01 STRUCTURAL ISOMERISM

IUPAC Nomenclature
&
Structural Isomerism
Contents
Topic Page No.
Theory 01 - 07
Exercise - 1 08 - 23
Answer Key 32 - 33
Syllabus
Hybridisation of carbon; Sigma and pi-bonds; Shapes of simple organic molecules
& structural isomerism, IUPAC nomenclature of simple organic compounds (only
hydrocarbons, mono-functional and bi-functional compounds);
Name : ____________________________ Contact No. __________________

IUPAC NOMENCLATURE & STRUCTURAL ISOMERISM
KEY CONCEPTS
Classification of organic compounds
IUPAC Nomenclature :
Groups :
Atom or a group of atoms which possess any 'charge' on it or any 'free valency' are called as Groups.
Alkyl group : When a hydrogen is removed from saturated hydrocarbon then alkyl group is formed. It is
represented by R & its general formula is CnH2n + 1. A bond is vacant on alkyl group on which any functional
group may come.
CH4  H CH3 – Methyl
CH3 – CH3 

H CH3 – CH2 – Ethyl
(a) C3H7 has following two isomers
(i) Normal propyl CH3–CH2–CH2–
(ii) Isopropyl (1-methyl ethyl) CH3–CH–
CH3
(b) C4H9 has following four structures :
(i) n-butyl H3C–CH2–CH2–CH2–
(ii) Iso butyl (2-methyl propyl) CH3–CH–CH2–

CH3
Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota IUPAC NOMENCLATURE AND
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
STRUCTURAL ISOMERISM
#1
B.Tech. IIT Delhi M.Sc. IT-BHU
(iii) Secondary butyl (1-methyl propyl) CH3–CH2–CH–
CH3
CH3
(iv) Tertiary butyl (1,1-dimethyl ethyl) CH3–C–
CH3
Alkenyl group :
CH2 = CH – Ethenyl
CH2 = CH – CH2 – Propenyal
CH3 – CH = CH – Propenyl(1-propenyl)
CH3–C=CH2 Isopropenyl (1-methyl-1-ethenyl)

C
Alkynyl group :
CH  C– Ethynyl
Retained Name :
Normal group :
(a) It is represented by 'n'.
(b) Straight chain of carbon atom is known as normal group.
(c) Free bond will come either on 1st carbon atom or on last carbon atom.
n-butyl C–C–C–C–
n-propyl C–C–C–
Iso group :
It is represented by following structure C–C–
C
Neo group :
(a) When two methyl group are attached to second last carbon atom group is named as neo group.
(b) It is represented by following structure -
For eg. Neo pentyl

#2
ALLOTMENT OF IUPAC NOMENCLATURE
Table : The Word Root of Unbranched Alkanes
Number of
Name
Carbon Atoms
1 Methane
2 Ethane
3 Propane
4 Butane
5 Pentane
6 Hexane
7 Heptane
8 Octane
9 Nonane
10 Decane
11 Undecane
12 Dodecane
13 Tridecane
14 Tetradecane
15 Pentadecane
16 Hexadecane
17 Heptadecane
18 Octadecane
19 Nonadecane
20 Eicosane
21 Heneicosane
22 Docosane
23 Tricosane
30 Triacontane
31 Hentriacontane
40 Tetracontane
50 Pentacontane
60 Hexacontane
70 Heptacontane
80 Octacontane
90 Nonacontane
100 Centane or Hectane

#3
Rules for Naming the compound having poly functional groups : -
If any organic compound possess more than one functional group, then functional group of highest priority
is taken in longest chain along with maximum number of substituents. The priority order of the final groups
is as under
Table : Functional Groups in decreasing order of seniority
Class Name Suffix Prefix

– ammonium (R4N+) ammonio –
1. Cations ------------------- – phosphonium (R4P+) phosphonio –
– sulphonium (R3S+) sulphonio –
2. R – COOH Alkanoic Acid – oic Acid (carboxylic acid) Carboxy
3. R – SO3H Alkane sulphonic Acid – sulphonic Acid sulpho
4. R–C–O–C–R Alkanoic Anhydride – anhydride ------------

|| ||
O O
5. R – COOR Alkyl Alkanoate – alkanoate (carboxylate) Alkoxy carbonyl
6. R–C–X
Alkanoyl halide – oyl halide (carbonyl halide) halo carbonyl
||
O
7. R – C – NH2
Alkanamide – amide (carboxamide) Carbamoyl
||
O
8. Alkanenitrile – nitrile (carbonitrile) cyano

R–CN
9. R–C–H
Alkanal – al (carbaldehyde) formyl
||
O
10. R – C – R Alkanone – one Oxo / Keto

||
O
11. R – OH Alkanol hydroxy

– ol
12. R – SH Alkanethiol – thiol mercapto
13. R – NH2 Alkanamine – amine amino
Isomerism
Organic compounds having same molecular formula but differing from each other at least in some physical or
chemical properties or both are known as isomers (Berzelius) and the phenomenon is known as isomerism.
The difference in properties of isomers is due to the difference in the relative arrangements of various atoms
or groups present in their molecules. Isomerism can be classified as follows:

#4
Constitutional or structural isomerism
(1) Chain, nuclear or skeleton isomerism : This type of isomerism arises due to the difference in the nature
of the carbon chain (i.e., straight or branched) which forms the nucleus of the molecule.
Examples :
(i) C4 H1 0 : CH3  CH 2  CH2  CH3 , CH3  CH  CH3

n Butane |
CH3
Isobutane
CH3
|
(ii) C5 H12 : (Three) CH3  CH2  CH2  CH2  CH3 , CH3  CH  CH2  CH3 , CH3  C  CH3
| |
n Pentane
CH3 CH3
Isope ntane
Neop entane
 Except alkynes chain isomerism is observed when the number of carbon atoms is four or more than four.
 Chain isomers differ in the nature of carbon chain, i.e., in the length of carbon chain.
 The isomers showing chain isomerism belong to the same homologous series, i.e., functional group,
class of the compound (Cyclic or open) remains unchanged.
 Chain and position isomerism cannot be possible together between two isomeric compounds. If two
compounds are chain isomers then these two will not be positional isomers.
(2) Position isomerism : It is due to the difference in the position of the substituent atom or group or an
unsaturated linkage in the same carbon chain.
C 3 H6 Cl2 : CH3  CCl2  CH3 , CH3  CH2  CHCl2 , CH3  CH  CH 2 , CH2  CH2  CH2
2,2 Dichloro propane, 1,1Dichloro prop ane | | | |
(gemdihalide ) (gemdiha lide) Cl Cl Cl Cl
1,2 Dichloro propane 1,3 Dichloro propane
(, -dihali de)
(Vicdih alid e)
 Aldehydes, carboxylic acids (and their derivatives) and cyanides do not show position isomerism.
 Monosubstituted alicylic compounds and aromatic compounds do not show position isomerism.
 Structural isomers which differ in the position of the functional group are called regiomers.
For example, (i) CH3  CH2  CH2  OH (ii) CH3  CH CH3
|
OH

#5
(3) Functional isomerism : This type of isomerism is due to difference in the nature of functional group
present in the isomers. The following pairs of compounds always form functional isomers with each other.
Examples :
(i) Alcohols and ethers (Cn H2 n+2O)
C2 H6 O : CH3  CH2  OH ; H3 C  O  CH3
Ethyl alcoho l Dimethyl ether
C3 H8 O : CH3  CH2  CH 2  OH ; C2H5  O  CH3

n  p ropyl alcoh ol Ethyl methyl ether
C4 H1 0O : CH3  CH2  CH2  CH2  OH ; C2H5  O  C 2H5

nButyl alcohol Diethyl ether
(ii) Aldehydes, ketones an d unsaturated alcohols …etc. (Cn H2n O)

O
||
C3 H6 O : CH3  CH2  CHO ; CH3  C  CH3 ; CH2  CH CH3 ; CH2  CH  CH2OH
Propi onal dehyde Acetone Allyl alcohol
O
1,2 Epoxy propa ne
(iii) Acids, esters and hydroxy carbonyl compounds …etc. (Cn H2 n O2)
C2 H4 O2 : CH3 COOH ; HCOOCH3
Acetic a cid Methyl forma te
O
||
C3 H6 O2 : CH3  CH2  COOH ; CH3 COOCH3 ; H3C CH CHO ; CH3  C CH2  OH
Prop ionic a cid Methyl a cetate 1 Hydroxy propan-2-o ne
OH
2-Hydroxypr opanal
(iv) Alkynes and alkadienes (C n H2n-2 )

C4 H6 : CH3  CH2  C  CH ; H2 C  CH  CH  CH2 ; CH3  C  C  CH3 ; H2C  C  CH  CH3
1 Butyn e 1,3  Butadien e 2 Bu tyne 1,2 Butadie ne
(v) Nitro alkanes and alkyl nitrites (  NO2 and  O  N  O )
O
C2 H5 NO2 : C2H5  N ; C2H5  O  N  O
Ethyl ni trite
O
Nitro ethane
(vi) Amines (Primary, secondary and tertiary)

H CH3
C3 H9 N : CH3  CH2  CH2  NH2 ; CH3  CH2  N ; CH3  CH  CH3 ; CH3  CH2  N
Propan -1- amine |
CH3 NH2 CH3
NMethyl ethan amine Propan -2 - amine N,N Dimethyl methan amine
(vii) Alcohols and phenols

CH2 OH OH
CH3
C7 H8 O :
Benzyl alcohol o-Cresol

(viii) Oximes and amides
O
||
C2 H5 NO : CH3  CH  NOH ; CH3  C NH2
Acetald oxime Aceta mide

#6
(4) Ring-chain isomerism : This type of isomerism is due to different modes of linking of carbon atoms, i.e.,
the isomers possess either open chain or closed chain sturctures.
C
H2
H2C CH 2 H 2C CH2
C6H 12 : CHCH3 ; CH CH CH CH CH  CH
H2C CH 2 ; 3 2 2 2 2
1 He xene
H 2C CH2
C Met hylcyclopentane
H2
Cyclohexane
 Ring – chain isomers are always functional isomers.

(5) Metamerism : This type of isomerism is due to the difference in the nature of alkyl groups attached to the
polyvalent atoms or functional group. Metamers always belong to the same homologous series.
Compounds like ethers, thio-ethers ketones, secondary amines, etc. show metamerism.
CH3 C 2H5
(i) C5 H13 N : C3H7  N ; C2H5  N
CH3 CH3
Dimethyl propyl amine Diethyl methyl amine
(ii) C6 H15N : C3H7  NH  C3H7 ; C2H5  NH  C 4H9

Dipropyl amine Butyl ethyl amine
 If same polyvalent functional group is there in two or more organic compounds, then chain or position
isomerism is not possible, there will be metamerism e.g.,
(a) CH3  C CH2  CH2  CH3 ; CH3 CH2  C CH2 CH3 are metamers and not position isomers.
| | ||
O O
(Pe n tan  2  one ) (Pen tan  3  on e)
(b) CH3  C CH2CH2CH3 ; CH3  C  CH  CH3 are metamers and not chain isomers.
|| || |
O O CH3
(Pentan 2 one) (3-Methylbutan-2-one)
Note : Alkenes donot show metamerism.

#7
PART - I : OBJECTIVE QUESTIONS
* Marked Questions are having more than one correct option.
Section (A) : Fundamental of Organic Chemistry

A-1. In homologous series :
(A) Molecular formula is same (B) Structural formula is same
(C) Physical properties are same (D) General formula is same
A-2. How many secondary carbon atoms does methyl cyclopropane have?
(A) None (B) One (C) Two (D) Three
A-3. Which of the following is the first member of ester homologous series ?
(A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D)Ethyl methanoate
A-4. How many carbons are in simplest alkyne having two side chains ?
(A) 5 (B) 6 (C) 7 (D) 8
A-5. How many 1º carbon atom will be present in a simplest hydrocarbon having two 3º & one 2º carbon atom?
(A) 3 (B) 4 (C) 5 (D) 6
A-6.* The pair of compounds having the same general formula :
(A) and (B) and
(C) and (D) and H–CC–CC–H
A-7. (a) and (b)
True statement for the above compounds is:

(A) (A) is phenol while (B) is alcohol (B) Both (A) and (B) are primary alcohol
(C) (A) is primary and (B) is secondary alcohol (D) (A) is secondary and (B) is primary alcohol
A-8. The total number of secondary H-atoms in the structure given below are :
(CH3)2CHCH2C2H5
(A) 1 (B) 4 (C) 3 (D) 2
A-9. Which of the following is the triad of a homologous series -

(A) CH3NH2, (CH3)2NH, (CH3)3 N (B) C2H5OH, (CH3)2CHOH, (CH3)3COH
(C) Both the above (D) CH2 = CH2, CH3 – CH = CH2, C2H5 – CH = CH2
A-10. The homologue of phenol is -

CH2OH OH OH OH
CH3 OH
(A) (B) (C) (D)

#8
A-11. What is not true about homologous series ?
(A) All the members have similar chemical properties
(B) They have identical physical properties
(C) They can be represented by a general formula
(D) Adjacent members differ in molecular mass by 14
A-12. An organic compound has molecular formula C9H18. It is a saturated hydrocarbon and its all hydrogen
atoms are identical. Its structural formula can be :
(A) (B)
(C) (D)
Section (B) : Classification and General Rules of IUPAC Nomenclature
B-1. C4H6O2 does not represent:

(A) A diketone (B) A compound with two aldehyde
(C) An alkenoic acid (D) An alkanoic acid
B-2. As per IUPAC rules, which one of the following groups, will be regarded as the principal functional group?
(A) –CC– (B) –OH (C)  C  (D)  C  H

|| ||
O O
B-3. The group of hetrocylic compounds is:
(A) Phenol, Furane (B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane, Aniline
B-4. Which of the following is a heterocyclic compound
HC  CH HC  COOH HC  CH HC  CH
(A) | (B) | (C) | (D) |
HC  CH HC  COOH HC  CH HC  CH
B-5. The number of sigma and pi-bonds in 1-butene 3-yne are:

(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi (C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
B-6. Which is an acyclic compound :

(A) Methane (B) Benzene (C) Pyrrole (D) Cyclobutane
B-7. Which of the following is not an alicyclic compound ?
(A) (B) (C) (D)

#9
B-8. Which of the following has not bridgehead carbon :
(A) (B) (C) (D)
B-9. Which of the following compounds is unsaturated hydrocarbon.
(A) (B) CH3–CN (C) (D)
Section (C) : IUPAC-Nomenclature of Alkane

C-1. The compound which has one isopropyl group is:
(A) 2,2,3,3-tetramethyl pentane (B) 2,2-dimethyl pentane
(C) 2,2,3-trimethyl pentane (D) 2-methyl pentane
C-2. The IUPAC name of the compound Br(Cl) IC. CF3 is:
(A) 2-bromo-2-chloro-2-iodo1,1,1-trifluoroethane
(B) 1,1,1-trifluoro-2-bromo-2-chloro-2-iodo ethane
(C) 2-bromo-2-chloro-1,1,1-trifluoro-2-iodo ethane
(D) 1-bromo-1-chloro-1-iodo-2,2,2-trifloro ethane
C-3. The IUPAC name of the following structure is [CH3CH(CH3)]2 C(CH2CH3)C(CH3) C(CH2CH3)2
(A) 3,5-diethyl-4,6-dimethyl-5-[1-methylethyl]-3-heptene
(B) 3,5-diethyl-5-isopropyl-4,6-dimethyl-2-heptene
(C) 3,5-diethyl-5-propyl-4,6-dimethyl-3-heptene
(D) None of these
F Cl
C-4. The IUPAC name of this compound is : | |
CH3  C  CH2  C  CH3
(A) 2-fluoro-4-chloro-2,4-diethyl pentane
| |
(B) 3-fluoro-5-chloro-3-methyl-5-ethyl hexane CH 2 CH 3 CH 2CH3
(C) 3-chloro-5-fluoro-3,5-dimethyl heptane

(D) 3,5-dimethyl-5-fluoro-3-chloro heptane
C-5. The IUPAC name of is -
(A) 2-bromo-4-isopropylpentane (B) 2, 3-dimethyl-5-bromohexane

(C) 2-bromo-4, 5-dimethylhexane (D) 5-bromo-2, 3-dimethylhexane
C-6. Give the IUPAC name of
CH3
|
H3 C  C  CH3
|
CH3  CH2  CH2  CH  CH  CH2  CH2  CH3
|
H3 C  CH
|
CH3
(A) 4-isopropyl-5-ter. butyl octane (B) 4-ter. butyl-5-isopropyl octane
(C) 2-methyl-3-propyl-4-ter. butyl heptane (D) 2, 2-dimethyl-3-propyl-4-isopropyl heptane
C-7. Which alkane would have only the primary and tertiary carbon ?
(A) Pentane (B) 2-Methylbutane
(C) 2, 2-Dimethylpropane (D) 2, 3-Dimethylbutane
C-8. In the structure of 4-Isopropyl-2, 4, 5-trimethylheptane, number of 1°, 2° & 3° H's are respectively :
(A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4

# 10
Section (D) : IUPAC-Nomenclature of Alkene & Alkyne
D-1. The IUPAC name of the compound having the formula is:
CH 3
|
H 3C  C  CH  CH 2
|
CH 3
(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene
(C) 3,3-dimethyl-1-butene (D) 2,2-dimethyl-3-butene
D-2. The IUPAC name of the compound CH2=CH–CH(CH3)2 is:

(A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene
(C) 2-vinyl propane (D) None of the above
D-3. The correct IUPAC name of the compound :
(A) 5-ethyl-3, 6-dimethyl non-3-ene (B) 5-ethyl-4, 7-dimethyl non-3-ene

(C) 4-methyl-5, 7-diethyl oct-2-ene (D) 2,4-ethyl-5-methyl oct-2-ene
D-4. The correct IUPAC name of :
CH3 – C  C – CH3
| |
C2H5 C2H5
(A) 1, 2-diethyl butane (B) 2-ethyl 3-methylpentane

(C) 3, 4-dimethyl-3-hexene (D) none is correct
D-5. The IUPAC name of the compound CH3CH = CHCH=CHCCCH3 is:

(A) 4,6-octadiene-2-yne (B) 2,4-octadiene-6-yne
(C) 2-octyn-4,6-diene (D) 6-octyn-2,4-diene
D-6. The correct IUPAC name of 2-ethyl-3-pentyne is:

(A) 3-methyl hexyne-4 (B) 4-ethyl pentyne-2 (C) 4-methyl hexyne-2 (D) None of these
D-7. The molecular formula of the first member of the family of alkenynes and its name is given by the set
(A) C3H2, alkene (B) C5H6, 1-penten-3-yne
(C) C6H8, 1-hexen-5-yne (D) C4H4, butenyne
D-8. The IUPAC name of is -
(A) 2-ethyl-3-methyl-1-penten-4-yne (B) 2-ethyl-3-methyl-4-pentyn-1-ene

(C) 4-ethyl-3-methyl-1-pentyn-4-ene (D) 4-ethyl-3-ethyl-4-penten-1-yne
D-9. The IUPAC name of
CH  CH3
||
HC  C  C  C  C  CH2  CH3 is :
(A) 5-ethyl- 5-heptene-1, 3- diyne (B) 3-ethyl- 2-heptene-4, 6- diyne
(C) 5-ethenyl-1, 3- heptatriyne (D) 3-ethenyl-4, 6-heptatriyne

# 11
D-10.
The IUPAC name of the above structure is :

(A) 2, 4, 5 - Triethyl-3-nonene (B) 5, 6 - Diethyl -3- methyl -4-decene
(C) 2, 4, 5 - Triethyl -3- octene (D) 3 - Heptyl - 5- methyl-3- heptene
D-11. IUPAC name of the compound is :
(A) 3-Ethyl-4-chloropenta-1, 4-diene (B) 2-Chloro-3-ethylpenta-1, 4-diene

(C) 4-Chloroethenylpent-1-ene (D) 3-Ethenyl-4-chloropent-4-ene
Section (E) : IUPAC-Nomenclature of Cyclic Compounds
E-1. The IUPAC name of the compound is -
(A) 1-chloro-2-bromocylohexane (B) 1, 2-bromochlorocyclohexane

(C) 4-bromo-3-chlorocyclohexane (D) 1-bromo-2-chlorocyclohexane
E-2. The IUPAC name of the given compound
is -
(A) Octylcyclopentane (B) 3-cyclopentyloctane

(C) cyclopentaneoctane (D) 6-cyclopentyloctane
E-3. The IUPAC name of CH  CH  CHCH 2CH 3 is:

|
CH 3
(A) 1-cyclohexyl-3-methyl-1-pentene (B) 3-methyl-5-cyclohexyl-pent-ene
(C) 1-cyclohexyl-3-ethyl-but-1-ene (D) 1-cyclohexyl-3,4-dimethyl-but-1-ene
E-4. The correct IUPAC name for the compound
C2H5
CH3
is -
(A) 6-Ethyl-1-methylcyclohex-1-ene (B) 3-Ethyl-2-methylcyclohex-1-ene

(C) 1-Ethyl-2-methylcyclohex-2-ene (D) 2-Ethyl-1-methylcyclohex-1-ene
E-5. The name of the compound is -
(A) bicyclo [2.2.1] octane (B) bicyclo [1.1.1] octane

(C) 1, 4-bismethylenecyclohexane (D) bicyclo [2.2.2] octane

# 12
E-6. Which of the following structures represents bicyclo [3.2.0] heptane -
(A) (B) (C) (D)
E-7. The IUPAC name of compound is -
(A) Bicyclo [2.2.1] hept-2-ene (B) Bicyclo [2.2.1] hept-5-ene

(C) Bicyclo [2.1.2] hept-2-ene (D) Bicyclo [1.2.2] hept-2-ene
E-8. The IUPAC name of compound is -
(A) Spiro [5.3] nonane (B) Spiro [3.5] nonane (C) Spiro [5.4] nonane (D) Spiro [4.5] nonane
E-9. The IUPAC name of is -
(A) 3-cyclopropyl-3-ethyl-2-propene (B) 1-cyclopropyl-1-ethylpropene

(C) 3-cyclopropyl-2-pentene (D) (1-ethyl-1-propenyl) cyclopropane
E-10. The IUPAC name of is -
(A) 3-cyclobutylcyclopropane (B) 1-cyclopropyl-3-methylcyclobutane

(C) 1, 3-cyclopropylmethylcyclobutane (D) 2-methylbicyclo [4.3.0] heptane
E-11. IUPAC name for is :
(A) Sec-butyl cyclobutane (B) 2-(n-butyl)cyclobutane

(C) 2-Cyclobutylbutane (D) 1-Cyclobutylbutane
E-12. The correct IUPAC name of is :
(A) 1, 4-Diethyl-2-methyl-5-propylcyclohexane (B) 1, 4-Diethyl-5-methyl-2-propylcyclohexane

(C) 2, 5-Diethyl-1-methyl-4-propylcyclohexane (D) 2, 5-Diethyl-4-methyl-1-propylcyclohexane

# 13
E-13. The correct IUPAC name of the compound
(A) 1-Ethenylcyclohexa (B) 5-Ethenylcyclohexa-1, 3-diene

(C) 6-Ethenylcyclohexa-1, 3-diene (D) Cyclohexa-2, 4-dienylethene
Section (F) : IUPAC-Nomenclature of Functional I groups
F-1. The IUPAC name of the compound CH 2  CH  CH 2 is:

| | |
OH OH OH
(A) 1,2,3-tri hydroxy propane (B) 3-hydroxy pentane-1,5-diol
(C) 1,2,3-hydroxy propane (D) Propane-1,2,3-triol
Ph
|
F-2. The IUPAC name of the compound is CH 3  CH  CH  NH 2
|
CH 3
(A) 1-amino-1-phenyl-2-methyl propane (B) 2-methyl-1-phenyl propane-1-amine

(C) 2-methyl-1-amino-1-phenyl propane (D) 1-isopropyl-1-phenyl methyl amine
F-3. The IUPAC name of the given compound is:
(A) 1,1-dimethyl-3-hydroxy cyclohexane (B) 3,3-dimethyl-1-hydroxy cyclohexane

(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1-dimethyl-3-cyclohexanol
F-4. The IUPAC name of acetyl acetone is:

(A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione
F-5. IUPAC name of is:
(A) 5-methyl hexanol (B) 2-methyl hexanol

(C) 2-methyl hex-3-enol (D) 4-methyl pent-2-en-1-ol
F-6. The IUPAC name of CH 3 CH 2  N  CH 2CH 3 is:

|
CH3
(A) N-methyl-N-ethylethylamine (B) diethyl methylamine
(C) N-ethyl-N-methyl ethanamine (D) methyl diethylamine
F-7. The IUPAC name of the compound:
(A) Propylene Oxide (B) 1,2-Oxo propane

(C) 1,2-Epoxy propane (D) 1,2-Propoxide

# 14
F-8. The IUPAC name of is
(A) 3-Methyl cyclobut-1-en-2-ol (B) 4-Methyl cyclobut-2-en-1-ol

(C) 4-Methyl cyclobut-1-en-3-ol (D) 2-Methyl cyclobut-3-en-1-ol
F-9. Ethyl methyl vinyl amine has the structure -
(A) CH3 CH2  N  CH2 CH  CH2 (B) CH3 CH2  N  CH  CH2

| |
CH3 CH3
(C) CH2  CH  N  CH  CH2 (D) CH3  N  CH  CH2

| |
CH3 CH3
F-10. The IUPAC name of is -

(A) 4-oxopentan-2-ol (B) 4-hydroxypentan-2-one
(C) pentane-4-ol-2-one (D) pentane-2-one-4-ol
F-11. All the following IUPAC names are correct except:

(A) 1-chloro-1-ethoxy propane (B) 1-amino-1-ethoxypropane
(C) 1-ethoxy-2-propanol (D) 1-ethoxy-1-propanamine
F-12. The IUPAC name of is -
(A) bicyclo [3.2.0] hexan-2-ol (B) spiro [3.2] hexan-1-ol

(C) spiro [3.2] hexan-4-ol (D) spiro [2.3] hexan-4-ol
F-13. The IUPAC name of camphor is -
(A) 6-oxo-1,2,2- trimethyl bicyclo [2,2,1] heptane (B) 1,7,7-trimethyl bicyclo [2,2,1] heptan-2-one
(C) 1,5,5-trimethyl bicyclo [2,1,1] hexan-2-one (D) 1,7,7-trimethyl bicyclo [2,1,2] heptan-2-one
Section (G) : IUPAC-Nomenclature of Functional groups
G-1. The correct IUPAC name of compound :

CH 3  CH 2  C  CH  CHO
|| |
O CN
(A) 2-cyano-3-oxopentanal (B) 2-formyl-3-oxopentanenitrile
(C) 2-cyano-1,3-pentanedione (D) 1,3-dioxo-2-cyanopentane

# 15
O CH 3
|| |
G-2. The IUPAC name of compound CH 3  C  CH  CH  CH  CH 3 is:
| |
CH 3 CHO
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal

(C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above
HO  C  O CH 3
| |
G-3. The IUPAC name of compound CH 3  C  C — C  H is:
| |
NH 2 Cl
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid (B) 3-amino-4-chloro-2-methyl-2-pentenoic acid

(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid (D) All of the above
G-4. The IUPAC name of the structure is:
H 2 N  CH  CH  CHO
| |
HOOC COOH
(A) 3-amino-2-formyl butane-1, 4-dioic acid (B) 3-amino-2, 3-dicarboxy propanal
(C) 2-amino-3-formyl butane-1, 4-dioic acid (D) 1-amino-2-formyl succinic acid
G-5. Which of the following compound is wrongly named?

(A) CH 3CH 2 CH 2 CHCOOH ; 2-Chloro pentanoic acid
|
Cl
(B) CH 3C  CCHCOOH ; 2-Methyl hex-3-enoic acid
|
CH 3
(C) CH3CH2CH=CHCOCH3 ; Hex-3-en-2-one
(D) CH 3  CHCH 2CH 2CHO ; 4-Methyl pentanal

|
CH 3
G-6. The IUPAC name of (C2H5)2 NCH 2 CH.COOH is:

|
Cl
(A) 2-chloro-4-N-ethylpentanoic acid (B) 2-chloro-3-(N,N-diethyl amino)-propanoic acid
(C) 2-chloro-2-oxo diethylamine (D) 2-chloro-2-carboxy-N-ethyl ethane
G-7. The correct IUPAC name of CH 3  CH 2  C  COOH is:

||
CH 2
(A) 2-methyl butanoic acid (B) 2-ethylprop-2-enoic acid
(C) 2-carboxybut-1-ene (D) None of the above

# 16
G-8. IUPAC name will be CH 2  CH  CH 2
| | |
CN CN CN
(A) 1,2,3-Tricyano propane (B) Propane trinitrile-1,2,3
(C) 1,2,3-cyano propane (D) Propane-1,2,3-tricarbonitrile
G-9. The IUPAC name of compound
(A) 1,2,3-tricarboxy-2-propanol (B) 2-hydroxy propane-1,2,3 tricarboxylic acid

(C) 3-hydroxy-3-Carboxy-1,5-pentane dioic acid (D) None
G-10. Which of the following is crotonic acid:

(A) CH2= CH–COOH (B) C6H5–CH=CH–COOH
(C) CH3–CH=CH–COOH (D) CH  COOH
||
CH  COOH
G-11. The IUPAC name of
CH2  CHO
|
OHC  CH2  CH2  CH  CH2  CHO is :
(A) 4, 4-di(formylmethyl) butanal (B) 2-(formylmethyl) butane-1, 4-dicarbaldehyde
(C) hexane-3-acetal-1, 6-dial (D) 3-(formylmethyl) hexane-1, 6-dial
G-12. is named as :
(A) 2, 3-Dimethylenebutanal (B) 2, 3-Dimethylbutanal

(C) 3-Methyl-2-methylenebut-3-enal (D) 2, 3-Dimethylenebutanone
Section (H) : IUPAC-Nomenclature of Functional groups
H-1. The IUPAC name of BrCH 2  CH  CO  CH 2  CH 2 CH 3 is:

|
CONH 2
(A) 2-bromomethyl-3-oxo hexanamide (B) 1-bromo-2-amino-3-oxo hexane
(C) 1-bromo-2-amino-n-propyl ketone (D) 3-bromo-2-propyl propanamide
H-2. One among the following is the correct IUPAC name of the compound
H
|
CH 3CH 2  N  CHO
(A) N-Formyl aminoethane (B) N-Ethyl formyl amine
(C) N-Ethyl methanamide (D) Ethylamino methanal

# 17
H-3. The IUPAC name of compound
H 3COOC  CH  COOCH 3
|
CH 2OH
(A) methyl 2-hydroxymethylpropandioate (B) Methyl methyl-2-hydroxypropandioate
(C) dimethyl-2-hydroxy methyl propandioate (D) 2-hydroxy methyl-dimethyl propandioate
H-4. The IUPAC name of is:
(A) 2-chlorocarbonyl ethylbenzoate (B) 2-carboxyethyl benzoyl chloride

(C) ethyl 2-(chlorocarbonyl) benzoate (D) ethyl 1-(chlorocarbonyl) benzoate
H-5. Structural formula of isopropyl methanoate is:
(A) CH 3  C  O  CH  CH 3 (B)
|| |
O CH 3
(C) CH3  C  O  CH 2  CH 2 (D) H  C  O  CH  CH 3
|| | || |
O CH 3 O CH 3
H-6. The IUPAC name of CH  C  O  CH 2  C  OH is:

|| ||
O O
(A) 1-acetoxy acetic acid (B) 2-acetoxy ethanoic acid
(C) 2-ethanoyl oxyacetic acid (D) 2-ethanoyloxyethanoic acid
H-7. The correct systematic name of the above compound is:

CH3  O  C  CH 2  COOH
||
O
(A) 2-acetoxy ethanoic acid (B) 2-methoxy carbonyl ethanoic acid
(C) 3-methoxy formyl ethanoic acid (D) 2-methoxy formyl acetic acid
H-8. The IUPAC name of the compound is :

(A) Propanoic anhydride (B) Dipropanoic anhydride
(C) Ethoxy propanoic acid (D) 1-Oxopropyl propanoate
H-9. The IUPAC name of the compound is :
(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride
(C) Cyclobutanedicarboxylic anhydride (D) Butanedioic anhydride
H-10. Ethyl ethanoyloxyethanoate is :
(A) (B) (C) (D)

# 18
H-11. The correct IUPAC name of the compound is :
(A) 1, 2, 3-Triaminobutane-1, 3-dione
(B) 2, 4-Diamino-3-oxobutanamide
(C) 1, 3-Dioxobutane-1, 2, 4-triamine
(D) 1, 3, 4-Triaminobutane-2, 4-dione
Section (I) : IUPAC-Nomenclature of Aromatic Compounds
I-1. The IUPAC name of is:
(A) 2-methoxy-4-nitro benzaldehyde (B) 4-nitro anisaldehyde

(C) 3-methoxy-4-formyl nitro benzene (D) 2-formyl-4-nitro anisole
I-2. The IUPAC name of C 6H5  CH  CH2  CCl3 is ;

|
C 6H5
(A) 1,1,1-trichloro-3,3-diphenyl propane (B) 1,1-diphenyl-3,3,3-trichloro propane
(C) both (A) and (B) (D) none of these
I-3. The IUPAC name of is -
(A) 1-amino-2-carboxybenzene (B) 2-amino-1-carboxybenzene

(C) 1-amino-2-benzenecaroxylic acid (D) 2-aminobenzenecarboxylic acid
I-4. IUPAC name of
(A) 4-Chlorophenyl benzoate (B) Phenyl 4-chlorobenzenecarboxylate

(C) Benzyl 4-chlorobenzenecarboxylate (D) 4-Chloro diphenylcarboxylate
I-5. The correct IUPAC name of the compound.
(A) N–Formyl-4-chlorobenzenamine (B) N–Formyl-4-chloroaniline

(C) N–(4-chlorophenyl)methanamide (D) N–(Parachlorophenyl)–N–formylaniline
Section (J) : Structural Isomerism
J-1. Esters are fiunctional isomers of:

(A) Hydroxy aldehyde (B) Ketone (C) Diketone (D) Diols
J-2. Which of the following is the first member of ester homologous series?
(A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D) Ethyl methanoate

# 19
J-3. & are called as –
(A) Position isomers (B) Chain isomers

(C) Function isomers (D) Ring chain isomers
J-4. Possible number of dichlorobenzene isomers is –

(A) 1 (B) 2 (C) 3 (D) 4
J-5. Functional isomer of CH3COOCH3 is –

(A) CH3CH2COOH (B) HOCH2—CH2CHO (C) Both of the above (D) None of the above
J-6. Propene and cyclopropane are –

(A) Chain isomers (B) Position isomers (C) Geometrical isomers (D) None of the above
J-7. Metamerism is shown by -

(A) Diethyl ether and n-propyl methyl ether (B) Ethyl alcohol and diethyl ether
(C) Acetone and propionaldehyde (D) Propionic acid and acetic acid
J-8. Which of the following pairs of compounds are not metamers ?

(A) CH3OCH2CH2CH3 and CH3CH2OCH2CH3
(B) CH3CH2OCH2CH3 and CH3OCH(CH3)2
(C) CH3NHCH2CH2CH3 and CH3CH2NHCH2CH3
(D) CH3NHCH2CH2CH3 and CH3NHCH(CH3)2
J-9. Which compound is not the isomer of 3-Ethyl-2-methylpentane ?
(A) (B) (C) (D)
J-10. What is the correct relationship between the following compounds ?
(A) Chain isomers (B) Position isomers (C) Functional isomers (D) Identical
J-11. Which one of the compound is not isomer of others ?
(A) (B) (C) (D)
J-12. Which of the given set of molecules have similar molecular formula :
(A) Nonane, 2-methylheptane (B) 3-Isopropylcyclopent-1-ene, 3-methylhexane
(C) 3-Methylcyclopent-1-ene, penta-1, 3-diene (D) Ethylcyclohexane, oct-2-ene
J-13. Molecular formula C4H10O represent :

(A) Two primary alcohol (B) One secondary alcohol
(C) One tertiary alcohol (D) All of these
J-14. Aldehydes show with each other :

(A) Chain isomers (B) Position isomers
(C) Functional isomers (D) Both (A) and (B)

# 20
J-15. Which of the following is not an isomer of 1-butyne ?
(A) but-2-yne (B) buta-1, 3-diene (C) but-2-ene (D) methyl cyclopropene
COOH
OCOH
J-16. & functional isomer
OMe OEt
Et
& metamers
Me
CH2 – CH2 – OH CH2 – O – CH3
& metamers
Me – N – Me CH2 – NH – CH3
& Functional isomers
(A) TFTF (B) FTTF (C) TTFT (D) TFFT
J-17. Which of the following is not the correct relationship
Me Me Me
Me Me
Me Me
O – Me O–Me
OH OH
I II III IV
(A) II & IV are metamer (B) I & II are functional isomer

(C) I & III are chain isomer (D) I and IV are positional isomer
J-18. Which of the following is not an isomer of compound CH3 – CH2CHO ?
(A) (B) (C) (D) CH2=CH–CH2–OH
Section (K) : Number of Structural Isomers

K-1. How many positional isoemrs are possible for dimethylcyclohexane :
(A) 3 (B) 4 (C) 5 (D) 6
K-2. How many positional isoemrs are possible for 3-ethylpentane (including it self)
(A) 1 (B) 2 (C) 3 (D) 4
K-3. The total number of unsaturated cyclic structure possible for a compound with the molecular formula C4H6
is:
(A) 3 (B) 4 (C) 5 (D) 6
K-4. Total number of 2° amine isomers of C4H11N would be (only structural) :

(A) 4 (B) 3 (C) 5 (D) 2

# 21
K-5. How many structural isomers of all the tertiary alcohols with molecular formula C6H14O.
(A) 2 (B) 3 (C) 4 (D) 5
K-6. The number of structural isomers for C5H10 is :

(A) 8 (B) 6 (C) 9 (D) 10
K-7. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9N
respectively:
(A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1
PART - II : MISCELLANEOUS QUESTIONS
Comprehensions Type :
Comprehension
The international group IUPAC has developed a detailed. system of nomenclature that we call the IUPAC
rule. Which are accepted throughout the world as the standard method for naming organic compounds. In
this system Alkyl groups are named by replacing the ‘-ane’ suffix of alkane name with ‘-yl’ like methyl ethyl
etc. complex alkyl groups are named. by a systematic method using the longest alkyl chain as the base
alkyl group. The base alkyl group is numbered beginning with the carbon atom bonded to the main chain.
The substitutes on the base alkyl group are listed with appropriate number and parentheses are used to
set off the name of the complex alkyl group.
1. Give the IUPAC name of following alkyl group
CH3
CH3 CH CH CH2
CH3
(A) (Di-isohexyl) (B) (2,3-dimethyl butyl) (C) (2,2-dimethyl butyl) (D) (2,-methyl-3-ethylbutyl)
CH2 CH CH2
2. Choose the correct IUPAC name of following alkyl group
OH CH3
(A) (2-methyl-3-Propanoyl) (B) (3-hydroxy-2-methyl propyl)
(C) (2-methyl-3-hydroxy propyl) (D) (1-hydroxy-2-methyl propyl
3. The structure of (2,2-dimethyl-3-ethylpentyl) group is -
CH3 CH3
(A) CH3 C CH CH2 CH2 (B) CH3 CH C CH2 CH2

CH3 C2H5 C2H5 CH3
CH3
(C) CH3 CH2 CH C CH2 (D) None of these

C2H5 CH3
4. (2-propenyl) group is -
(A) CH2=CH–CH2– (B) CH3–CH=CH–
(C) Both (A) and (B) (D) None of these

# 22
Assertion / Reasoning Type
DIRECTIONS :
Each question has 5 choices (A), (B), (C), (D) and (E) out of which ONLY ONE is correct.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
(E) Statement-1 and Statement-2 both are False.
H
5. Statement-1 : CN is called cyclohexanenitrile.
Statement-2 : : It contains six carbon atoms in the ring and CN as the functional group.
6. Statement-1 : The locant (2,8,7) is preferred over the locant (3,4,9).

Statement-2 : The first term, i.e., 2 in the first set is lower than the first term, i.e, 3 in the second set.
7. Statement-1 : The IUPAC name of CH3CH=CH–CCH is pent-3-en-1-yne and not pent-2-en-4-yne.

Statement-2 : While deciding the locants for double bond and triple bonds. lowest locant rule for multiple
bonds is followed.
8. Statement-1 : The IUPAC name for the compound C2H5 C CH2OH is -

CH2
2-ethylprop-2-en-1-ol.
Statement-2 : Ethyl (C2H5) rather than methylene (=CH2) is considered as the substituent group because
‘e’ of ethyl comes first in alphabetically order than ‘m’ of methylene.
9. Statement-1 : The IUPAC name for O is 7-oxabicyclo [4. 1. 0] heptane.
Statement-2 : The prefix oxo is used for the C=O group.

# 23
PART - I : MIXED OBJECTIVE
Br
|
1. The IUPAC name of CH3  CH  CH2  CH2  CH2  C  CH3 is
| |
OH Br
(A) 6, 6-Dibromo heptan-2-ol (B) 2, 2-Dibromo heptan-6-ol
(C) 6, 6-Dibromo heptan-2-al (D) None of these
2. IUPAC name of 4-Isopropyl m-xylene is :

(A) 1-Isopropyl 2, 4-dimethyl benzene (B) 4-Isopropyl-m-xylene
(C) 1-Isopropyl-3, 5-dimethyl benzene (D) 4-Isopropyl-3, 5-dimethyl benzene
3. The structure of 2-(3-oxobutyl)cyclohexanone is :
(A) (B)
(C) (D)
4. The compounds with molecular formula C100H202 can show

(A) Metamerism (B) Position and chain isomerism
(C) Functional isomerism (D) Ring-chain isomerism
5. How many primary amines are possible for the formula C8H11N (only Aromatic structural isomers)
(A) 4 (B) 6 (C) 7 (D) 14
6. The total number of aromatic isomeric ethers of molecular formula C8H10O is

(A) Six (B) Seven (C) Four (D) Five
7. How many structural isomers could be obtained from molecular formula C2FCl BrI
(A) Four (B) Five (C) Six (D) Three
8. Which type of isomerism is observed between I and II.
and
(A) Functional isomerism (B) Metamerism

(C) Optical isomerism (D) Geometrical isomerism
9. Which of the following compound does not have molecular formula C6H6
(A) Hexa-1, 3-dien-5-yne
(B) 3-(2-cyclopropenyl)cycloprop-1-ene(or Bicyclopropenyl)
(C) Cyclohexa-1, 3-diene-5-yne
(D) Cyclohexa-1, 3, 5-triene

# 24
10. IUPAC name of is
(A) 3, 5-Dimethylcyclohex-1-ene (B) 4, 6-Dimethylcyclohex-1-ene

(C) 1, 5-Dimethylcyclohex-2-ene (D) none of these
11. Which of the following are isomers
(A) I, II only (B) III, IV only (C) I, II, III (D) All
12. Total number of structurally different dichloropropanes is

(A) 2 (B) 3 (C) 4 (D) 5
13.* Consider the following structures :
CH3 Cl
CH3 – CH2 – CH2 – CH2 – Cl CH3 – C – CH3
– CH2 – Cl
Cl
I III IV
II
(A) I & II are chain isomers (B) I & III are functional isomers
(C) II & IV are functional isomers (D) III & IV are chain isomers
PART - II : SUBJECTIVE QUESTIONS
Allot the IUPAC name to the following compounds :
1. 2. 3.
4. 5. 6.
CH2 CH2
|| ||
7. 8. CH2=CH– C=CH–CH=CH2 9. CH3  C  C  C  C  CH3
|
Br
10. 11. 12. CH2 = CH – CH2 – N C

# 25
13. 14. 15.
16. CH3OCH2OCH2CH2OCH3 17. 18. CH3 – CH2 – O – C(CH3)3
19. 20. 21. CH3  O  CH2  CH2  N  CH3

|
H
22.
23. Identify the molecular weight of the compound ‘X’ containing carbon and hydrogen atoms only with 3 and
2 bonds in one molecule.
24. Find the hybridization state of each carbon atoms in following compound.
CH2 = C = CH – CH2 – C  C – CH2 – NH2
25. Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon atoms
only.
26. Which isomerism is shown by and
27. The ring chain functional isomer of compound But-2-ene are.
PART - I : IIT-JEE PROBLEMS (PREVIOUS YEARS)

1. Write IUPAC name of the following : [JEE-2002]
2. Which of the following represents the given mode of hybridisation, sp2 – sp2 – sp – sp, from left to right?
[JEE-2003]
(A) H2C = CH – C  CH (B) CH  C – C – C  CH
(C) H2C = C = C = CH2 (D)

# 26
3. Write IUPAC name of the following : [JEE-2004]
O
||
4. IUPAC name of C 6H5  C  Cl [JEE-2006]
(A) Benzoylchloride (B) Benzenecarbonylchloride
(C ) Chlorophenyl ketone (D) phenylchloroketone
5. The number of structural isomers for C6H14 is : [JEE-2007]

(A) 3 (B) 4 (C) 5 (D) 6
6. What is the IUPAC name of the following compound? [JEE-2008]
(A) 4-bromo-3-cyanopheol (B) 2-bromo-5-hydroxbenzonitrile

(C) 2-cyano-4-hydroxybromobenzene (D) 6-bromo-3-hydroxybenzonitrile
7. The total number of cyclic possible for a hydrocarbon with the molecular C4H6 is /are : [JEE-2010]
PART - II : AIEEE PROBLEMS (PREVIOUS YEARS)
1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]

 CH3 – CH2 – CH2 – C – O – CH2 – CH3
||
O
ethyl butanoate
 CH3 – CH – C – CH – CH3
| || |
CH3 O CH3
2,4 dimethyl -3- pentanone
CH3
|
 H3C – CH – CH – CH3
|
OH
2-methyl -3- butanol
IV CH3 – CH2 – CH2 – CHO
butanal
(1)  (2)  (3)  (4) IV
2. The general formula CnH2nO2 could be for open chain : [AIEEE-2003]

(1) diketones (2) carboxylic acids (3) diols (4) dialdhydes.

# 27
3. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003]
(1) 4-methylisopropyl ketone (2) 3-methyl-2-butanone
(3) Isopropylmethyl ketone (4) 2-methyl-3-butanone
4. The IUPAC name of the compound [AIEEE-2004]
is -
(1) 3,3 -dimethyl-1-hydroxy cyclohexane (2) 1, 1 – dimethyl–3– hydroxy cyclohexane

(3) 3,3-dimethyl-1-cyclohexanol (4) 1,1 - dimethyl - 3- cyclohexanol
5. Write IUPAC name of the following : [AIEEE-2005]
6. The IUPAC name of the compound shown below is - [AIEEE 2006]
(1) 6-bromo-2-chlorocyclohexene (2) 3-bromo-1-chlorocyclohexene

(3) 1-bromo-3-chlorocylohexene (4) 2-bromo-6-chlorocycohex-1-ene
7. The IUPAC name of [AIEEE 2007]
is –
(1) 1, 1-diethyl-2-dimethylpentane (2) 4, 4-dimethyl-5, 5-diethylpentane

(3) 5, 5-diethyl-4, 4-dimethylpentane (4) 3-ethyl-4, 4 dimethylheptane
8. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC
system of nomenclature is [AIEEE 2008]
(1) –SO3H, –COOH, –CONH2, –CHO (2) –CHO, –COOH, –SO3H, –CONH2
(3) –CONH2, –CHO, –SO3H, –COOH (4) –COOH, –SO3H, –CONH2, –CHO
9. The IUPAC name of the following compound is : [AIEEE-2009, 3/160]
(1) 4-Bromo-3-cyanophenol (2) 2-Bromo-5-hydroxybenzonitrile

(3) 2-Cyano-4-hydroxybromobenzene (4) 6-Bromo-3-hydroxybenzonitrile
10. The IUPAC name of neopentane is : [AIEEE-2009]

(1) 2, 2-dimethylpropane (2) 2-methylpropane
(3) 2, 2-dimethylbutane (4) 2-methylbutane

# 28
NCERT QUESTIONS
1. Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary,
secondary , tertiary), vinyl or aryl halides :
(i) (CH3)2CHCH(Cl)CH3 (ii) CH3CH2CH(CH3)CH(C2H5)Cl
(iii) CH3CH2C(CH3)2CH2I (iv) (CH3)3CCH2CH(Br)C6H5
(v) CH3CH(CH3)CH(Br)CH3 (vi) CH3C(C2H5)2CH2Br
(vii) CH3C(Cl)(C2H5)CH2CH3 (viii) CH3CH=C(Cl)CH2CH(CH3)2
(ix) CH3CH=CHC(Br)(CH3)2 (x) p-CIC6H4CH2CH(CH3)2
(xi) m-CICH2C6H4CH2C(CH3)3 (xii) O-BR-C6H4CH(CH3)CH2CH3
2. Give the IUPAC names of the following compounds :

(i) CH3CH(Cl)CH(Br)CH3 (ii) CHF2CBrClF
(iii) ClCH2C  CCH2Br (iv) (CCl3)3CCl
(v) CH3C(p-ClC6H4)2CH(Br)CH3 (vi) (CH3)3CCH=ClC6H4I-p
3. Write IUPAC names of the following compounds :
(i) (ii) (iii)
(iv) (v) (vi)
(vii) (viii) (ix)
(x) C6H5–O–C2C2H5 (xi) C6H5–O–C7H15(n–) (xii)

# 29
4. Write structures of the compounds whose IUPAC names are as follows :
(i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol
(iii) 3, 5-Dimethylhexane-1, 3, 5-triol (iv) 2, 3-Diethylphenol
(v) 1-Ethoxypropane (vi) 2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol
(ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol.
5. Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names.
6. Name of the following compounds according to IUPAC system of nomenclature :

(i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl
(iii) CH3CH=CHCHO (iv) CH3COCH2COCH3
(v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p
7. Draw the structures of the following compounds :

(i) 3-Methylbutanal (ii) p-Nitropropiophenone
(iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-ene-2-one
(v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid
(vii) p, p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid
8. Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give also common
names:
(i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2(CH3)CHO
(iii) CH3(CH2)5CHO (iv) Ph–CH=CH–CHO
(v) (vi) PhCOPh
9. Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary
amines.
(i) (CH3)2CHNH2 (ii) CH3(CH2)2NH2 (iii) CH3NHCH(CH3)2
(iv) (CH3)3CNH2 (v) C6H5NHCH3 (vi) (CH3CH2)2NCH3
(vii) m-BrC6H4NH2
10. Write structures of different chain isomers of alkanes corresponding to the molecular formula C6H14. Also
write their IUPAC names.

(i) (CH3)3CCH2C(CH3)3 (ii) (CH3)2C(C2H5)2 (iii) tetra – tert – butylmethane

# 30
(i) (ii)
(iii) CH2=C(CH2CH2CH3)2 (iv)
13. Write structures and IUPAC names of different structural isomers of alkenes corresponding to C5H10.
14. Draw cis and trans isomers of the following compounds. Also write their IUPAC names :
(i) CHCl=CHCl (ii) C2H5CCH3=CCH3C2H5
15. Write structures of different isomers corresponding to the 5th member of alkyne series. Also write IUPAC
names of all the isomers. What type of isomerism is exhibited by different pairs of isomers ?

(a) CH3CH=C(CH3)2 (b) CH2=CH–C  C–CH3 (c)
(d) (e) (f)
(g)
17. For the following compounds, write structural formulas and IUPAC names for all possible isomers having
the number of double or triple bond as indicated :
(a) C4H8 (one double bond) (b) C5H8 (one triple bond)

# 31
EXERCISE # 1
PART # I
A-1. (D) A-2. (C) A-3. (C) A-4. (B) A-5. (B) A-6.* (ABD) A-7. (D)
A-8. (B) A-9. (D) A-10. (B) A-11. (B) A-12. (B) B-1. (D) B-2. (D)
B-3. (B) B-4. (A) B-5. (B) B-6. (A) B-7. (D) B-8. (D) B-9. (D)
C-1. (D) C-2. (C) C-3. (A) C-4. (C) C-5. (B) C-6. (B) C-7. (D)
C-8. (B) D-1. (C) D-2. (B) D-3. (A) D-4. (C) D-5. (B) D-6. (C)
D-7. (D) D-8. (A) D-9. (A) D-10. (A) D-11. (B) E-1. (D) E-2. (B)
E-3. (A) E-4. (A) E-5. (D) E-6. (C) E-7. (A) E-8. (B) E-9. (C)
E-10. (B) E-11. (A) E-12. (A) E-13. (B) F-1. (D) F-2. (B) F-3. (C)
F-4. (B) F-5. (D) F-6. (C) F-7. (C) F-8. (B) F-9. (B) F-10. (B)
F-11. (B) F-12. (D) F-13. (B) G-1. (B) G-2. (C) G-3. (B) G-4. (C)
G-5. (B) G-6. (B) G-7. (B) G-8. (D) G-9. (B) G-10. (C) G-11. (D)
G-12. (C) H-1. (A) H-2. (C) H-3. (A) H-4. (C) H-5. (D) H-6. (D)
H-7. (B) H-8. (A) H-9. (D) H-10. (D) H-11. (B) I-1. (A) I-2. (A)
I-3. (D) I-4. (B) I-5. (C) J-1. (A) J-2. (C) J-3. (A) J-4. (C)
J-5. (C) J-6. (D) J-7. (A) J-8. (D) J-9. (B) J-10. (A) J-11. (D)
J-12. (D) J-13. (D) J-14. (A) J-15. (C) J-16. (C) J-17. (D) J-18. (A)
K-1. (B) K-2. (A) K-3. (B) K-4. (B) K-5. (B) K-6. (D) K-7. (C)
PART # II
1. (B) 2. (B) 3. (C) 4. (A) 5. (D) 6. (A) 7. (A)
8. (C) 9. (B)
EXERCISE # 2
PART # I
1. (A) 2. (A) 3. (B) 4. (B) 5. (D) 6. (D) 7. (D)
8. (B) 9. (C) 10. (A) 11. (C) 12. (C) 13.* (AD)
PART # II
1. 3-(1-Chloroethyl)-4-methyl-4-phenylpentan-2-one 2. 2-Cyclopropyl-4-ethylhex-1-ene
3. 6-isopropylcyclodec-1-yne 4. 1-Chloro-2, 3-epoxypropane
5. 3-Mercaptobenzoic acid 6. N, N-Diethyl cyclohexanecarboxamide
7. 3–Cyclopropyl-3-methylbutanal 8. 3–Bromohexa–1, 3, 5–triene
9. 2–Methyl–3–methylenehex–1–en–4–yne 10. 3–Methoxy–5, 5–dimethylcyclohex–2–en–1–ol
11. 2–Bromo–1–chloro–3–iodocyclohexane 12. Carbylamineprop-2-ene
13. 1, 1, 1–Trichloro-2, 2-bis(4–chlorophenyl)ethane 14. 1–(3–bromophenyl)–6–phenylhexa–1,3,5–triyne
15. 3–Methyl–2–(3–oxobutyl)cyclohexan-1-one 16. 2, 4, 7-Trioxaoctane
17. 1, 3, 5, 7-Tetraoxacyclooctane 18. 2-Ethoxy-2-methylpropane

# 32
19. N-Methylbenzamide 20. 3-Ethylphenyl ethanoate
21. N-Methyl-2-methoxy-1-ethanamine 22. Pentano-5-lactone
23. H – C º C – H, Mol wt. = 26 24.
25. H2C = C = CH2 ; M.W. = 40. 26. Metamerism 27. ,
EXERCISE # 3
PART # I
1. (4-Hydroxyphenyl) ethanal 2. (A) 3. 3-Aminobenzoic acid 4. (B)
5. (C) 6. (B) 7. 5
PART # II
1. (3) 2. (2) 3. (2) 4. (3) 5. 4-Methylbenzenesulphonic acid
6. (2) 7. (4) 8. (4) 9. (2) 10. (1)
EXERCISE # 4
NCERT QUESTIONS
10. (i) CH3–CH2–CH2–CH2–CH2–CH3 n-Hexane (ii) CH3– CH –CH2–CH2–CH3 2-Methylpentane
|
CH3
(iii) CH3–CH2– CH –CH2–CH3 3-Methylpentane (iv) CH3– CH – CH –CH3 2, 3-Dimethylbutane

| | |
CH3 CH3 CH3
CH3
|
(v) CH3– C –CH2–CH3 2, 2-Dimethylbutane
|
CH3
11. (i) 2, 2, 4, 4-Tetramethylpentane (ii) 3, 3-Dimethylpentane (iii) 3, 3-Di-tert-butayl-2, 2, 4, 4-tetramethylpentane
12. (i) 2, 8-Dimethyl-3, 6-decadiene ; (ii) 1, 3, 5, 7 Octatetraene ;
(iii) 2-n-Propylpent-1-ene ; (iv) 4-Ethyl-2, 6-dimethyl-dec-4-ene ;
13. (a) CH2=CH–CH2–CH2–CH3 Pent-1-ene (b) CH3–CH=CH–CH2–CH3 Pent-2-ene

(c) CH3– C =CH–CH3 2-Methylbut-2-ene (d) CH3– CH –CH=CH2 3-Methylbut-1-ene
| |
CH3 CH3
(e) CH2= C –CH2–CH3 2-Methylbut-1-ene

|
CH3
14. (i) (ii)
15. 5th member of alkyne has the molecular formula C6H10. The possible isomers are :

# 33

01 STRUCTURAL ISOMERISM

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IUPAC Nomenclature

Name : ____________________________ Contact No. __________________

Classification of organic compounds

CH3 – CH3 

(a) C3H7 has following two isomers

(i) Normal propyl CH3–CH2–CH2–

(ii) Isopropyl (1-methyl ethyl) CH3–CH–

(i) n-butyl H3C–CH2–CH2–CH2–

(ii) Iso butyl (2-methyl propyl) CH3–CH–CH2–

Physical & Inorganic By Organic Chemistry By

CH2 = CH – CH2 – Propenyal

CH3–C=CH2 Isopropenyl (1-methyl-1-ethenyl)

(a) It is represented by 'n'.

(b) Straight chain of carbon atom is known as normal group.

For eg. Neo pentyl

Physical & Inorganic By Organic Chemistry By

Physical & Inorganic By Organic Chemistry By

Table : Functional Groups in decreasing order of seniority

Class Name Suffix Prefix

2. R – COOH Alkanoic Acid – oic Acid (carboxylic acid) Carboxy

3. R – SO3H Alkane sulphonic Acid – sulphonic Acid sulpho

4. R–C–O–C–R Alkanoic Anhydride – anhydride ------------

5. R – COOR Alkyl Alkanoate – alkanoate (carboxylate) Alkoxy carbonyl

8. Alkanenitrile – nitrile (carbonitrile) cyano

10. R – C – R Alkanone – one Oxo / Keto

11. R – OH Alkanol hydroxy

12. R – SH Alkanethiol – thiol mercapto

13. R – NH2 Alkanamine – amine amino

Physical & Inorganic By Organic Chemistry By

(i) C4 H1 0 : CH3  CH 2  CH2  CH3 , CH3  CH  CH3

Physical & Inorganic By Organic Chemistry By

C3 H8 O : CH3  CH2  CH 2  OH ; C2H5  O  CH3

C4 H1 0O : CH3  CH2  CH2  CH2  OH ; C2H5  O  C 2H5

(ii) Aldehydes, ketones an d unsaturated alcohols …etc. (Cn H2n O)

(iv) Alkynes and alkadienes (C n H2n-2 )

(v) Nitro alkanes and alkyl nitrites (  NO2 and  O  N  O )

(vi) Amines (Primary, secondary and tertiary)

(vii) Alcohols and phenols

Benzyl alcohol o-Cresol

Physical & Inorganic By Organic Chemistry By

 Ring – chain isomers are always functional isomers.

(ii) C6 H15N : C3H7  NH  C3H7 ; C2H5  NH  C 4H9

Note : Alkenes donot show metamerism.

Physical & Inorganic By Organic Chemistry By

* Marked Questions are having more than one correct option.

Section (A) : Fundamental of Organic Chemistry

A-6.* The pair of compounds having the same general formula :

(A) and (B) and

(C) and (D) and H–CC–CC–H

A-7. (a) and (b)

True statement for the above compounds is:

A-9. Which of the following is the triad of a homologous series -

A-10. The homologue of phenol is -

Physical & Inorganic By Organic Chemistry By

Section (B) : Classification and General Rules of IUPAC Nomenclature

B-1. C4H6O2 does not represent:

(A) –CC– (B) –OH (C)  C  (D)  C  H

B-4. Which of the following is a heterocyclic compound

B-5. The number of sigma and pi-bonds in 1-butene 3-yne are:

B-6. Which is an acyclic compound :

B-7. Which of the following is not an alicyclic compound ?

(A) (B) (C) (D)

Name : __________ Contact No.