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Elementary Problems in Organic Chemistry For JEE by M S Chouhan
Elementary Problems in Organic Chemistry For JEE by M S Chouhan
1
Organic Chemistry:
Some Basic Principles and Techniques
H H H
(a) (b) H — C — C — C — H
H H H
(c) CH 3 — CH 2 — CH 3 (d)
(a) (b)
O
(a) 3 (b) 4 (c) 1 (d) 5
9.
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
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)
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:
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.
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?
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:
10. ; How many methyl —CH 3 group are present in given alkane?
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
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
CHO
(c) (d) Br
O
3. What is the common name of the following compound ?
O
||
CH 3 CHCH 2 COH
|
Cl
OH CH2CH2OH
7. (i) and (ii)
Cl
|
9. The IUPAC name of CH 3 — C — CH 2 CH == CHCH 3 is:
|
OH
CH3
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
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
CH2Cl OCH2Cl Cl
(iii) (iv) (v)
O O O O
|| || || ||
(iii)CH 3 COH (iv) CH 3 COOH (v) CH 3 CO CCH 3
O
(a) n-propyl ethanoate (b) ethyl propanoate
(c) pentanoic anhydride (d) n-propyl propanoate
HO—C==O CH3
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
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
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
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)
COOC2H5
5. The IUPAC name of is :
COCl
CO—O—C2H5
CO—Cl
[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?
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) chain isomers (b) positional isomers (c) metamers (d) functional isomers
Cl Cl
Cl
16. ; ( A) and ( B ) are:
Cl
(A) (B)
(a) chain isomers (b) positional isomers (c) metamers (d) functional isomers
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
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
O
1.
O O
(A) (B)
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)
HO OH HO OH
(i) (ii)
HO OH HO O HO O
(iii) (iv) (v)
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
(a) i (b) ii (c) iii (d) iv (e) v
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
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) (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
(I) (II)
H H CH3 H
H H
H
H C2H5 H
CH3 CH3
(III) (IV)
H H H H
H H
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H
H
(V)
CH3
H H C2H5
(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
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)
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
?
Cl Cl
(a) 0 (b) 1 (c) 2 (d) 3
16. How many geometrical isomers are possible for
CH 3 — CH == C == CH — CH == CH — CH 3 ?
(a) 0 (b) 1 (c) 2 (d) 3
17. How many geometrical isomers are possible for
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
CH3 CH3
21. How many geometrical isomers are possible for H H ?
Optical Isomerism
1. Determine the relationship between the two molecules shown.
O O
CH CH3
3
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
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
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
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
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Cl Br
(c) (d) I C H
Cl Cl
(A) (B)
(a) Diastereomers (b) Enantiomer (c) Identical (d) Structural isomer
Cl
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
(a) (b)
(c) (d)
H H
19. How many planes of symmetry are present in H C == C H ?
CO2H
O
¾¾® (b) (Number of chiral center)
CO2H
sum of ( a + b = ?) :
(a) 3 (b) 4 (c) 5 (d) 6
(a) H H (b) HO H
CH3 CH3 CH2OH
CH3
OH
(c) (d) All of these
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 ?
H
27. H
Cl
Cl
How many plane of symmetry is present in above compound ?
(a) 0 (b) 1 (c) 2 (d) 3
28.
29. Which of the following compound has plane of symmetry and center of symmetry ?
F F F
F F F F F F
Cl O
(A)
CH3
34.
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
CO2H
H OH
40. Number of chiral centers present in tartaric acid is:
H OH
CO2H
(a) 1 (b) 2 (c) 3 (d) 4
H C Cl and C
H
H
CH3 CH2Cl
(a) Constitutional isomers (b) Enantiomers
(c) Diastereomers (d) Conformational isomers
(e) Superimposable without bond rotation
H Br
and
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
H H CH3 CH3
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
49. What is the relationship between the structures shown below?
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
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
58. What is the relationship between the following compounds?
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
59. What is the relationship between the following compounds?
CH3 CH3
Cl H H Cl
and
Cl H Cl H
CH3 CH3
H OH
H OH
HO H
CH2OH
(a) 2 (b) 4 (c) 6 (d) 7 (e) 8
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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
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
CH3
N
O H
(a) 0 (b) 1 (c) 2 (d) 3
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)
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
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
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)
CH3 r CH3
C CH3 rC CH3
(c) (d)
H CH3
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
(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
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)
+ +
H
(c) C (d) CH2
H
(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
21.
How many resonating structure are possible for Napthalene (lacking formal charges) ?
(a) 1 (b) 2 (c) 3 (d) 4
r
H—C—H
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:
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
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Organic Chemistry: Some Basic Principles and Techniques 51
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
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
r
CH2
CH3
r r r
(a) (b) (c) (d)
r
NH2
CH2
r r
(a) (b) (c) (d)
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
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
CH3 CH3
Å Å
III. and
O .. O ..
..
..
..
..
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
(a) I (b) II (c) III (d) IV
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
.. ..
.. OH
.. O ..
..
.. O ..
s
..
..
57. Which is the most important contributing resonating structure of the following ?
O s
CH2—N—O
.. O ..s O ..
..
..
..
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
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?
61. Which of the following compounds has localized lone pair of electrons?
s
NH2 CH2 — NH2 CH — CH3
O
NH—CH3 CH3
C—H
(a) (b) (c) (d)
NO2
NH2
(c) (d)
67. Which of the following carbocations has maximum number of resonating structures ?
r r r r
(a) (b) (c) (d)
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
r r r r
CH2 CH—CH3 CH3— C—CH3 CH3— C—CH3
CH3 CH3
(a) (b) (c) (d)
r
(c) r > H2N CH2
s s
CH2 < CH2
(d) Cl F
r r r r
CH2 CH2 CH2 CH2
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
F Cl CH3
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
NO2 NO2
CH3 CH3 CH3
(c) (d)
96. In which of the following lone pair of nitrogen is not involved in resonance?
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)
(c) (d)
Hyper Conjugation
1. Which of the following is the most stable diene?
a b c d
(a) c > a (b) a > c (c) d > c (d) b > a
(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)
r
(c) H2C—CH—CH2 (d)
r
r
(a) r (b) (c) r (d)
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
(a) I (b) II (c) III (d) IV (e) V
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
(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)
(IV) (V)
(a) I (b) II (c) III (d) IV (e) V
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
; ;
Hb
Ha
(a) Ha > Hb > Hc > Hd (b) Hb > Hc > Ha > Hd
(c) Hb > Hc > Hd > Ha (d) Hd > Ha > Hc > Hb
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
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 :
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)
(1,2-Dimethyl cyclohexane)
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
3. 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 highest energy?
benzene =
I II III
IV V VI
(a) orbital I (b) orbital II (c) orbital III (d) orbital IV
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. + –
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
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
H H
S N O
(iii) (iv) r (v)
S
(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
(a) i (b) ii (c) iii (d) iv (e) v
28. Which of the following compound will undergo dimerization?
(a) (b) (c) (d)
O
(a) AlCl 3 (b) HCl (c) H 2 SO 4 (d) Na
36. To convert given compound into aromatic best reagent is:
+ 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
NH2 NH2
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 ?
(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
NH2
NH2 NH3
r
16. Rank the following in decreasing order of acidity :
NH2 N
(c) (d)
(a) (b)
O2N NO2
NO2 NO2
OH OH
NO2 NO2
(c) (d)
NO2
NO2 NO2
(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
(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
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)
(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
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
36. Which of the following is strongest base ?
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
r r
NMe3 H1 PMe3 H2
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.
OH OH CO2H CO2H
44.
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
58. Rank the following compound in order of increasing acidic strength :
(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
59. Rank the following compound in order of increasing acidic strength :
(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
60. Rank the following compound in order of increasing acidic strength :
(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
F Cl
(a) i > ii > iii (b) ii > iii > i (c) iii > ii > i (d) iii > i > ii
(a) (b)
r
Ha H NMe3
(c) (d)
r
H PMe3 H CH3
O O
(a) (b) O S
Ha
Ha
H
S S
(c) (d) CH3—S—C—S—CH3
Ha O CH3
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
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)
(a) i > ii > iii (b) i > iii > ii (c) iii > i > ii (d) iii > ii > i
CF3
(a) (b) (c) (d) N CF3
CF3
(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
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)
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
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
For More Material Join: @JEEAdvanced_2024
Organic Chemistry: Some Basic Principles and Techniques 91
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 :
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
(a) (b)
(c) (d)
5H2/Ni
9. Energy
H2/Ni
DH=– 350 kJ /mol
(DH=– 120 kJ /mol)
3H2/Ni
Answers
[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)
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)
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)
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)
Miscellaneous Problems
1. (c) 2. (b) 3. (a) 4. (b) 5. (d) 6. (c) 7. (a) 8. (c) 9. (b) 10. (a)
(c) (d)
(c) ¬
¾® (d) ¬
¾®
r
8. In which of the following compounds lone pair of nitrogen is involved in resonance?
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)
|
||
OH
O NH2
(a) alcohol (b) ketone (c) carboxylic acid (d) amide
17. Which of the following is aromatic?
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
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
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)
:OMe
:
r
(a) (b)
r
OMe OMe
(c) (d)
r OMe OMe
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
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
Me
(a) (p) 11
(b) (q) 12
O
|
(c) (r) 13
O
|
(d) (s) 14
(t) 15
O
||
(c) Metamers (r)
CH 3 — C — O — CH 2 — CH 3 ,
O
||
CH 3 — CH 2 — C — O — CH 3
Column-I Column-II
s
(c) O (r) No relation
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
s (s) Homologous
(d) CH 3 — CH 2 — CH 3 , CH 3 — CH 2 — CH 2
Cl
HO
Cl
( 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
Me Me
Me Me
OH
Br
Br Br
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
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
CH2–Cl
CH2–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
24. How many carbon atom present in the parent chain in the given following compound ?
O
CH3
Cl
28. Total number of a-hydrogen in the given compound is:
r
(3) + (4) (5) (6)
N N
| |
H H
r
(7) (8)
r
r
30. x = Types of functional group
y = Double bond equivalent
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)
O
42. X = Number of a-Hydrogen,
(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
H3C O2N Br
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
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
10. C 3 H 6 Cl 2
13. C 5 H 12
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
8. Find the number of Stereocenter and Chiral center in all structural isomers of given molecular
formula:
S.No. Molecular Formula Stereocenter Chiral Center
(iii) C 6 H 14
(iv) C 3 H 6 Cl 2
(v) C 5 H 12
(vii) C 5 H 11 Br
(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
(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
CH3 CH 3 CH3
Cl
1. CH3 2. 3.
CH 3
CH3 CH3
Cl Cl
4. 5. 6.
7. 8. 9.
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
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
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
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 CMe3
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
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
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
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
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.
Br I
7.
I Br
Elementary Organic Chemistry
Organic Chemistry: Some Basic Principles and Techniques 137
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
8. 2,3-dichloropentane
9. 1,2-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
27. State different types of gases evolved in the following given blocks :
a. EtOH
b. H — C ºº C — H
c.
d. Ph—OH
e. Ph — CO 2 H
f. Ph — SO 3 H
g.
h.
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.
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.
9.
10.
33.
Huckel Rule Complete
S.N. Compounds Planarity Cyclic Nature
( 4n + 2) pe - delocalisation
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.
O O
OH Cl
1. 2.
O NH2 O CH3
O
3. 4.
O
N
CH3
O
5. 6.
O
7.
OH
35. Write the IUPAC name of the compounds given in the blank box.
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.
36. Write the IUPAC name of the compounds given in the blank box.
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
37. Write the IUPAC name of the compounds given in the blank box.
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
+
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?
S. Resonating S. Resonating
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
S. Resonating S. Resonating
Compounds Compounds
No. Structure No. Structure
H3C
O
-
CH
14. 15.
O
-
O O
CH3
16. H3C 17.
O
O
18. H3C
OH
40. Write the IUPAC name of the compounds given in the blank box.
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
41. Write the IUPAC name of the compounds given in the blank box.
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
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
42. Write the IUPAC name of the compounds given in the blank box.
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
43. Write the IUPAC name of the compounds given in the blank box.
S. S.
Compounds Compounds
No. No.
HO O OH
O S O
CH3 CH3
1. O O 2.
O O
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
44. Write the IUPAC name of the compounds given in the blank box.
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
45. Write the IUPAC name of the compounds given in the blank box.
S. S.
Compounds Compounds
No. No.
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.
46. Write the IUPAC name of the compounds given in the blank box.
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
47. Write the IUPAC name of the compounds given in the blank box.
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
48. Write the IUPAC name of the compounds given in the blank box.
S. S.
Compounds Compounds
No. No.
1. 2.
N N
H3C CH3
H3C
CH3
3. 4.
N
CH
CH3
H3C
CH3
5. 6.
N
CH
CH3
7.
N
49. Write the IUPAC name of the compounds given in the blank box.
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
O OH
H3C CH3
H3C CH3
9. Br 10.
Br HO O
CH
S. S.
Compounds Compounds
No. No.
H3C
H3C
H3C CH3 CH3
O OH
CH3
H3C
CH3 CH3
13. 14.
O
HO
CH3
15.
O
HO
50. Write the IUPAC name of the compounds given in the blank box.
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.
51. Write the IUPAC name of the compounds given in the blank box.
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
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.
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
56. Write the IUPAC name of the compounds given in the blank box.
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
57. Write the IUPAC name of the compounds given in the blank box.
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.
58. Write the IUPAC name of the compounds given in the blank box.
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
59. Write the IUPAC name of the compounds given in the blank box.
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
60. Write the IUPAC name of the compounds given in the blank box.
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
61. Write the IUPAC name of the compounds given in the blank box.
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
O
CH3 Cl
H3C
H3C
CH3
7. 8.
O CH2 Br
62. Write the IUPAC name of the compounds given in the blank box.
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)
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
Å Å
+ +
Cl
2. + enantiomer
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
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
10. C 3 H 6 Cl 2 4
13. C 5 H 12 3
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
, * ,
, , [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
*
(vi) [S.C. = 2; C.C. = 2]
*
Br
Br *
(vii) * Br
Br Br
Br
Br
* Br [S.C. = 3; C.C. = 3]
CH2
* *
*
(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
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
(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) *
CH3
OH
(1) cis– –
CH3—CH2—C == C—CH2CH3 (2) trans– –
CH3 total- 6
Total enols possible are 6.
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.
1. ✕ ✓ ✕ ✕ ✕ ✕ ✕
2. ✕ ✕ ✕ ✓ ✓ ✓ ✕
3. ✕ ✓ ✕ ✕ ✕ ✕ ✕
4. ✕ ✓ ✕ ✕ ✕ ✕ ✓
5. ✕ ✓ ✕ ✕ ✕ ✕ ✕
6. ✕ ✕ ✕ ✓ ✓ ✓ ✕
7. ✓ ✕ ✕ ✓ ✓ ✓ ✓
8. ✓ ✕ ✕ ✓ ✓ ✓ ✓
25.
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
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
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
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
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
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
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.
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)
Alkanes
Br Na
1. ¾¾2®( A) ¾ ¾¾
¾®( B ). Product B is:
hv Dry ether
O
s r electrolysis
2. C—O K ¾¾¾¾® (A) ; Major-product ( A) is :
(Major)
(a) (b)
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 ?
Br
Br 2Na
5. ¾¾¾®
dry ether
(A) ; Product A is:
Br
Br
Br Br
OH
Cl Cl
Cl Cl
(I) CH2CH2CH2CH2CH2CH2 (II) (III)
Cl
Cl
Cl
(IV) (V)
Cl
Cl
(a) I (b) II (c) III (d) IV (e) V
15. Compare the heats of combustion of the following compounds:
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
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
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
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?
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)
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
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 +
O and HCHO
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
(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?
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
O
15. ¾¾3® ( A); Product ( A) is:
Zn
OH
CH2OH CH3 CH3
(I) (II) (III) OH
CH3
CH3
(IV) (V)
OH HO
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
(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
20. What is the major product of the following reaction?
NBS
+ heat
?
Br
NBS NBS Br Br
(I) (II) NBS (III) (IV) Br (V)
Br
CH3 CH2Br
(I) (II)
CH3 CH3
CH3
(III) (IV) (V)
Br Br Br
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)
H—Br KSH
¾¾¾®
Peroxide
(A) ¾¾¾® (B)
O
SH
SH
SH
(a) (b) (c) (d)
+ Br2/CCl4 ?
Br
D rs
(1) NaH
32. ¾ ¾¾ ¾® P , Product formed in this reaction is:
D ( 2) - H 2O
D D
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
37. How many different products are obtained upon the ozonolysis of the following C 20 -tetraene?
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)
44. Which alkene will give only optically active product upon catalytic hydrogenation (H 2 /Pd)?
4 eq. H , Pd
2
¾¾¾¾¾® ?
(a)
+
(b)
+
(c)
+
(d)
+
I II III IV
(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
Br+ O +O Br–
H
52. What is the major product of the following reaction?
CH3
Br2
+ ?
H2O
OH OH H CH
(i) (ii) (iii) (iv) CH
OH OH
O
Br
56. ¾¾2®
H 2O
Cl Cl
CH3 CH3 CH3 Cl
CH3
(I) (II) (III) (IV) (V) CH3
Cl
Cl
Cl
(a) I (b) II (c) III (d) IV (e) V
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
ColdKMnO
62. 4
¾¾¾¾¾® (A)
2 4 Br /CCl
¾¾¾¾¾® (B)
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
4. What is the product of the following reaction?
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) (b) OH
H
H
H
(c) (d)
H
O HO
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 d
b c
(a) a (b) b (c) c (d) d
2. Identify the site where electrophilic aromatic substitution takes place ?
O
a d
b c
(a) a (b) b (c) c (d) d
3. Identify the site where electrophilic aromatic substitution takes place ?
c O
b O
a
H—N
O
(a) a , b (b) b, c (c) a , c (d) b
4. Identify the site where electrophilic aromatic substitution takes place ?
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)
For More Material Join: @JEEAdvanced_2024
Hydrocarbon (Aliphatic and Aromatic Hydrocarbons) 227
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
8. Based upon your understanding of the basic principles of molecular orbitals it should be
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®
10. Which of the following represents the best reagent(s) for the electrophilic nitration of
benzene?
? NO2
¾¾¾®
FeBr
3
¾¾¾®
Br 2
HNO 3
¾¾¾®
H SO
2 4
NO2
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
Na
15. ¾¾¾® (A); product ( A) is:
dry ether
Br
Br
Br 4Na
16. ¾¾¾®
dry ether (A). Product ( A) of the reaction:
Br
Br
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
21. Which of the compound will not undergo Friedel Craft reaction ?
O
CH3 CH3
E r Er
22. ¾¾® ortho-complex ( r1 ) ; ¾¾® meta-complex ( r2 ).
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 ?
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) (b)
(c) (d)
(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:
37.
HNO
3
+ ¾¾¾®
H SO
?
2 4
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
3anhydrous AlCl
+ ICl ¾¾¾¾¾® X is:
I
Cl I Cl
COOH CH3
(i) (ii)
CH3CH2 HOOC
KMnO 4
¾¾¾®
H+, heat
?
COOH
COOH
(a) (b) COOH
COOH
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
NH—C—CH3 NH—C—CH3
(c) (d)
Br
Br Br Br
1
2
O
2 Br
49. ¾¾® substitution take place at the position.
3 Fe
4
O O
NH—C—CH3 NH—C—CH3
(a) (b) O
C—CH2—Cl
CH2—C—Cl
O
(c) (d) O
CH2—C—Cl
C—CH2—Cl
O
51. Give the major product of the following reaction:
O
O O
NHPh NHPh
(a) (b)
H3C
CH3
NHCOPh NHCOPh
(c) (d)
H3C
CH3
Answers
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)
HO OH
(a) (b)
OH OH
OH OH
(c) (d)
OH OH
O O
O
2. ¾¾3® Identify all possible product:
Zn
4. In which of the following electron density on phenyl ring is more than benzene?
CH3 OH Cl NO2
Br
5. ¾¾2® Identify the products.
CCl 4
Br
Br
(a) Et (b) Et
Br Br
Et
Br
Br
(c) (d) Br
8. Which of the following compounds when react with AlCl 3 aromatic compound will form ?
Cl Cl Cl Cl
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
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
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) a > b > c > d (b) b > a > c > d (c) d > b > c > a (d) d > b > a > c
(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
Br CH2—Br
(c) (d)
NBS
¾¾
¾®
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®
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.
r
(a) — NR 3 (p) shows +I effect
O
(b) || (q) shows +H effect
— C— H
..
(c) — O—
.. Me (r) shows +M effect
OH
(p) Group attached with benzene ring is +M
(a) group.
NO2
(q) Group attached with benzene ring is -M
(b) group.
SO3H
(s) Group attached with benzene ring is +I.
(d)
OH
(a) (p) +M
NO2
(b) (q) -M
O
C—CH3 (r) -I
(c)
O
O—C—CH3 (s) +I
(d)
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
Ni / D 2
¾¾ ¾
¾® Ni / D 2
9. 10. ¾¾ ¾
¾®
COOH
Br2 , CCl4 Br2 , CCl4
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
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®
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
CH
(cis)
CH
CH3
13. CH3
Cold KMnO 4
H Br ¾¾ ¾¾¾ ¾®
CH
(trans)
CH
CH3
8.
1.
2.
3.
4.
5.
, ,
6.
, ,
7.
, ,
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
Comprehension Based Problems:
Passage-1: 1. (c) 2. (d) 3. (b)
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
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
3
Haloalkanes and
Haloarenes
1. NaS
Br ¾¾¾¾¾¾¾® ?
2. H2, Pd
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
Free Free
(a) Energy (b) Energy
Free Free
Energy Energy
(c) (d)
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
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262 Elementary Organic Chemistry
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:
(a) Is > Br s > Cl s > F s (b) F s > Cl s > Br s > 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:
(a) Is > Br s > Cl s > F s (b) F s > Cl s > Br s > Is
(c) Is > Cl s > Br s > F s (d) F s > Is > Br s > Cl s
KOH KOH
Reaction-1: ¾¾¾® ; Reaction-2: ¾¾¾¾®
H2O Crown ether
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
(a) No change (b) Doubles the rate
(c) Triples the rate (d) Quadruples the rate (e) Rate is halved
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
rs
36. K SH ( P ) ; Major product ( P ) is:
¾¾®
Br
SH SH
CH2
Br Br
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
CH2—Cl
sr
Ph—S Na
49. ¾¾¾® (A), Structure of product ( A) is:
Br
Cl SPh SPh
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
Br Br
Br Br
(a) (b) (c) (d)
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
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
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
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
Br Br Br
Br Br Br
Br Br CH2—Br
Br Br Br
(i) (ii) (iii)
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
(a) I (b) II (c) III (d) IV (e) V
I I I
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)
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
CH3 NH3
r
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
51. What is the product of the following reaction?
O
3 CH CH OH
2
S ¾¾¾¾¾®
O
O
OCH2CH3
(a) OCH2CH3
OCH2CH3
NBS HBr Mg
1. CH 3 — CH == CH 2 ¾ ¾
¾® (A) ¾ ¾® (B) ¾¾®(C )
ROOR
Product (C) is:
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)
6. What is the product of the following reaction?
CH2CH3
TsCl Cl–
CH3 OH
H
CH2CH3 CH2CH3
(a) CH3 Cl (b) CH3 OTs
H H
CH2CH3 CH2CH3
(a) CH3 Cl (b) CH3 OTs
H H
NaOH
(c) Br ¾¾¾¾® (d) Br NaI
¾¾¾¾®
H2O/EtOH
Cl
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 CH3
CH—C—CH3 CH == C—CH3
IV. V.
OH H
CH 3
|
(a) CH 3 CH 2 OC — CH 3 (b) CH 2 == CH 2
|
CH 3
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
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)
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
(a) (b) (c) (d) None of these
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
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
Br
H3C H H3C H
(a) (b)
H CH3 H3C H
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
Ph KOH
40. ¾¾¾® (A), A is:
EtOH
F
CH2 CH3 CH3
(a) Ph (b) Ph (c) Ph (d) Ph
OEt
CH 3
|
41. CH 3 — C — Br CH 3 — CH — Br CH 3 — CH 2 — CH 2 Br
| | (c)
CH 3 CH 3
( a) (b)
Reactivity toward E 1 :
(a) a > b > c (b) b > a > c (c) b > c > a (d) c > b > a
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
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
CH3
–
52. r
OH
¾¾¾® Olefinic product.
NMe3 D
H H
OH O
(a) Br Cl (b) Br Cl
Cl
Cl
(c) Br Cl (d) Br Cl
OCl
(a) (b)
Br Br
(c) (d)
Br
56. H ¾alc.
¾¾
KOH
¾® (A) ; Product (A) is:
D
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
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
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
I
r r r
(iii) N (iv) N (v) N Is
CH3 I CH3 CH3 CH3 CH3
CH3 CH3 CH3
2 Ag O heat
r + ¾¾® ¾¾® ?
H2O
N
CH3 CH3 Is
CH3
(i) (ii)
Cl
(a) S N 2 (b) S N1 without rearrangement
(c) S N1 with rearrangement (d) E 2 (e) E 1
8. What mechanism predominates in the reaction below?
CH3OH, D
CH2CH3
Cl
(a) S N 2 (b) S N1 without rearrangement
(c) S N1 with rearrangement (d) E 2 (e) E 1
9. What mechanism predominates in the reaction below?
NaOCH3, CH3OH
CH2CH3
Cl
(a) S N 2 (b) S N1 without rearrangement
(c) S N1 with rearrangement (d) E 2 (e) E 1
CH 3
|
10. CH 3 — C — Br CH 3 — CH — Br CH 3 — CH 2 — CH 2 Br
| | (c)
CH 3 CH 3
( a) (b)
Reactivity toward E 2 :
(a) a > b > c (b) b > a > c (c) b > c > a (d) c > b > a
[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)
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
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)
[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)
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
Br
rs
KSH
5. ¾¾¾® Correct statement regarding given reaction will be:
(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
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
Answers
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
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
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)
(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.
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
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
Cl
(b) (q) Elimination reaction
F
(c) (r) S N1 reaction
NO2
Cl
(d) (s) S N 2 reaction
(a) CH 3 — CH 2 — Br (p) 10 -5
(b) Me — CH 2 — CH 2 — Br (q) 10 -2
Me
|
Me — C — CH 2 — Br (s) 1
(d)
|
Me
Cl
(a) (p) 172
Cl
(q) 157
(b)
Cl
Cl
(d) (s) 1
CH3
(a) HO r + R — CH 2 — I ¾® (p) 1
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
(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
Br
H3C
CH3
(b)
NO2
NO2
NO2
(a) Br (p) 0
alc. KOH
¾ ¾ ¾¾®
D
Br
(c) Br (r) S N 2 reaction
aq. KOH
¾¾¾
¾®
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
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
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
CH3—Li(excess)
O CH3 O
+
(1) Al(Mg) H (1) CH3MgBr
C—CH3 K C— C — CH3 L
(1) CH3MgBr
(2) H+
M
O+ P N Q+R
(2) H+
309
310 Elementary Organic Chemistry
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
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
NO2 CH3
3.
1.
2.
3.
4.
5.
6.
7.
8.
9.
11.
12.
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
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:
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
Br OH MgBr
Br Br
(E) (F) (G) (H)
CH3 OH CH3 OH O
(L) (M) (N) (O)
D
OD
(S) (T) D Cl (U) D D
O
COOEt
(V) (W) CH2—C—OH
COOEt
O O
(Z) CH2—NH2+CO2
2.
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
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
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)
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.
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
, (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
Cl Cl
(a) + enantiomer (b) Cl
Cl
(c) + (d) optically active
Br
(c) (d) +
4. Which is not a likely product formed when the following alcohol is treated with sulfuric acid?
OH
OH H HO
(a) (b) (c) (d)
OH HO OH OH
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
10. What is the major product of the following reaction?
4 2 NaBH , H O
O ¾¾¾¾¾¾® ?
(a) O (b) OH
+ enantiomer
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
16. What is the major product of the following reaction?
O
1. NaBH4, MeOH
2. Dilute acid, heat
O OH ¾¾¾¾¾¾¾® ?
O
O
O O
(a) OH (b) (c) (d)
O O O CN OH
Cl
(a) NC (b) (c) (d)
CN
OH
19. Identify which of the compound having 2° alcohol ?
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
CH2—OH H
r
27. ¾¾® (A) ; Product (A) is:
D
CH2—OH
H+
28. ¾® (A) ; Product ( A) is:
¾¾
D
CH3
CH3
Conc. H SO
2 4
30. In the given reaction ¾ ¾¾¾¾ ® A. The product A is:
OH
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Alcohols, Phenols and Ethers 331
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
32. Which of the following alcohols is least reactive towards acid-catalysed dehydration?
OH OH OH
OH
OH
Hr
33. ¾ ¾®( A) ; Product (A) is:
D
Hr
34. ¾¾®( A); Product (A) is:
D
HO
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
(a) I (b) II (c) III (d) IV (e) V
38. Which of the following alcohols dehydrates most readily ?
OH
(I) CH3 OH (II)
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
CH3 OH
H2SO4
40. ? , Major product of the reaction is :
heat
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
(e) none of the above
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
OH
H+
50. ¾¾® A, major product A is:
D
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
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
O NH H2N NH
(a) (b)
O OH O O
(b) O (d)
NH2 H2N
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Alcohols, Phenols and Ethers 337
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)
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
OH OH
+ Al2O3
H (C) ; (D)
¾¾®
D
¾¾®
D
(A)
69. ¾¾® ; Reagent (A) is :
r s s
(a) H 3 O (b) H + D (c) HO (d) NH 2
[B] Phenols
1. What is the major product of the following reaction ?
OH
FeBr3
+Br2 ¾¾¾® ?
CH3
OH
OH
OCl Br
OH
(c) (d) (e)
CH3 CH3
CH3 Br
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
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
(a) i (b) ii (c) iii (d) iv (e) v
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
O
||
OH O—C— Me
CHO COOH
(a) (b)
OMe OH O
||
COOH C—OCH3
(c) (d)
OH NO2
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
CH3
OH OH
OH OH OH
OH
OH O O
CO2H
(a) ; C—O—C—CH3
OH OH O
CO2H
H
(b) ;
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:
[C] Ethers
1. O Ph ¾ ¾¾® A+B, So A and B would be:
dil. HI
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
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
I OH
OH OH
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
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
OH O
O O
HOs
22. CH 3 — O — CH 3 ¾ ¾¾® ; Product of the reaction is:
H 2O
r
3 H O
23. ¾¾¾® ; Product of the reaction is:
O OEt
, EtOH ,EtOH
(a) HO OH (b) HO O
CH3
s
(a) O + Br (b) Br + Os
(c) Os + OH (d) Os + Os
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
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)
CH3
Nitrating mixture
9. +CH 3 — C — Cl ¾® ( A) ¾ ¾¾¾¾¾
¾® ( B)
|| possible products
O
Answers
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
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
1. Structure of ( A) is:
OH OH
OH OH
2. Structure of ( B ) is:
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
2. Structure of ( B ) is:
Ph Ph Ph
Ph
(a) (b) (c) (d)
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
H H
(a) (b) H (c) (d)
H
OH O O O
(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®
O
(c) (d) O
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)
2. Structure of ( B ) is:
O O
3. Structure of (C ) is:
O O
O O
(b) O (q) 3
HI
¾¾®
O
(c) O (r) 5
HI
¾¾®
O
HI
(d) Et — O — Et ¾¾® (s) 6
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
O—CH2—CH3
r
H O
3
(d) O ¾¾¾® (s) CH 3OH
(b) OHs
NO2
AlCl3
(c) Cl (r) Carbocation intermediate
OH
(Y)
(d) Br (s) Free-radical
Br
2 NaI
¾¾® ¾¾¾® substitution
CCl4 Acetone, D
Br
(X) (Y)
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
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 (B) gas
(ii) Ph — C — OH + NaHCO 3 ¾®
Sum of molecular mass of A+B=?
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
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
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
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®
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
5HIO
35. CH 2 OH — CHOH — CHOH — CHOH — CHOH ¾ ¾¾4®
Aldopentose (glucose)
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
Cl
/ AlCl3
O
(f)
Br2/Fe Cl2/Fe HNO3 + conc. (e)
H2SO4 H2SO4
(a) (b) (c) (d) CH2CH2CH3
(H2/Ni)
(s) NH2
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
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
OH
+
(c) H P3
D
OH
+
(c) H P3
D
49. Sum of a-hydrogen in products ( P1 + P2 + P3 = ?)
OH
OH
+
(a)
+
(b) H P2
H P1 D
D
+
H P3
(c) D
OH
Answers
OH
CHO
(iv) , : CCl 2 , substitution
(ortho and para)
OH
CO2H
(v) , Carbocation, substitution
(ortho and para)
OH
Br Br
(vii) , Carbanion, substitution
Br
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
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
O
12. R — CH — CH — R + C 6 H 5 COOH
13.
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.
MeO – CH
H – COOH + CHO
O
37.
CHO
H–C
CH2OH
Acetaldialdehyde
MeO – CH
CHO
38. O
CHO
HC
CHO + HCHO + HCO2H
(v)
42.
Br Cl NO2 SO3 H
a= ; b= ; c= ; d=
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
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
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
(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
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
+
N N N N
(a) (b) (c) (d)
7. 1. LDA
¾¾¾¾¾® ? ; Product of the reaction is:
2. CH3CH2I
O O
O O
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
|| || || ||
(c) R — C — Cl (d) R — C — O — C — R (e) R — C — OH
11. Which of the following compounds is a hydrazone ?
CH3
NHNH2 N
CH3
(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
D O/DOs
2
¾ ¾¾¾
¾®
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
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
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
CH3 CH3
O O O
(a) (b) (c) (d) None of these
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
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
OH
C2H5 N—C2H5
(i) N (ii)
C2H5 C2H5
r
N—C2H5 N—C2H5 CH2CH3
(iii) (iv) (v)
C2H5 C2H5
CH2CH3 NCH2CH3
(i) (ii)
CH2CH3 OH
(iii) (iv) (v) NHCH2CH3
NHCH2CH3
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
NaOH
¾¾¾¾® ?
6. O Heat Product of the reaction is :
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
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)
O O
HO OH
|| ||
(iii)HOCH 2 CH 2 CH 2 CH (iv) OH (v) H — C — Os
HO
CH3
O
OH O
CH3 CH3
CH3 CH3 CH3
(iii) (iv) (v)
CH3
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
O O OH O O
OH
(a) (b) CH3 (c) (d)
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
|| ||
(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
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
2. What is the product of the following reaction?
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
|| || || ||
(c) R — C — Cl (d) R — C — O — C — R (e) R — C — OH
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
(a) i (b) ii (c) iii (d) iv (e) v
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
CH2CH2
(i)
HOOC COOH
CH2CH2O COOH
(ii)
HOOC
O O
CCH2CH2C
(iii)
O O
COCH2CH2OC
(iv)
O O
C—C OCH2CH2OH
(v)
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
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
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
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
3. What is the product of the following reaction?
O
O
2NaOH, H O
Cl O ¾¾¾¾¾¾® ?
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
(a) O (b) O
O
O
(c) O (d)
O
8. What is the major product of the following reaction ?
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 O
|| ||
(a) C — CH 3 (b) C — OH
(c) C (d) C — CH 2 CH 3
||
O O
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
NO2
Decarboxylation
1. Which of the following compounds loses carbon dioxide upon heating to 100°C?
OH OH OH OH
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
3. What is the product of the following reaction?
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
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
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
(a) i (b) ii (c) iii (d) iv (e) v
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
(c) (d)
CO2H
HO CO2H
O
Answers
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)
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)
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
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
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)
O O O
|| ||
KOH ( aq.)
23. CH 3 — C — CH 2 — CH 2 — CH 2 — C — CH 3 ¾ ¾ ¾¾®
D
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
(a) (b) (c) (d) None of these
Answers
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)
Passage-3:
O
1. HCN ||
AlCl3 dil. KOH 2. H3O+ Ph
A + B ¾¾® C + HCHO ¾¾¾® D ¾¾¾® O (Lactone)
3. D HO
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:
CHO
O
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.
(a) (b)
(c) (d)
2. Structure of Q is:
O
(a) H (b) O
Ph
H O
(c) (d)
H
3. Structure of ' S' is:
O
O OH O H O
O H H
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.
1. Structure of ( A) is:
(a) O (b) O (c) OH (d) O
2. Structure of ( B ) is:
O OH
|| |
(a) (b) (c) EtOH (d) CH 3 — CHO
3. Structure of (C ) is:
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
Passage-9:
OH
H3 Or OH
KCN
( A) ¾¾® ( B) ¾¾®
O
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
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
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
OH
CH ==NH
(c) (d)
CH2—NH2
(c) (d)
N
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
O O
(a) (b) (c) (d)
O O O
H OH
(a) (b) (c) (d)
Passage-14:
O conc. KOH
CH == CH 2 ¾¾3® ( A) + ( B) ¾ ¾¾¾¾® (C ) + ( D )
Zn D
1. Structure of (C ) is:
(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
1. Structure of ( A) is:
O O
OH OH
(a) (b)
O O
O
O
2. Structure of ( B ) is:
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
1. Structure of ( A) is:
(a) (b) (c) (d) (a) and (b) both
2. Structure of ( B ) is:
O O O
O
(a) (b) (c) (d)
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
(c) (r) Isomer of But-2-en-l-ol
O
Electrophilic addition
(b) CH3 (1) LiAlH4 (q)
¾¾¾¾®
+
(2) H
reaction
r
H3O
¾¾¾® Formation of 3° alcohol take
(c) (r)
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
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
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
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
7.
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
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
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
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
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
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)
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
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:
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)
O
X X
X X
(a) (b) (c) (d)
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
··
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)
CH2—NH2
HNO
2
36. ¾¾®(A) ; Product (A) is :
OH OH
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
OH
2 HNO
39. (A) ¾¾® ; Structure of (A) is:
NH—CH3 NH2 N
40. Which of the following compound will not undergo amine inversion?
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
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:
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
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
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
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
O O
Passage-2:
HNO2 H2SO4
(A) (B) D
(C)
(major) (major)
HBr
Br
1. Compound (A) is:
NH NH NH2
(a) NH2 (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
Passage-4:
NHCH3
CH3
1. Structure of ( A) is:
O NH O NH—CH3 O NH2
2
(a)
(c)
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
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®
(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
(s) NH2
Answers
Comprehension Based Problems:
Passage-1: 1. (b) 2. (a) 3. (d)
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
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
OH
OH H2N
(c) H2N (d) O
+
O H
OH
CH2
NH2
NH
C ==NH
NH2
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
H CH2OH
OH O OH O
(c) CH2OH (d) H
H OH OH H H OH
H H
OH H OH OH
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
H OH
H OH
3 HNO
H OH ¾¾¾®
H OH
CH2OH
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
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
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
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
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
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
HO OH
H OH
H H
(a) a ketohexose (b) an aldohexose (c) an a-furanose (d) an a-pyranose
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
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
OH
HOCH2 O HOCH2 O OH
(iv) (v)
HO OCH3 HO OCH3
OH OH
CH2OH CH2OH
HOCH2 O OH OH O OH OH O OCH3
OH OH OH OH OH
(a) i (b) ii (c) iii (d) iv (e) v
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
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
119. What is the major organic product of the following reaction ?
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
—
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
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)
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
HO H OH OH
H OH
HO
CH2OH
OH O O
OH
(c) H (d)
HO OH
HO OCH3
OH OCH3
Answers
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
HC—OH
C—OH
HO H
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
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
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
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.
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 ?
HC==O HC==O
H OH HO H
H OH H OH
CH2OH CH2OH
D-erythrose D-threose
Answers
3 CH2C6H5
1 4
3. H2N—–CH—–CONH—–CH—–COO CH3
2
CH2—–COOH
Aspartamine
—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
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
8
Polymers
F F F F F F
F F
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
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
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
O O
O O
O O
(a) Polyester (b) Polycarbonate
(c)Polyurethane (d) Polyamide
O N N O
H H
(a) Polyester (b) Polycarbonate
(c) Polyurethane (d) Polyamide
10. To which functional group class does the following polymer belong?
O
O O
O
O
O O
O
(a) Polyester (b) Polycarbonate
(c) Polyurethane (d) Polyamide
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)
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 ?
CH3 CH3
CH3 CH3
CH3 CH2BF2
r s
(iv) BF + CH2 == CH ¾¾® CH2CHBF3
3
CH3 CH3
s r
(v) BF3 + CH2 == CH ¾¾® F3BCH2CH
CH3 CH3
(a) i (b) ii (c) iii (d) iv (e) v
40. Which of the following is more likely to undergo both radical and cationic polymerization ?
CH == CH2
(i) CH 2 == CH 2 (ii)
OCH3 NH2
CH == CH2 CH == CH2
(iv) (v)
CH3 O2N
CH == CH2 CH == CH2
(ii) (iii)
OCH3 NH2
CH == CH2 CH == CH2
(iv) (v)
CH3 O2N
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
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
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
Answers
1. (c, d) 2. (c, d)
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
Answers
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
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
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)
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 ?
(V) CººCCH2CH2CH2OH
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
(a) i > ii > iii (b) i > iii > ii (c) ii >i > iii (d) iii > ii > i
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508 Elementary Organic Chemistry
22. f CH3
Et
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
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
O
1. MgBr
(i) CH3CH2C—OCH3 ¾¾¾¾¾®
r 2. H3O
O
1. MgBr
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
Cl O OH
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
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.
1. PhMgBr + 2-propanol
2. PhMgBr + Ph — CH 2 — OH
3. PhMgBr + CH 3 — SH
4. PhMgBr + CH 3 — C ºº CH ¾®
6. PhMgBr +
O
7. ||
PhMgBr + Ph — C — Ph ¾®
PhMgBr + CHO
8.
9.
PhMgBr +
CHO
10. PhMgBr +
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
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
NH2
OCH3
OH
O O
OEt HS O
(a) (b)
Cl
Cl
O
O O–C–O–Ph
O O
Answers
Unified Conceptual Problems:
1.
OH
OH Ph Ph OH
(5) (6) (7) (8)
Ph Ph Ph Ph
OH
OH CH3 OH
Ph
(9) (10) (11) (12)
(13) HO
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Grignard Reaction 519
H OH
H OH
3. (a)
Ph HO
r1 > r2 > r3
H OH
(b) CH 3 CH 2 OH , r1 > r2
H OH
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
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
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
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522 Elementary Organic Chemistry
Miscellaneous Problems
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
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
C
CH
COs
2
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)
OH O
S—O—H
(c) (d)
O
NO2
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)
Miscellaneous Problems
1. (c) 2. (b) 3. (b) 4. (b) 5. (b) 6. (d) 7. (d) 8. (a)
Answers
1. (b, c, d)
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
7. Select the correct statement:
(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
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)
2. H2N S—NHR
O
Above drug is an example of :
(a) sulpha drug (b) sulphonamide (c) analgesic (d) tranquilizer
3. Select the correct statement:
(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)