A] Alcohols
1. (b) 2. (d) 3. (b) 4. (a) 5. (d) 6. (d) 7. (c) 8. (b) 9. (b) 10. (b)
11. (d) 12. (d) 13. (a) 14. (c) 15. (a) 16. (d) 17. (d) 18. (d) 19. (b) 20. (b)
21. (d) 22. (b) 23. (c) 24. (b) 25. (d) 26. (b) 27. (b) 28. (b) 29. (a) 30. (d)
31. (c) 32. (b) 33. (a) 34. (b) 35. (a) 36. (c) 37. (b) 38. (c) 39. (d) 40. (b)
41. (e) 42. (a) 43. (b) 44. (b) 45. (d) 46. (b) 47. (c) 48. (c) 49. (c) 50. (b)
51. (c) 52. (b) 53. (b) 54. (b) 55. (a) 56. (b) 57. (d) 58. (a) 59. (a) 60. (d)
61. (d) 62. (d) 63. (a) 64. (c) 65. (c) 66. (b) 67. (c) 68. (b) 69. (b)
[B] Phenols
1. (e) 2. (b) 3. (c) 4. (e) 5. (c) 6. (b) 7. (c) 8. (a) 9. (d) 10. (c)
11. (b) 12. (b) 13. (b) 14. (a) 15. (c) 16. (b)
[C] Ethers
1. (c) 2. (b) 3. (a) 4. (b) 5. (d) 6. (c) 7. (d) 8. (b) 9. (b) 10. (c)
11. (b) 12. (b) 13. (c) 14. (d) 15. (a) 16. (c) 17. (a) 18. (b) 19. (b) 20. (b)
21. (b) 22. (a) 23. (b) 24. (a) 25. (b) 26. (b) 27. (a) 28. (d)

O O
(i) CH MgBr
3 (i) CH MgBr
3
1. ¾ ¾¾¾¾®( A ) ; ¾ ¾¾¾¾®( B )
H3C CH3 (ii) Hr H CH3 (ii) Hr
Which of the following reagent can be used to differentiated between A and B ?

(a) FeCl 3 (b) Active metal Na (c) Lucas reagent (d) K 2 Cr 2 O 7
2. Which of the following compounds gives benzene when reacts with PhMgBr?
OH
(a) CH 3 OH (b) CH 4 (c) CH 3 — C ºº CH (d)
3. Which of the following compounds when reacts with PhMgBr (excess) followed by
acidification will yield 3º alcohol ?
O O
|| ||
(a) CH 3 — C — Cl (b) Et — O — C — O — Et
O O
||
(c) O O (d) H — C — O — Et
4. In which of the reaction ring expansion take place when protic acid is added in it ?
OH OH
CH3 OH
OH
(a) (b) (c) (d)
5. Which of the following compounds may undergo Reimer-Tiemann reaction ?

OH NO2
OH
OCH3
(a) (b) (c) (d)
6. Which of the following compounds do/does not react with NaHCO 3 ?

OH
OH OH
(a) (b) (c) (d) CH 3 — C ºº C — H
CH3

Grignard Reaction 351
7. Which of the following compounds reacts with Na?
(a) CH 3 OH (b) CH 3 — C ºº CH (c) Ph — OH (d)

8. Which of the following is/are weaker acid than methanol?
(a) CH 3 — C ºº CH (b) (c) OH r

(d) CH —O—H
OH 3
H
O—H
Nitrating mixture
9. +CH 3 — C — Cl ¾® ( A) ¾ ¾¾¾¾¾
¾® ( B)
|| possible products
O
Possible structure(s) of ( B ) is/are:

OCOCH3 OCOCH3
OCOCH3
NO2
NO2
NO2
Answers
1. (c, d) 2. (a, c, d) 3. (a, b, c) 4. (a, b) 5. (a, b) 6. (a, b, c, d)

7. (a, b, c) 8. (a, b, c) 9. (b, c)

Passage-1:
Compound ( A) tertiary alcohol when it reacts with conc. H 2 SO 4 gives alkene
( B). B on O 3 Zn followed by reaction with dil. KOH and heating gives (C ). (C )
on reaction with NaOH followed by acidification gives D.
O
C—OH
D=
1. Compound A is:
OH OH
OH
(a) (b) (c) (d)

HO
2. Compound B is:
(a) (b) (c) (d)
3. Compound C is:
O
O O
|| || CH3
CH3
(a) (b) (c) (d)
CHC3
Passage-2:
A tertiary alcohol ( A) C 7 H 14 O on reaction with conc. H 2 SO 4 gives ( B) C 7 H 12 .
( B) on ozonolysis give (C ) C 7 H 12 O 2 . (C ) gives both Haloform and Tollen’s
reagent test. When (C ) reacts with sodium methoxide gives ( D ) C 7 H 10 O. ( D ) on
OH
reaction with H 2 Ni give ( E ) . ( E ) on reaction with conc. H 2 SO 4

gives ( A)

1. Structure of ( A) is:
OH OH
OH OH
(a) (b) (c) (d)
2. Structure of ( B ) is:
(a) (b) (c) (d)
3. Which statement is true about D ?

(a) Formed from Cannizaro reaction
(b) Formed from Perkin reaction
(c) Formed from cross Aldol reaction
(d) Formed from intramolecular Aldol reaction
Passage-3:
A tertiary alcohol ( A) on acid catalysed dehydration gives ( B). Which on
ozonolysis gives (C ) and ( D ). C upon reaction with KOH gives ( E ). D upon
reaction with SeO 2 followed by reaction with conc. KOH and acidification give
( F ).
Structure of ( E ) and ( F ) are , and Ph — CH — C — OH
| ||
OH O
O
respectively.
1. Compound ( A) is obtained by:
O O
||
(a) MgBr + Ph — C — CH 3 ¾® (b) CH3 + PhMgBr
(c) CH 3 MgBr + Ph (d) All of these

Ph Ph Ph
Ph
(a) (b) (c) (d)
3. Structures of (C ) and ( D) are respectively:

O O
O
||
(a) , Ph — CHO (b) , Ph — C — CH 3
(c) , Ph — CH 2 — CHO (d) All of these
Passage-4:
An alcohol P, which gives positive iodoform test, undergoes reaction with 2
moles of PCC (pyridinium chloro chromate) and gives compound Q.
Compound Q on reaction with dil. KOH followed by heating gives compound
R. Ozonolysis of R leads to formation of a tricarbonyl compound S, which on
reaction with LiAlH 4 gives compound T. The structure of compound T is as
given below.
CH2—OH
CH2—OH
O
2 moles of PCC 3 (i)OHs
4 (i) O LiAlH
P ¾ ¾¾¾¾¾¾® Q ¾ ¾¾¾® R ¾ ¾¾
¾ ® S ¾ ¾¾¾ ®T
(ii)D (ii) Zn,H 2O
1. The structure of the carbonyl compound Q is :

O O O O
H H
(a) (b) H (c) (d)
H
OH O O O

2. The structure of the carbonyl compound R is :

OH
(a) (b)
OH
O O
(c) (d)
O O
3. The structure of the carbonyl compound S is :
O O
H
(a) (b) O
CHO
O O
O O
H
(c) (d)
O O
O
Passage-5:
A organic compound P on reaction with concentrated HI gives products Q and
R. Both compound Q and R gives alkene on reaction with respectively
alcoholic KOH and concentrated H 2 SO 4 (followed by heating).
conc. HI
P ¾¾¾® Q + R
¾¾®
¾¾®
alc. KOH H2SO4

D D
1. Structure of compound P will be:

O O
(a) (b)
O
(c) (d) O

2. Structure of compound Q will be:

I
I
(a) (b) I (c) I (d)
3. Structure of compound R will be:

OH OH
OH OH
(a) (b) (c) (d)
Passage-6:
OAc O
|| O
||
Cl Cl PCC (1) NaOI2 4 H SO
HOs
(A) (B) ¾¾¾®
r (C) ¾¾¾®
(2) H D
O
1. Compound ( A) is optically active so the structure of ( A) is:
OH OH
(a) (b)
OH
(c) OH (d)
O O
(a) (b) (c) O (d) (a) and (b) both
3. Structure of (C ) is:
O O
(a) ONa (b) OH
O O
(c) OH (d) ONa


Column-I Column-II (Moles of HI Consumed)
(a) O—CH3 (p) 2

HI
¾¾®
O—CH3
(b) O (q) 3
HI
¾¾®
O
(c) O (r) 5
HI
¾¾®
O
HI
(d) Et — O — Et ¾¾® (s) 6

Column-I Column-II
(Reaction) (Moles of HI consumed)
O—CH3 Conc. HI
(a) ¾¾¾® (p) No reaction
O—CH3 Conc. HI
(b) ¾¾¾® (q) 1
O Conc. HI
(c) ¾¾¾® (r) 2
OCH3
Conc. HI
¾¾¾®
(d) OCH3 (s) 3
OCH3


Column-I (Reaction) Column-II (Product)
(a) O—Et r
H O
3
O
O—Et ¾¾¾® (p)
O—CH2—CH3
(b) r (q) EtOH

H O
3
¾¾¾®
r
3H O
(c) O ¾¾¾® (r) OH
r
H O
3
(d) O ¾¾¾® (s) CH 3OH

Column-I Column-II
(a) CH2OH
(p) Nucleophilic substitution reactionc with HBr
(b) (q) Elimination reaction with H 2 SO 4

OH
OH (r) Geometrical isomer will formed when reaction
(c) with H 2 SO 4
(d) OH (s) No reaction with H 2 SO 4
5. Match the reactions in Column-I with appropriate types of steps/reactive intermediate

involved in these reactions as given in Column-II:
Column-I Column-II
r s s (p) Nucleophilic aromatic substitution

HO
OH+ C6H5N2Cl (pH= 10–11)
(a)
Cl (q) Electrophilic aromatic substitution
(b) OHs
NO2

AlCl3
(c) Cl (r) Carbocation intermediate
OH
(s) Carbanion intermediate

(d) H+
(t) Coupling reaction

6. Match the reactions with appropriate types of reactions and intermediates involved in
formation of ( X ) and (Y ).
Column-I Column-II
(a) OH OH OH (p) Nucleophilic
Br Br Br Br Br substitution reaction
Br
2 2
¾¾® ¾¾®
H2O hn
CH3 CH3 CH2—Br

(X) (Y)
(b) Br OH OH (q) Electrophilic
NO2 substitution reaction
(1) HOs 3 HNO
¾¾¾®
r ¾¾¾®
(2) H H2SO4
NO2 NO2 NO2

(X) (Y)
(c) O (r) Electrophilic addition
O
Cl reaction
3 AlCl
+ Cl—C—CH2—CH2—Cl ¾¾®
(X)
O
aq. KOH
OH
(Y)
(d) Br (s) Free-radical
Br
2 NaI
¾¾® ¾¾¾® substitution
CCl4 Acetone, D
Br
(X) (Y)
(t) Elimination reaction

1. How many isomers of C 4 H 10 O are possible which can undergo oxidation reaction with
K 2 Cr 2 O 7 (including stereoisomer) ?
O O—Et
X HI
2. ¾® ; How many ( X ) moles of HI consumed ?
¾¾
O O—Et
OH
(i) CHCl |KOH

3
3. ¾ ¾¾¾¾¾® ' X '
(ii) H 3Or
Identify the molecular weight of the product ' X ' give your answer in this way if molecular
weight is 121 means 1 + 2 + 1 = 4 answer possible.
4. (i) Ph — OH + Na ¾
¾® (A) gas
(ii) CH 3 OH + Na ¾®
¾ (B) gas
Sum of molecular mass of gas (A+B=?)
5. (i) Ph — OH + K ¾
¾® (A) gas
(ii) Ph — OH + KH ¾®
¾ (B) gas
Sum of molecular mass of A+B=?
6. (i) Ph — OH + Na ¾
¾® (A) gas
(ii) Ph — OH + NaH ¾®
¾ (B) gas
(iii) Ph — OH + NaNH 2 ¾®
¾ (C) gas
Sum of molecular mass of A+B+C=?
O
||
7. (i) Ph — C — OH + NaHCO 3 ¾ ¾® (A) gas
14
O
||
¾ (B) gas
(ii) Ph — C— OH + NaHCO 3 ¾®
14

O
||
¾® (A) gas
8. (i) Ph — S — OH + NaHCO 3 ¾
||
O
O
||
¾ (B) gas
(ii) Ph — C — OH + NaHCO 3 ¾®
O
CH == O
4 moles of PCC
9. ( A) ¾ ¾¾¾¾¾®
CH == O
O
Maximum number of moles of Ac 2 O consumed by reactant ( A) is:
1. Which of the following alcohols, when heated with H 2 SO 4 , will undergo dehydration more
rapidly? Explain.
CH—CH3 CH—CH3
(a) or (b)
OH OH

2. Identify product, Intermediate & Type of reaction (Substitution, Elimination, Addition)
Type of reaction
S.No. Reaction Product Intermediate
(S/E/A)
M. A .
¾¾
¾®
(i)
M. A .= mixed acid
O
(ii) Cl
¾¾¾®
AlCl3
r
N ºº NCls
(iii) 2 H O ( boil )
¾ ¾¾¾®
OH
(iv) CHCl
¾ ¾¾3®
KOH
OH
(v) (1) CO , NaOH

2
¾ ¾¾¾¾Å
¾®
( 2) H
OH
Å
(vi) Ph — N ºº N
¾ ¾¾¾
s
¾®
HO
OH
(vii) Br
¾¾2®
H 2O
+ Cl ¾AlCl
¾¾3®
(viii)
OH
(ix) H+
¾¾®
D

3. This question gives you idea about solubility of compound is Na, NaOH, NaHCO 3 .
Evolve H2 gas React with aq. React with
S.No. Compound
with Na metal NaOH NaHCO 3
1. Ph — CO 2 H
2. Ph — OH
3. Ph — CH 2 — OH
4. Ph — CH 2 — CO 2 H
5. Ph — CH 2 — OCH 3
6. Ph — CH 2 — CH 2 — OH
7. Ph — SO 3 H
O
||
8. CH 3 — C — OH
9. CH 3 — CH 3
O
10. ||
CH 3 — C — O — CH 3
O
11. O
12. CH 3 — C ºº N
13. CH 3 — C ºº CH
14. HO NO2
O OH
15.
O OH

1. LAH, ether
4. ¾ ¾¾¾¾®
2. H 3Or
1. LAH, ether
5. CH 2 — (CH 2 ) 14 — COOH ¾ ¾¾¾
r¾® (LAH = LiAlH 4 )
2. H 3O
Palmitic acid
1. LAH, ether
6. CH 3 — CH — CH — COOH ¾ ¾¾¾
r¾®
Croxtonic 2. H 3O
acid
1. LAH, ether
7. CH 2 (NH 2 ) CH 2 COOH ¾ ¾¾¾
r¾® 2. H 3O
b- Alanine
1. LAH, ether
8. (i) Acids chlorides CH 3 COCl ¾ ¾¾¾
r¾® 2. H 3O
1. LAH, ether
(ii) Acid anhydrides (CH 3 CO) 2 O ¾ ¾¾¾
r¾® 2. H 3O
1. LAH, ether
(iii)Esters CH 3 — CH — CH — COOC 2 H 5 ¾ ¾¾¾
r¾® 2. H 3O
LAH
9. CH 3 — CH — CH — CH 3 ¾ ¾
¾®
Ether
O
10. 4 ROH + LiAlH 4 ¾®
LiAlD
11. (i) LiAlD 4 + 4C 6 H 5 — CH — CH 3 ¾® (ii) ¾ ¾¾4®
|
Br
12. R — CH == CH — R + C 6 H 5 CO 3 H ¾®
C H CO H
6 5 3
13. ¾ ¾¾¾ ¾ ®
CHCl 3
NaBH
¾4®
14. CH 3 COCH 2 COOC 2 H 5 ¾ ¾¾
Ethyl- g- ketopen tanoate

NaBH
¾4®
15. C 6 H 5 × CO × CH 2 × CH 2 × COOH ¾ ¾¾
b- Benzyol propanoic acid
NaBH
¾4®
16. CH 3 × CO × CH 2 × CH 2 × CO × CH 3 ¾ ¾¾
Hexan- 2, 5- dione
NaBH
¾4®
17. CH 2 OH ×(CHOH) 4 × CHO ¾ ¾¾
Glucose
NaBH
¾4®
18. C 6 H 5 CH == CH — CHO ¾ ¾¾
Cinnamaldehyde
NaBH
¾4®
19. NC × CH 2 × CH 2 × CHO ¾ ¾¾
3-Cyanopropionaldehyde
NaBH
¾4®
20. R × CO × Cl ¾ ¾¾
Acid chloride
21.
- HIO
22. R — CHOH — CH 2 OH + HIO 4 ¾ ¾¾3®
- HIO
23. R — CHOH — CHOH — R ¢ + HIO 4 ¾ ¾¾3®
- HIO
24. R 2 C(OH) — CHOH — R ¢ + HIO 4 ¾ ¾¾3®
-2HIO
¾3®
25. R — CHOH — CHOH — CHOH — R ¢ + 2HIO 4 ¾ ¾¾
- HIO
26. R ¢— CO — CHOH — R + HIO 4 ¾ ¾¾3®
- HIO
27. CH 2 OH — CO — CH 2 OH + HIO 4 ¾ ¾¾3®
- HIO
28. R ¢ — CO — CHOH — R + HIO 4 ¾ ¾¾3®
- HIO
29. CH 2 OH — CO — CH 2 OH + HIO 4 ¾ ¾¾3®
- HIO
30. R — CO — CO — R ¢ + HIO 4 ¾ ¾¾3®
- HIO
31. RCHNH 2 — CHOH — R ¢ + HIO 4 ¾ ¾¾3®
HIO
32. R — CHOH — CH 2 — CHOH — R ¾ ¾¾4®
33. CH 2 OH — CHOH — CHOH — CHOH — CHO + 4HIO 4 ¾®
Aldopentose
34. CH 2 OH — CHOH — CHOH — CHOH — CHOH — CHO + 5HIO 4 ¾®

Aldopentose
5HIO
35. CH 2 OH — CHOH — CHOH — CHOH — CHOH ¾ ¾¾4®
Aldopentose (glucose)

4HIO
36. CH 2 OH — CHOH — CHOH — CHOH — CO — CH 2 OH ¾ ¾¾4®
Ketohexose (fructose)
2HIO4
37.
MeO – CH
CHOH
2HIO4
38. CHOH O
CHOH
HC
CHOH
CH2OH
Methyl glucoside (II)
Colddil.KMnO 4
NaOIO4
39. CH2 (A) (B)
KMnO
¾4®
40. CH 3 — (CH 2 ) 7 — CH — CH — (CH 2 ) 7 — COOH ¾ ¾¾
Oleic acid NalO 4
Ni - H Ni - H
41. (i) CH 2 — CH 2 ¾ ¾¾¾® (ii) HC ºº CH ¾ ¾¾¾®
Room temp. Room temp.
Ni – H
Ni - H ¾¾ ¾ ¾ ¾¾®
(iii) ¾ ¾¾¾® (iv) 120 –150°C, Pr ess
100°C, Press
Ni—H, 150°C
(v)
200-300 atm

42. Provide necessary reagents in the following road-map :
Cl
/ AlCl3
O
(f)
Br2/Fe Cl2/Fe HNO3 + conc. (e)
H2SO4 H2SO4
(a) (b) (c) (d) CH2CH2CH3
(H2/Ni)
NBS hot KMnO4 (n)

or Br2/hn
(g) (h)
(m)
NH2 (k)
(i)
conc.
(j) H2SO 4/D
HOOC
(l) alc.
KOH (q)
N2Cl
CH=CHCH3
HBr/peroxide
(p)
HBr / CCl4
HBF4 CuCl HBr Kl CuCN H2O H3PO 2

/HCl / CuBr / boil
(t) (u) (v) (w) (x) (y) (z)
(s) NH2

43. Sum of a-hydrogen in products ( P1 + P2 + P3 + P4 = ?).

CH3
+
(a) CH3 – CH2 – C – CH3 H P1
D
OH
CH3
(b) CH3 – CH2 – C – C H3 H+
P2
D
OH
CH3
+
(c) CH 3 – C – CH – C H2 – OH H P3
D
CH3 CH3
+
H P4
(d) CH3 – CH2 – CH2 – CH2 – OH D
44. Propose mechanisms for the following reactions.

OH H SO
2 4
(a) D
cyclopentanol cyclopentene
OH
H2SO4
(b) +
D
2-pentanol 1-pentene 2-pentene
OH
H2SO4
+ +
D
(c) CH3 CH3 CH3 CH2
2-methylcyclohexanol 1-methylcyclohexene 3-methylcyclohexene methylenecyclohexane
45. Sum of a-hydrogen in products ( P1 + P2 + P3 + P4 = ?)

CH2OH
OH
H3PO4 H2SO4
(a) P1 (b) P2
D D

OH OH
H2SO4
H2SO4
(c) D P3 (d) P4
D
46. Dehydration of 2-methylcyclopentanol gives a mixutre of three alkenes. Propose mechanisms

to account for these three products.
CH3 CH3 CH3 CH2
H2SO4
+ +
OH D
2-methylcyclopentanol major minor minor
47. Sum of a-hydrogen in products ( P1 + P2 + P3 = ?)

OH
OH
+ +
(a) H P1 (b) H P2
D D
OH
+
(c) H P3
D

+ +
H P1 H P2
(a) D (b) D
OH OH
OH
+
(c) H P3
D
OH
OH
+
(a)
+
(b) H P2
H P1 D
D
+
H P3
(c) D
OH

Answers

Passage-1: 1. (b) 2. (a) 3. (a)
Passage-2: 1. (b) 2. (b) 3. (c)
Passage-3: 1. (d) 2. (b) 3. (b)
Passage-4: 1. (b) 2. (c) 3. (a)
Passage-5: 1. (a) 2. (d) 3. (c)
Passage-6: 1. (a) 2. (a) 3. (c)

1. (a)® r; (b)® q; (c)® s; (d)® p
2. (a)® q; (b)® r; (c)® p; (d)® s
3. (a)® p, q; (b)® p, q; (c)® q, r; (d)® q
4. (a)® p; (b)® p, q, r; (c)® s; (d)® p, q
5. (a) ® q, s, t; (b) ® p, s; (c) ® q, r; (d) ® q, r
6. (a) ® q,s; (b) ® p,q; (c) ® p,q; (d) ® r,t

1. 5 2. 2 3. 5 4. 4 5. 4 6. 21 7. 90 8. 88 9. 4

1. (b) will undergo dehydration more rapidly because it produces a secondary benzylic
carbocation, which is more stable than secondary carbocation due to resonance.
2.
NO2 O
+
(i) , Carbocation, substitution (ii) , CH 3 — C == O , substitution
OH
(iii) , Carbocation, substitution

OH
CHO
(iv) , : CCl 2 , substitution
(ortho and para)
OH
CO2H
(v) , Carbocation, substitution
(ortho and para)
(vi) HO N==N , Carbanion, substitution
OH
Br Br
(vii) , Carbanion, substitution
Br
(viii) , Carbocation, substitution
(ix) , Carbocation, substitution
3.
Evolve H2 gas with Na metal React with aq. NaOH React with NaHCO 3
1. 3 3 3
2. 3 3 7
3. 3 7 7
4. 3 3 3
5. 7 7 7
6. 3 7 7
7. 3 3 3
8. 3 3 3

9. 7 7 7
10. 7 3 7
11. 7 3 3
12. 7 3 7
13. 3 7 7
14. 3 3 3
15. 3 3 3
4.
5. CH 3 — (CH 2 ) 14 — CH 2 OH
Hexadecanol-1(cetyl alcohol)
6. CH 3 — CH — CH — CH 2 OH
Crotyl alcohol
7. CH 2 — (NH 2 )CH 2 CH 2 OH
3- Aminopropanol-1
8. (i) CH 3 CH 2 OH (ii) 2CH 3 CH 2 OH (iii) CH 3 — CH — CH — CH 2 OH

But- 2- ene-1- ol
æ CH 3 ö
ç | ÷ sr
ç ÷
9. ç CH 3 — CH 2 — CH — O ÷— AlLi ¾® 4CH 3 — CH 2 — CH(OH) — CH 3
ç ÷
ç ÷
è ø4
sr
10. ( RO) 4 AlLi + 4H 2
11. (i) 4 C 6 H 5 — CH — CH 3 + LiAlBr 4 (ii)

|
D
O

12. R — CH — CH — R + C 6 H 5 COOH

13.
14. CH 3 × CH(OH) × CH 2 × CH 2 × COOC 2 H 5

Ethyl- 4- hydroxypen tanoate
15. C 6 H 5 × CH(OH) × CH 2 × CH 2 × COOH

7- Hydroxy- 4- phenylbutanoic acid
16. CH 3 × CH(OH) × CH 2 × CH 2 × CH(OH) × CH 3

Hexan- 2, 5- diol
17. CH 2 OH ×(CHOH) 4 ×(CHOH) 4 × CH 2 OH

Sorbitol
18. C 6 H 5 × CH — CH × CH 2 OH
Cinnamyl alcohol
19. NC × CH 2 × CH 2 × CH 2 OH
4- Hydroxybutyronitrile
20. R ×CH 2 OH
Alcohol
21.
22. R — CHO + HCHO

23. R — CHO + R ¢CHO
24. R 2 CO + R ¢CHO
25. RCHO + HCOOH + R ¢CHO
26. R ¢— COOH + R — CHO
27. 2HCHO + CO 2
28. R ¢— COOH + R — CHO
29. 2HCHO + CO 2
30. R — COOH + R ¢— COOH
31. RCHO + R ¢CHO + NH 3
32. No reaction
33. 4HCOOH + HCHO + 4HIO 3
34. 5 HCOOH + HCHO + 5HIO 3
35. 5HCOOH + HCHO + 5HIO 3
36. 2HCHO + 3HCOOH + CO 2

MeO – CH
H – COOH + CHO
O
37.
CHO
H–C
CH2OH
Acetaldialdehyde
MeO – CH
CHO
38. O
CHO
HC
CHO + HCHO + HCO2H
39. (A) (B)
40. CH 3 — (CH 2 ) 7 — CHO + OHC — (CH 2 ) 7 — COOH

n- Nonaldehyde Half aldehyde of azelaic acid
41. (i) CH 3 — CH 3 (ii) CH 3 — CH 3 (iii) (iv)
(v)
42.
Br Cl NO2 SO3 H
a= ; b= ; c= ; d=

O
e = CH 3 CH 2 CH 2 Cl FeCl 3 f= ; g = Sn / HCl
(1) Cl / AlCl
2
h = CF3 CO 3 H ; i = NaNO 2 / HCl / H 3 PO 2 j = ¾ ¾¾¾¾¾3®
( 2) NaNH 2
Br OH
k= ; l = NaNO 2 / HCl ; m= n = hot KMnO 4
Br
o = hot KMnO 4 ; p= q= Br ;r = OH
F Br
s = LAH or H 2 Ni; t= u= v=
I CN OH
w= x= y= z=
43. 9 + 9 + 11 + 6 = 35
45. 4 + 7 + 8 + 8 = 27
47. 8 + 8 + 4 = 20
48. 6 + 5 + 8 = 19
49. 7 + 8 + 8 = 23

5
Aldehydes, Ketones and
Carboxylic Acids
[A] Aldehydes and Ketones
Methods of Preparation
1. Predict which of the following compounds will have a lower boiling point than 1-butanal.
(a) 1-butanol (b) 2-butanol (c) 1-butene (d) butanoic acid
2. Predict the product of the following reaction.
PhCH 2 OH + PCC (pyridinium chlorochromate/methylene chloride) ®
(a) benzophenone (b) benzoic acid (c) benzaldehyde (d) benzyl chloride
3. Give the expected product of the following reaction.
O 1.ExcessMeMgBr
O ¾¾¾¾¾¾¾®
2.H 2O,neutralize
?
HO
O OH O OH
(a) (b)
H3CO CH3 HO CH3
CH3 CH3
H3C H3C OH
(c) O (d)
HO HO CH3
O
O 1. DIBAL-H, hexane, –78°C

4. ¾¾¾¾¾¾¾¾¾® ? Major product of the reaction is:
2. H O
2
O

Aldehydes, Ketones and Carboxylic Acids 377
(a) O (b) O
O O
O
O
(c) O O (d) O
O
5. Di-isobutylaluminium hydride (DIBAL-H) can be used to carry out which of the following
conversions ?
(a) ester to aldehyde (b) carboxylic acid to ester
(c) 2° alcohol to ketone (d) aldehyde to carboxylic acid (e) ester to ketone
Properties of Carbonyl Compounds

1. Which of the following sets of reaction conditions will give the product indicated?
O OCH3
OCH3
¾¾¾¾®
HO HO
s
(a) (CH 3 O) 2 Ag , heat (b) CH 3 OH , HO, separate water
(c) (1) CH 3 ONa ,(2) MeI (d) CH 3 OH , H + , separate water
2. What are the starting materials needed for the following reaction?
O
HCl O
¾¾¾¾®
OH
O O
(a) + OH (b) + O
OH
OH
O
(c) + (d) + O
HO
OH
O
HCl
3. OH ¾¾¾¾® ? ; Product of the reaction is:
OH
(a) O (b) OH (c) OH (d)
O O O O

O O r
2 HOCH CH OH, H
2
4. ¾¾¾¾¾¾¾®? ; Product of the reaction is:
O O
O O
(a) (b)
O
O O
O O
(c) (d) O O
3 CH NH
2
5. ¾¾¾¾® ? ; Product of the reaction is:
pH 4.5
CH3 H CH3 CH3

N N H—N
HO NH2 OH
(a) (b) (c) (d)
6. Cyclohexanone + Pyrrolidine + Tosic acid¾® ? ; Product of the reaction is:
+
N N N N
(a) (b) (c) (d)
7. 1. LDA
¾¾¾¾¾® ? ; Product of the reaction is:
2. CH3CH2I
O O
O O
(a) (b) (c) (d)

8. Which compound is formed when the enolate of 2-methylcyclohexanone, formed from lithium
diisopropylamide (LDA), reacts with methyl iodide?
O O OH
a b c d
(a) a (b) b (c) c (d) d
9. Which of the following compounds is most reactive toward nucleophilic acyl substitution ?
O O
|| ||
(a) R — C — NH 2 (b) R — C — OCH 3
O O O O
|| || || ||
(c) R — C — Cl (d) R — C — O — C — R (e) R — C — OH
10. Which of the following compounds is the least reactive toward nucleophilic acyl substitution ?
O O
|| ||
(a) R — C — N H 2 (b) R — C — OCH 3
O O O O
|| || || ||
11. Which of the following compounds is a hydrazone ?
CH3
NHNH2 N
CH3
(i) (ii)
NH—NH N—NH2 NH2

(iii) (iv) (v)
12. The compound :

O
||
HOCH 2 CH 2 CH 2 CH 2 CH
can form a hemiacetal by reacting with itself in solution. What is the structure of this
hemiacetal?
HO H HO H
O O
(i) (ii)

HO OH
OH
(iii) (iv) CH 3 CH 2 CH 2 CH 2 CH OH (v) CH 3 CH 2 CHOCH 3
|
OH

13. How many hydrogens are replaced by deuterium in the following reaction?
O
D O/DOs
2
¾ ¾¾¾
¾®
(a) 1 (b) 2 (c) 3 (d) 4
5(i) xPCl
14. ¾ ¾¾¾¾¾ ® CH 3 — C ºº C — CH 3
O (ii) y - moles NaNH 2
Sum of ( x + y = ?) .
(a) 2 (b) 3 (c) 4 (d) 5
15. PhMgBr act as a nucleophile with:
O O
|| ||
(a) CH 3 SH (b) CH 3 — C ºº CH (c) CH 3 —C — OH (d) H — C — H
O O
|| || D
RO—C
A C Find correct order of the reactivity of carbonyl groups with LiAlH 4 is:
16.
CHO
|
B COCl
(a) A > B > C > D (b) B>C>D>A
(c) D>C>B>A (d) B>D>C>A
O
LiAlH
17. ¾ ¾¾4® ; Which type of mechanism is followed this reaction?
Hr
(a) Electrophilic addition (b) Nucleophilic addition
(c) Nucleophilic substitution (d) Electrophilic substitution
18. What is/are the major product(s) of the following reaction ?
O
||
CH 3 MgBr + HOCH 2 CH ¾¾® ?
(One mole)

O OMgBr
|| |
(a) HO — CH 2 CCH 3 + HMgBr (b) HO — CH 2 CH
|
CH 3
O O
|| ||
(c) CH 4 + BrMgOCH 2 CH (d) BrMgCH 2 CH + CH 3 OH (e) No reaction
19. Which of the following reagents does not form an alcohol from an aldehyde as shown below ?
O
||
?
R —C—H¾ ¾® R — CH 2 — OH
(a) H 2 Pt (b) 1. NaBH 4 /2. H 3 O +
(c) 1. LiAlH 4 /2. H 3 O + (d) 1. Ag 2 O, NH 3 /2. H 3 O + (e) H 2 /Raney Ni
20. Which of the following compound undergo nucleophilic addition with RMgBr?
O O
|| ||
(a) CH 3 — C — CH 3 (b) CH 3 — C — Cl (c) CH 3 — Cl (d) H 2 C == CH 2
21. Compare rate of reaction of following with RMgBr :
O O O
|| || ||
(i) H — C — H (ii) CH 3 —C — H (iii) CH 3 — C — CH 3
(a) i>ii>iii (b) ii>i>iii (c) iii>i>ii (d) i>iii>ii
O
||
22. CH 3 — C — Et + PhMgBr ¾®
¾ A ¾® ¾ r B ; Product of the reaction is:
(2)H
OH OH
| |
(a) CH 3 — C — Ph (b) Ph — C — Ph (c) (d)
| | OH
Et CH 3
O
||
(i) KCN
23. H ¾ ¾¾
¾®‘ P’
(ii) H 3Or
Find out the incorrect statement about the above given reaction:
(a) It is a nucleophilic addition reaction
(b) Product obtained is present in racemic mixture
(c) If the hydrolysis of obtained product give a-hydroxy acid
(d) It is a electrophilic addition reaction

24. The K eq. values for the HCN addition reaction with the following aldehydes are in the order:
O O O
H H H
MeO Me2N
(i) (ii) (iii)
(a) i > ii > iii (b) ii > iii > i (c) iii > i > ii (d) ii > i > iii
25. Arrange the following compounds in decreasing order of K eq for hydrate formation:
O
(1) C 6 H 5 COCH 3 (2) Cl C—CH3
O O
(3) NO2 C—CH3 (4) CH3 C—CH3
(a) 3>2>1>4 (b) 2>1>3>4 (c) 3>1>2>4 (d) 4>2>1>3

OH
| K1
O
26. (1) CH 3 — C — CN +HCN
|
CH 3
OH O
| K2
(2) CH 3 — C — CN +HCN
| H
H
Relation between K 1 and K 2 is:
(a) K 1 = K 2 (b) K 1 > K 2 (c) K 2 > K 1 (d) K 1 = K 2 = 1
O OH
H+
27. + (excess) ¾¾® ? Major product of the reaction is:
(i) O (ii) OH
O OH OH
(iii) O (iv) OH (v) O

28. What sequence of reactions would best accomplish the following conversion ?
O O OH O
|| || | ||
?
CH 3 — C — CH 2 — C — H ¾ ¾¾® CH 3 CHCH 2 CH
(a) NaBH 4 H 3 O + (b) HOCH 2 CH 2 OH H + ; NaBH 4 ; H + H 2 O
(c) KMnO 4 HO – ; heat (d) LiAlH 4 H 3 O + (e) H 2 Pt; PCC
29. Which of the following compounds will give a positive iodoform test ?
(a) propanal (b) 2-pentanone
(c) 3-pentanone (d) benzophenone (e) cyclohexanone
30. Which of the following reagents is best used for the conversion shown below ?
O OH
C—H H
?
¾¾¾® D
CH3
(a) 1. NaBH 4 2. D 3 O + (b) 1. NaBD 4 2. H 3 O +
(c) 1. LiAlH 4 2. D 3 O + (d) 1. H 2 Pt 2. D 2 O (e) 1. LiAlH 4 2. H 3 O +
Ph OH H 2SO 4
31. ¾ ¾¾ ®( A) ; Product (A) is:
CH3 C ==N
O O
|| ||
(a) Ph — C — NH — CH 3 (b) CH 3 — C — NH — Ph
O O
(c) NH2 (d) NH—CH3
32. Benzaldehyde is more reactive than.......... towards nucleophilic attack.

O O O CHO
|| || ||
(a) H — C — H (b) CH 3 — C — H (c) Ph — C — Ph (d)
NO2
OH H+
33. Product is :
CHO
(a) cyclic acetal (b) cyclic hemiacetal

(c) open chain acetal (d) open chain hemiacetal
34. The end product of the reaction is:
O
2Cl (1 eq) 4 NaBH
¾¾¾® (A) ¾¾¾®
–
(B)
hn OH
CH3

CH3 CH3
O O O
Ph
35. Cl Alcoholic KOH
¾¾¾¾¾® (C), C is:
O
O
Ph
(a) C2H5O (b) Ph
O
CH3
(c) —C—Ph (d) CH3
OH
O C2H5O
36. Rank the acid derivatives with respect to their reactivity with water.
Hint: Most reactive >least reactive
(a) acid halide > ester > acid anhydride > amide
(b) acid anhydride > amide > acid halide > ester
(c) amide > ester > acid anhydride > acid halide
(d) acid halide > acid anhydride > ester > amide
O
37. O—Et
O O
Number of functional group reduced by NaBH 4 and LiAlH 4 respectively are:

(a) 2, 2 (b) 2, 3 (c) 3, 3 (d) 1, 3
O
38.
O
NO2
Number of functional groups that are reduced by LiAlH 4 and NaBH 4 is:
(a) 3, 0 respectively (b) 3, 1 respectively (c) 3, 2 respectively (d) 2, 2 respectively
39. Which of the following is not a reduction reaction ?
O O
|| ||
H Br
(i) R — C — Cl ¾¾2® CH 3 — C — H (ii) CH 2 == CH 2 ¾¾2® CH 2 — CH 2
CCl 4
| |
Br Br

O O OH
|| || |
NH 2NH 2 1. NaBH
(iii) CH 3 — C — CH 3 ¾ ¾¾ ¾® CH 3 CH 2 CH 3 (iv) R — C — R ¾ ¾¾¾4® R — CH — R
OH, heat 2. H 3O +
O
Zn(Hg)
(v) ¾¾¾®
HCl

40. Which of the following is an enamine ?
N—CH3 NCH3
(i) (ii)
CH3
CH3
N N== NH N—N
CH
(iii) OH 3 (iv) (v)

O + CH CH NHCH CH ¾¾® ?
3 2 2 3
OH
C2H5 N—C2H5
(i) N (ii)
C2H5 C2H5
r
N—C2H5 N—C2H5 CH2CH3
(iii) (iv) (v)
C2H5 C2H5

O + CH CH NH ¾¾ H2
® ?
3 2 2
Pt
CH2CH3 NCH2CH3
(i) (ii)
CH2CH3 OH
(iii) (iv) (v) NHCH2CH3
NHCH2CH3

Aldol and Cannizaro Reactions

O
10%NaOH,H
2 O
1. ¾¾¾¾¾¾® ? Product of the reaction is :
5°C
HO HO
(a) (b) O
O
OH
(c) HO (d)
O
O
O
HCl, H O
2
2. ¾¾¾¾® ? Product of the reaction is :
O
O O OH O O
(a) (b) (c) (d)
OH
3. What is the starting material used in the following reaction?
O Ph
OH
10%NaOH,H
2 O
? ¾¾¾¾¾¾®
O
O
(a) 2 (b) 2 OH (c) 2 (d) 2
O
4. Which of the following compounds is the product of an aldol condensation reaction?
O
O OH O O
HO OH
(a) (b) (c) (d)
OH
O
O + NaOH,H 2O
5. 100°C
¾¾¾¾¾¾® ? Product of the reaction is :
HO O
O O O
(a) (b) (c) (d)

NaOH
¾¾¾¾® ?
6. O Heat Product of the reaction is :
O
(a) O (b) (c) (d)

O
O O
7. Which of the following is not the product of an intramolecular aldol condensation?
O O O O
(a) (b) (c) (d)
8. Which product(s) should be formed in the following reaction?

O
NaOH, H O
2
¾¾¾¾¾®
O
O O
O O
a b c d
(a) a and b (b) a , b , and c (c) c and d (d) c only
9. Which is the major product of the following reaction?
O O
EtO– Na+, EtOH, Heat
¾¾¾¾¾¾¾¾®
H3C H
O O O O
a b c d
(a) a (b) b (c) c (d) d
O
10. dil. KOH

¾¾¾® (A) ; Product ( A) is:
D
O OH
O O OH
(a) (b) (c) (d)
OH

O CH == O
CH3 NaOH
11. + ¾¾¾® (A) 99% yield. Product ( A) is:
H O; D
2
NO2
O O NO2
|| ||
(a) Ph — C — CH == CH — Ph (b) Ph — C — CH == CH
O
||
(c) Ph — C — CH == CH NO2 (d) Ph — CH 2 — CH == CH — Ph
12. What is the major organic product of the following aldol addition ?
O
CH
OH–
2 ¾¾® ?
O
OH
O CH
OH
CH
(i) (ii)
O
CH OH O
OH
CH
(iii) (iv)
OH
O
CH
CH
(v)

13. What is the major organic product of the following addition ?
O O
|| ||
OHs
CH 3 CH 2 CH + H — C — H ¾ ¾
¾® ?
(excess)

O OH O
|| | ||
(i) CH 3 CH 2 CHCH (ii) CH 3 C — CH
| |
OH CH 3
O O
HO OH
|| ||
(iii)HOCH 2 CH 2 CH 2 CH (iv) OH (v) H — C — Os
HO

base/ D
14. Ph — CH == CH — CH == O + CH 3 — CH == CH — CH == O ¾ ¾¾®( A) aldol-condensation
product. How many geometrical isomer of ( A) will formed ?
(a) 4 (b) 6 (c) 8 (d) 16
O
CH3
1. LDA/THF
¾¾¾¾¾® ?
2. CH3I
O O
CH3 CH3
(i) CH3 (ii)
CH3
O
OH O
CH3 CH3
CH3 CH3 CH3
(iii) (iv) (v)
CH3

16. Which of the following aldehydes does not undergo an aldol addition when mixed with base ?
O
O
|| CH2CH
(i) H — C — H (ii)
O
O O
|| || CH
(iii)CH 3 CH (iv) CH 3 CH 2 CH (v)

CHO ¾¾¾¾®
conc. KOH Hr
17. (A) ¾® (B) ; Structure of ( B ) is:
CHO D D
cyclic product
O O
COOH O COOK
(a) O (b) (c) (d)
CH2OH CH2OH
OH
PCC dil. KOH

18. ¾¾® (A) + HCHO ¾¾¾¾® (B) ; Structure of ( B ) is:
O O OH O O
OH
(a) (b) CH3 (c) (d)
19. can be synthesised from which of the following in presence of base:
CHO
O
CHO C—CH3 O
(a) (b) CHO (c) (d)
CHO
CHO CHO CHO
20. is final product when one of following is allowed to react with base. Select the
CH3
compound.
O O
|| ||
(a) CH 3 — C — CH 2 — CH 2 — CH 2 — C — CH 3
O O
|| ||
(b) CH 3 — CH 2 — CH 2 — C — CH 2 — C — CH 3

O O
|| ||
(c) CH 3 — C — CH 2 — CH 2 — CH 2 — CH 2 — C — CH 2 — Cl
O O
|| ||
(d) CH 3 — C — CH 2 — CH == CH — C — CH 3
21. Which of the following reactant on reaction with conc. NaOH followed by acidification gives
the following lactone as the only product ?
O
||
O
O
||
C—OCH3 CO2H
(a) (b)
CO2H CHO
CHO CO2H
(c) (d)
CHO CO2H
22. Identify which of the following reactant (I) is best for the following conversion ?
OH
O dil.KOH LiAlH
(I) ¾¾3® (II) ¾ ¾¾
¾® (III) ¾ ¾¾4®
(Zn) D
(a) (b) (c) (d)

[B] Carboxylic Acids and Their Derivatives
Esterification
1. What is the acid anhydride that is hydrolyzed?
O O
+
3H O ,H O
2 OH + HO
? ¾¾¾¾¾¾®
O O
O O
(a) (b) O
O
O O O O
(c) O (d) N
H
O
+
O H O ,H O
3 2
O ¾¾¾¾¾¾® ?
O
O O
OH
(a) HO (b) HO OH
O O
O
O O
OO O
(c) HO OH (d)
HO
3. Which of the following compounds is hydrolyzed most rapidly in aqueous NaOH ?
O O
|| ||
(a) R — C — NH 2 (b) R — C — OCH 3
O O O O
|| || || ||

4. Which of the following compounds is hydrolyzed most slowly in aqueous NaOH ?

O O O
|| || ||
(a) R — C — O — C — CH 3 (b) R — C — NH 2
O O O
|| || ||
(c) R — C — OCH 2 (d) R — C — OCH 3 (e) R — C — Cl
5. Esters and amides are most easily made by nucleophilic acyl substitution reaction on:
(a) alcohols (b) acid anhydrides
(c) carboxylates (d) carboxylic acids (e) acid chlorides
6. 4-Oxobutanoicacid is reduced with Na-borohydride and the product is treated with aqueous
acid. The final product is:
O O O OH CH3
(a) (b) COOH (c) (d)
O
7. The hydrolysis of esters in base is called :
(a) the Fischer esterification (b) the Hunsdiecker reaction
(c) the Dieckmann condensation (d) transesterification
(e) saponfication
8. Which of the following conditions will drive the equilibrium of the Fischer esterification
towards ester formation ?
(a) addition of water (b) removel of water as it is formed
(c) addition of an inorganic acid as a catalyst (d) addition of alcohol
(e) both (b) and (d)
9. What is the product of the following reaction ?
O
O 18
H +
+ H2O ¾¾® ?
18O
18 ||
(i) HOCH 2 CH 2 CH 2 CH 2 COH
O O
18 || 18 ||18
(ii) HOCH 2 CH 2 CH 2 CH 2 COH (iii) HOCH 2 CH 2 CH 2 CH 2 COH
18
O O
||18 18 ||
(iv) HOCH 2 CH 2 CH 2 CH 2 COH (v) HOCH 2 CH 2 CH 2 CH 2 COH

10. Which of the following is most reactive toward Grignard reagent ?

O O
|| ||
(a) CH 3 — C — H (b) CH 3 — C — Cl
O O
|| ||
(c) CH 3 — C — CH 3 (d) CH 3 — C — O — Et
11. Typically, amides will hydrolyze under ............. conditions than esters.
(a) milder (b) more dilute
(c) more vigorous (d) less vigorous (e) more saline
12. Which of the following esters undergoes hydrolysis in basic medium most easily ?
(a) CH 3 CH 2 CO 2 CH 3 (b) (CH 3 ) 2 CHCH 2 CO 2 CH 3
(c) C 6 H 6 O 2 CCH 3 (d) p - CH 3 C 6 H 4 O 2 CCH 3 (e) p - NO 2 C 6 H 4 O 2 CCH 3
13. What is the product obtained from the following reaction ?
O
C—OH 18
H r
+ CH3OH ¾¾® ?
O O
18
C—O—CH3 18 C—O—CH3 18
(i) +H 2O (ii) +H 2O
18
O O
18
C—O—CH3 18 C—O—CH3
(iii) +H 2O (iv) +H 2O
18
O
18
C—O—CH3 18
(v) +H 2O

COOH
Hr
2 +HOCH 2CH2OH ¾¾®?
CH2CH2
(i)
HOOC COOH

CH2CH2O COOH
(ii)
HOOC
O O
CCH2CH2C
(iii)
O O
COCH2CH2OC
(iv)
O O
C—C OCH2CH2OH
(v)

CO2H
NaBH Hr
15. 4
¾¾¾® (A) ¾¾¾®
D (B)
CH2—CHO Cyclic
Compound ( B ) is:
O O
COOH
O
(a) (b) (c) O (d) (a) and (c) both
OH
CO2H
18
2CH OH
16. 3
¾¾¾®
r (A)
H
CO2H
Product ( A) is:
18
O O
O 18
18 C—O—CH3 C—O—CH3
C—O—CH3
CO2CH3
(a) (b) (c) (d)

18 C—OCH3 C—OCH3
C—OCH3
CO2CH3
O O
O 18 18

17. Which of the following carboxylic acid derivatives is most easily hydrolyzed?
O O O O O
(a) OCH3 (b) Cl (c) NHCH3 (d) O
18. Which of the following carboxylic acid derivatives is most difficult to hydrolyze?
O O O O O
(a) Cl (b) NHCH3 (c) O (d) OCH3
r
19. Which of the following compounds will not undergo hydrolysis ? (H 3 O)
O
||
(a) CH 3 — C ºº N (b) CH 3 — CH == NH (c) CH 3 — C — NH 2 (d) CH 3 — NH 2
PI KCN Hydrolysis
20. C 2 H 5 OH ¾¾3® A ¾ ¾
¾® B ¾ ¾¾¾®(C), (C) is:
(a) CH 3 — COOH (b) CH 3 — CH 2 — COOH
(c) CH 3 — (CH 2 ) 2 — COOH (d) CH 3 H — COOH
Carboxylic Acids and Their Derivatives

1. HBr, peroxide
2. Mg, Et2O
3. CO , Et O
2 2
¾¾¾¾¾¾¾¾®
+ ?
4. H O , H O
3 2
5. SOCl2, pyridine
O O
Cl O
(a) (b) (c) (d)
O Cl Cl
2. Which of the following compounds is not an acid anhydride?
O O
O O
(a) (b) (c) O (d)
O O
O O
O
O
O
O
2NaOH, H O
Cl O ¾¾¾¾¾¾® ?

O O O O
OH ONa
(a) Cl OH (b) Cl ONa
O O
O O O O
HO OH ONa
NaO
(c) OH (d) ONa
O O
4. Which of the following is not an acid derivative?
O O O
O
(a) (b) Cl (c) (d) O
O
5. Which of the following is the strongest acid? O
Cl
COOH COOH
(I) (II)
Cl
Cl Cl Cl COOH
COOH COOH
(III) (IV) (V)
Cl Cl
Cl Cl Cl Cl
6. What is the major organic product obtained from the following sequence of reactions ?
O
||
SOCl CH 3OH
CH 3 — C — OH ¾ ¾¾2® ¾ ¾¾ ¾® ?
O O
|| ||
(a) CH 3 — C — O — CH 3 (b) CH 2 — C — O — CH 3
|
Cl
O O O
|| || ||
(c) CH 3 — O — C — H (d) CH 3 — O — C — H (e) CH 3 — C — O — Cl


O
O O
4LiAlH
¾¾¾® ¾¾¾¾¾®
O—CH3 + H + H
O O
(a) O (b) O
O
O
(c) O (d)
O
O
CNH2
1. LiAlH
4
¾¾¾¾®
r ?
2. H3O
r r
NH3 CH2NH3
(i) (ii)
OH O
r Li
C—NH3 C—N CH2OH
AlH2
(iii) H (iv) (v)

O
||
P2O 5 (i) CH 3 MgBr (i) I2 + Ca(OH)2
9. C — NH 2 ¾ ¾ ¾® A ¾ ¾¾¾¾ ® B ¾ ¾¾¾¾ ¾® C; Product is:
(ii) H 3Or (ii) D
O O
|| ||
(a) C — CH 3 (b) C — OH
(c) C (d) C — CH 2 CH 3
||
O O

O
P4O10
10. —C—NH2 ¾¾® (A) ; Product (A) is :
D
OH
(a) —CH—NH2 (b) —Cºº N (c) —CH2—NH2 (d) —NH2
11. Which of the following reagents would reduce carboxylic acids and esters into alcohols ?
(a) H 2 /Raney Ni (b) 1. LiAlH 4 /2. H 3 O +
(c) Na NH 3 (d) 1. NaBH 4 /2. H 3 O + (e) Zn(Hg) / H +
12. When the lactone below is treated with LiAlH 4 , the major organic product is ................. .
O
O
(a) a cyclic ether (b) a cyclic alcohol
(c) a cyclic ketone (d) an acyclic aldehyde (e) an acyclic diol
O
HNO
13. ––O—C–– ¾ ¾¾3®( A) ; Major product ( A) is:
H 2SO 4
O O
(a) O2N— —C—O— (b) —C—O—
NO2
O O
(c) O2N— —O—C— (d) —C—O—
NO2
Decarboxylation
1. Which of the following compounds loses carbon dioxide upon heating to 100°C?
OH OH OH OH
(a) O (b) O (c) O (d) O
O
O OH
2. Which of the following compounds loses carbon dioxide upon heating to 100°C?
O
O O
(a) (b)
O

O O O
(c) OH (d) OH
OH
O O
HO OH
Heat
¾¾¾¾® ?
O O
O HO O
O O
O
(a) HO (b)
OH HO
O
O
O O
(c) (d) HO

O O
Heat
¾¾¾¾® ?
OH
(a) 3-methyl-2-butanone (b) 3,3-dimethylmalonic acid
(c) propane (d) 3,3-dimethyl-2,4-pentadione
Heat
CH—COOH ¾¾¾¾® ?
|
COOH
(a) toluene (b) benzoic acid
(c) phenylacetic acid (d) cyclohexylacetic acid
6. Which of the following is phthalic acid ?
COOH COOH
(i) (ii)
HOOC
COOH
COOH
COOH HOOC COOH
COOH
(iii) (iv) (v)
COOH
COOH COOH

7. Which is the best method for carrying out the following reaction ?
COOH
¾¾¾¾®
NO2
+
(a) COOH;HNO 3 H 2 SO 4
(b) CH 3 Cl AlCl 3 ;HNO 3 H 2 SO 4 ;KMnO 4 H + , heat
(c) CH 3 Cl AlCl 3 ;KMnO 4 H + , heat; HNO 3 H 2 SO 4
(d) HNO 3 H 2 SO 4 ;CH 3 Cl AlCl 3 ;KMnO 4 H + , heat
(e) HNO 3 H 2 SO 4 ; + COOH
O
8. POCl3
Ph—C—NH2 ¾¾®
P O /D
(A) ; Product (A) is:
2 5
OH
(a) Ph — NH 2 (b) Ph — CH 2 — NH 2 (c) Ph—CH—NH (d) Ph — C ºº N
2
O O
|| ||
(i) CH 3 MgBr (ii) H +
9. Ph — C — CH 2 — C — OH ¾
¾®( A) + ( B ) ¾ ¾¾¾¾¾¾ ¾®(C )
14 D
(gas)
Product (C ) is:
14 14 14 14
(a) CH 3 — CO 2 H (b) CH 3 CO 2 H (c) CH 3 CO 2 H (d) CH 3 CO 2 H
O
||
( 2) H +
10. Ph — C — OH + NaHCO 3 ¾® ( A) + PhMgBr ¾ ¾¾®( B )
14 Gas
Product ( B ) is:
O O
|| ||
(a) Ph — C — OH (b) Ph — C — OH (c) Ph — OH (d) Ph — CH 3
14

O
C—OH
heat
¾¾® ?
C—OH
O

O O
C—OH
+ CO2 O +H 2O
(i) (ii)
O
O
OH OH
(iii) + CO2 (iv) +H 2O (v)
OH C—OH
O O
12. In which of the following reaction CO 2 (carbondioxide) is not released ?
O O
O O
|| || OH ¾
(a) ¾
¾® (b) ¾®
D OH D
OH
O
O
(c) || NaHCO 3
(d) OH ¾
H ¾ ¾¾¾® ¾®
O OH D
13. Compound ( A) evolves CO 2 gas with NaHCO 3 ,

Compound ( A) evolves H 2 gas with Na ,
Compound ( A) gives +ive Iodoform test,
Structure of ( A) is:
OH O
CO2H
(a) (b)
HO CHO
OH
O OCH3
(c) (d)
CO2H
HO CO2H
O

Answers
[A] Aldehydes and Ketones

Methods of Preparation
1. (c) 2. (c) 3. (b) 4. (b) 5. (a)
Properties of Carbonyl Compounds

1. (b) 2. (a) 3. (b) 4. (b) 5. (c) 6. (b) 7. (c) 8. (b) 9. (c) 10. (a)
11. (d) 12. (b) 13. (c) 14. (b) 15. (d) 16. (b) 17. (b) 18. (c) 19. (d) 20. (a)
21. (a) 22. (a) 23. (d) 24. (d) 25. (a) 26. (b) 27. (c) 28. (b) 29. (b) 30. (b)
31. (a) 32. (c) 33. (b) 34. (c) 35. (c) 36. (d) 37. (b) 38. (c) 39. (b) 40. (b)
41. (a) 42. (e)
Aldol and Cannizaro Reactions

1. (a) 2. (a) 3. (d) 4. (c) 5. (c) 6. (d) 7. (c) 8. (d) 9. (c) 10. (b)
11. (a) 12. (b) 13. (d) 14. (c) 15. (a) 16. (a) 17. (a) 18. (a) 19. (b) 20. (a)
21. (c) 22. (b)
[B] Carboxylic Acids and Their Derivatives

Esterification
1. (b) 2. (c) 3. (c) 4. (b) 5. (e) 6. (a) 7. (e) 8. (e) 9. (d) 10. (b)
11. (c) 12. (e) 13. (d) 14. (d) 15. (a) 16. (b) 17. (b) 18. (b) 19. (d) 20. (b)
Carboxylic Acids and Their Derivatives

1. (a) 2. (b) 3. (d) 4. (c) 5. (e) 6. (a) 7. (c) 8. (b) 9. (c) 10. (b)
11. (b) 12. (e) 13. (c)
Decarboxylation
1. (a) 2. (c) 3. (d) 4. (a) 5. (d) 6. (c) 7. (d) 8. (d) 9. (a) 10. (b)
11. (b) 12. (d) 13. (d)

1. Which of the following compound easily undergo decarboxylation on heating ?

O O O
CO2H
O
(a) (b) (c) (d)
CO2H CO2H
HO2C CO2H
2. Which of the following compound reacts with NaHCO 3 to evolve CO 2 gas ?
OH
O OH OH
O == S == O
C—OH
(a) (b) (c) (d)
3. Which of the following compound undergo Cannizzaro reaction ?

O
O
|| H
(a) H — C — H (b)
CH 3 O O
| || ||
(c) CH 3 — C — C — H (d) Ph — CH 2 — C — H
|
CH 3
4. In which of the following intramolecular aldol condensation reaction more than two products
are possible ?
O O
|| ||
KOH
(a) CH 3 — C — CH 2 — CH 2 — CH 2 — CH 2 — C — H ¾ ¾ ¾®
D
CH2—CH == O
KOH
(b) ¾¾
¾®
D
CH2—C—CH3
O

O O
|| ||
Ca(OH)2
(c) H — C — CH 2 — CH 2 — CH 2 — CH 2 — C — H ¾ ¾ ¾¾®
D
O
Ba(OH)
(d) ¾2®
¾¾¾
D
O
5. Which of the following pair is differentiated by iodoform test ?
O
||
(a) H — C — H, CH 3 CHO
O O
|| ||
(b) CH 3 — C — CH 3 , H — C — H
O OH
(c)
(d)
O O
6. Among the following which compound gives haloform test ?
O O
|| ||
(a) Ph — C — CH 3 (b) Ph — C — CH 2 — CH 3
O
(c) (d) CH3

OH
7. Which of the following gives positive test with 2, 4 - DNP ?

O O O O
|| ||
(a) (b) (c) CH 3 — C — H (d) H — C — H
8. Which of the following gives positive iodoform test?

O OH
(a) (b) (c) OH (d) OH

9. Which of the following gives negative iodoform test?

O
||
(a) Ph — CHO (b) Ph — C — Ph
O O
|| ||
(c) Ph — C — CH 3 (d) Ph — C — CH 2 — CH 3
10. Which of the following compounds undergo self aldol?
O O O O
|| || || ||
(a) CH 3 — C — H (b) CD 3 — C — H (c) Ph — C — H (d) H — C — H
11. Which of the following compounds give geometrical isomers when reacts with NH 2 — OH ?
O O O O
|| || || ||
(a) Ph — C — CH 3 (b) CH 3 — C — CH 3 (c) H — C — H (d) CH 3 — C — H
12. Which of the following compound easily undergo decarboxylation on heating?
O O O
|| || ||
(a) Ph — C — CH 2 — C — OH (b) CH 3 — C — OH
O O
CO2H || ||
(c) CH3—CH (d) CH 3 — C — CH 2 — C — OH
CO2H
13. Which of the following compounds will undergo cannizaro reaction?

O O O O
|| || || ||
(a) H — C — H (b) Ph — C — H (c) CH 3 — C — H (d) D — C — D
14. Which of the following gives positive Tollen’s test?
O
|| O
(a) CH 3 CHO (b) Ph — CHO (c) Ph — C — CH 3 (d)
15. Which of the following compounds reacts with NaHSO 3 ?
H
O
(a) (b) O
O
(c) O (d)
16. Which of the following reaction is esterification ?
O O O
|| + || ||
H
(a) EtOH + CH 3 — C — OH ¾¾® (b) EtOH + CH 3 — C — O — C — CH 3 ¾
¾®
D D
O
||
(c) EtOH + CH 3 — C — Cl ¾® (d) EtOH + HCl ¾®

17. Which of the following compounds is/are hemiacetal?

OH OH OEt
OH OEt OEt
OH
(a) (b) (c) (d) OEt
18. Which of the following compounds is/are acetal?

OCH3 OCH3 OH OH
OCH3 OEt OH OEt
(a) (b) (c) (d)
19. Which of the following is/are more reactive than acetone toward Grignard reagent?
O O O O
|| || || ||
(a) H — C — H (b) CH 3 — C — H (c) Ph — C — CH 3 (d) Ph — C — Ph
20. Which of the following compounds has active methylene group?
O O O O
|| || || ||
(a) CH 3 — C — CH 2 — CH 2 — C — CH 3 (b) CH 3 — C — CH 2 — C — CH 3
O O O O
|| || || ||
(c) CH 3 — C — C — CH 3 (d) CH 3 — C — CH 2 — C — OEt
21. Which of the following acids is/are stronger acid than benzoic acid?
CO2H CO2H CO2H
CO2H
NO2
CH3
(a) (b) (c) (d)
NO2 OCH3 NO2

22. Which of the following is/are ketoxime ?
Ph
(a) N—OH (b) N—OH (c) N—OH (d) N—NH2
CH3
O O O
|| ||
KOH ( aq.)
23. CH 3 — C — CH 2 — CH 2 — CH 2 — C — CH 3 ¾ ¾ ¾¾®
D
CH3
Correct statement regarding given reaction is:

(a) It is a dehydration reaction (b) Carbanion is intermediate
(c) One of the step is nucleophilic addition (d) One of the step is electrophilic addition

24. In which of the following reaction aldehyde will form ?

3 H Or
(a) Stephen’s reduction R — C ºº N + SnCl 2 + HCl ¾ ¾ ¾®
CH3
CrO Cl
(b) Etard reaction 2 2
¾¾¾®
H O 2
AlCl
(c) Gattermain’s formylation ¾3®
+CO + HCl ¾ ¾
3 H Or
(d) Ph — CH == N — CH 3 ¾ ¾ ¾®
O
25. ¾¾3® ( A) + ( B )
Zn
Compound ( A) and ( B ) is differentiated by
(a) NaOI (b) Tollens reagent (c) Fehling solution (d) Na-metal
O
NaOI
26. ( A) ¾ ¾
¾® ( B ) ¾
¾® + CO2 ; Structure of ( A) is:
D
Hr
CO2H
O O O OH
O
Answers
1. (b, c) 2. (a, c) 3. (a, b, c) 4. (a, b) 5. (a, b, d) 6. (a, d)

7. (a, b, c, d) 8. (a, b, c) 9. (a, b, d) 10. (a, b) 11. (a, d) 12. (a, c, d)
13. (a, b, d) 14. (a, b) 15. (a, b, c) 16. (a, b, c) 17. (b, d) 18. (a, b)
19. (a, b) 20. (b, d) 21. (a, b, d) 22. (a, c) 23. (a, b, c) 24. (a, b, c, d)
25. (b, c) 26. (b, c)

Passage-1:
Carbonyl group show characteristic reaction of nucleophilic addition in which
nucleophile attack in rate determing step on carbonyl carbon.
1. Which pH is suitable for oxime formation ?
(a) 4 - 5 (b) 1 - 2 (c) 8 - 10 (d) 12 - 14
2. Which of the reactant show geometrical isomerism when it react with hydrazine
(NH 2 — NH 2 )?
O
O || O
|| ||
|| O
(a) (b) (c) (d)
H H
CH == O
PCl PhMgBr NH — NH
3. ¾5® w ¾ ¾ ¾
¾¾ ¾® x ¾ ¾2¾ ¾
¾2® y
C—OH
||
O
Identify final product ‘ y’ of the above given reaction:
(a) (b)
Ph
Ph
N
N N
(c) (d)
N
Ph Ph
Passage-2:
O OH
||
O3 ( 1 ) CH3 Mg Br
¾¾¾® O + CH3 —CH ¾¾¾¾¾®
Zn r
(2) H
( A) ( B) ( C) ( D)
1. Compound ( B ) and (C ) is differentiated by:

(a) Iodoform test (b) 2, 4-DNP (c) Tollen’s reagent (d) All

2. Which compound give negative iodoform test ?

(a) A (b) B (c) C (d) D
3. When (C ) reacts with hydroxylamine then formed product is:
(a) CH 2 == N — OH (b) CH 3 — CH == N — OH
(c) CH 3 — CH == N — NH 2 (d) N—OH
Passage-3:
O
1. HCN ||
AlCl3 dil. KOH 2. H3O+ Ph
A + B ¾¾® C + HCHO ¾¾¾® D ¾¾¾® O (Lactone)
3. D HO
1. Compound A and B is:

O
AlCl3 AlCl
3
(a) + Cl ¾¾® (b) + ¾¾®
Cl
OH
3 AlCl
Cl ¾¾® 3AlCl
(c) + (d) + ¾¾®
O
2. Compound C is:
O O
|| ||
(a) Ph — C — CH 3 (b) Ph — C — CH 2 — OH
O O
|| || CHO
(c) Ph — C — CH 2 — C — H (d)
3. Compound D is: CH2—OH
O O O
|| || ||
(a) Ph — C — CH 2 — OH (b) Ph — C — CH 2 — C — H
O O
||
CH3
(c) Ph — C — CH 2 — CH 2 — OH (d)
CH2—OH

Passage-4:
O3 conc.KOH
A ¾® B + C.¾¾¾¾® Benzyl alcohol + salt of benzoic acid
O
dil.KOH
¾¾¾¾® CH3—CH—CH2—C—H
HCN
OH
H3Or
D ¾¾¾¾®
D E
1. Structure of A is:
(a) H 2 C == CH — CHO (b) Ph — CH == CH — CH 3
(c) Ph — C == CH 2 (d) Ph — CH == C — CH 3
| |
CH 3 CH 3
2. Structure of ( B ) and (C ) differentiated by:
(a) FeCl 3 (b) Fehling solution (c) 2,4-DNP (d) NaHSO 3
3. Structure of E is:
Me
OH OH
OH
(a) (b) (c) (d)
O O O O O O O
HO O
Passage-5:
A compound ( A) gives positive test with Br2 CCl 4 . When ( A) undergoes
reductive ozonolysis product ( B) is obtained. When ( B) reacts with dil. KOH
followed by heating (C ) will obtained (C ) gives positive Tollens test. When (C )
reacts with NH 2 — NH 2 KOH / D product ( D ) will obtained.
( D) = CH3
1. Compound ( A) is:
(a) (b)
CH2
(c) (d)

2. Compound ( B ) is:
O
CH CH2—CHO
(a) (b)
CH2—CH2—CH == O CH2—CHO
(c) (d) O == CH — CH == O
3. Compound (C ) is:
(a) CHO (b)
CHO
O
(c) (d) CHO
Passage-6:
An organic compound ' P ' (C 15 H 14 ) on ozonolysis in the presence of Zn give
Q (C 8 H 8 O) and R(C 7 H 6 O). R either react with tollen's reagent as well as conc.
KOH following by acidic medium give same product S. Q reacts with dil. KOH to
give T product. Q also give test with I 2 s OH and obtained product is S.
1. Structure of ' P ' is:
(a) (b)
(c) (d)
2. Structure of Q is:
O
(a) H (b) O
Ph

O
H O
(c) (d)
H
3. Structure of ' S' is:
O
O OH O H O
O H H
(a) (b) (c) (d)

OH
Passage-7:
OH
+
3 H O dil. KOH
2 H
(A) ¾ ¾¾ ¾®( B) + (C ) ¾ ¾¾¾
¾®( D ) ¾ ¾
¾ ®
D Ni
( B) give positive iodoform.
(a) O (b) O (c) OH (d) O
O OH
|| |
(a) (b) (c) EtOH (d) CH 3 — CHO
O OH
|| O |
(a) (b) (c) == O (d)
Passage-8:
3
Compound ( A) gives mole of H 2 gas with Na.
2
Compound ( A) reacts with NaHCO 3
Compound ( B) reacts with amm. AgNO 3
Compound ( B) gives 1-mole of H 2 gas with Na
Compound (C ) highly reactive towards Na
Compound ( D ) does not reacts with Na.
1. Compound ( A) is:
(a) HO — CH — C ºº CH (b) HO — CH — C ºº C — CH 3
| |
CHO OH

O O
|| ||
(c) H — O — C — CH — C ºº C — CH 3 (d) HO — C — CH — C ºº CH
| |
OH OH
2. Compound ( B ) is:
O
||
(a) HO — CH 2 — C — H (b) HO — CH 2 — C ºº CH
O
||
(c) HO — CH — C — CH 3 (d) HO — CH 2 — C ºº C — CH 3
|
OH
3. Compound (C ) is:
(a) CH 3 OH (b) OH (c) (d)
OH OH
4. Compound ( D) is:
OH
(a) CH 3 OH (b) CH 3 — C ºº CH (c) CH 4 (d)
Passage-9:
OH
H3 Or OH
KCN
( A) ¾¾® ( B) ¾¾®
O
1. Compound (A) is:

O O O
|| || ||
(a) CH 3 — C — CH 3 (b) CH 3 — C — H (c) H — C — H (d) EtOH
2. Compound (B) is:
OH OH
OH
(a) CH3—C—CH3 (b) CN (c) H—C—CH3 (d) Et — CN
CH3 H
CH3 H

Passage-10:
Acid derivatives ( RCOX ) undergo nucleophilic reactions at the carbonyl group.
The rate of such a reaction depends on the group X.
The reaction proceeds via the following steps.
s
:O: – :O: O
+ Nu: + :X
–
R X R X R Nu
Nu
1. The compound which would undergo nucleophilic substitution fastest would be:
(a) CH 3 CH 2 CONH 2 (b) CH 3 CH 2 COOCH 3
O O
|| ||
(c) CH 3 CH 2 COCl (d) CH 3 — C — O — C — CH 3
2. Based on the above mechanism, following four probable potential energy diagrams can be
drawn.
E E E E
Reaction coordinate Reaction coordinate Reaction coordinate Reaction coordinate

A B C D
Identify the potential energy diagrams for the best and the poorest leaving groups among
O
||
—NH 2 , — OC 2 H 5 and —Cl, — O — C — CH
Best Poorest
3. The correct order of resonance stabilization is:
(a) Acid chloride > Amide > Ester (b) Ester > Amide > Acid chloride
(c) Amide > Ester > Acid chloride (d) Acid chloride > Ester > Amide
(e) Amide > Acid chloride > Ester (f) Ester > Acid chloride > Amide
4. Oxygen atom of the carbonyl group is most basic in:
(a) Amide (b) Ester (c) Acid chloride (d) None of these
Passage-11:
O r
PCl H O
¾ ( A) ¾ ¾¾5®( B) ¾ ¾
+NH 2 — OH ¾® 3
¾®(C ) + CH 3 — NH 2
1. Compound (A) is:

(a) NH (b) N—OH (c) O (d) N—NH2

2. Compound (B) is:

O O O
(a) NH2 (b) NH— (c) CH2—NH2 (d) None of these
3. Compound (C) is:

OH
(a) EtOH (b) CH 3 — CO 2 H (c) (d) CH 3 — CH 3
Passage-12:
®
N == C
Br2 CHCl 3
¾ ( B) ¾ ¾®(C ) ¾ ¾¾®( D ) Compound (D) is
( A) + NH 3 ¾®
D KOH KOH
1. Compound (A) is:

O
OH C ºº N
(a) (b)
OH
CH ==NH
(c) (d)
2. Compound (B) is:

O
NH2 NH2
(a) (b)
CH2—NH2
(c) (d)
N
3. Compound (C) is: H

CH2—NH2 NH2
(a) (b)
NH—CH3
(c) (d)
N
H

Passage-13:
A derivative of acid ( A), C 7 H 12 O 2 on reduction with LiAlH 4 (lithium
alluminium halide) gives ( B) on reaction with SOCl 2 gives (C ) C 6 H 11Cl. (C ) on
reaction with Mg/ether and CO 2 following by H 3 O r gives ( D ) C 7 H 12 O 2 . ( D ) on
reacts with ammonia and after dehydration with P2 O 5 gives ( E ) C 7 H 11N. ( E )
after reduction with LAH gives C 7 H 15 N( F ). ( F ) on reaction with NaNO 2 × HCl
OH
gives (G ). G is and ( F ) on reaction with CHCl 3 × KOH gives foul like

smell.
1. The structure of the A is:

O OH
O O O O
O O
(a) (b) (c) (d)
2. The structure of D is:

OH O OH O
O O O
H OH
(a) (b) (c) (d)
3. The structure of E is:

N N
N N
(a) (b) (c) (d)
Passage-14:
O conc. KOH
CH == CH 2 ¾¾3® ( A) + ( B) ¾ ¾¾¾¾® (C ) + ( D )
Zn D
(a) HCHO (b) HCOOK (c) HCOOH (d) CH 3 OH
2. Structure of ( D) is:
(a) (CH 3 ) 3 — CCHO (b) (CH 3 ) 3 — CCOOH
(c) (CH 3 ) 3 — CCH 2 OH (d) (CH 3 ) 3 — CCOOK

Passage-15:
O
(1) AlCl Zn(Hg) conc.H SO
+ O ¾ ¾¾¾3® ( A) ¾ ¾¾ 2
¾® ( B) ¾ ¾¾¾¾¾4®
(2) Hr HCl D
O O
O O
OH OH
(a) (b)
O O
O
(c) (d) None of these
O
OH
(a) (b)
O
O
OH
(c) (d)
O
Passage-16:
Br O NH — NH
¾2¾ ( A) ¾ ¾¾
Meso product ¬¾ 3 2
¾®( B) ¾ ¾¾¾¾
¾2
® (C )
CCl 4 Zn, H 2O KOH, D
Compound (B) gives positive iodoform test
(a) (b) (c) (d) (a) and (b) both
O O O
O
(a) (b) (c) (d)


Column-I Column-II
conc. KOH
s r (p) A gives positive
(a) ( A) ¾ ¾¾¾ ¾® Ph — CH 2 OH + Ph — CO 2 K Tollen’s test
O OH (q)
( A) ¾ ¾¾¾®
dil. KOH A gives positive
(b)
C 3 H 6O D Fehling test
O O O (r) A gives positive

|| || ||
CH 3 — C —O— C —CH 3 iodoform test
(c) ( A) ¾ ¾¾¾¾¾¾¾
¾®Ph — CH == CH — C — OH
s r
(1) CH 3 CO 2Na/ D
(2) H 3Or
O O (s) A gives positive

||||
CH 3 — C —OH 2-4-DNP test
(d) ( A) ¾ ¾¾¾¾
¾® CH 3 — C — O — CH 2 — CH 3
H + ,D
(t) A when reacts with

R — NH 2 then formed
product is Schiff-base

Column-I Column-II
Reacts with NaBH 4 to given

(a) (p)
O secondary alcohol
Silver mirror react with

(b) O (q) Ag(NH 3 ) +21
O
(c) (r) Isomer of But-2-en-l-ol
CHO When reacts with PhMgBr

(d) (s)
tertiary alcohol will form.


Column-I Column-II
O
(1)CH 3MgBr
Nucleophilic addition
(a) CH3 ¾¾¾¾® (p)
(2)H + reaction
O
Electrophilic addition
(b) CH3 (1) LiAlH4 (q)
¾¾¾¾®
+
(2) H
reaction
r
H3O
¾¾¾® Formation of 3° alcohol take
(c) (r)
place
HBr Formation of 2° alcohol take

(d) ¾¾¾® (s)
H2O place.
Column-I Column-II
O
(a) r® 1° alcohol
PhMgBr + ( x) ¾ ¾¾
( 2 )H (p) ||
H — C— H
O
(b) r® 2° alcohol
PhMgBr + ( y) ¾ ¾¾
( 2 )H (q) ||
CH 3 — C — H
O
(c) r® 3° alcohol
PhMgBr + ( z ) ¾ ¾¾
( 2 )H (r) ||
CH 3 — C — CH 3
(d) PhMgBr + ( p) ¾ ¾¾
r® (s) EtOH
( 2 )H

1. ( x) isomer of carbonyl compound of C 5 H 10 O give positive iodoform test (including

stereoisomer) ?
2. How many compound give positive Tollen’s test ?
D-Glucose, D-Fructose,
O O O
||
CH 3 — C — H, Ph — CH 2 — OH, CH 3 — CH 3 ,H OH, OH
3. How many isomer C 4 H 10 O give positive Iodoform test ?
(Excluding stereoisomer)
4. How many moles of RMgX consumed in the given compound ?
H O
O OEt
Cl
OH O
5. Among the following how many compound reacts with NaBH 4 ?
O O O
|| || ||
(i) CH 3 — CHO, (ii) CH 3 — C — CH 3 , (iii) CH 3 — C — O — Et, (iv) CH 3 — C — Cl
O O
|| ||
(v) CH 3 — C — O — C — CH 3 , (vi) CH 3 — CH 3 , (vii) H 2 C == CH 2
HgSO dil.
¾4®( A) ¾¾®( B ) ; total number of ‘C’ atom in the product B is:
6. HC ºº CH ¾ ¾¾
H 2SO 4 NaOH
7. In the scheme given below, the total number of intramolecular aldol condensation products
formed from ‘ Y ’ is:
1. O
3 1. NaOH ( aq )
¾ ¾¾
¾ ® Y ¾ ¾¾¾¾¾®
2. Zn, H 2O 2. heat
O HO O OH
||
KOH C
8. CH 3 — C — CH 3 + xHCHO ¾ ¾
¾®
HO OH
HO HO
X = moles of HCHO consumed.
Value of ( X ) will be:
O O
|| ||
KOH ( aq.)
9. CH 3 — C — CH 3 + CH 3 — CH 2 — C — CH 3 ¾ ¾¾¾®( X )
D

X = number of aldol condensation product (including stereoisomer).

Find out the value of ( X )
10. How many isomers of C 4 H 10 O give positive iodoform test ? (include stereoisomer)
O
HO2C CO2H
11. ¾® ( X ) moles of CO 2 evolved during given reaction?
¾
HO2C CO2H D
CO2H CO2H
So the value of ( X ) is:
12. Among the following compounds how many gives positive Tollen’s test?
O
O
(a) (b) (c)
(d) CH 3 — C ºº C — CH 3 (e) CH 3 — CH 2 — C ºº CH
HO OEt
HO OEt O O
(f) (g) OEt (h) (i)
OH O
(j) EtOH (k) (l) H
OH
OH
13. How many isomers having molecular formula C 7 H 14 O give cannizaro reaction?
CH == O
conc. KOH Hr
1. ¾ ¾¾¾ ¾®( A) ¾ ¾®( B ) cyclic
D
CH == O
Find the value of x
molecular weight of( B )
where x =
2
2. Propose a sequence of steps to carry out the following conversion:
O
HO CH3
¾¾®
CHO CHO

3. Provide the structure of the major organic product of the following reaction sequence .
O O
1. LiAlH
O 4
¾¾¾¾¾®
2. H2O
O
|| 14
NaHCO Na
4. Ph — C — OH ¾ ¾¾¾3®( A) gas; Ph — OH ¾¾®( B ) gas
Sum of molecular mass of gas ( A + B = ?)
5. Identify A to Z in the following:
Zn(Hg)
B C
HCl
a H+|CH3OH
NH2—NH2
Se
O
D
KOH, D
2 /D
A
(Hunsdiecker rxn.)
CH3OH/H
I2 Hr (1) AgOH
NaOH
E + F H
(2) Br2/CCl4
KOH
b D r
O NH2—CH3
Br2/Hr 1° amine
N G
c (pH=4-5)
CaO/D
Red P+I2/H2O
(H.V.Z. rxn.)
NH2OH
P+I2 Al(OCHMe2)3 O
e d (pH=4-5) J
OH PCC
OH D
OH
f P K
Hr I
l
SOC 2
aq. KOH
D2O/DOs CH2N2
g Q
Prolonged
heating MCPBA
/D L M
PO4 h
H 3 n.) PhCHO, KOH
-rx R
(E 1 Cross aldol
i
HCN H3Or
S T
Peroxide HCl HBr Peroxide
j k
Cl2+Ca(OH)2 D
U + V Y
Ag heat D LAH
HIO4
W X Z Z1

6. Identify ( A) to (Y ) in the following:

O
O N
CH3—C—Cl
Pyridine
I NH2NH2 CH3O– SNAr
Excess of
G Br2 H
L M
Hoffmann’s bromamide
Cl
3 C—
CH
HNO3
O,
Reaction
H
2 SO
4
LiAlH4
F J
K
Cl2/Fe
or SO2Cl2/hn
(Reed rxn.)
POCl3
D E
Cl2/hn
or P2O5
or P4O10
Heat
CH3Cl in presence
NH3 [O] of AlCl3
C B alk. KMnO4
A Friedal Craft’s
reaction
Complete Nitration
NaOH
in presence of
conc. H2SO4
BENZENE
Q
Gattermann-Koch
CO+HCl (Gas)
Sodalime
heat
3Cl2/hn
S P
R
Fenton reagent
3H2/Ni
X
Fe+2/H2O2
T
Zn(dust)
high temp/pressure
Perkin’s Reaction
in presence of
W
(CH3CO)2O
CH3COONa
n in
itratio
lete N
Comp . H NO 3
HNO3 f conc
nce o
U V prese
(1) Conc. H2SO4

(2) HNO3/D (Better method for preparation of Picric acid) Y

7.
Reaction with aq. Reaction with Positive test with

S.No. Compound
NaOH H3Or Tollen’s reagent
H OH
1.
H OEt
OEt
2.
OEt
O
3.
O—Et
4. CH 3 — C ºº N
5. R — O — R
6. CH 3 — CH 2 — OH
7. Ph — O — Ph
8. Ph — O — CH 3
O OMe
9.
O OH
10.
CH2OH
O
H H
H
11. OH H
HO OH
H OH
O
12.
H O
13. CH 3 — CHO
14. Ph — COCH 3
15.
OCOCH3

Answers

Passage-1: 1. (a) 2. (d) 3. (c)
Passage-2: 1. (c) 2. (a) 3. (b)
Passage-3: 1. (b) 2. (a) 3. (c)
Passage-4: 1. (a) 2. (d) 3. (c)
Passage-5: 1. (b) 2. (a) 3. (a)
Passage-6: 1. (c) 2. (b) 3. (a)
Passage-7: 1. (b) 2. (c) 3. (a)
Passage-8: 1. (d) 2. (b) 3. (a) 4. (c)
Passage-9: 1. (b) 2. (b)
Passage-10: 1. (c) 2. —Cl, — NH2 3. (c) 4. (a)
Passage-11: 1. (b) 2. (b) 3. (b)
Passage-12: 1. (a) 2. (b) 3. (b)
Passage-13: 1. (a) 2. (a) 3. (b)
Passage-14 1. (b) 2. (c)
Passage-15 1. (a) 2. (b)
Passage-16 1. (b) 2. (a)

1. (a) ® p,s,t; (b) ® r,s,t; (c) ® p,s,t; (d) ® r
2. (a)® p, r, s; (b)® q, r; (c)® p, s; (d)® q, r
3. (a)® p, r; (b)® p, s; (c)® q, s; (d)® q, r
4. (a)® p; (b)® q; (c)® r; (d) d® s
1. 2 2. 4 3. 1 4. 6 5. 3 6. 4 7. 3 8. 6 9. 9 10. 2
3
11. 5 12. 13. 3
(a,e,k)

1. 67
2. (i) HOCH 2 CH 2 OH, H + (ii) CH 3 CH 2 CH 2 MgBr (iii) H 3 O +
OH
3. OH + CH3CH2CH2CH2OH
(Racemic)
4. 46 + 2 = 48
5.
OH OCH3
(A) (B) (C) (Clemmensen reduction)
OCH3 OCH3
(Hemiacetal) (Acetal)
s Å
(D) (E, F) CHI 3 + CH 3 CO 2 Na (G) CH 3 — CO 2 H
(Wolff-Kishner reduction) (Iodoform rxn.)
O
|| O
(H) CH 3 — Br (I) I — CH 2 — CO 2 H (J) (CH 3 C O) -2 Ca (K) + CaCO3
O O
OH
(L) (M) Et (N) N—CH3 (O) N
O (lmine)
(Schiff-base)
..
(Leukarat rxn.)
O O H OH
O || CN
(P) (Q) CD 3 — C — CD 3 (R) Ph (S)
O Cyanohydrin
Cyclic Acetal
OH O
CO2H ||
(T) (U, V) CHCl 3 + (CH 3 C O) -2 Ca (W) HC ºº CH
O
O OH O
+ CaCO3 O—C CH2OH
(X) (Y) (Z) (Z 1 )
C—O +HCHO
O
(Lactide)

O O O O
|| ||
(a) H 2 O + Se + CH 3 — C — C — H (b) (c) CH2—Br
(Aldol-condensation)
OH I OH
Cl
H H
(d) (e) (f) (g) HCl+SO2+
Cl Cl
Br
(h) (i) (j) (k)
(Markovnikov rule) (Anti-markovnikovrule)
6.
CH3 COOH COONH4 CONH2
(A) (B) (C) (D)

Tolueneor BenzoicAcid Ammonium Benzamide
MethylBenzene Benzoate
NH2 NH2
Br Br
(E) Ph — C ºº N (F) Ph — CH 2 — NH 2 (G) (H)
Aniline
Br
Tribromo
Aniline
O CH2Cl Cl
NH—C—CH3
(I) (Acetanilide) (J) (K)
(Acetylation Reaction) BenzylChloride
Cl OCH3 NHNH2
(L) (D.D.T.) (M) (N) (O)
NO2 NO2 NO2

COONa
CH3
O2N NO2
(P) (Q) (R)
Sod. Benzoate Benzene
NO2
Trinitro-toluene (Explosive)
(TNT)
OH
H Cl
Cl H
(S) H Cl (T) (U)
Cl H Cyclohexane
H Cl NO2
Cl H
Benzene-hexachloride or Gammaxine
(C6H6Cl6 or 6, 6, 6 insecticide)
OH OH
O2N NO2
(V) (W)
Phenol
NO2
Picric acid
CHO CH==CHCOOH
(X) (Y)
Benzaldehyde a, b-Unsaturated acid or
Cinnamic acid (PAAUA)
7.
Product when react with Product when react with Positive test with Tollen’s
aqueous NaOH H3Or reagent
1. 3 3 3
2. 7 3 7
3. 3 3 7
4. 3 3 7
5. 7 3 7
6. 7 7 7

7. 7 7 7
8. 7 3 7
9. 7 3 7
10. 3 3 3
11. 3 3 3
12. 3 3 7
13. 3 3 3
14. 3 3 7
15. 3 3 7

Organic Compounds Containing Nitrogen 431
6
Organic Compounds
Containing Nitrogen
NH OH H SO
1. ¾ ¾2¾® ( A) ¾ ¾¾
2 4
®( B ). Product B is:
N—OH NH O O
O NH NH
(a) (b) (c) (d)
O
|| ND 3 Br
¾®( A) ¾¾2®( B ) ; Product (B) is:
2. CH 3 — C — OH ¾ ¾
D KOH
O O
(a) CH 3 — ND 2 (b) CH 3 — NH 2 (c) (d)
OH
O O
|| ||
KOBr LAH
3. CH 3 — C — NH 2 ¾ ¾
¾® ( A) ; CH 3 — C — NH 2 ¾ ¾® ( B )
Relation between ( A) and ( B ) is:
(a) Chain isomer (b) Homologues
(c) Functional isomer (d) Identical
4. Which of the following will not undergo Hoffmann bromamide reaction?
O
||
(a) Ph — C — NH — Br (b)

O
(c) (d) CH3—C—NH2
5. Number of moles of Br 2 consumed in Hoffmann bromamide reaction is:

(a) 1 (b) 2 (c) 3 (d) 4
O
|| Br
6. CH 3 — C — NH 2 ¾ ¾ 2¾® ( A) ; Product (A) is:
KOD/ D 2O
(a) CH 3 — NH 2 (b) CH 3 — ND 2 (c) CH 3 — OH (d) CH 3 — O — D

O
O ||
Cl CH —C — Cl
7. ¾¾2®( A) ¾ ¾3 ¾ ¾¾®( B ) ; Product (B) is:
NH2 NaOH
O O
|| O O
(a) CH 3 — C — NH 2 (b) NH—Et (c) (d)
NH—CH3 NH—CH3
O
NH—Br
Ba(OH)
8. ¾2®( A) ; Product (A) is:
¾¾¾
O
NH2 NH2
(a) (b)
NH—CH3 CH2—NH2
(c) (d)
O
C—NH2
KOBr
9. ¾®( A); Product (A) is:
¾¾
O
NH2 C—OH
NH2 NH2
(a) (b) (c) (d)

O
||
H 2SO 4
10. ( A) ¾ ¾¾® f —C — NH — CH 3 [f = Ph] ; Reactant (A) is:
f OH CH3 OH
(a) (b) C ==N
CH3 C ==N f
O
|| f NH2
(c) CH 3 — C — NH — f (d) C ==N
Et
11. Which of the following is syn aldoxime ?

H OH CH3 OH
(a) C == N (b) C == N
H H
H OH
(c) CH C == N (d) All of these
3
12. Which of the following give positive isocyanide test?
(a) (b) CH 3 — NH 2 (c) CH 3 — NH — CH 3 (d) N

N
H CH3
13. An isocyanide on reduction with hydrogen in the presence of platinum gives:

(a) amide (b) primary amine (c) secondary amine (d) alcohol
14. Which of the following reducing agents is best used in the reaction shown below ?
O
||
?
CH 3 — C — NH 2 ¾®¾ CH 3 CH 2 NH 2
(a) H 2 /Raney Ni (b) 1. LiAlH 4 /2. H 3 O +
(c) Na NH 3 (d) 1. NaBH 4 /2. H 3 O + (e) Zn(Hg) / H +
KOH LiAlH
¾®( B ) ¾ ¾¾4® CH 3 CH 2 NHCH 3
15. ( A) ¾ ¾
CHCl 3 Hr
Identify compound A:
O O
|| ||
(a) CH 3 — CH 2 — C — OH (b) CH 3 — CH 2 — C — NH 2
O
||
(c) CH 3 — CH 2 — C — Cl (d) CH 3 — CH 2 — NH 2

16. A nitrile can be made by dehydrating an amide. However, for this reaction to occur, the amide
must be:
(a) primary (b) secondary
(c) tertiary (d) N-methylated (e) part of a lactam
17. CH 3 — CH 2 — NH 2 + CHCl 3 + KOH ¾
¾®( A) ; Product ( A) is:
(a) CH 3 — CH 2 — C ºº N ®
(b) CH 3 — CH 2 — N ==C
(c) CH — N = ®
=C (d) N 2
3
NH2
s
18. + x + HO ¾® isocyanide. Reagent x is:
(a) CH 4 (b) CCl 4 (c) CHCl 3 (d) CH 2 Cl 2

NH2
19. + CHCl 3 + xKOH ¾® ®C

N ==
Moles of KOH used in the reaction are :

(a) 1 (b) 2 (c) 3 (d) 4
O
15
20. NH2 ¾Br
¾2®( A) ; Product (A) is:
KOH
15 15
(a) Ph — NH 2 (b) Ph — CH 2 — NH 2 (c) Ph — CO 2 H (d) Ph — CH 2 — OH
21. OH ¾NH Br
¾3® (A) ¾¾2® (B) ; Product (B) is:
¾
D KOH
CH2—NH2 NH2
(a) (b)
OH
(c) (d)

NH Br CHCl
22. ¾3®( A) ¾¾2®( B ) ¾ ¾¾3®(C ) ; Product (C) is:
¾¾
D KOH KOH
®
(a) N == C (b)
(c) (d)
s
CO2
Br
23. ( A) ¾¾2® ; Reactant (A) is:
KOH
NH2
(a) (b)
(c) (d)
r
3 H O 2 Br + KOH
24. Ph — C ºº N ¾¾
¾ ® ( A) ¾ ¾ ¾¾®( B ) ; Product (B) is:
(Partial hydrolysis)
(a) Ph — CH 2 — NH 2 (b) Ph — OH (c) Ph — NH 2 (d) Ph — CH 3

25. Which one of the following compounds when heated with KOH and p-amine gives
carbylamine test?
(a) CHCl 3 (b) CH 3 Cl (c) CH 3 OH (d) CH 3 CN
26. Which energy diagram corresponds to a reaction in which an intermediate would build up to a
significant concentration?
(a) (b) (c) (d)

27. Which of the following compounds is an imine?

O O
N
(a) N (b)
|
H
H
|
CN N
(c) (d)
O
28. What is the product of the following reactions?
1. Mg, Et2O
2. CO2, Et2O
+
3. H O , H O
Br 3
¾¾¾¾¾¾¾¾® 2
?
4. SOCl , pyridine
2
5. NH3 (Solvent)
O
Cl
NH2
(a) (b) (c) (d) NH2
NH NH
29. Which of the following alkyl halides is not a reasonable substrate for the Gabriel synthesis?
O
1. KOH
2. RX
NH ¾¾¾¾¾¾¾¾¾® R—NH2
3. NH2NH2, EtOH, reflux
O
X X
X X
(a) (b) (c) (d)
30. What is the molecular formula of urea ?

O O
(a) H — C — NH — NH2 (b) NH2—CH 2—C—H
O
(c) NH2— C — NH2 (d) NH 2 — NH — CH 2 — OH
31. Which of the following is a tertiary amine?
··
(a) CH 3 — CH — CH 2 — NH 2 (b) CH 3 — CH — CH — CH 3
| | |
CH 3 CH 3 NH 2
··

CH 3 CH 3
| | ··
(c) CH 3 — C — CH 3 (d) CH 3 — C — CH 3 (e) CH 3 — N — CH 3
| | |
NH 2 NH — CH 3 CH 3
··
32. How many moles of Grignard reacts with following compound ?

O
H—C
C ºº N
HS
Cl
(a) 2 (b) 3 (c) 4 (d) 5
33. Which of the following is a quaternary ammonium ion ?
R R
| |r
(a) R — C — R (b) R — C — R
|
R
R R R
| | |r
(c) R — N — R (d) R — N — R (e) R — N — R
.. | |
R R
HNO
2
34. ¾¾¾® (A) ; Product ( A) is:
NH2 (Major)
(a) (b) OH (c) OH (d) All of these

OH
HNO
35. CH 3 — CH — CH 2 — NH 2 ¾ ¾¾2® ( A) ; Major product (A) is:
|
CH 3
OH
(a) OH (b) OH (c) (d)
CH2—NH2
HNO
2
36. ¾¾®(A) ; Product (A) is :

OH OH
(a) (b) (c) (d)
CH 3 CH 3
| |
HNO
37. CH 3 — C — C — CH 3 ¾ ¾¾2® ? Product of the reaction is:
| | D
OH NH 2
O O O
(a) (b) (c) (d)
NH2
OH
HNO2
38. ¾¾®D
(A) ; Product (A) is:
O O O
(a) (b) (c) (d)
OH
2 HNO
39. (A) ¾¾® ; Structure of (A) is:
NH—CH3 NH2 N
(a) (b) (c) (d)
40. Which of the following compound will not undergo amine inversion?
(a) (b) CH 3 — NH — CH 3 (c) NH 3 (d)

N
NH2
41. The nitrogen atom in the following cyclic compounds can be removed as trimethylamine by
successive Hoffmann eliminations (involving exhaustive methylation followed by heating
with AgOH). The amine which will require a greater number of Hoffmann eliminations is:
CH3 CH3
N CH3
CH3
N N
(a) (b) (c) (d)
N

r s
OH NººNCl
42. + ¾¾®
s ? Product of the reaction is:
HO
OCH3
OH
N == N
(a) (b)
CH3O
OCH3
OH
N == N N== N
(c) (d)
HO
OCH3
OH
(e)
OCH3
OH N2+Cl–
OH -
43. Consider the reaction; + ¾® X ; here X is:
¾¾
NH2
OH
OH
N
N N
(a) (b) NH2
N
NH2

OH
OH
(c) (d)
N == N
NH2
HO CH3
NaNO2
44. ¾¾¾¾® (A) ¾¾¾¾¾¾¾¾® ( B ), Product ( B ) is:
HCl(0–5°C) mild-basic
OH OH
(a) (b)
N == N—Ph
CH3 CH3
OH OH
N == N—Ph PH
(c) (d)
CH3 CH3
45. Find out a reaction in which product obtained gives positive isocyanide test
O O
|| ||
LiAlH 4 NaBH 4
(a) NH2 ¾ ¾¾ ® (b) NH2 ¾ ¾¾®
NH LiAlH NH NaBH
(c) || ¾ ¾¾4® (d) || ¾ ¾¾4®
O O
CH2—NH2
HNO
46. 2
¾¾¾® (A) . Product ( A) is:
(a) Ph — CH 2 — OH (b) Ph — OH (c) Ph — CH == O (d) Ph — CO 2 H

47. In which of the reaction formation of Diazonium salt takes place ?

NH2 NH—CH3
NaNO2 NaNO2
(a) ¾¾¾®
2HCl
(b) ¾¾¾®
2HCl
2 NaNO
NaNO
2 ¾¾¾®
(c) ¾¾¾® (d) 2HCl
2HCl
N N
H CH3
NaNO
48. Ph — CH 2 — NH 2 ¾ ¾¾2®( A)(Major) ; Product (A) is:
2HCl
(a) Ph — OH (b) Ph — CH 2 — OH (c) Ph — CH 2 — Cl (d) Ph — CH — CH 3
|
Cl
NH2
H—Cl
49. ¾¾¾® ; Product formed in this reaction is:
(1-mole)
CH2—NH2
NH2
r s NH2
NH2Cl NH2
(a) (b) (c) s r (d)

CH—Cl s
r s NH3Cl
CH2—NH2 CH2—NH3Cl NH3 r
r
Answers
1. (d) 2. (b) 3. (b) 4. (c) 5. (a) 6. (b) 7. (c) 8. (b) 9. (a) 10. (a)
11. (c) 12. (b) 13. (c) 14. (b) 15. (d) 16. (a) 17. (b) 18. (c) 19. (c) 20. (a)
21. (b) 22. (a) 23. (b) 24. (c) 25. (a) 26. (b) 27. (b) 28. (d) 29. (d) 30. (c)
31. (e) 32. (b) 33. (e) 34. (b) 35. (c) 36. (a) 37. (b) 38. (a) 39. (b) 40. (d)
41. (b) 42. (c) 43. (a) 44. (c) 45. (a) 46. (a) 47. (a) 48. (b) 49. (b)

1. Which of the following compounds will not undergo Hoffmann bromamide reaction?
O O
|| ||
(a) CH 3 — C — NH — CH 3 (b) Ph — C — NH — Ph
O O
||
(c) NH2 (d) Ph — C — NH 2
2. Which of the following gives positive carbylamine reaction ?
NH2 NH2
CH3—CH—NH2
(a) (b) (c) (d) N
CH3
H
3. Which of the following gives positive carbylamine reaction ?

C
|
(a) (b) (c) NH2 (d) C — C — NH 2
N |
CH3 C
NH2
4. Which of the following is/are primary amine?
C
(a) (b) (c) NH2 (d) C—C—NH2

N
C
NH2 CH3
5. Which of the following compound reacts with ammonical AgNO 3 ?

r s
NH3Cl
O
|| O
(a) (b) CH 3 — C — CH 3 (c) CH 3 — C ºº CH (d) ||
Ph H
Answers
1. (a, b) 2. (a, b, c) 3. (a, c, d) 4. (a, c, d) 5. (a, c, d)

Passage-1:
Hoffmann bromamide reaction involves conversion of a carboxylic acid amide
into an amine with a loss of one carbon atom on treatment with aqueous
sodium hypobromite. Thus Hoffmann result in shortening of a carbon chain.
O
||
Br2
R — C — NH 2 ¾ ¾¾® R — NH 2 + NaBr + Na 2 CO 3
NaOH
Mechanism of the reaction is:
s
O O
NaOH
R—C—NH2 ¾¾® R—C == NH+Br—Br
O
R—C—NH—Br
HOs
O == C == N—R¬¾¾R—C—Ns—Br
H 2O
Na2CO3 + R—NH2 ¬¾¾
1. Which of the following most reactive towards Hoffmann bromamide reaction ?

O O O O
15
C—NH2 C—NH2 C—NH2 C—NH2
(a) (b) (c) (d)
CH3 OCH3 NO2

O
O ||
Br2 Ph— C —O— Et
2. C—NH2 ¾¾® ( A) ¾ ¾ ¾ ¾ ¾¾® ( B ) major. Product B is:
KOH
O O
|| ||
(a) Ph — NH — C — Ph (b) Ph — C — NH — CH 2 — Ph
O O O
|| || ||
(c) Ph — C — C — Ph (d) EtO — C — NH — Ph

3. Which of the following will not give Hoffmann bromamide reaction ?

O O
||
(a) CH 3 — C — NH 2 (b) C—NH—Br
O O
(c) C—NH2 (d) C—NH—CH3
Passage-2:
HNO2 H2SO4
(A) (B) D
(C)
(major) (major)
HBr
Br
1. Compound (A) is:
NH NH NH2
(a) NH2 (b) (c) (d)
2. Compound (B) is:

O
(a) (b) OH (c) (d) CH3
OH OH
3. Compound (C) is:
(a) (b) (c) (d)
Passage-3:
LiAlH
4 LiAlH
( A) ¾ ¾ ¾
¾ ® ( B) ; ¾4® ( D )
(C ) ¾ ¾ ¾
(A) and (C) are isomers while (B) and (D) are isomers.
1. Compound (A) is:
O O
|| ||
(a) CH 3 — C — OH (b) CH 3 — C — NH 2 (c) CH 3 — C ºº N (d) H 2 C == CH — NH 2
2. Compound (B) is:
(a) CH 3 — CH 2 — OH (b) CH 3 — CH 2 — NH 2
(c) CH 3 — NH — CH 3 (d) CH 3 — CH 2 — NH — CH 3
3. Compound (C) is:
O
(a) (b) CH 3 — C ºº N (c) CH 3 — N ®
== C (d) H 2 C == CH —NH 2
NH2

4. Compound (D) is:

(a) CH 3 — CH 2 — OH (b) CH 3 — CH 2 — NH 2
(c) CH 3 — NH — CH 3 (d) CH 3 — O — CH 3
5. Which of the following gives positive isocyanide test?
(a) A (b) B (c) C (d) D
Passage-4:
NHCH3
KOBr CHCl LiAlH

( A) ¾ ¾¾® ( B) ¾ ¾ ¾3® (C ) ¾ ¾ ¾
¾4
®
KOH
CH3
O NH O NH—CH3 O NH2
2
(a) (b) (c) (d) none of these

CH3
CH3 CH3
CN NC NC
NC
CH3
(a) (b) (c) (d)
CH3
CH3 CH3

1. Which of the compound react with the following reagent ?

Column-I Column-II
NH2 (p) Positive isocyanide test
(a)
O (q) Undergo Reimen Teimann reaction

(b) ||
Ph — C — CH 3
OH (r) Hoffmann bromamide reaction
(c)
O (s) 2 , 4 DNP (Positive test)

(d) ||
Ph — C — NH 2
(t) Reacts with CH 3 MgBr and evolve CH 4 gas.

1. ¾¾® x is total number of HEM (Hoffman Exhaustive Methylation and

N
elimination) to remove nitrogen from given compound.
alc. KOH
¾® y is total number of possible product (including stereoisomer)
¾¾¾
Br
Sum of x + y = ?
CººN
3 H Or
2. (1) ¾¾ ¾®( A) + NaHCO 3 ¾® ( B ) gas
CººN
LiAlH HNO
(2) ¾ ¾¾4® (C ) + ¾ ¾¾2® ( D) gas
æB+Dö
Find out the sum of molecular mass of gas çç ÷÷ = ?
è 12 ø
1. Provide the major organic product(s) of the reaction below.

CH3
1. CH I(excess), K CO
3 2 3
¾¾¾¾¾¾¾¾¾®
N 2. Ag2O , H2O
3. Heat
H

2. Find missing reagent & Name of reaction:

S.No. Reaction Missing Reagent Name of reaction
O
(i) ||
R — C — NH 2 ¾¾® R — NH 2
(ii) ®
Ph — NH 2 ¾¾® Ph — N == C
OH OH
CO2H
(iii)
¾¾®
OH OH
CHO
(iv)
¾¾®
Ph OH
C == N ¾¾®
CH3
(v) O
||
Ph — C — NH — CH 3
O
(vi) ||
Ph — C ºº CH ¾¾® Ph — C — CH 3
Br
(vii)
¾¾®
Br
(viii) ¾¾®

3. Find the (a) to (z).

O
(f)
(a) (b) (c) (d) (e)
Br Cl NO2 SO3H CH2CH2CH3
(k) (o)
(g) (h) OH (n)
Br
(i) NH2 HOOC
(j)
(l) (p) (m)
N2Cl
Br
CH==CHCH3
(q)
(r)
OH
(t) (u) (v) (w) (x) (y) (z)

F Cl Br I CN OH
(s) NH2

Answers
Passage-1: 1. (b) 2. (a) 3. (d)
Passage-2: 1. (a) 2. (a) 3. (b)
Passage-3: 1. (c) 2. (b) 3. (c) 4. (c) 5. (b)
Passage-4: 1. (a) 2. (b)

1. (a) ® p, t; (b) ® s; (c) ® q,t; (d) ® r, t
1. 6 2. 6
1.
N
2.
(i) Br 2 + NaOH ; Hoffmann’s Bromamide
(ii) CHCl 3 + KOH ; Isocyanide Test/Hoffmann’s Carbyl amine test
(iii) CO 2 + KOH ; Kolbe schmidt
(iv) CHCl 3 + KOH ; Reimer-Tiemann reaction
(v) H + /PCl 5 /SO 3 ; Beckmann rearrangement
(vi) HgSO 4 dil. H 2 SO 4 ; Kucherov’s reaction
(vii) HBr; Markovnikov’s addition
(viii) HBr, Peroxide; Anti Markovnikov’s addition
3. (a) = Br 2 Fe ; (b) = Cl 2 Fe ; (c ) = HNO 3 + H 2 SO 4 ; (d) = conc . H 2 SO 4 ;
(e) = CH 3 CH 2 CH 2 Cl FeCl 3 ; (f ) = CH 3 CH 2 CH 2 COCl AlCl 3 ;
(g ) = Sn HCl ; (h) = CF3 CO 3 H; (i) = NaNO 2 HCl , H 3 PO 2 ; ( j) = Cl 2 AlCl 3 , NaNH 2 ;
(k ) = NBS; (l) = NaNO 2 HCl ; (m) = conc . H 2 SO 4 D ; (n) = NaBH 4 LAH(H 2 / Ni);
(o) = hot KMnO 4 ; (p) = alc . KOH; (q) = HBr peroxide ; (r ) = BH 3 : THF H 2 O 2 ;
(s) = LAH; (t ) = HBF4 ; (u) = CuCl HCl ; ( v ) = HBr CuBr ; ( w) = KI; ( x) = CuCN;
( y ) = H 2 O boil ; (z ) = H 3 PO 2

Biomolecules 451
7
Biomolecules
1. Which of the following is the only naturally occurring amino acid with the R configuration at
the (-carbonyl stereogenic centers?
(a) serine (b) arginine (c) cysteine (d) proline
2. What is the major structure of aspartic acid present at pH = 7 in aqueous solution?
O NH2 O NH2
OH O–
(a) HO (b) HO
O O
O NH+
3 O NH2
O– O–
– –
(c) O (d) O
O O
3. What is the major structure of glycine present at pH = 1 in aqueous solution?

+ OH + O–
H
(a) 3 N H
(b) 3 N
O O
OH
OH H2N
(c) H2N (d) O
+
O H

4. Which of the following amino acids has pI ~ 9.8?

O
(a) H2N—CH—C—OH Tyrosine:

CH2 pKa1(COOH)=2.2
pKa2(NH 2)=9.1
pKa3( R) = 10.1
OH
(b) H2N—CH—C—OH Lysine:

CH2 pKa1 (COOH) = 2.2
pKa2 (NH2) = 9
CH2
pKa3 (R) = 10.5
CH2
CH2
NH2
(c) H2N—CH—C—OH Arginine:

pKa2 (NH2) = 9
CH2
pKa3 (R) = 12.5
CH2
NH
C ==NH
NH2
(d) H2N—CH—C—OH Cysteine:

pKa2 (NH2) = 10.8
SH
pKa3 (R) = 8.3

Biomolecules 453
5. Which of the following structures is called a Zwitter ion?

O
r H O
H3N—C—C—Os r H
| H3N—C—C—OH
CH2 |
(a) (b) CH2
|
O == C |
| COOH
O s
O
O H
r H H3N—C—C—Os
H3N—C—C—O s |
| CH2
(c) CH2 (d)
|
| O == C
COOH |
Os
6. Which descriptors fit the following sugar best?
O OH
OH
HO
HO OH
(a) ketose, furanose, a (b) ketose, furanose, b
(c) aldose, pyranose, b (d) aldose, pyranose, a
7. Which of the following is the correct Fischer representation of D-galactose?
Hint: The structure of b-D-galactopyranose is provided.
OH OH
H O
H
HO OH
H OH
H H
CHO CHO
HO H HO H
HO H H OH
(a) (b)
H OH H OH
H OH H OH
CH2OH CH2OH

CHO CHO
H OH H OH
HO H HO H
(c) (d)
HO H H OH
H OH H OH
CH2OH CH2OH
8. Which of the following structures is the correct Haworth representation of D-idose?

CHO
HO H
H OH
HO H
H OH
CH2OH
CH2OH CH2OH
OH O OH O
(a) H (b) H
OH H OH H OH OH
H H
H OH OH H
H CH2OH
OH O OH O
(c) CH2OH (d) H
H OH OH H H OH
H H
OH H OH OH
9. Which of the following compounds does not undergo mutarotation?

(a) glucose (b) sucrose (c) ribose (d) fructose
10. D-Mannose is epimeric with D-glucose at C 2 . Which of the following structures represents
b-D-mannopyranose?
OH
HO OH
HO CH2OH HO HO O
O O
HO O
OH HO
OH HO OH OH
HO HO
HO HO
(a) (b) (c) (d)
(a) a (b) b (c) c (d) d

Biomolecules 455
11. A glycoside is shown below. What is the structure of the carbohydrate from which it was
formed?
HOH2C O OMe
HCl
H OH Open chain form ?
H CH2OH
OH H
CHO CH2OH
H OH ==O
HO H HO H
(a) H OH (b) H OH
H OH H OH
CH2OH CH2OH
CH2OH
CHO ==O
HO H H OH
(c) H OH (d) HO H
H OH H OH
CH2OH CH2OH
12. A glycoside is the carbohydrate form of an

(a) ether (b) acetal
(c) aglycone (d) alcohol
13. Which of the following structures is not going to give a positive test with Benedict’s reagent?
CHO
H OH
H OH
3 HNO
H OH ¾¾¾®
H OH
CH2OH

COOH CH2OH COOH CN

H OH H OH H OH H OH
H OH H OH H OH H OH
(a) (b) (c) (d)
H OH H OH H OH H OH
H OH H OH H OH H OH
CH2OH CH2OH COOH CH2OH

CHO
H OH
H OH
Br /H O
2 2
H OH ¾¾¾¾®
H OH
CH2OH
COOH CH2OH
H OH H OH
H OH H OH
(a) (b)
H OH H OH
H OH H OH
CH2OH CH2OH
COOH CN
H OH H OH
H OH H OH
(c) (d)
H OH H OH
H OH H OH
COOH CH2OH
15. Reduction of hexose A (molecular formula C 6 H 12 O 6 ) with sodium borohydride gives

compounds B and C. Compound B is optically inactive, whereas compound C is optically
active. Which of the following is compound A?
(a) D-fructose (b) D-glucose (c) D-mannose (d) D-galactose

Biomolecules 457
16. Which of the following disaccharides fulfills the two requirements stated below?
1. a-(1, 2) glycosidic linkage
2. Not a reducing sugar
H OH
OH
O
(a) HO
H H
H H OH
OH O O CH2OH
H OH
OH
HO H
H OH
(b) OH
O
HO
H O O CH2OH
H H
OH H H OH
OH
HO H
H OH
OH
O
(c) HO
H H
H H OH
OH O O CH2OH
H OH
H
HO H
HOH2C
O CH2OH
(d) H OH
OH H H OH
O OH
HO
O H
H
H H
OH H

OH OH
O O
MeOH, HCl
O ¾¾¾¾¾® ?
HO H
H OH
OH OH
O O
(a) + HO
HO OCH3
OCH3
OCH3 OCH3
O O
(b) + H CO
H3CO OH 3 H
H OH
OCH3 OCH3
O O
(c) O
H3CO H
H OH
OH OH
O O
(d) O
HO H
H OMe

Biomolecules 459
18. Which statements are correct about the following disaccharide?

Ring A
OH
OH Ring B
HO O
OH
HO
O O
OH
HO OH
(a) Ring A is an acetal in the a configuration; ring B is a hemiacetal in the b configuration
(b) Ring A is an acetal in the b configuration; ring B is a hemiacetal in the a configuration.
(c) Ring A is a hemiacetal in the a configuration; ring B is an acetal in the b configuration.
(d) Ring A is a hemiacetal in the b configuration; ring B is an acetal in the a configuration.
19. How many aldose and ketose, and furanose and pyranose units are present in maltose?
OH
H
H2C H
O
HO H H
H OH
HO H
H OH HO OH
H
O
O
Maltose CH2 OH
H
(a) 0 aldose, 2 ketose, 0 furanose, 2 pyranose

(b) 1 aldose, 1 ketose, 1 furanose, 1 pyranose
(c) 2 aldose, 0 ketose, 0 furanose, 2 pyranose
(d) 2 aldose, 0 ketose, 1 furanose, 2 pyranose
20. Given structure is :
HC == O
|
H—C—OH
|
H—C—OH
|
H—C—OH
|
CH2OH
D-ribose
(a) Aldopentose (b) Aldohexose (c) Ketopentose (d) Aldotetrose


CH2OH
|
C == O
|
HO—C—H
|
H—C—OH
|
H—C—OH
|
H—C—OH
|
CH2OH
D-sedoheptulose
(a) Aldopentose (b) Aldohexose (c) Ketoheptose (d) Ketohexose
HC == O
|
HO—C—H
|
HO—C—H
|
H—C—OH
|
H—C—OH
|
CH2OH
D-mannose
(a) Aldopentose (b) Ketohexose
(c) Ketoheptose (d) Aldohexose
23. Which of the following is D-glyceraldehyde ?
HC == O H
(a) HOCH2 OH (b) HO CH2OH
H HC == O
CH2OH
(c) HO H (d) Both (a) and (b)
HC == O
Br
24. D-Glucose ¾¾2®
H 2O
(a) Aldonic acid (b) Adaric acid (c) Alditol (d) Tartaric acid

Biomolecules 461
25. D-Glucose will form same osazone with:

(a) D-Mannose (b) D-Fructose (c) D-Allose (d) Both (a) and (b)
26. Relation between D-Glucose and D-Fructose is:
(a) C 2 -epimer (b) C 3 -epimer (c) Functional isomer (d) Positional isomer
27. Which of following is Oligosaccharides ?
(a) Glucose (b) Fructose (c) Sucrose (d) Starch
28. Which of the following is D-Glyceraldehyde ?
CH2OH CHO CHO CHO
(a) H OH (b) H OH (c) H OH (d) HO H
CH CH2—OH CH3 CH3
29. C 2 -epimer of D-Glucose is:

(a) D-Glucose (b) D-Allose (c) D-Altrose (d) D-Mannose
30. C 3 -epimer of D-Glucose is:
(a) D-Glucose (b) D-Allose (c) D-Altrose (d) D-Mannose
31. Which of the following carbohydrates is Aldohexose ?
(a) D-Mannose (b) D-Glucose
(c) D-Fructose (d) Both (a) and (b)
Br
32. D-Glucose ¾¾2®; Product is known as:
H 2O
(a) D-Glucitol (b) D-Gluconic acid

(c) D-Glucaric acid (d) Tartaric acid
HOs HOs
33. D-Glucose D-Fructose ( X ); ( X ) is:
(a) D-Allose (b) D-Altrose (c) D-Mannose (d) D-Glucose
5HIO 4
34. D-Glucose ¾ ¾¾®; Product is:
(a) 4HCO 2 H , HCHO (b) 5HCO 2 H , HCHO
(c) 4HCO 2 H , CO 2 , HCHO (d) 5HCHO , HCO 2 H
35. Which of the following pairs give same Osazone ?
(a) D-Glucose, Fructose (b) D-Glucose, D-Mannose
(c) D-Allose, D-Altrose (d) All of these
36. a-D-Glucose and b-D-Glucose are:
(a) Epimers (b) Anomers
(c) Enantiomers (d) Acetals
37. Identify the non-reducing sugar :
OH OCH3
O H3CO O
OH
H H H
(a) HO H (b)
OH OH H3CO OH
H H3CO

CH2OH
OH
O OH O
H OH
H H
(c) OH H (d)
H OCH3
OH OH
OH HO
H
CH2OH
|
C == O
H OH (i) NaBH
4
38. HO ¾¾¾¾® (P)
H +
(ii) H , H2O
H OH
CH2OH
D-sorbose
Number of stereoisomer of product ( P ) is:

(a) 4 (b) 10 (c) 12 (d) 16
39. The main structural features of proteins is:
(a) Ester linkage (b) Ether linkage (c) Peptide linkage (d) All of these
40. Which compound can exist in a dipolar (Zwitter ion) structure ?
(a) C 6 H 5 CH 2 CH(N == CH 2 )COOH (b) (CH 3 ) 2 CHCH(NH 2 )COOH
(c) C 6 H 5 CONHCH 2 COOH (d) HOOCCH 2 CH 2 COCOOH
41. Vitamin C is chemically :
(a) Ascorbic acid (b) Citric acid (c) Aspirin (d) Aspartic acid
42. In an amino acid, the carboxylic group ionises at pK a1 = 2 .34 and ammonium ion at
pK a2 = 9.60. The isoelectric point of the amino acid is at pH :
(a) 5.97 (b) 2.34 (c) 9.60 (d) 6.97
43. Which statement is incorrect about peptide bond ?
(a) C — N bond length in proteins is longer than usual bond length of C — N bond
(b) Spectroscopic analysis shows planar structure of — C — NH — bond
||
O
(c) C — N bond length in proteins is smaller than usual bond length of C — N bond
(d) None of these
44. A triglyceride can have how many different acyl groups ?
(a) 3 (b) 2 (c) 1 (d) 4
45. Glycosidic linkage is present in:
(a) Sucrose (b) Maltose (c) Lactose (d) All of these
46. Which of the following amino acid has lowest isoelectric point ?
(a) Lysine (b) Aspartic acid (c) Glycine (d) Alanine

Biomolecules 463
47. Protein on hydrolysis gives:

(a) a-amino acid (b) b-amino acid (c) g-amino acid (d) All of these
48. Which of the following amino acid is optically inactive ?
(a) Glycine (b) Alanine (c) Valine (d) Leucine
49. Peptide linkage is present in:
(a) Protein (b) Nylon-66 (c) Sucrose (d) Both (a) and (b)
50. Product obtained by hydrolysis of lactose are:
(a) Glucose and fructose (b) Glucose and mannose
(c) Mannose and fructose (d) Galactose and Glucose
51. Which of the following is amino acid ?
(a) NH 2 — CH 2 — CO 2 H (b) NH 2 — CH 2 — CH 2 — CO 2 H
(c) NH 2 — CH 2 — CH 2 — CH 2 — CO 2 H (d) All of these
52. Which of the following is structure of b-D-Glucopyranose ?
CH2—OH CH2—OH
O O
H H H OH
H H
(a) OH H (b) OH H
HO OH HO H
H OH H OH
HOCH2 O OH CH2—HO O CH2—HO

(c) H H (d) OH H
H H H OH
OH OH H OH
53. Maximum number of monosaccharide units present in oligosaccharides is:

(a) 8 (b) 15 (c) 10 (d) 40
54. Which one of the following is non-reducing sugar ?
(a) Glucose (b) Arabinose (c) Fructose (d) Sucrose
55. Which one of the following is reducing sugar ?
(a) Starch (b) Cellulose (c) Glycogen (d) Fructose
56. In aqueous solution glucose exist in how many isomeric forms ?
(a) Two (b) Sixteen (c) Three (d) Four
57. Reducing property of monosaccharide is due to the presence of:
(a) —OH group (b) Keto group
(c) Acetal group (d) Anomeric hydroxyl group (a Hemiacetal)
58. Which one of the following carbohydrates will show mutarotation ?
(a) Sucrose (b) Maltose (c) Lactose (d) Both (b) and (c)
59. Glucose and mannose are:
(a) Anomers (b) Positional isomer
(c) Functional isomers (d) Epimers

60. Which of the following pairs are epimers ?

CH2OH CHO
| |
CHO CHO C == O H—C—OH
| | | |
H—C—OH HO—C—H HO—C—H HO—C—H
| | | |
(a) H—C—OH and HO—C—H (b) H—C—OH and H—C—OH
| | | |
H—C—OH HO—C—H H—C—OH HO—C—H
| | | |
CH2OH CH2OH CH2OH CH2OH
CHO CHO CHO CHO

| | | |
H—C—OH H—C—OH H—C—OH HO—C—H
| | | |
(c) H—C—OH and HO—C—H (d) H—C—OH and HO—C—H
| | | |
H—C—OH H—C—OH HO—C—H H—C—OH
| | | |
CH2OH CH 2OH CH2OH CH 2OH
61. Glucose molecule reacts with ‘ X ’ number of molecule of phenylhydrazine to yield osazone.
The value of X is:
(a) Three (b) Two (c) One (d) Four
62. Which of the following reagents cannot distinguish between glucose and fructose ?
(a) Tollens’ reagent (b) Fehling’s solution (c) Benedict’ solution (d) All of these
63. Cellulose is a polymer of:
(a) Glucose (b) Fructose (c) Ribose (d) Sucrose
64. Which of the following is an example of Ketohexose ?
(a) Mannose (b) Galactose (c) Maltose (d) Fructose
65. When glucose reacts with bromine water, the main product is :
(a) Acetic acid (b) Saccharic acid (c) Glyceraldehyde (d) Gluconic acid
66. All monosaccharide ..............Tollens’ reagent :
(a) oxidises (b) reduces (c) condense with (d) add to
67. The number of chiral centres in (+) glucose is:
(a) 4 (b) 3 (c) 2 (d) 1
68. Protein is polymer of:
(a) Amino acid (b) a-amino acid (c) g-amino acid (d) b-amino acid
69. Amino acid may be:
(a) Neutral (b) Basic (c) Acidic (d) Any one of these

Biomolecules 465
70. The given structure of a-amino acid will exist at which pH ?

COOH
r |
NH3—C—H
|
R
(a) 7 (b) 14 (c) 0 (d) 12
71. Peptide linkage is:
O O O O
|| || || ||
(a) — C — O — (b) — C — NH 2 (c) — C — NH — NH 2 (d) — C — NH —
72. Complete hydrolysis of cellulose gives:
(a) L-glucose (b) D-fructose (c) D-ribose (d) D-glucose
73. Number of chiral carbons in b -D-(+)-glucose is:
(a) six (b) three (c) four (d) five
74. The pair of compounds in which both the compounds give positive test with Tollens’ reagent
is:
(a) glucose and sucrose (b) fructose and sucrose
(c) acetophenone and hexanal (d) glucose and fructose
75. D-Glucose and L-Glucose are:
(a) Enantiomers (b) Diastereomers (c) Epimers (d) Anomers
76. Identify the pair of Epimers:
(a) D-glucose and D-fructose (b) D-glucose and L-glucose
(c) D-glucose and D-mannose (d) D-glucose and D-gulose
77. The number of stereogenic centres in a-D-Glucose are:
(a) 4 (b) 5 (c) 3 (d) 2
78. Which of the following pairs give positive Tollens’ test ?
(a) Glucose, sucrose (b) Glucose, fructose
(c) Hexanal, acetophenone (d) Fructose, sucrose
79. The two forms of D-glucopyranose obtained from the solution of D-glucose are called :
(a) isomer (b) anomer (c) epimer (d) enantiomer
80. Cellulose upon acetylation with excess acetic anhydride/H 2 SO 4 (catalytic) gives cellulose
triacetate whose structure is:
AcO
H O O—
AcO H
O OAc H H
H O
AcO H
O OAc H H OAc
H O H
H
OAc H H OAc
(a) —O H
H OAc

AcO
H O O—
AcO H
O OH H H
H O
AcO H
O OH H H OH
H O H
H
H H OH
(b) —O OH H
H OH
AcO AcO AcO

H O H H O H H O O—
H H H
(c) OAc H OAc H OAc H
—O O O H
H OAc H OAc H OAc
AcO AcO AcO

H O H H O H H O O—
H H H
(d) H H H H H H
—O O O H
OAc OAc OAc OAc OAc OAc
81. The correct statement about the following disaccharide is:

CH2OH
O CH2OH O H
H H
H
OH H H HO
HO OCH2CH2O CH2OH
H OH OH H
(i) (ii)
(a) Ring (i) is pyranose with a-glycosidic link (b) Ring (i) is furanose with a-glycoside link
(c) Ring (ii) is furanose with a-glycosideic link (d) Ring (ii) is pyranose with b-glycosidic link
82. The following carbohydrate is:
H OH
H O
HO
HO OH
H OH
H H
(a) a ketohexose (b) an aldohexose (c) an a-furanose (d) an a-pyranose

Biomolecules 467
83. Which of the following is the structure of L-glucose ?

CHO CHO CHO
HO H H OH H OH
H OH HO H HO H
(a) HO H (b) H OH (c) H OH (d) None of these
HO H H OH HO H
CH2OH CH2—OH CH2—OH
HC—OH
||
C—OH
HO H
84. , the given enol form is:
H OH
H OH
CH2OH
(a) D-glucose (b) D-mannose (c) D-fructose (d) All of these
85. Component of starch is:
(a) Amylose (b) Allose (c) Fructose (d) Mannose
86. A carbohydrate composed of three to ten sugar molecules is called a (n) :
(a) single carbohydrate (b) disaccharide
(c) oligosaccharide (d) polysaccharide (e) monosaccharid
87. Which of the following best describes the sugar D-galactose,
O == CH
H OH
HO H
HO H
H OH
CH2OH
(a) D-aldohexose (b) D-ketohexose
(c) L-aldohexose (d) L-ketohexose (e) D-aldopentose
88. Which of the following compounds is a D-sugar ?
CH == O
O == CH
H OH
H OH
(a) H OH (b)
HO H
HO H
CH2OH
CH2OH

O == CH CH2OH CH2OH
HO H
(c) (d) HO H (e) H OH
HO H
O == CH O== CH
CH2OH
89. What is the relationship between the following compounds ?
HC ==O O ==CH
H OH HO H
and
H OH HO H
CH2OH CH2OH
D-erythrose L-erythrose
(a) conformational isomers (b) constitutional isomers

(c) identical (d) enantiomers (e) diastereomers
90. At which carbon are the following sugars epimers of each other ?
HC == O HC ==O
H OH HO H
HO H HO H
H OH H OH
CH2OH CH2OH
(a) C-1 (b) C-2 (c) C-3 (d) C-4 (e) C-5
91. At which carbon are the following sugars epimers of each other ?
HC == O HC == O
H OH H OH
HO H HO H
H OH HO H
H OH H OH
CH2OH CH2OH
D-Glucose D-Galactose
(a) C-1 (b) C-2 (c) C-3 (d) C-4 (e) C-5
92. How many chirality centers are there in an aldohexose ?
(a) 2 (b) 3 (c) 4 (d) 5 (e) 6
93. How many chirality centers are there in a 2-ketohexose ?
(a) 2 (b) 3 (c) 4 (d) 5 (e) 6
94. How many stereoisomers are possible for a 2-ketohexose ?
(a) 2 (b) 4 (c) 8 (d) 16 (e) 32

Biomolecules 469
95. Which of the following sugars yields the same alditol upon reduction with NaBH 4 as does
D-glucose ?
(a) L-glucose (b) D-mannose
(c) L-gulose (d) D-arabinose (e) none of these
96. Which of the following is/are product(s) obtained from the reduction of D-fructose ?
CH2OH CH2OH
H OH HO H
HO H HO H
(a) D-Glucitol (b) D-Mannitol
H OH H OH
H OH H OH
CH2OH CH2OH
HC == O
H OH
HO H
(c) D-Glucose (d) (a) and (b) (e) (a) and (c)
H OH
H OH
CH2OH
97. Which of the following monosaccharides will form D-glucaric acid upon oxidation with nitric
acid ?
COOH
H OH
HO H
H OH
H OH
COOH
HC == O CH2OH
H OH H OH
HO H H OH
(a) D-Glucose (b) L-Glucose
H OH HO H
H OH H OH
CH2OH HC == O

CH2OH
H OH
HO H
(c) D-Glucitol (d) (a) and (b) (e) (a) and (c)
H OH
H OH
CH2OH
98. Reduction of a 2-ketohexose with NaBH 4 yields:

(a) a single aldohexose (b) a mixture of acetals
(c) a mixture of alditols (d) a mixture of cyclic hemiacetals
(e) a single pyranose
99. When two aldohexoses yield the same osazone upon treatment with phenylhydrazine, then
they are:
(a) enantiomeric (b) epimeric at C-2
(c) epimeric at C-3 (d) epimeric at C-5 (e) both necessarily D-sugars
100. Which of the following pairs of monosaccharides will form the same osazone when reacted
with phenylhydrazine ?
(a) D-glucose and L-glucose (b) D-glucose and D-gulose
(c) D-glucose and D-fructose (d) D-glucose and D-allose
(e) D-glucose and D-galactose
101. Which of the following is the Haworth projection b-D-galactopyranose ?
CH2OH CH2OH
OH O OH OH O OH
(i) OH H (ii) OH H
H H H OH
H OH H OH
CH2OH CH2OH CH2OH

OH O H H O H H O OH
(iii) H H (iv) H H (v) H OH
H OH OH OH OH H
OH OH OH OH OH H

102. When a monosaccharide reacts to give the pyranose form from its open-chain form, how many
distinct pyranose forms are possible ?
(a) 1
(b) 2

Biomolecules 471
(c) 2 n , where n is the number of carbons present

(d) 4n + 2 , where n is the number of carbons present
(e) 4
103. Anomers of D-glucopyranose differ in their stereochemistry at:
(a) C-1 (b) C-2 (c) C-3 (d) C-4 (e) C-5
104. A pyranose with the hydroxyl group on the anomeric carbon pointing up in the Haworth
structure is designated:
(a) a (b) b (c) a (d) b (e) f
105. Which of the following is methyl-a-D-glucoside ?
OCH3
HOCH2
O
(i)
HO OH
OH
OH
HOCH2 O OCH3 HOCH2 O
(ii) (iii)
HO OH HO OH
OH OH
OH
HOCH2 O HOCH2 O OH
(iv) (v)
HO OCH3 HO OCH3
OH OH
106. Which of the following compounds is a nonreducing sugar ?

OH
HOCH2 O OH HOCH2 O
(i) (ii)
HO OH HO OH
OH OH
CH2OH CH2OH
HOCH2 O OH OH O OH OH O OCH3
(iii) (iv) OH (v)
OH OH OH OH OH

107. Which of the following statements regarding methyl-b-L-glucopyranoside is correct ?

(a) This glycoside is a reducing sugar
(b) This glycoside undergoes mutarotation in aqueous base
(c) This glycoside will undergoes no reaction with treated with excess CH 3 I Ag 2 O
(d) This glycoside will be hydrolyzed to the cyclic hemiacetal in dilute aqueous acid
(e) This glycoside will readily undergoes Killani-Fischer chain elongation
108. Which of the following would give a positive Tollen's test ?
(a) a-D-glucopyranose
(b) methyl b-D-glucopyranoside
(c) sucrose
(d) methyl a-D-ribofuranoside
109. How many different proteins containing 100 amino acid can be made from the 20 naturally
occuring amino acids ?
(a) 100 20 (b) 20 100 (c) 100 - 20 (d) None
110. The maximum concentration of zwitter ion of given amino acid will be at
r
NH 3 — CH 2 — CO 2 H
( pK a = 9. 8) ( pK a1 = 2 . 3)
(a) 1 (b) 11 (c) 6 (app.) (d) 5 (app.)

111. Which of the following molecules is the skeletal structure of an amino acid ?
s s
(a) R — C == CH — COO (b) R — CH — CH 2 — COO
| |
ONH 3 NH 3
r r
O O
s || s || r
(c) R — CH — COO (d) R — CH — C — COO (e) R — CH — C — NH 3
| | |
NH 3 NH 3 COO s
r r
112. Which of the following is an L-amino acid ?
s s
COO COO
r r
(i) H3N H (ii) H3N H
H R
s s
COO COO H
r r r
(iii) H NH3 (iv) H3N R (v) R NH3
s
R H COO

Biomolecules 473
113. Which of the following best represents the structure of an amino acid in basic solution
(pH = 11) ?
s
(a) R — CH — COO (b) R — CH — COOH
| |
NH 2 NH 2
s
(c) R — CH — COOH (d) R — CH — COO
| |
rNH 3 rNH 3
114. Which of the following is a Zwitter ion ?
s
(a) R — CH — COO (b) R — CH — COOH.
| |
NH 2 NH 2
s
(c) R — CH — COOH (d) R — CH — COO
| |
rNH 3 rNH 3
115. Which of the following amino acids has the highest isoelectric point ?
(a) lysine (b) aspartic acid
(c) glycine (d) proline (e) phenylalanine
116. What is the pI of glycine ? The structure and pKa values are shown below.
H
¾¾®
H—C—COOH pKa = 2.34
NH
r 3
¾¾®
pKa = 9.60
(a) 7.26 (b) 5.97 (c) 3.63 (d) 7.50 (e) 11.94
117. Which of the following amino acids has its isoelectric point at the lowest pH ?
(a) glutamic acid (b) lysine
(c) valine (d) glycine (e) methionine

118. What is the pI of arginine ? The structure and pKa values are shown below.
H H
NH2—C—NH———C—COOH pKa = 2.17
NH3 NH3
r r
¾¾®
¾¾®
pKa = 12.48 pKa = 9.04
(a) 10.76 (b) 7.90 (c) 5.61 (d) 7.33 (e) 9.67
O
||
1. Br2 P excess
CH 3 — C — OH ¾ ¾¾ ¾® ¾ ¾¾® ?
2. H 3O + NH 3
O
|| s
(a) CH 3 CNH 2 (b) CH 2 COO
|
NH 3
r
O O Br
|| || |
(c) CH 2 CNH 2 (d) CH 2 CNH 2 (e) CH 3 C == NH
| |
Br NH 3
r
120. What is the name of the amino acid produced when propanoic acid is subjected to the
following sequence of reagents :
1. PBr 3 , Br 2 ;
2. H 2 O
3. NH 3 , D ?
(a) alanine (b) aspartic acid
(c) glutamic acid (d) valine (e) asparagine
HC == O
121. H OH ¾2HIO
¾¾4®
CH2—OH
Product formed is:

(a) 2HCHO,HCO 2 H (b) HCHO,2HCO 2 H
(c) CO 2 ,HCHO (d) CO 2 ,HCO 2 H

Biomolecules 475
122. Which of the following is Zwitter ion ?

r
r s NH3
NH3 Cl
r s r s
(a) (b) O Cl (c) (d) NaCl
—
H
SO
s 3
123. Which of the following compound can form Zwitter ion?
NH2 NH2 CO2H CO2H
(a) H CH3 (b) H NH (c) H
2
NH2 (d) H CO2H
OH Ph CH3 CH3
124. Which of the following is D-carbohydrate ?
CHO CHO CH2OH CH2OH
(a) H OH (b) H OH (c) H OH (d) H OH
CHO CH2OH CHO CH2OH
125. Which of the following pair will form same osazone ?

(a) D-Glucose, D-Allose (b) D-Glucose, D-Altrose
(c) D-Alose, D-Altrose (d) D-Fructose, D-Galactose
126. Total number of stereoisomers possible for ketohexose are :
(a) 4 (b) 8 (c) 16 (d) 32
127. Name the following compounds and indicate whether each is a reducing sugar:
HO
CH2OH CH2OH
O O
HO
(a) OCH2CH2CH3 (b)
HO OH
OH
HO OCH3
HO HOCH2
CH2OH O OCH2CH3
O
(c) OH (d) CH2OH
HO
OH OH
OH

Answers
1. (c) 2. (c) 3. (a) 4. (b) 5. (c) 6. (b) 7. (c) 8. (b) 9. (b) 10. (c)
11. (b) 12. (b) 13. (b) 14. (c) 15. (a) 16. (c) 17. (a) 18. (a) 19. (c) 20. (a)
21. (c) 22. (d) 23. (d) 24. (a) 25. (d) 26. (c) 27. (c) 28. (b) 29. (d) 30. (c)
31. (d) 32. (b) 33. (c) 34. (b) 35. (d) 36. (b) 37. (d) 38. (b) 39. (c) 40. (b)
41. (a) 42. (a) 43. (a) 44. (a) 45. (d) 46. (b) 47. (a) 48. (a) 49. (d) 50. (d)
51. (d) 52. (b) 53. (c) 54. (d) 55. (d) 56. (c) 57. (d) 58. (d) 59. (d) 60. (c)
61. (a) 62. (d) 63. (a) 64. (d) 65. (d) 66. (b) 67. (a) 68. (b) 69. (d) 70. (c)
71. (d) 72. (d) 73. (d) 74. (d) 75. (a) 76. (c) 77. (b) 78. (b) 79. (b) 80. (a)
81. (a) 82. (b) 83. (a) 84. (d) 85. (a) 86. (c) 87. (a) 88. (d) 89. (d) 90. (b)
91. (d) 92. (c) 93. (b) 94. (c) 95. (c) 96. (d) 97. (e) 98. (c) 99. (b) 100. (c)
101. (a) 102. (b) 103. (a) 104. (d) 105. (a) 106. (e) 107. (d) 108. (a) 109. (b) 110. (c)
111. (c) 112. (b) 113. (a) 114. (d) 115. (a) 116. (b) 117. (a) 118. (a) 119. (b) 120. (a)
121. (b) 122. (c) 123. (c) 124. (b) 125. (c) 126. (b) 127. (c)

Biomolecules 477
1. Which of the following pairs forms the same osazone with phenylhydrazine ?
(a) D-Glucose and D-Fructose (b) D-Fructose and D-Mannose
(c) D-Glucose and D-Mannose (d) D-Glucose and D-Galactose
2. Which of the following compounds give positive Tollens’ test ?
OH OH
OH OH
O O
(a) OH (b) OCH3
OH OH
OH OH
OH OH CH2OH
OH OCH3
H O
O
H H O
(c) OCH3 (d) H OH OH H
OH
OH OH H H OH
3. The correct statement(s) about the following sugars X and Y is (are):
CH2OH
CH2OH O
CH2OH H H
H
H H HOH2C O H O H HO
H H O OH
OH H H HO H
O CH2OH
HO OH H OH H
HO H
H OH OH H
H OH
(X) (Y)
(a) X is a reducing sugar and Y is a non-reducing sugar
(b) X is a non-reducing sugar and Y is a reducing sugar
(c) The glucosidic linkages in X and Y are a and b, respectively
(d) The glucosidic linkages in X and Y are b and a, respectively
4. Which of the following is reducing sugar ?
(a) Sucrose (b) Maltose
(c) Lactose (d) a-D-Glucopyranose
5. In which of the following polymer there is presence of peptide linkage ?
(a) Starch (b) Cellulose (c) Protein (d) Terylene

6. Which of the following is reducing sugar ?

CH2—OH CH2—OH
H O H H O OH
(a) H (b) H
OH H OH H
HO OH HO H
H OH H OH
CH2—OH CH2—OH CH2—OH
H O OCH HO O O OH
3
(c) H (d) H H
OH H OH H O OH H
HO H H H
H OH H OH H OH
7. Which of the following compound will show mutarotation ?
CH2—OH
H OH
O
HOCH2 O OH
H
(a) (b)
OH H HH HH
HO H OH OH
H OH
HO
CH2OH
OH O O
OH
(c) H (d)
HO OH
HO OCH3
OH OCH3
Answers
1. (a, b, c) 2. (a, b, d) 3. (b, c) 4. (b, c, d) 5. (c) 6. (a, b, d)

7. (a, b)

Biomolecules 479
Passage-1:
It is convenient at times to represent the cyclic structures of a
monosaccharide without specifying whether the configuration of the
anomeric carbon atom is a or b. When we do this, we shall use formulas such as
the following
CH2OH CH2OH
H O HO O
H
HO H OH
HO HO OH
H OH OH
Indicates a or b (three-dimensional view not specified)
1. Which of the following represents the anomer of the compound shown ?
HOCH2 O H
H H
H OH
HO OH
HOCH2 O H HOCH2 O OH
(a) HO H (b) H H
H OH H H
H OH HO OH
H O OH
(c) OH HO (d) None of these
HOCH2 H
H H
2. What is the structure of L-Glucose ?
CHO CHO CHO
HO H H OH H OH
H OH HO H HO H
(a) HO H (b) H OH (c) H OH (d) None of these

HO H H OH HO H
CH2OH CH2—OH CH2—OH

HC—OH
C—OH
HO H
3. H OH, the given is enol form of:

H OH
CH2OH
(a) D-glucose (b) D-mannose
(c) D-fructose (d) All of these
Passage-2:
CH2—OH CH2—OH
O O
H H H OH
H H
(A) OH H (B) OH H
HO OH HO H
H OH H OH
OH O OCH3 HO—CH2 O OH
(C) OH H (D) OH H
H CH2—OH H H
H OH H OH
1. Relation between (A) and (B) is:

(a) Anomers (b) Positional
(c) Functional isomer (d) Enantiomer
2. Structure of b-D-Glucopyranose is:
(a) (A) (b) (B)
(c) (C) (d) (D)
3. Which of compound not undergo mutarotation ?
(a) (A) (b) (B)
(c) (C) (d) None of these
4. How many mole of acetic anhydride will consumed when it reacts with compound ( A ) ?
(a) 3 (b) 4
(c) 5 (d) 6

Biomolecules 481

Column-I Column-II
CH2—OH (p) It will undergo osazone formation
(a) H O H
H
OH H
HO OH
H OH
CH2—OH (q) When undergo acetylation reaction
H O OH with acetic anhydride molecular
H weight increases by 210
(b) OH H
HO H
H OH
CH2—OH (r) It is reducing sugar
H O OCH
3
(c) H
OH H
HO H
H OH
CH2—OH CH2—OH (s) It is known as a-D-Glucopyranose
HO O O OH
H H
(d) OH H O OH H
H H
H OH H OH
(t) Non-reducing sugar


Column-I Column-II
CH2OH CH2OH
H O O OH
H H
H H (p) Reducing sugar
(a) OH H OH H
O
OH H
H OH H OH
CH2OH
O OH
HOCH2 H
H
HO O (q) Used as a monomer of
O OH H
(b) H H cellulose
OH H H H OH
H
H OH
CH2OH
H O OH
H
(c) OH H (r) Presence of Glycosidic
HO H linkage
H OH
CH2OH
H O OEt
H
(d) OH H (s) It will undergo
OH H mutarotation
H OH
(t) When reacts with acetic

anhydride 4 moles will
consumed

Biomolecules 483

Column-I Column-II (Reagent used is)
r
(a) Sucrose ¾H¾¾
3O
® (p) Product is glucose + Fructose
r
(b) Maltose ¾H¾¾
3O
® (q) Product is 2 Glucose
r
(c) Lactose ¾H¾¾
3O
® (r) Product is Glucose + Galactose
(s) Oligo saccharides

CH2OH
H OH
O
1. O
HO OH
L-ascorbicacid
vitaminC
Explain why the C-3 OH group of vitamin C is more acidic than the C-2 OH group.
2. Give the structures of the products in the following reaction
+
Sucrose ¾H¾® A + B
3. Aspartame, an artificial sweetener, is a peptide and has the following structure:
CH 2C 6H 5
|
H 2 N — CH —CONH — CH — COOCH 3
|
CH 2 — COOH
(i) Identify the four functional groups.
(ii) Write the Zwitter ionic structure.
(iii) Write the structure of the amino acids obtained from the hydrolysis of aspartame.
(iv) Which of the two amino acids is more hydrophobic?
4. Write the structure of alanine at pH = 2 and pH = 10.
5. Following two amino acids lysine and glutamine form dipeptide linkage. What are two
possible dipeptides ?
NH2 NH2
H2N COOH + HOOC COOH

6. The structure of D-glucose is as follows :
CHO
H OH
HO H
H OH
H OH
CH2OH
(a) Draw the structure of L-glucose.
(b) Give the reaction of L-glucose with Tollens’ reagent.

Biomolecules 485
7. Which of the following disaccharide will not reduce Tollens’ reagent ?

CH2OH CH2OH
HO O O OH
H H
H HO H HO
O
H H
OH H OH H
CH2OH CH2OH
OH O O OH
H H
H HO OH H
O
H H
OH H H OH
8. What is the total number of basic groups in the following form of lysine ?
H3N+—CH2×CH2×CH2×CH2 O
CH—C
H2N O–
9. A decapeptide (Mol. wt. 796) on complete hydrolysis gives glycine (Mol. wt. 75), alanine and
phenylalanine. Glycine contributes 47.0% to the total weight of the hydrolysed products. The
number of glycine units present in the decapeptide is :
10. How many compound which is given below is isomer of D-Glucose ?
D-Mannose, D-Fructose, D-Gulose, D-Idose, D-Galactose, D-Arabinose, D-Ribose
11. How many acidic group is present in given amino acid ?
r
NH 3 — CH — CH 2 — CH 2 — CO 2 H
|
CO -2
CHO
H OH
H OH
HIO
12. HO H ¾ ¾¾4®
H OH
CH2OH
16-isomer of above compound when reacts with periodic acid (HIO 4 ).- How many mole of
periodic acid will consumed ?

486
CH==O
H OH
CH2—OH
D-glyceraldehyde
HC==O HC==O
H OH HO H
H OH H OH
CH2OH CH2OH
D-erythrose D-threose
HC==O HC==O HC==O HC==O

H OH HO H H OH HO H
H OH H OH HO H HO H
H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH
D-ribose D-arabinose D-xylose D-lyxose
13. On the basis of given comprehension, answer the given questions.
HC==O HC==O HC==O HC==O HC==O HC==O HC==O HC==O

H OH HO H H OH HO H H OH HO H H OH HO H

H OH H OH HO H HO H H OH H OH HO H HO H
H OH H OH H OH H OH HO H HO H HO H HO H
H OH H OH H OH H OH H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH
D-allose D-altrose D-glucose D-mannose D-gulose D-idose D-galactose D-talose
1 2 3 4 5 6 7 8
Elementary Organic Chemistry
Biomolecules 487
(i) Are D-erythrose and L-erythrose enantiomers or diastereomers?

(ii) Are L-erythose and L-threose enantiomers or diastereomers?
(iii) Which sugar is the C-3 epimer of D-xylose?
(iv) Which sugar is the C-5 epimer of D-allose?
(v) Which sugar is the C-4 epimer of L-gulose?
(vi) How many stereoisomers are possible for:
(a) a 2-ketoheptose? (b) an aldoheptose? (c) a ketotriose?
Answers

Passage-1: 1. (b) 2. (a) 3. (d)
Passage-2: 1. (a) 2. (b) 3. (d) 4. (c)

1. (a) - p,q,r,s; (b) - p,q,r; (c) - t; (d) - p,r
2. (a) - p,r,s; (b) - p,r,s; (c) - p ,q , s; (d) - t
3. (a) - p,s; (b) - q,s; (c) - r,s


1. Due to the stability of conjugate base.
H+
¾® D-glucose + D-fructose
2. Sucrose ¾ ¾
H 2O
CHO CH2OH
|
H OH CO
HO H HO H
H OH H OH
H OH H OH
CH2OH
CH2OH
3 CH2C6H5
1 4
3. H2N—–CH—–CONH—–CH—–COO CH3
2
CH2—–COOH
Aspartamine
(i) NH 2 — gp. (1) – amino gp.

—COOH gp. (2) – carboxyl gp.
—CONH gp. (3) – 2º– amide gp.
—COOH gp. (4) – ester gp.
CH 2 C 6 H 5
+ |
(ii) H 3 N— CH — CONH — CH — COOCH 3
|
CH 2 COO -
CH2C6H5
HO H OH H Hydrolysis
(iii) H2N—CH—CO NH—CH—CO O CH3 ¾¾¾¾® H2N—CH—COOH
CH2COOH CH2COOH
(A)
CHC6H5
+ H2N—CH—COOH+ CH3OH
(B)
(iv) B is more hydrophobic due to presence of larger organic gp., benzyl gp. (C 6 H 5 CH 2 — ) .
r
4. At pH = 2, NH 3 — CH — CO 2 H
|
CH 3

Biomolecules 489
s
At pH = 10, NH 3 — CH — CO 2
|
CH 3
O
||
5. Peptide linkage is —NH — C — and it is formed by the condensation between —NH 2 group
and —COOH group as follows:
—C — O — H + H — NH — ¾ ¾¾® —C—NH—
- H 2O
||
O O
In given amino acids lysine and glutamine, the two possible dipeptides are formed as follows:
NH H H NH
a
(i) H2N a + –2H2O
C—OH HO—C COOH ¾¾®
O
O O COOH
HN
NH
H2N
O
(ii) When a-NH 2 of both amino acids is used but in one terminal —COOH gp. lacking a-NH 2
gp. is used.
O O
2–2H O
HN H HO —C C—OH ¾¾®
H2N C— OH H HN
O
O
O == C COOH
HN NH
H2N C
O

6. (a) L-glucose is mirror image of D-glucose .

CHO CHO
H OH HO H
HO H H OH
H OH HO H Mirror image (L)
H OH HO H
CH2OH CH2OH
D-glucose L-glucose
CHO COOs
HO H HO H
H OH Tollens’ reagent H OH
(b) ¾¾¾¾¾®
HO H HO H
HO H HO H
CH2OH CH2OH
L-glucose
7. In structure (a), one ring has a free hemiacetal group, will hydrolyse into open chain in
aqueous solution and therefore will reduce Tollen’s reagent. Structure (b) has only acetal
groups, will not hydrolyse in aqueous solution into open chain, will not reduce Tollens’
reagent.
8. 2
9. 6
10. 5
11. 2
12. 80
13.
(i) Enantiomers (ii) Diastereomers (iii) D-ribose
(iv) L-talose (v) L-allose (vi) (a) 16, (b) 32, (c) 0

Polymers 491
8
Polymers
1. When a carbohydrate reacts with NaBH 4 , the product is an:

(a) alditol (b) aldaric acid (d) aldonic acid (d) aglycone
2. Where are the isoprene subunits in the following terpene?
(a) (b) (c) (d)
3. The following chain-growth polymer is made up of how many difluoroethylene monomer

units?
F F F F F F
F F
(a) 1 (b) 2 (c) 3 (d) 4
4. Which of the following is the correct structure for the monomer that is used to make the
following chain-growth polymer?
H H H H
| | | |
—CH2—C—CH2—C—CH2—C—CH2—C—
| | | |
CONH2 CONH2 CONH2 CONH2

(a) CH 2 — CH — CH 2 — CONH 2 (b) CH — CH 2 — CH 2 — CONH 2

(c) CH 2 — C — CH 3 (d) CH 2 — CH — CONH 2
|
CONH 2
5. What is the structure of one of the compounds used in synthesis of the following step-growth
polymer?
H O O H
N N
N N
O O H H O
O
OCCH3
H2N
(a) NH2 (b)
OCCH3
O
NH2 O
OH
(c) (d) HO
O
NH2
6. Draw the structure of the monomer used to produce this polymer through anionic
polymerization.
O O
O
O
Cl
(a) (b) OH
O
H
(c) (d) Cl OH

Polymers 493
7. Which two monomers would react to give a good yield of the following polymer?
O
O O O O
O O
Cl Cl HO OH HO OH Cl
I II III IV
(a) I and III (b) II and IV

(c) I and IV (d) II and III
8. To which functional group class does the following polymer belong?
O O
O O
O O
(a) Polyester (b) Polycarbonate
(c)Polyurethane (d) Polyamide

O O
O N N O
H H
(c) Polyurethane (d) Polyamide
O
O O
O
O
O O
O
(c) Polyurethane (d) Polyamide

11. Which percentage of sulphur is used in the vulcanization of rubber ?

(a) 3% (b) 5% (c) 30% (d) 55%
12. Reductive ozonolysis of polymer of 1, 3-butadiene will mainly form :
CHO CH 2 — CHO
(a) HCHO (b) | (c) | (d) CH 3 — CHO
CHO CH 2 — CHO
13. Which one of the following is natural polymer ?
(a) Starch (b) Nylon-6 (c) Teflon (d) Buna-S, SBR
14. Which of the following is homopolymer ?
(a) Starch (b) Polystyrene (c) Orlon (d) All of these
15. Which of the following monomers can undergoes radical, cationic as well as anionic
polymerisation with equal ease ?
(a) CH 3 — C == CH 2 (b) C 6 H 5 — CH == CH 2
|
CH 3
(c) CH 2 == CH — CN (d) CH 2 == CH 2
16. Zieglar-Natta catalyst is:
(a) R 3 Al (b) TiCl 4 (c) R 3 Al + TiCl 4 (d) R 3 B + TiCl 2
17. Monomer of Teflon is :
(a) Monochloroethene (b) 1, 2-Difluoroethene
(c) 1, 1, 2-Trifluoroethene (d) Tetrafluoroethene
18. Orlon is polymer of:
(a) Styrene (b) CF2 == CF2 (c) Vinyl chloride (d) Acrylonitrile
19. Intermolecular force present in nylon-6,6 is:
(a) van der Waals (b) Hydrogen bond
(c) Dipole-Dipole interactions (d) Sulphide linkage
20. Nylon-6,6 is made by using:
(a) Phenol (b) Benzaldehyde
(c) Adipic acid (d) Succinic acid
21. Polymer which has amide linkage is:
(a) Nylon-6,6 (b) Terylene (c) Teflon (d) Bakelite
22. Bakelite is prepared by the reaction between:
(a) Phenol and formaldehyde
(b) Ethylene glycol and dimethylphthalate
(c) Urea and formaldehyde
(d) Tetramethylene glycol and hexamethylene diamine
23. Natural rubber is a polymer of:
(a) Butadiene (b) Ethyne (c) Styrene (d) Isoprene
24. Terylene is a condensation polymer of ethylene glycol and:
(a) Benzoic acid (b) Phthalic acid
(c) Salicylic acid (d) Terephthalic acid
Polymers 495
25. Cellulose acetate is a:

(a) Natural polymer (b) Semisynthetic polymer
(c) Synthetic polymer (d) Plasticiser
26. A condensation polymer among the following polymers is:
(a) Teflon (b) Polystyrene (c) PVC (d) Dacron
27. In elastomer, intermolecular forces are:
(a) Nil (b) Weak (c) Strong (d) Very strong
28. Which one of the following is a polyamide ?
(a) Teflon (b) Nylon-6,6 (c) Terylene (d) Bakelite
29. Which of the following is fully fluorinated polymer ?
(a) Neoprene (b) Teflon (c) Thiokol (d) PVC
30. The monomer of the polymer
CH3 CH3
| |r
CH2—C—CH2—C is:
| |
CH3 CH3
CH3
(a) CH2 == C (b) CH 3 — CH == CH — CH 3
CH3
(c) CH 3 — CH == CH 2 (d) CH3—C == C—CH3
| |
CH3 CH3
31. Buna-S is a polymer of:
(a) butadiene only (b) butadiene and styrene
(c) styrene only (d) butadiene and nitryl
32. Among cellulose, polyvinyl chloride, nylon and natural rubber, the polymer in which the
intermolecular force of attraction is the weakest, is :
(a) polyvinyl chloride (b) natural rubber (c) nylon (d) cellulose
33. What is the structure of the monomer from which the following polymer is made ?
—CH—CH—CH—CH—CH—CH—CH—CH—
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3
(a) CH 3 CH 3 (b) CH 2 == CH 2
(c) CH 3 CH == CH 2 (d) CH 2 == CHCH == CH 2 (e) CH 3 CH == CHCH 3
34. What is the structure of the monomer from which the following polymer is made ?
—CHCH2—CHCH2—CHCH2—CHCH2—

CH2CH3
(a)
CH == CH2 CH2CH2CH3
(b) (c)
CH == CHCH3 CH == CHCH == CH2

(d) (e)
35. Which of the following addition polymers results from the reaction below ?
Catalyst
¾® ?
nCF2 == CF2 ¾ ¾¾
(a) [—CF — CF—]n (b) [CF3 — CF3 ]n
(c) [—CF2 CH — CHCF2 —] n (d) [—CF2 — CF2 —]n
36. Chain-growth polymerization proceeds by which of the following mechanisms ?
(a) radical polymerization (b) cationic polymerization
(c) anionic polymerization (d) (a) and (b) (e) (a), (b) and (c)
37. Which of the following species can best serve as a radical initiator for radical polymerization ?
(a) ROH (b) ROR
(c) ROOR (d) RCOOR (e) RCOOH
38. Which of the following species can best serve as an initiator for cationic polymerization ?
(a) ROOR (b) ROH
(c) ROR (d) AlCl 3 (e) RCOOR
39. Which of the following is the chain-initiating step in the cationic polymerization of propene ?
(i) BF3 + CH2 == CH ¾¾® F2BCH == CH + HF
CH3 CH3
(ii) BF3 + CH2 == CH ¾¾® CH2 == CBF2 + HF
CH3 CH3
(iii) BF3 + CH2 == CH ¾¾® CH2 == CH + HF
CH3 CH2BF2
r s
(iv) BF + CH2 == CH ¾¾® CH2CHBF3
3
CH3 CH3

Polymers 497
s r
(v) BF3 + CH2 == CH ¾¾® F3BCH2CH
CH3 CH3
40. Which of the following is more likely to undergo both radical and cationic polymerization ?
CH == CH2
(i) CH 2 == CH 2 (ii)
(iii)CH 2 == CHCl (iv) CH 2 == CHC ºº N (v) CH 2 == CCH 3

|
COOR
41. Which of the following monomers has the greatest ability to undergo cationic polymerization ?
CH == CH2 CH == CH2
CH == CH2
(i) (ii) (iii)
OCH3 NH2
CH == CH2 CH == CH2
(iv) (v)
CH3 O2N

42. Which of the following monomers has the greatest ability to undergo anionic polymerization ?
CH == CH2
(i)
CH == CH2 CH == CH2
(ii) (iii)
OCH3 NH2
CH == CH2 CH == CH2
(iv) (v)
CH3 O2N

43. Which of the following is a step-growth polymer ?

(a) polyethylene (b) polyester
(c) polypropylene (d) polystyrene (e) plexiglass
44. What monomers formed the following polymer ?
O O O
—C C—NH NHC NH—
O O
(i) H2N NH2 + HOC COH
O
(ii) 2HOC NH2
O O
(iii) H2NC NH2+HO COH
O O
(iv) 2H2NC CNH2
O O
(v) HO OH+H 2NC CNH2

45. Which dimer (step-growth dimerization) will form from the following monomer ?
O
||
CH 2 — C — OH ¾¾®
|
NH 2
O O O O O O
|| || || || || ||
(a) CH 2 COCCH 2 (b) CH 2 CONHCOH (c) CH 2 CNHCH 2 COH
| | | |
NH 2 NH 2 NH 2 NH 2
O O O O
|| || || ||
(d) HOCCH 2 NHNHCH 2 COH (e) HOCCH 2 N == NCH 2 COH

Polymers 499
46. The joining together of many monomers to form a very large molecule is called ?
(a) polymerization (b) monomerization
(c) dimerization (d) hydroxylation (e) homogenization
47. Amide linkage is present in :
(a) Nylon-6,6 (b) Bakelite (c) Sucrose (d) Starch
48. When phenol reacts with formaldehyde in the presence of acidic medium then obtained
polymer will be:
(a) Resin (b) Bakelite (c) Dacron (d) Teflon
49. Polymer of b - D -Glucopyranose is:
(a) starch (b) cellulose (c) amylose (d) sucrose
50. Among cellulose, polyvinyl chloride, nylon and natural rubber, the polymer in which the
intermolecular force of attraction is weakest is:
(a) nylon (b) polyvinyl chloride (c) cellulose (d) natural rubber
51. Which of the following polymer, not having C—C bond formation during polymerisation.
(a) Teflon (b) Bakelite (c) Natural rubber (d) Terylene
Answers
1. (a) 2. (c) 3. (d) 4. (d) 5. (a) 6. (a) 7. (a) 8. (b) 9. (c) 10. (a)
11. (b) 12. (c) 13. (a) 14. (d) 15. (b) 16. (c) 17. (d) 18. (d) 19. (b) 20. (c)
21. (a) 22. (a) 23. (d) 24. (d) 25. (b) 26. (d) 27. (b) 28. (b) 29. (b) 30. (a)
31. (b) 32. (b) 33. (e) 34. (b) 35. (d) 36. (e) 37. (c) 38. (d) 39. (e) 40. (b)
41. (c) 42. (e) 43. (b) 44. (a) 45. (c) 46. (a) 47. (a) 48. (b) 49. (b) 50. (d)
51. (d)

1. The correct functional group X and the reagent/ reaction conditions Y in the following scheme
are:
(i) Y
X – (CH2)4 – X ¾¾¾¾¾¾¾¾® Condensation polymer
O O
(ii) C—(CH2)4—C
HO heat OH
(a) X = COOCH 3 ,Y = H 2 Ni heat (b) X = CONH 2 ,Y = H 2 Ni heat

(c) X = CONH 2 ,Y = Br 2 NaOH (d) X = CN,Y = H 2 Ni heat
2. In which of the following polymer there is presence of amide linkage?
(a) Starch (b) Cellulose
(c) Protein (d) Nylon-6,6
Answers
1. (c, d) 2. (c, d)

Polymers 501

Column-I Column-II
(a) Nylon-6,6 (p) Condensation polymerization
(b) Styrene (q) Addition polymerization
(c) Bakelite (r) Homo-polymer
(d) Teflon (s) Co-polymer

Column-I Column-II
(a) Terylene (p) Condensation polymerization
(b) Styrene (q) Addition polymerization
(c) Bakelite (r) Homo-polymer
(d) Teflon (s) Co-polymer

Column-I Column-II
(a) Cellulose (p) Natural polymer
(b) Nylon-6,6 (q) Synthetic polymer
(c) Protein (r) Amide linkage
(d) Sucrose (s) Glycoside linkage

Column-I Column-II
(a) Natural polymer (p) Nylon-6,6
(b) Synthetic polymer (q) Protein
(c) Amide-linkage (r) Cellulose
(d) Glycosidic linkage (s) Starch


Column-I Column-II
(a) Protein (p) Natural polymer
(b) Starch (q) Synthetic polymer
(c) Cellulose (r) Amide-linkage
(d) Nylon-6,6 (s) Glycosidic linkage
1. Write the names of monomers of the following polymers:

H H O O
| | || ||
(i) —
[ N—(CH2)6—N—C—(CH2)4—C — ]n
O H
é
ê || |
(ii) —
ë C—(CH )
2 5 —N —n (iii)
2. Classify the following as addition and condensation polymers: Terylene, Bakelite, Polyvinyl
chloride, Polythene.
3. Arrange the following polymers in increasing order of their intermolecular forces.
(i) Nylon-6,6, Buna-S, Polythene (ii) Nylon-6, Neoprene, Polyvinyl chloride
4. Give the structures of the products in the following reaction :
NOH
H+ Polymerisation
¾¾® C ¾ ¾¾ ¾¾
¾® [ D ]n
5. Write down the heterogeneous catalyst involved in the polymerization of ethylene.

6. Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of
CH 3 COCHO.
(a) Deduce the structure of A.
(b) Write the structure of “ all cis”- form of polymer of compound A.

Polymers 503
Answers

1. (a) ® p,s; (b) ® q,r; (c) ® p,s; (d) ® q,r
2. (a) ® p,s; (b) ® q,r; (c) ® p,s; (d) ® q,r
3. (a) ® p,s; (b) ® q,r; (c) ® p,r; (d) ® s
4. (a) ® q,r, s; (b) ® p; (c) ® p,q; (d) ® r, s
5. (a) ® p,r; (b) ® p,s; (c) ® p,s; (d) ® q,r

1. (i) Hexamethylene diamine and adipic acid, (ii) Caprolactum, (iii) Tetrafluoroethene
2. Addition polymers: Polyvinyl chloride, Polythene
Condensation polymers: Terylene, Bakelite
3. in increasing order of intermolecular forces.
(i) Buna-S, Polythene, Nylon-6,6, (ii) Neoprene, polyvinyl chloride, Nylon-6.
N—OH
O O
H+ Polymerisation
4. ¾¾® NH ¾¾¾¾¾® —C—(CH2)5—NH—n
Nylon-6 (D)
Caprolactum
(C)
R 3 Al + TiCl 4
¾® —CH
5. nCH 2 == CH 2 ¾ ¾¾ ¾ ¾¾ ¾ ( 2—CH2—
)n Ziegler-Natta catalyst (R 3 Al + TiCl 4 ) acts as
Ziegler- Natta Catalyst
heterogenous catalyst. While Wilkinsons’ catalyst ((Ph 3 P) 3 .RhCl) acts as homogenous
catalyst.
CH 3 O
| O3 ||
6. (a) H 2 C == C — CH == CH 2 ¾ ¾¾ ¾® 2HCHO + CH 3 — C — CHO
Zn - H 2O
Isoprene
CH2 CH2—CH2 CH2
(b) Isoprene ¾® C == C C == C
H3C H H3C H
Natural rubber

9
Grignard Reaction
1. What are the major products of the following reaction?

1.EtMgBr ,Et O
2
O ¾¾¾¾¾¾® + ?
2.H O,H O
2 3
Opticallyactive
Et Et OH Et
(a) + (b) +
OH OH Et OH
OH Et OEt
(c) + (d) +
Et OH OEt
2. Which of the following compounds would not give tert-butyl alcohol when treated with excess
methylmagnesium bromide?
(a) Acetyl chloride (b) Acetaldehyde (c) Methyl acetate (d) Acetic anhydride
3. Which of the following reagents, when treated with phenylmagnesium bromide followed by
acid workup, will yield 2-phenylethanol?
(a) Ethanol (b) Oxirane (c) Acetaldehyde (d) Ethylene
4. What is the major product of the reaction sequence shown ?
O
CH3CHCH3 Mg, ether H2C——CH2 H O+
3
¾¾¾¾® ¾¾¾¾¾® ¾¾®
Cl
(a) (CH 3 ) 2 CHCH 2 CH 2 OH (b) (CH 3 ) 2 CHCHOHCH 3
(c) CH 3 CH 2 CH 2 CH 2 CH 2 OH (d) CH 3 CH 2 CH 2 CHOHCH 3
5. In which of the reaction CH 4 formation takes place ?
(a) CH 3 MgBr + Ph — CH == O (b) CH 3 MgBr + CH 3 — CH == O

O
||
(c) CH 3 MgBr + CH 3 — C — CH 3 (d) CH 3 MgBr + EtOH
6. PhMgBr + (x) ¾¾® ; ( x) is:

CH 3
| O
(a) CH 4 (b) CH 3 — C — OH (c) (d) ether
|
CH 3
7. The product/s of the following reaction is/are:
OH ether
+ CH 3 CH 2 MgBr ¾ ¾¾®
OMgBr
(a) (b) +
CH2CH3 OH
OMgBr O
(c) + CH 3 CH 3 (d)
O
||
Mg (2)
8. CH 3 — Br ¾ ¾¾¾®( A) + Ph — C — H ¾ ¾
¾r
®( B ); Product ( B ) is:
ether H
OH
|
(a) CH 3 — C — Ph (b) CH 3 — CH — Ph
||
O
O
||
(c) CH 3 — CH — CH 3 (d) Ph — CH 2 — C — H
|
Ph
OH
|
9. The product CH 3 — C — Ph is obtained in the reaction. (Assume acidification at the end of the
|
Ph
reaction)
O O
|| ||
(a) CH 3 MgBr + Ph — C — Ph (b) PhMgBr + CH 3 —C — Ph

O
||
(c) 2PhMgBr + CH 3 — C — O — Et (d) All of these
10. Reaction with PhMgBr + H — O — CH — CH 3 gives:
|
CH 3
OH
O—Ph
(a) (b) (c) H (d)
11. Compare reactivity toward Grignard reagent :
O O O
(a) (b) (c)
(a) c > b > a (b) b > c > a (c) a > b > c (d) none of these
¾¾®
12. PhMgBr + ( x) 2 Hr Ph — CH 2 — CH 2 — OH ; Reactant ( x) is:
O
(a) CH 3 — CH == O (b) O (c) EtOH (d)
O OH
13. +x CH3MgBr ¾¾® CH 3 — CH — CH 2 — CH 2 — CH 2 — CH 2 .
H r | |
OH OH
The value of x is:
(a) 1 (b) 2 (c) 3 (d) 4
s
14. Compare rate of reaction of the following with OH / H 2 O
O O O
(a) (b) (c)
(a) c > b > a (b) a > b > c (c) b > a > c (d) b > c > a
15. What is the product of the following reaction sequence?
O
CH3MgBr H3O+
CººCH ?
(I) CººCH3 (II) CººCCH2CH2OCH3

(III) CººCCH2OCH2CH3 (IV) CººCCH2CH2OH
(V) CººCCH2CH2CH2OH

16. Which of the following reactions can be used to prepare 3-methyl-3-hexanol,
OH
|
CH 3 CH 2 CCH 2 CH 2 CH 3 ?
|
CH 3
O O
|| ||
1. CH 3 MgBr 1. CH 3CH 2MgBr
(a) CH 3 CH 2 CCH 2 CH 2 CH 3 ¾ ¾¾¾¾ ® (b) CH 3 CCH 2 CH 2 CH 3 ¾ ¾¾¾¾¾ ¾®
2. H 3Or 2. H 3Or
O
||
1. CH 3CH 2CH 2MgBr
(c) CH 3 CCH 2 CH 3 ¾ ¾¾¾¾¾¾ ¾® (d) (a) and (b) (e) (a), (b) and (c)
2. H 3Or
O
O
Cl
RMgX
17. ¾ ¾¾®
H 3Or
CHO
How many molecules of RMgX are consumed in the above given reaction ?
(a) 2 (b) 4 (c) 5 (d) 6
18. Which of the following compound when reacts with CH 3 MgBr formation of 3° alcohol take
place ?
O O O O
|| || ||
(a) H — C — H (b) CH 3 — C — H (c) CH 3 — C — CH 3 (d) C—H
19. Which of the following is least reactive toward Grignard reagent ?

O O
|| ||
(a) H — C — H (b) CH 3 — CH == O (c) Et — CH == O (d) CH 3 — C — CH 3
20. Compare reactivity toward Grignard reagent ?
O O
|| O ||
CH 3 — C — H C—H CH 3 — C — CH 3
(i) (iii)
(ii)
(a) i > ii > iii (b) i > iii > ii (c) ii >i > iii (d) iii > ii > i
21. Which of the following is most reactive toward Grignard reagent ?

(a) H — O — H (b) CH 3 OH
O
||
(c) CH 3 — C — OH (d) CH 3 — S — O — H
|| ||
O O
OH
22. f CH3
Et
The above 3° alcohol can be prepared by [f = Ph (phenyl ring)] :

O O
|| ||
(a) f — MgBr + CH 3 — C — Et (b) EtMgBr + f — C — CH 3
O
||
(c) CH 3 MgBr + f — C — Et (d) All of these
OH
|
23. PhMgBr +( x) ¾ ¾¾ ¾® Ph — C — Ph; ( x) is:
( 2 ) Hr |
Ph
O O O O
|| || || ||
(a) Ph — C — H (b) Ph — C — Ph (c) Ph — CH — C — H (d) Ph — C — CH 3
|
Ph
24. Which of the following compound react with CH 3 MgBr ?
O O
(a) (b) (c) (d)
O
25. PhMgBr act as a base with :
O O O
|| || ||
(a) CH 3 —C — CH 3 (b) CH 3 — C — CH 2 — C — CH 3
O O O
|| || ||
(c) CH 3 —C — OEt (d) CH 3 — C — O — C — CH 3

O
||
26. CH 3 — C — OH; the given carboxylic acid is prepared by:
14
14
(a) C H 3 MgBr + O == C == O ¾ ¾¾
r® (b) CH 3 MgBr + O == C == O ¾ ¾¾
r®
( 2) H 14 ( 2) H
14 14
(c) CH 3 MgBr + CH 3 OH ¾® (d) C H 3 MgBr + CH 3 OH ¾®
27. When CH 3 MgBr reacts with dry ice followed by acidification product will be :
O
||
(a) CH 3 — C — OH (b) CH 3 — CH 2 — OH
O
||
(c) CH 3 — CH 2 — C — H (d) CH 3 OH
O
r
H
28. MgBr + Et—O—C—O—Et ¾® (A) ¾®(B) ; Final product ( B ) is :
(excess)
O OH
(a) C (b) C
(c) PhCH (d) Ph — CH — Ph

|
O OH
29. MgBr + Cl—C—CH3 ¾¾®

r
(2) H
(excess)
Final product of above reaction is:
OH OH O
| | ||
(a) Ph — CH — CH 3 (b) Ph — C — CH 3 (c) Ph — C — CH 3 (d) Ph 3 CH
|
Ph
O
30. CH3—C—O—Et + BrMg —CH2—CH2—CH2—CH2—MgBr r (A) ; Product ( A) is:
(2) H
OH CH2—OH CH3 O
CH3
OH CH3
(a) (b) (c) (d)

O
31. Et—O—C—O—Et + BrMg —CH2—CH2—CH2—CH2—MgBr ; Product ( P ) is :
(P)
OH O O
OH
(a) (b) (c) (d)
O
32. MgBr + H—C—O—Et ¾¾®
r (A) ; Product ( A) of the above reaction is:
(2) H
(excess)
O OH
(a) C—CH3 (b) CH
O
(c) C—H (d)
O O
33. CH3—C—(L.G.)+CH 3MgBr ¾¾® (L.G. = leaving group)
CH3 CH 3
Rate of reaction will be maximum when leaving group is:
O
||
(a) —OEt (b) —O — C — CH 3 (c) —Cl (d) —CH 3
34. Most reactive towards Grignard reagent is :
O O O O
(a) (b) H (c) Cl (d) OEt
(1) 2CH MgBr Hr

35. 3
¾¾¾¾¾®
r (A) ¾¾® ( B ); Product ( B ) is:
(2) H D
O O
O
(a) (b) (c) OH (d)
O O

36. Which of the following reactions can be used to prepare :

OH
CH3CH2C
O
1. MgBr
(i) CH3CH2C—OCH3 ¾¾¾¾¾®
r 2. H3O
O
1. MgBr
(ii) CH3CH2C ¾¾¾¾¾®

r
2. H3O
O
C
1. CH CH MgBr
3 2
(iii) ¾¾¾¾¾¾®
r
2. H3O
(a) i (b) ii (c) iii (d) ii and iii (e) i, ii and iii
37. Which of the following alcohols can be prepared by the reaction of methyl formate with excess
Grignard reagent ?
(a) 1-pentanol (b) 2-pentanol
(c) 3-pentanol (d) 2-methyl-2-pentanol (e) 3-methyl-3-pentanol
O
||
38. Et — O — C — O — Et+PhMgBr ¾¾®( A) ; Product (A) is:
(excess) (2)Hr
OH O OH
| || |
(a) Ph — CH — Ph (b) Ph — C — Ph (c) Ph — C — Ph (d) Ph — CH 2 — OH
|
Ph
39. How many mole of Grignard reacts with following compound ?
O
HO
Cl
CH3
HS
O
(a) 3 (b) 4 (c) 5 (d) 6

(1)2PhMgBr
40. ¾ ¾¾¾¾® (A); Final product (A) is:
(2)Hr
Ph O
Ph Ph O
O O
(a) O (b) (c) (d) None of these
Ph
O Ph Ph
O
||
41. CH 3 — C — O — Et + PhMgBr ¾ ¾ ¾® ( A); Product ( A) is:
(excess) (2) Hr
O OH OH
|| | | OH
(a) CH 3 — C — Ph (b) CH 3 — C — Ph (c) CH 3 — C — Ph (d)
| |
CH 3 Ph
OH OH
42. + xCH3MgBr ¾¾¾®

r ; The value of x is:
(2) H
Cl O OH
(a) 1 (b) 2 (c) 3 (d) 4

43. How many moles of Grignard reagent will consumed when following compound reacts with
it?
O
HO
HO O—Et
O
(a) 2 (b) 3 (c) 4 (d) 5
Cl
Cl
44. +x CH3MgBr. The value of x is:
OH
CH3 O
(a) 1 (b) 2 (c) 3 (d) 4

O
45. O—C—O +x PhMgBr ¾¾®
r 3°alcohol.
(2) H
The value of x is:

(a) 2 (b) 3 (c) 4 (d) 5
O
46. O
O +x PhMgBr ¾¾®
(excess)
Cl
Moles of Grignard reagent consumed is:
(a) 3 (b) 4 (c) 5 (d) 6
47. + xPhMgBr ¾
¾® 3 ºalcohol
2Hr
Value of x is:
(a) 2 (b) 3 (c) 1 (d) 4
48. Which of the following is least reactive toward RMgBr?
O O O O
|| || || ||
(a) CH 3 — C — Et (b) CH 3 — C — Ph (c) Ph — C — Ph (d) Ph — C — H
49. PhMgBr + O == C == O ¾¾®( A) ; PhMgBr + O == S == O ¾¾®( B )
r
(2) Hr || (2)H
O
Product (A) and (B) respectively are:
(a) Ph — CO 2 H,Ph — SO 2 H (b) Ph — OH,Ph — SO 3 H
(c) Ph — CO 2 H,Ph — SO 3 H (d) Ph — SO 3 H,Ph — CO 2 H
Answers
1. (a) 2. (b) 3. (b) 4. (a) 5. (d) 6. (b) 7. (c) 8. (b) 9. (d) 10. (b)
11. (c) 12. (b) 13. (a) 14. (b) 15. (d) 16. (e) 17. (b) 18. (c) 19. (d) 20. (b)
21. (d) 22. (d) 23. (b) 24. (d) 25. (b) 26. (b) 27. (a) 28. (b) 29. (b) 30. (a)
31. (a) 32. (b) 33. (c) 34. (c) 35. (b) 36. (e) 37. (c) 38. (c) 39. (c) 40. (a)
41. (c) 42. (c) 43. (d) 44. (c) 45. (b) 46. (b) 47. (b) 48. (c) 49. (c)

1.
S.No. Reaction Product
1. PhMgBr + 2-propanol
2. PhMgBr + Ph — CH 2 — OH
3. PhMgBr + CH 3 — SH
4. PhMgBr + CH 3 — C ºº CH ¾®
5. PhMgBr + Acetic acid

O
6. PhMgBr +
O
7. ||
PhMgBr + Ph — C — Ph ¾®
PhMgBr + CHO
8.
9.
PhMgBr +
CHO
10. PhMgBr +
11. CH 3 MgBr + Butanone ¾®
12. CH 3 MgBr + 2-Pentanone ¾®
13. CH 3 MgBr + 3-Pentanone

2. Find the value of x in each reaction ?

(a) x PhMgBr + OH (b) x PhMgBr + OH (c) x PhMgBr + CH=O
SH OH H OH
NH2 OH H OH
CH2–CºCH OH HO H
CH2–O–CH3 CH2–OH
OH
3. Identify product and compare rate of reaction ?
(a) O
CH3MgBr + CH3 – C – H r1
O
CH3MgBr + Ph – C – H r2
CH 3MgBr + r3
O
(b) O
CH 3MgBr + H – C – H r1
O
CH 3MgBr + H r2
(c) CH=O
CH 3MgBr + r1
CH=O
CH3MgBr + r2
CH3O
CH=O
CH3MgBr + r3
NO2

(d) O
PhMgBr+ r1
O
PhMgBr+ r2
PhMgBr + r3
O
(e) O
PhMgBr + r1
PhMgBr + Ph–CH=O r2
O
PhMgBr + r3
PhMgBr + r4
(f)
PhMgBr +
O r3
PhMgBr + r3
O
PhMgBr +
O r3

4. Write the product of following reactions.
S.No. Reaction Product

O
||
1. PhMgBr + Ph — C — Cl ¾®
(excess)
O
||
2. PhMgBr + Ph — C — OEt ¾®
(excess)
O
||
3. PhMgBr + Ph — C — NH 2 ¾®
(excess)
O
||
4. PhMgBr + EtO — C — OEt ¾®
(excess)
O
||
5. PhMgBr + Et — S — C — Cl ¾®
(excess)
PhMgBr + Ph — C ºº N ¾®
6. (excess)
Cl
7. PhMgBr +
(excess)
OH
PhMgBr + CH 3 — Cl ¾®
8.
PhMgBr + Br — Br ¾®
9.

5. Propose the all suitable routes to prepare given alcohol by the help of grignard reagent ?
OH OH
(a) Et (b) (c) CH3 CD3
OH CT3
6. Find the value of x ? (x = mole of RMgX consumed).
NH2
OCH3
OH
O O
OEt HS O
(a) (b)
Cl
Cl
O
O O–C–O–Ph
O O
Answers
1.
(1) (2) (3) (4)
OH
OH Ph Ph OH
(5) (6) (7) (8)
Ph Ph Ph Ph
OH
OH CH3 OH
Ph
(9) (10) (11) (12)
(13) HO
2. (a) x =5 (b) 4 (c) 5
H OH
H OH
3. (a)
Ph HO
r1 > r2 > r3
H OH
(b) CH 3 CH 2 OH , r1 > r2
H OH
(c) r3 > r1 > r2

NO2
Ph
(d) r1 > r2 > r3
HO H HO Ph
HO Ph
OH OH Ph
(e) r1 > r2 > r3 > r4
H Ph
OH
(f) Ph Ph OH No reaction r1 > r2 > r3
4.
O
OH Ph OH Ph
1. (2) (3) + Ph Ph
Ph Ph Ph Ph
OH Ph OH Ph O
(4) (5) (6)
Ph Ph Ph Ph Ph Ph

(7) (8) Ph — CH 3 (9) Ph — Br
MgBr
5. (a)
O H3 O r
EtMgBr
H3 O r
O
O MgBr
H3 O r
MgBr
O
H3 O r
(b)
MgBr
CHO
H3 O r
O
CT3MgBr
(c) CH CH3
3 H Or
3
O
CD3MgBr
CH3 CT3 H Or
3
O
CH3MgBr
CD3 CT3 H Or
3
6. (a) 7 (b) 8

Practical Organic Chemistry 521
10Practical Organic
Chemistry
1. Among the following which metal(s) is/are used to prepare sodium extract ?
(a) Li (b) Na (c) K (d) all of these
2. In organic analysis N is identified as:
(a) CN - (b) NO -2 (c) CNO - (d) none of these
3. The ammonia evolved from the treatment of 0.30g of an organic compound for the estimation
of nitrogen was passed in 100 mL 0.1 MH 2 SO 4 . The excess of acid required 20 mL of 0.5M
NaOH solution for complete neutralisation. The organic compound is :
(a) Thio urea (b) Benzamide (c) Urea (d) Acetamide
4. If a compound contains both N and S, the ions present in the Lassaigne’s extract are:
(a) CN - + S 2- (b) CNS - (c) N 3- + S 2- (d) CNS - + NO -2
5. Before testing halogens by Lassaigne’s extract, sodium extract is boiled with HNO 3 to:
(a) make the medium acidic (b) remove CN - or S 2- ions if present
(c) suppress the dissociation of AgNO 3 (d) avoid co-precipitation
6. Which of the following compounds interfere in the Beilsteins test for halogens ?
(a) Urea (b) Thiourea (c) Pyridine (d) All of these
7. Which halogen can't be tested by Beilstein test ?
(a) F - (b) Cl - (c) Br - (d) I -
8. There are several criteria of purity for organic compounds out of the following which is
considered to be the best ?
(a) Melting point (b) Mixed melting point
(c) Microscopic examination (d) Colour
9. Aniline has high boiling point, high vapour pressure at 100°C and is insoluble in water. Aniline
is therefore, separated by:
(a) Steam distillation (b) Simple distillation
(c) Distillation at low pressure (d) Sublimation
10. In paper chromatography:
(a) Mobile phase is liquid and stationary phase is solid
(b) Mobile phase is solid and stationary phase is liquid
(c) Both phases are liquids
(d) Both phases are solids
11. Absolute alcohol is prepared from rectified spirit by:

(a) Fractional distillation (b) Steam distillation
(c) Azeotropic distillation (d) Vacuum distillation
12. Azeotropic mixture are:
(a) Boils at different temperature (b) Are mixture of solids
(c) Are constant boiling mixtures (d) None of these
13. Anhydrous formic acid cannot be obtained from its aqueous solution by simple fractional
distillation because:
(a) Pure HCOOH is unstable
(b) HCOOH forms hydrogen bonds with water
(c) Boiling point of HCOOH is very close to that of water
(d) Constant boiling azeotropic mixture is formed with water
14. Glycerol boils at 290° C with slight decomposition, impure glycerine can be purified by:
(a) Steam distillation (b) Simple distillation
(c) Vacuum distillation (d) Extraction with a solvent
15. Absolute alcohol cannot be obtained by simple fractional distillation because:
(a) Pure C 2 H 5 OH is unstable
(b) C 2 H 5 OH forms hydrogen bonds with water
(c) Boiling point of C 2 H 5 OH is very close to that of water
(d) Constant boiling azeotropic mixture is formed with water
16. A bottle containing two immiscible liquids is given to you. They may be separated by using a:
(a) Fractionating column (b) Separating funnel
(c) Vacuum distillation (d) Steam distillation
17. The process of distillation involves all the following processes except:
(a) Change of state (b) Boiling (c) Condensation (d) Oxidation
18. Fractional crystallisation is carried out to separate such mixtures:
(a) Organic solids mixed with inorganic solids
(b) Organic solids highly soluble in water
(c) Organic solids having small difference in their solubilities in suitable solvent
(d) Organic solids having great difference in their solubilities in suitable solvent
19. An organic substance from its aqueous solution can be separated by:
(a) Distillation (b) Extraction with solvent
(c) Steam distillation (d) Fractional distillation
20. Two volatile and miscible liquids can be separated by fractional distillation into pure
components under the condition:
(a) They have low boiling points
(b) The difference in their boiling points is large
(c) The boiling points of the liquids are close to each other
(d) They do not form azeotropic mixture
21. For the separation of two miscible liquids which method is used ?
(a) Chromatography (b) Fractional column
(c) Fractional distillation (d) Separating funnel
22. Which reagent to useful in separating benzoic acid from phenol?
(a) Dil. HCl (b) Dil. H 2 SO 4 (c) 5% NaOH (d) 5% NaHCO 3
23. The most suitable method for separation of 1: 1 mixture of ortho and para nitrophenols is:
(a) Distillation (b) Crystallisation (c) Sublimation (d) Chromatography
24. In steam distillation, the vapour pressure of the volatile organic compound is:

(a) Equal to atmospheric pressure (b) Less than atmospheric pressure

(c) More than atmospheric pressure (d) None of these
25. Which of the following is used for removing moisture?
(a) Na 2 CO 3 (b) silica gel (c) FeSO 4 (d) Potash alum
26. 1.0 g of an organic compound containing nitrogen on Kjeldahlising required 58.0 mL of N /5
H 2 SO 4 for complete neutralization of ammonia. The percentage of nitrogen in the compound
is about:
(a) 38.31 (b) 14.82 (c) 16.24 (d) 21.62
27. 0.099 g of an organic compound when heated with fuming nitric acid in the presence of silver
nitrate in a Carius tube gave 0.287 g silver chloride. The percentage of chlorine in the
compound is about:
(a) 28.64 (b) 71.72 (c) 35.45 (d) 64.23
28. In Lassaigne’s test the organic compound is fused with sodium metal to:
(a) Ignite the compound (b) Oxidise the compound
(c) Convert the elements in ionic form (d) Reduce the compound
29. The fusion of nitrogen containing organic compounds with sodium results in the formation of:
(a) Sodium carbide (b) Sodium nitride (c) Sodium cyanide (d) Sodium carbonate
30. AgNO 3 solution does not give white ppt. with CCl 4 but with sodium extract of CCl 4 , AgNO 3
gives white precipitate because:
(a) CCl 4 is covalent compound
(b) CCl 4 is partially ionised
(c) Sodium extract of CCl 4 contains Cl - ions and Na+ ion
(d) Sodium extract of CCl 4 contains ClO -3 ions
31. In Kjeldahl method function of CuSO 4 is:
(a) B.P. elevator (b) catalyst
(c) freezing point depressator (d) none of these
32. In the estimation of nitrogen by Duma’s method 0.59 g of an organic compound gave 112 mL
N 2 at NTP. The percentage of nitrogen in the compound is about:
(a) 23.7 (b) 11.8 (c) 20.1 (d) 47.5
33. 0.20 g of hydrocarbon on combustion gave 0 .66 g CO 2 . The percentage of hydrogen in the
hydrocarbon is about:
(a) 33 (b) 45 (c) 10 (d) 90
34. 0.58 g of a hydrocarbon on combustion gave 0.9 g water. The percentage of carbon in the
hydrocarbon is about:
(a) 75.82 (b) 82.76 (c) 27.85 (d) 58.64
35. When sodium extract is prepared, generally the substance ignites is:
(a) Na (b) H 2 (c) Organic compound (d) O 2
36. The organic compound which does not give blue colour in Lassaigne’s test is:
(a) Aniline (b) Glycine (c) Hydrazine (d) Urea
37. 0.2 g of an organic compound containing C, H and O, on combustion gave 0.147 g CO 2 and
0.12 g water. The percentage of oxygen in organic compound is:
(a) 73.29% (b) 78.45% (c) 83.23% (d) 89.50%

1. Which of the following structures will give a positive test with Tollens’ reagent?
O
OH O
(a) (b) (c) O (d)
O
2. Which of the following pair is differentiated by iodoform test ?
O O O O
(a) (b) H H H
O O O O
||
I
(c) Ph H — C— H (d) CH2—I CH
I
3. What is(are) the final product(s) of the following reaction?
O
2I , NaOH
¾¾¾¾® ?
O O
ONa+CHI 3
(a) I (b)
O O
I
(c) (d) OH+CHI 3
4. Which of the following compounds would give a positive iodoform test?

O O O O
O
(a) (b) (c) (d)
O
C—OH
2NaNH
5. HO CH2—C SO3H ¾ ¾¾¾2® Product of the reaction is:
C
CH

CO2H
(a) HO CH2— C s
SO3
C
Cs
COs2
(b) HO CH2—C SOs

3
C
CH
COs
2
(c) sO CH2—C SO3H
CH
(d) None of these
6. Which of the following compound will not evolve H 2 gas with Na ?
O
||
(a) Ph —C — OH (b) Ph — OH
O O
|| ||
(c) CH 3 — C — CH 2 — C — CH 3 (d)
7. Which of the following compounds is most reactive with NaHCO 3 ?

OH
CO2H
(a) (b)

OH O
S—O—H
(c) (d)
O
NO2
8. Which compound does not give positive iodoform test ?

O
|| O
(a) CH 3 — C — OCH 3 (b)
O O O
|| || ||
(c) CH 3 — C — CH 2 I (d) CH 3 — C — CH 2 — C — CH 3
Answers
1. (b) 2. (a) 3. (c) 4. (b) 5. (b) 6. (d) 7. (a) 8. (b) 9. (a) 10. (a)
11. (c) 12. (c) 13. (c) 14. (c) 15. (d) 16. (b) 17. (d) 18. (c) 19. (b) 20. (d)
21. (c) 22. (d) 23. (a) 24. (b) 25. (b) 26. (c) 27. (b) 28. (c) 29. (c) 30. (c)
31. (b) 32. (a) 33. (c) 34. (b) 35. (b) 36. (c) 37. (a)
1. (c) 2. (b) 3. (b) 4. (b) 5. (b) 6. (d) 7. (d) 8. (a)
1. Among the following which compound can't be identified by Lassaigne’s test ?

(a) diazo compounds (b) NH 4 NO 3 (c) NH 2 × NH 2 (d) NH 2 OH
Answers
1. (b, c, d)

Chemistry in Everyday Life 527
11
Chemistry in
Everyday Life
1. Phenol is:
(a) antimicrobial (b) antiseptic (c) disinfectant (d) all of these
2. Select the correct statements:
(a) 2-3% alcohol-water mixture is known as tincture of iodine.
(b) Iodoform solution is antiseptic for wounds.
(c) Boric acid solution is antiseptic for eyes.
(d) All of these
3. Select the correct statement:
(a) Enzymes are proteins in nature and are biological catalysts
(b) Proteins which help in communication system are called receptors
(c) Polar molecules across the cell membrane are called carrier proteins
(d) All are correct
4. Some drugs interact with enzymes and make them biologically inactive. Such drugs are called:
(a) enzyme promoters (b) enzyme inhibitors (c) allogens (d) all of these
5. Drugs which do not bind to the enzyme’s active site, but to different site. This different site is
called :
(a) inhibition site (b) competitive site (c) allosteric site (d) none of these
6. Chemicals that are responsible for communication of message between neurons and muscles
are known as:
(a) messengers (b) allogens (c) antagonists (d) receptors
(a) Antagonists are the substances which inhibit the natural function of receptor site.
(b) Agonists are the drugs that mimic the natural messenger by switching on the receptor
(c) Substrates may bind to active site of enzyme through a variety of interactions such as ionic
bonding, H-bonding, van der Waals’ interaction or dipole-dipole interaction.
(d) All of these
8. Among the following which is not antacid ?
(a) Histamine (b) Cimetidine (c) Ranitidine (d) All are antacids
9. Histamine stimulates the secretion of pepsin and hydrochloric acid and antihistamines are
used to prevent the action of histamines.Among the following which are antihistamines ?
(a) Ranitidine (b) Terfenadine (c) Brompheniramine (d) All of these

10. Among the following, which is not a tranquilizer ?

(a) Noradrenaline (b) Chlordiazepoxide (c) Meprobamate
(d) Equanil (e) All are tranquilizers
11. Iproniazid and phenelzine are:
(a) antidepressants (b) tranquilizer (c) both (a) and (b) (d) none
12. Hypnotics are sleep producing drugs. Among the following select the hypnotics :
(a) Barbiturates (b) Valium (c) Serotonin (d) All of these
13. Among the following analgesics, select the odd one:
(a) codeine (b) morphine (c) aspirin (d) heroin
14. Morphine narcotics are obtained from:
(a) opium (b) avena (c) datura (d) all of these
15. Morphine and heroin, both are narcotic analgesics. Heroin may be obtained from morphine
by:
(a) nitration (b) acetylation (c) chlorination (d) none of these
Answers
1. (d) 2. (d) 3. (d) 4. (b) 5. (c) 6. (a) 7. (d) 8. (a) 9. (d) 10. (e)
11. (c) 12. (d) 13. (c) 14. (a) 15. (b)
1. Select the correct statements:

(a) Drugs are chemicals of low molecular mass.
(b) Drugs produce biological response.
(c) Drugs which are used to treat diseases are called medicines.
(d) Chemotherapy is the use of chemicals for therapeutic effect.
O
2. H2N S—NHR
O
Above drug is an example of :
(a) sulpha drug (b) sulphonamide (c) analgesic (d) tranquilizer
(a) Bactericidal antibiotics are those which kills the microbes.
(b) Bacteriostatic antibiotics are those which inhibits the growth of microbes.
(c) Ofloxacin is the bacteriostatic antibiotics.
(d) penicillin is bactericidal
Answers
1. (a, b, c, d) 2. (a, b) 3. (a, b, d)

Elementary Problems in Organic Chemistry For JEE by M S Chouhan

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Elementary Problems in Organic Chemistry For JEE by M S Chouhan

Uploaded by

Copyright:

Available Formats

For More Material Join: @JEEAdvanced_2024

For More Material Join: @JEEAdvanced_2024

[A] Classification and Nomenclature of Organic Compounds

(a) 4 (b) 6 (c) 8 (d) 10

4. Which of the following is homocyclic compound?

For More Material Join: @JEEAdvanced_2024

5. Which of the following is heterocyclic compound?

(c) (d) All of these

7. Which of the following is organometallic compound?

How many functional groups are present in above compound?

For More Material Join: @JEEAdvanced_2024

17. In homologous series, successive members differ by :

18. Degree of unsaturation for is:

(a) 6 (b) 7 (c) 8 (d) 9

(a) 12 (b) 13 (c) 14 (d) 15

For More Material Join: @JEEAdvanced_2024

21. Double bond equivalent of C 5 H 12 O is:

(a) (b) (c) (d) All of these

24. Difference of DBE in and is:

(a) 0 (b) 1 (c) 2 (d) 3

For More Material Join: @JEEAdvanced_2024

(a) 2 (b) 3 (c) 4 (d) 5

Hybridization and Bonding in Organic Molecules

(a) 1 (b) 2 (c) 3 (d) 4

(a) 6 (b) 12 (c) 18 (d) 24

For More Material Join: @JEEAdvanced_2024

7. In which of the following carbon is sp 2 hybridized state ?

How many p-electrons are contained in given molecule?

For More Material Join: @JEEAdvanced_2024

IUPAC Nomenclature of Alkanes

(a) 6C (b) 7C (c) 8C (d) 9C

For More Material Join: @JEEAdvanced_2024

(a) 2-methyl-3-ethylheptane (b) 3-ethyl-2-methylheptane

(a) isoprene (b) 3-methyl-1,3-butadiene

(a) 4 (b) 5 (c) 6 (d) 7

11. ; How many 2° carbon present in above compound?

(a) 4 (b) 5 (c) 6 (d) 7

15. ; Correct IUPAC name of the following compound is:

(a) 4-(1,1-dimethylethyl)-5-ethyloctane (b) 5-ethyl-4-(1,1-dimethylethyl) octane

For More Material Join: @JEEAdvanced_2024

IUPAC Nomenclature of Alkynes/Alkenes

(a) 3, 6-Dimethyl cyclohexene (b) 1, 6-Dimethyl cyclohexene

(c) 6,6-Dimethyl cyclohexene (d) 1,5-Dimethyl cyclohexene

2. Which pair of names refers to the same compound ?

For More Material Join: @JEEAdvanced_2024

(a) neohexyne (b) trimethylpropyne

7. The IUPAC name of is:

(a) 2-bromo-3-methylbut-3-ene (b) 4-bromo-3-methylpent-2-ene

(a) 3-methyl-1-hexen-5-yne (b) 4-methyl-5-hexen-1-yne

IUPAC Nomenclature of Alcohols/Aldehydes/Ketones/Acids

For More Material Join: @JEEAdvanced_2024

(a) 2-Methyl butanoic acid (b) 2-Ethylprop-2-enoic acid

True statement for the above compounds is :

(a) I (b) II (c) III (d) IV

For More Material Join: @JEEAdvanced_2024

(a) 5-chloro-2-hydroxyhexene (b) 2-chloro-5-hydroxyhexene

11. The IUPAC name of CH—OH is:

(a) 1-hydroxy-1-cyclopropylethane (b) 1-hydroxyethylcyclopropane

IUPAC Nomenclature of Acid Halides, Esters, Nitriles, Amines, Amides, Anhydrides

For More Material Join: @JEEAdvanced_2024

3. Which of the following compounds is an acyl chloride ?

(a) i (b) ii (c) iii (d) iv (e) v