JEE (Adv.

)-Chemistry IUPAC Nomenclature & structural Isomerism

PART-I : SUBJECTIVE QUESTIONS

Section (A) : Fundamentals and classification of organic compounds
A-1. Find the number of 1º, 2º & 3º hydrogen atoms in the following compounds?

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

A-2. Indicate the following as 1°, 2° and 3° alcohol.

CH3
(a) (b) (c) CH3–C–CH2–OH
CH3
A-3. Indicate the following as 1°, 2° and 3° amines.
CH3
(a) CH3–C–NH2 (b) Ph–CH–NH–CH3 (c) CH3 –CH2–N–CH3 (d)
CH3 CH3 CH3
A-4. What is the degree of marked carbon atoms in the following compounds?

(a) (b) (c)

A-5. How many sp2–sp2 C–C s bonds are present in the given structure ?

A-6. Write the number of s and p bonds in the following molecules.

CH3
(a) OH (b)

A-7. Calculate the number of 3° carbon atoms in the given compound.

A-8. Find the hybridization of each carbon atom in following compound.

8 7 6 5 4 3 2 1
CH2= C = CH – CH 2– C º C – CH 2 – COOH
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
A-9. Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon atoms
only.
A-10. Classify the following compounds as homocyclic, heterocyclic, alicyclic, aromatic, saturated and
unsaturated.

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

Section (B) : IUPAC-Nomenclature of alkanes and cycloalkanes

B-1. Write IUPAC name of the following compounds.

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

B-2. Write the common name of the following alkyl groups.

(a) (b) (c)

(d) –CH2–CH3 (e) CH3–CH2–CH2–

B-3. Write the IUPAC name of following compounds

(a)

(b)

(c)

(d)

(e)

(f)
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
B-4. Write the correct IUPAC name of the following hydrocarbon (alkyl) groups.

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

B-5. Write IUPAC name of the following compounds.

Cl I CH2 - CH2 - Cl
| | |
(a) Br - CH - CH - CH - CH - CH (b) CH3 - CH - CH - CH2 - CH3
2 2 3
|
CH3

Cl Br NO 2 Cl CH3 F
| | | | | |
(c) CH3 - CH2 - CH - CH - CH2 - CH - CH2 - CH3 (d) CH3 - C - CH2 - CH - CH - CH2 - CH3
|
Br

B-6. Write IUPAC names of the following hydrocarbons (use common naming for hydrocarbon groups.)

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

B-7. Identify the parent chain in the following compounds as ring or side chain.

(a) (b) (c)

(d) (e) (f)

B-8. How many carbon atoms are present in the parent chain of the given compound?

B-9. Write IUPAC name of the following compounds.

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

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
Section (C) : IUPAC Nomenclature of alkenes, cylcoalkenes, polyenes and alkynes
C-1. Write IUPAC name of the following compounds.

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

C-2. Write the IUPAC name of the following hydrocarbon groups.

CH3
|
(a) –CH=CH2 (b) –CºCH (c) — C = CH (d) –CH2–CH=CH2
2

CH3
(e) =CH–CH3 (f) |
= C - CH3

C-3. Write the general formula of alkenes. Give common and IUPAC names of first three members.
C-4. Write the general formula of alkynes. Give common and IUPAC names of first three members.
C-5. Write IUPAC name of the following compounds :

(a) (b) (c)

C-6. Write the IUPAC name of the following compounds:-

(a) CH3 – – C º C – CH3 (b) (c)

C-7. Write IUPAC names of the following.

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

C-8. What is the position of bromo in the given compound according to IUPAC?

C-9. Write the position of ethyl substituent in the IUPAC name of the following compound.

CH3 CH2 – CH3 CH3

–

–
–

CH3 – CH2 – CH – CH – CH – CH = C – CH3

– – – –

CH2
CH2
CH – CH3
CH3
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
Section (D) : IUPAC naming of non chain terminating functional groups containing
compounds
D-1. Write the priority order of given functional groups.
–COOH, –CN, –CHO, –OH, –COCH3, –NH2
D-2. Number of functional groups present in the following compounds are :

D-3. Write the correct IUPAC name of the followings.

(a) (CH3)2 CHCH = CHCH2OH (b)

(c) H3 C — N — CH — CH3 (d) Cl CH2COCH2

| |
CH3 CH3

(e) (f)

D-4. Draw the structures of the following compounds.

(a) 3-Methoxy-5, 5-dimethylcyclohex-2-en-1-ol (b) 5–Methyl-2-(methylethyl)cyclohexan-1-amine
(c) 2–Chloro–3–methylcyclohex–3–ene–1–thiol (d) 3 –Bromo– 4–methylcyclopentan-1-one
D-5. How many of following IUPAC names are correctly matched?

(a) 2-Chlorobutan-3-ol (b) 2-Ethylbut-3-en-1-ol

(c) 5-Aminomethyl-3-ethylheptan-2-ol

(d) 3-Butylpentane-2,4-dione (e) 3-Oxoheptane-5-sulphonic acid.

(f) 3-(2-Bromoethyl)hexan-2-ol

(g) 3-Bromo-4-methylpentane-2-sulphonic acid

(h) 3-Propylpent-4-en-2-one (i) 3-Ethenylpentane-2,4-dione

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
Section (E) : IUPAC naming of the chain terminating functional group containing
compounds

E-1. Write the structure of the following molecules :

(a) 4-Formyl-2-oxocyclohexane-1-carboxylic acid.
(b) 2-Cyano-3-oxopentanedioic acid
(c) 3-Methyl-2-methylenebut-3-enoic acid
(d) 5-Oxocyclohex-2-ene-1-carbonitrile

E-2. Write IUPAC names of the following compounds :

O
(a) CH3CH2 – CH – C – OCH3 (b) (c)
– –

CH2
CH3

E-3. In how many of the following compounds, correct parent chain is selected ?

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

(e) (f) (g)

E-4. In the given compound, number of carbon atoms in parent chain are X and locant position of double bond in
parent chain is Y. Report your answer as X + Y :

Section (F) : IUPAC-Nomenclature of aromatic compounds

F-1. Write IUPAC names of the following :

(a) (b) (c) Ph–CH2–Ph (d)

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
F-2. Write the correct IUPAC names of the following :

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

F-3. In how many of the following compounds, benzene ring is considered as parent chain ?

(a) (b)

(c) (d)

F-4. Write IUPAC names of following compounds.

(a) (b)

(c) (d)

F-5. Write IUPAC names of following compounds

(a) (b)

(c) (d)

F-6. Write IUPAC names of following compounds.

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

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
F-7. The number of compounds with correct IUPAC name is/are :

(a) (b)

2-Carboxyphenol 3-Ethyl-4-chloro-5-hydroxybenzenecarbonitrile

(c) (d)

3-Formyl-5-nitrobenzenecarboxylic acid 1-Hydroxy-3-methoxy-4-nitrobenzene

(e) (f) (g)

4-Amino-1-nitrobenzene 3-Methylphenol 2,4,6-Trimethylbenzenecarbonlychloride

Section (G) : Structural isomerism

G-1. Identify the relationship between the given compounds.

(a) and (b) and

(c) and

G-2. Identify the relationship amongst the following :

(a) (b)

(c) (d)
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
G-3. Identify the relationship between compound I, II and III.
H3C
H
H
CH2–CH=CH2
III
G-4. In how many of the following, correct isomeric relation is given?

(a) and are metamers

(b) and are functional isomers

(c) and are position isomers

(d) & are chain isomers

(e) & are functional isomers

(f) & are metamers

(g) & are position isomers

Section (H) : Number of structural isomers

H-1. What is the degree of unsaturation in a compound with molecular formula C9H6N4?
H-2. Degree of unsaturation of the following compound is ?
CN

CHO
O
H-3. How many esters are possible of formula C4H8O2? What is the relation between them?
H-4. The ring-chain functional isomers of compound But-2-ene are.
H-5. Write all structurally isomeric ethers with molecular formula C5H12O.
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART-II : OBJECTIVE QUESTIONS

Section (A) : Fundamentals & classification of organic compounds
A-1. How many 1°carbon atoms will be present in a simplest open chain hydrocarbon having two 3° and one 2°

carbon atoms ?

(A) 3 (B) 4 (C) 5 (D) 6

A-2. Alicyclic compounds are :

(A) Aromatic compounds (B) Aliphatic cyclic compounds

(C) Heterocyclic compounds (D) None of the above

A-3. A group of closely related compounds which can be expressed by a general formula & in which two consecutive

members differ by 14 in their molecular masses is called

(A) a heterogeneous series (B) a homologous series

(C) a homogeneous series (D) an electrochemical series

A-4. Which of the following is a heterocyclic compound?

HC = CH HC = COOH HC = CH HC = CH
(A) | S (B) | (C) | CH2 (D) | C=O
HC CH HC COOH HC CH HC CH
A-5. Number of 3º and 2º carbon atoms in the following compound are?

(A) 5, 6 (B) 5, 7 (C) 4, 6 (D) 6, 6

A-6. Molecular formula of naphthaquinone is ?

(A) C12H8O2 (B) C11H6O2 (C) C10H6O2 (D) C10H8O2

A-7.

Incorrect statement for the above structures is :

(A) I, II & III have CnH2n-2 general formula (B) I , II & III have same empirical formula
(C) I & II are homologue of compound III. (D) I, II & III have same molecular formula
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
A-8. Which of the following is not an alicyclic compound ?

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

N
|
H

A-9. The saturated heterocyclic compound is :

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

N
.. |
H

A-10. Which of the following does not have bridgehead carbon ?

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

Section (B) : IUPAC-Nomenclature of alkanes & cycloalkanes

B-1. Which of the following compound has isopropyl group ?

(A) 2,2,3,3-Tetramethylpentane (B) 2,2-Dimethylpentane

(C) 2,2,3-Trimethylpentane (D) 2-Methylpentane

B-2. IUPAC name of compound is :

CH2-CH3
CH3-CH-CH-CH3
CH2-CH3

(A) 2,3-Diethylbutane (B) 2-Ethyl-3-methylpentane

(C) 3-Methyl-2-ethylpentane (D) 3,4-Dimethylhexane

B-3. What is the correct systematic name (IUPAC) for the compound (CH3)2CHCH(CH2CH3)(CH2CH2CH3)?
(A) 3-Isopropylhexane (B) 2-Methyl-3-propylpentane
(C) Ethyl isopropyl propyl methane (D) 3-Ethyl-2-methylhexane

B-4. The correct structure of 6-Ethyl-2,3,5-trimethylnonane is :

(A) (B)

(C) (D)
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
B-5. The correct IUPAC name of the following compound is :

(A) 1-Bromo-1-ethyl-2-fluoro-2-iodo-1-nitroethane (B) 3-Bromo-4-fluoro-4-iodo-3-nitrobutane.

(C) 2-Bromo-1-fluoro-1-iodo-2-nitrobutane. (D) 1-Fluoro-1-iodo-2-bromo-2-ethyl-2-nitroethane.
B-6. A student named a certain compound as 2,3-Diethylbutane. Its correct IUPAC name is ?
(A) 2,3-Dimethylhexane (B) 3,4-Dimethylhexane
(C) 2-Ethyl-3-methylpentane (D) 2-Ethylbutane
B-7. The common and IUPAC names for the group, –CH2CH(CH3)2 respectively are
(A) Isobutyl & 2-methylpropyl (B) Isobutyl & 1-methylpropyl
(C) tert-Butyl & 1,1-dimethylethyl (D) sec-Butyl & 2-methylpropyl

B-8. In which of the following compound IUPAC numbering is correct?

(A) (B)

(C) (D)

Section (C) : IUPAC Nomenclature of alkenes, cylcoalkenes, polyenes and alkynes

CH 3 CH 3
| |
C-1. The correct IUPAC name of the compound CH 3 - CH 2 - C = C - CH - CH - CH 2 - CH 2 - CH 3 is :
|
C2H5

(A) 5-Ethyl-3,6-dimethylnon-3-ene (B) 5-Ethyl-4,7-dimethylnon-3-ene

(C) 4-Methyl-5,7-diethyloct-2-ene (D) 2,4-Dimethyl-5-ethyloct-2-ene

C-2. The molecular formula of the first member of the family of alkenynes and its name is given by the set

(A) C3H6, Alkene (B) C5H6, Pent-1-en-3-yne

(C) C6H8, Hex-1-en-5-yne (D) C4H4, Butenyne

C-3. The correct IUPAC name of 2-Ethylpent-3-yne is:

(A) 3-Methylhex-4-yne (B) 4-Ethylpent-2-yne

(C) 4-Methylhex-2 yne (D) None of these

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
C-4. The IUPAC name of the compound CH3CH = CHCH=CHCºCCH3 is:

(A) Octa-4,6-diene-2-yne (B) Octa-2,4-diene-6-yne

(C) Oct-2-yne-4,6-diene (D) Oct-6-yne-2,4-diene

C-5. Select the structure with correct IUPAC numbering in the chain?

(A) (B)

(C) (D)

C-6. The correct IUPAC name of the compound is -

F I
C

Cl C CH2
CH2 CH2 Br
(A) 4-Bromo-1-chloro-2-fluoroiodomethylbutene
(B) 4-Bromo-2-chloromethyl-1-fluoro-1-iodobut-1-ene
(C) 2-(2-Bromoethyl)-3-chloro-1-fluoro-1-iodoprop-1-ene
(D) 1-Bromo-3-chloromethyl-4-fluoro-4-iodobut-1-ene

C-7. The IUPAC name of is :

(A) 1,2-Dimethylcyclohexene (B) 1,6-Dimethylcyclohexene

(C) 1,2-Dimethylcyclohex-2-ene (D) 2,3-Dimethylcyclohexene

C-8. In which of the following, cyclic chain is the main chain ?

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

C-9. The correct IUPAC name of the compound is :

(A) 1-Ethenylcyclohexa-2,4-diene (B) 5-Ethenylcyclohexa-1,3-diene

(C) 6-Ethenylcyclohexa-1,3-diene (D) Cyclohexa-2,4-dienylethene

Section (D) : IUPAC naming of non chain terminating functional groups containing
compounds
D-1. The IUPAC name of CH 3 CH 2 - N - CH 2CH 3 is:
|
CH 3
(A) N-Methyl-N-ethylethanamine (B) Diethylmethanamine

(C) N-Ethyl-N-methylethanamine (D) Methyldiethylethanamine

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
D-2. The IUPAC name of acetyl acetone is :

(A) Pentane-2,5- dione (B) Pentane -2,4-dione

(C) Hexane-2,4-dione (D)Butane-2,4-dione

OH

D-3. The correct IUPAC name of

CH2–CºCH

(A) 3-Cyclohexanolpropyne (B) 3-[3-Hydroxycyclohexyl]propyne

(C) 3-Propynylcyclohexanol (D) 3-(2-Propynyl)cyclohexanol

D-4. The IUPAC name of the compound CH3 is:

HO CH3

(A) 1,1-Dimethyl-3-hydroxycyclohexane (B) 3,3-Dimethyl-1-hydroxycyclohexane

(C) 3,3-Dimethylcyclohexanol (D) 1,1-Dimethylcyclohexan-3-ol

D-5. The IUPAC name of is :

(A) 3-Methylcyclobut-1-en-2-ol (B) 4-Methylcyclobut-2-en-1-ol

(C) 4-Methylcyclobut-1-en-3-ol (D) 2-Methylcyclobut-3-en-1-ol

D-6. The correct IUPAC name of the compound is :

(A) 6-Ethyl-1-methyl-4-oxohept-6-ene-1-sulphonic acid

(B) 7-Ethyl-5-oxooct-7-ene-2-sulphonic acid
(C) 2-Ethyl-7-sulphooct-1-ene-4-one
(D) 7-Methylene-5-oxononane-2-sulphonic acid

D-7. The correct structure of 6-Amino-4-hydroxycylohex-2-ene-1-sulphonic acid?

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

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
Section (E) : IUPAC naming of the chain terminating functional group containing
compounds

E-1. IUPAC name of CH2=CH – CN is:

(A) Ethenenitrile (B) Vinyl cyanide (C) Cyano ethene (D) Prop-2-enenitrile

E-2. The correct IUPAC name of CH3 - CH 2 - C - COOH is:

||
CH 2

(A) 2-Methylbutanoic acid (B) 2-Ethylprop-2-enoic acid

(C) 2-Carboxybutene (D) None of the above

E-3. The IUPAC name of (C2H 5)2NCH 2CHCOOH 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-ethylethane

E-4. is named as :

(A) 2, 3-Dimethylenebutanal (B) 3-Methyl-2-methylenebut-3-enone

(C) 3-Methyl-2-methylenebut-3-enal (D) 2, 3-Dimethylenebutanone

E-5. The correct IUPAC name of compound is :

(A) 1-Chloropentane-1, 4-dione

(B) 4-Chlorocarbonylbutan-2-one
(C) 4-Oxopentanoylchloride
(D) 3-Oxobutanecarbonylchloride
E-6. The correct IUPAC name of following compound is :

COOH

OH
CH2NH2

(A) 4-Aminomethyl-3-hydroxycyclohex-5-ene-1-carboxylic acid

(B) 2-Aminomethyl-5-carboxycyclohex-3-en-1-ol
(C) 4-Aminomethyl-5-hydroxycyclohex-2-ene-1-carboxylic acid
(D) 3-Hydroxy-4-aminomethylcyclohex-5-en-1-oic acid
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

E-7. The IUPAC name of the compound is :

(A) Propanoic anhydride (B) Dipropanoic anhydride

(C) Ethoxypropanoic acid (D) 1-Oxopropyl propanoate

E-8. The IUPAC name of the compound is :

(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride

(C) Cyclobutanedicarboxylic anhydride (D) Butanedioic anhydride

E-9. The IUPAC name of is

(A) Ethoxymethanone (B) Ethyl 2-methylpropanoate

(C) Ethoxypropanone (D) 2-Methylethoxypropanone

Section (F) : IUPAC-Nomenclature of aromatic compounds

F-1. The IUPAC name of the following compound is :

(A) 5-Bromo-3-hydroxybenzenecarbaldehyde
(B) 3-Bromo-5-formylphenol
(C) 3-Bromo-5-hydroxybenzenecarbaldehyde
(D) 1-Bromo-3-formyl-5-hydroxybenzene

F-2. The IUPAC name of the compound is :

(A) 2-Cyano-1-formylbenzene-4-carboxylic acid (B) 3-Cyano-4-formylbenzene-1-carboxylic acid

(C) 4-Carboxy-2-cyanobenzene-1-carbaldehyde (D) 2-Formyl-5-carboxybenzene-1-carbonitrile

F-3. IUPAC name of

(A) 4-Chlorophenyl benzoate. (B) Phenyl 4-chlorobenzenecarboxylate.

(C) Benzyl 4-chlorobenzenecarboxylate. (D) 4-Chlorodiphenylcarboxylate.
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

F-4. The correct IUPAC name of the compound is

(A) N–Formyl-4-chlorobenzenamine (B) N–Formyl-4-chloroaniline

(C) N–(4-Chlorophenyl)methanamide (D) N–(Parachlorophenyl)–N–formylaniline

F-5. IUPAC name of the compound is

(A) 2-Chlorocarbonyl ethylbenzenecarboxylate (B) 2-Carboxyethylbenzoyl chloride

(C) Ethyl 2-(chlorocarbonyl)benzenecarboxylate (D) Ethyl 1-(chlorocarbonyl)benzenecarboxylate

F-6. The correct IUPAC name of the compound is :

(A) 2-Phenoxycarbonylbenzenecarboxylic acid

(B) Phenyl-2-carboxybenzenecarboxylate
(C) 2-Benzoyloxybenzenecarboxylic acid
(D) 2-Benzyloxycarbonylbenzenecarboxylic acid

Section (G) : Structural isomerism

G-1. Relation between compounds & is:

(A) Position isomers (B) Chain isomers (C) Identical (D) Functional isomers

G-2. Which type of isomerism is observed between I and II ?

(I) CH3 – CH2 – C – OCH3 , (II)
||
O
(A) Functional isomerism (B) Metamerism
(C) Position isomerism (D) Stereoisomerism
G-3. Which of the following is a pair of structural isomers?

(A) and (C) and

(C) and (D) and

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
G-4. Which one of the follwoing compound is not isomer of others?

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

G-5. What is the relation between 3-Ethylpentane and 3-Methylhexane ?

(A) Chain isomers (B) Position isomers (C) Functional isomers (D) No relation

G-6. Which type of isomerism is observed between I and II ?

(I) CH3 – CH2 – NH – CHO (II) CH3–CH–CHO

NH2
(A) Chain isomers (B) Position isomers (C) Functional isomers (D) Metamers
G-7. Which of the following pair is identical ?

(A) (B)

(C) (D)

Section (H) : Number of structural isomers

H-1. Degree of unsaturation (DU) & total number of different functional groups in given compound are?

CHO OH O
NC NH

NH
NC
O CH2OH

(A) 8, 7 (B) 9, 8 (C) 12, 8 (D) 12, 7

H-2. How many positional isomers are possible for dimethylcyclohexane?

(A) 3 (B) 4 (C) 5 (D) 6

H-3. How many aromatic isomers are possible for trichlorobenzene (C6H3Cl3) ?
(A) 2 (B) 3 (C) 4 (D) 5

H-4. The number of ether isomers represented by formula C4H10O is (only structural)?
(A) 4 (B) 3 (C) 2 (D) 1
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
H-5. Total number of 2° amine isomers of C4H11N would be (only structural)?
(A) 4 (B) 3 (C) 5 (D) 2

H-6. Find the total number of structurally isomeric 1° amides with molecular formula C5H11NO?
(A) 1 (B) 3 (C) 2 (D) 4

H-7. How many structural isomers of all the tertiary alcohols with molecular formula C6H14O are ?
(A) 2 (B) 3 (C) 4 (D) 5

H-8. Total number of structural isomers for C5H10 would be?

(A) 8 (B) 6 (C) 9 (D) 10

PART-III : MATCH THE COLUMN

1. Column – I Column – II

(A) and (p) Isomers

(B) and (q) Positional Isomers

(C) and (r) Functional Isomers

(D) and (s) Homologs

2. Column – I (Molecular formula) Column – II (Number of benzenoid isomers)

[X = Cl, Y = Br, Z = F]
(A) C6H2X4 (p) 3
(B) C6H4XY (q) 6
(C) C6H3XYZ (r) 10
(D) C6H3X2Y (s) 12
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART - I : OBJECTIVE QUESTIONS

1. A compound of molecular formula C6H12O3 can never have a functional group-
O
(A) Carboxylic acid -C-OH (B) Aldehyde –C
H
O
O
(C) Ester C O (D) Anhydride –C–O–C
O O

2. IUPAC name of the compound is :

O

(A) 1-Ethoxycyclohexa-1,3-diene (B) 1-Ethoxycyclohexa-1,5-diene

(C) 2-Ethoxycyclohexa-1,5-diene (D) 4-Ethoxycyclohexa-1,3-diene

Br CHO
3. Correct IUPAC name for the compound is :

OMe
(A) 3-Methoxy-5-bromobenzenecarbaldehyde (B) 3-Formyl-5-bromophenylmethylether
(C) 3-Formyl-5-bromo-1-methoxybenzene (D) 3-Bromo-5-methoxybenzenecarbaldehyde
4. Number of functional groups present in ASPARTAME are -
HO
H2 N O

O
O NH

ASPARTAME
(A) 4 (B) 5 (C) 7 (D) 6

5. IUPAC name of the compound is

(A) 2,2,5-Trimethyl-4-(1-methylpropyl)nonane
(B) 4,8,8-Trimethyl-6-(1-methylpropyl)nonane
(C) 3,5-Dimethyl-4-(1-methylene tertiary butyl)nonane
(D) 6,6-Dimethyl-2-propyl-4-(1-methylpropyl)heptane
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
6. In the structure of 4-Isopropyl-2,4,5-trimethylheptane, number of 10, 20 & 30 H’s are respectively-
(A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4

7. The correct IUPAC numbering in the compound is :

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

8. The correct IUPAC name of .

(A) 1-Ethylidenecyclohex-2-ene (B) 3-Ethylidenecyclohex-1-ene

(C) 2-Ethylidenecyclohex-1-ene (D) 3-Ethenylcyclohex-1-ene

9. 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

10. IUPAC name of the following molecule is

COOH

Br
COOH

(A) 2-Bromobenzene-1,4-dioic acid (B) 3-Bromobenzene-1,4-dicarboxylic acid

(C) 2-Bromobenzene-1,4-dicarboxylic acid (D) 3-Bromobenzene-1,6-dicarboxylic acid

11. What is the number of all structurally isomeric alkynes with molecular formula C6H10?
(A) 6 (B) 7 (C) 8 (D) 9

12. How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom in an
thracene ?
(A) 3 (B) 7 (C) 4 (D) 6
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
13. The number of structural isomers possible from the molecular formula C2H2FClBrI are-
(A) 3 (B) 5 (C) 7 (D) 9
14. Which of the following represent functional isomers ?

(A) OH (B) COOH

OH COOH
O

(C) (D)
O
O OH
15. Which one of the following is a functional isomer of CH3–CH2–CH2–CH2–NH2?
CH3
(A) CH3–CH2–NH–CH2–CH3 (B) CH3-CH-CH2-NH2
CH3
(C) CH3-C-NH2 (D) CH3-CH2-N-CH2-CH3
CH3 CH3
16. Number of structure isomers of molecular formula C5H10 having one p-bond are-
(A) 2 (B) 3 (C) 5 (D) 4

OH
17. Compound which is functional isomer of is-
O
O OH
OH O
(A) (B) (C) OH (D)
O O O O
PART - II : NUMERICAL TYPE QUESTIONS
1. Possible number of compounds with different structures and IUPAC name p1-bromo -p2-methyl butanoic acid.
Where pi represents position of side chains/substituents?
2. The number of structurally isomeric compound(s) possible with molecular formula C8H18 containing 5 carbons
in main chain and having methyl group(s) as side chain are -
3. Number of correct names in the given substituents are :

(a) (b) (c)

Ethylmethyl 1-Methylpropyl 2,3-Dimethylpropyl

(d) (e) = CH–CH3 (f)

2,3-Dimethylbutyl Ethylidene 2-Methylethenyl
(g) –C º CH (h) –CH2–CH=CH2 (i) –CH2–C º CH
Ethynyl 2-Propenyl Prop-1-ynyl
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
4. The number of isomeric pairs with correct relationship specified are :

(a) & Metamers

(b) & Functional isomers

(c) & Position isomers

(d) & Position isomers

(e) & Functional isomers

(f) & Functional isomers

5. How many number of all structurally isomeric dienes with molecular formula C5H8 are possible ?
6. How many cyclic structurally isomeric amines of molecular formula C3H7N are possible?
7. How many structurally isomeric ethers with molecular formula C5H12O are possible?
8. How many structurally isomeric esters with molecular formula C5H10O2 are possible?
9. How many structurally isomeric ketones with molecular formula C6H12O are possible?
10. How many number of all aldehydes (structurally isomeric) with molecular formula C5H10O are possible?
11. How many benzenoid structural isomers are possible for C7H8O ?

CH3
|
12. Observe the compound CH3– CH –CH=CH– CH–CH2–CH3 and answer the given question.
|
COOH
x = Number of carbon atoms in principal carbon chain
y = locant of methyl group
z = locant of C = C
Write your answer as x+y+z.

13. Total number of benzenoid isomers of molecular formula C9H12 would be-
14. How many structural alkenes of formula C2FClBrI are possible ?
15. How many structural isomers can be obtained by the replacement of one hydrogen atom of propene with
chlorine ?
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART - III : ONE OR MORE THAN ONE OPTION CORRECT TYPE

1. Select the pair of compounds having same general formula?

(A) and (B) and

(C) and (D) and H—CºC—CºC—H

2. Which functional groups are not present in given compound ?

(A) Amide (B) Alcohol (C) Amine (D) Aldehyde

3. Select the correct IUPAC name :

(A) Methane-1,1,1,1-tetracarboxylic acid
(B) 5-Carbonyl-heptane-1,7-dioic acid
(C) 2-Chloro ethanoyl chloride
(D) 1-Bromo-3-fluoro-4-methyl cyclohexane
4. Which of the following are correct common names ?

—C—
(A) Acetophenone
O
(B) CH3COCH3 Acetone
(C) PhCOCH3 Benzophenone
COOH
OCOCH3
(D) Aspirin (Acetyl salicylic acid)

5. Which of the following IUPAC name(s) is/are incorrect ?

(A) 4-Chloro-3-methyl cyclopentanol
(B) 1-Amino-3-bromohexan-1-one
(C) 4-chloro-3-methylcyclohexane carboxylic acid
(D) 3-Bromo-1-methylhexan-1-ol

6. Which of the following represent correct pair of homologues ?

(A) & (B) Me–OH & MeCH2CH2OH

(C) & (D) CH3–CH2–NH2 &

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
7. Which of the following IUPAC names are correct?

(A) 2-Methylcyclopentanecarboxamide.

(B) Cyclohexanoyl chloride.

(C) 2-Methylcyclobutanecarbonitrile

(D) Methyl 2-bromocyclohexanecarboxylate

8. Which of the following pairs of structures represent the constitutional isomers ?

(A) CH2=CHCH2CH3 and

(B) CH3OCH2CH3 and

(C) (CH3)3CCH2CH2CH2OH and (CH3)2 CHCH2OCH2CH2CH3

(D) CH2ClCHClCH2CHO and CHCl2CH=CH–CH2–OH

9. Which of the following is/are the correct relationship ?

NH2
NHCH3 CH2 – CH2 – NH2 CH2 – NHC2H5
CH3 CH3

CH3 CH3 CH3

CH3
I II III IV
(A) I & II are functional isomers. (B) II & IV are metamers.
(C) I & IV are position isomers. (D) I & III are chain isomers.

10. Which of the following are functional isomers of methyl ethanoate ?

O O O
|| || ||
(A) CH3 – CH2 – COOH (B) CH3 C (C) CH3 – O – CH 2 – C – H (D) CH2 – C – CH3
CH H |
| OH
OH
11. Which of the following can be the isomer(s) of C8H8O ?

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

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART - IV : COMPREHENSION
Comprehension # 1 (Questions 1 to 3)
A saturated hydrocarbon (P) has six membered ring. Three alkyl groups attached to the ring are alternate
to each other.
(i) First group has only two carbon atoms.
(ii) Second group has four carbon atoms and its all hydrogen atoms are chemically same.
(iii) Third group has total five carbon atoms. Its main chain contains three carbon atoms with ethyl as a
substituent.
1. How many 3° hydrogen atoms are present in the hydrocarbon (P) ?
(A) 2 (B) 3 (C) 4 (D) 5
2. How many 2º carbon atoms are present in the compound (P)?
(A) 10 (B) 12 (C) 6 (D) 8
3. IUPAC name of hydrocarbon (P) is
(A) 1–(1–Ethylpropyl)–3–ethyl–5–(1,1–dimethylethyl)cyclohexane
(B) 1–Ethyl–3–(1–ethylpropyl)–5–(1,1–dimethylethyl)cyclohexane
(C) 1–(1,1–Dimethylethyl)–3–ethyl–5–(1–ethylpropyl)cyclohexane
(D) 1–(1,1–Dimethylethyl)–3–ethyl–5–(2–ethylpropyl)cyclohexane
Comprehension # 2 (Questions 4 to 6)
There are three isomeric compounds P, Q, R with molecular formula C4H6O3. Compound P is a saturated
hydroxy carboxylic acid compound Q is a symmetrical anhydride while R is an aldehydic ester.

4. Which of the following is P ?

(A) (B)

(C) (D)

5. Which of the following is the metamer of Q ?

(A) (B)

(C) (D)

6. Which of the following is R ?

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

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART- I : JEE ADVANCE PROBLEMS (PREVIOUS YEARS)

1. The IUPAC name of the following compound is : [IIT-JEE-2009]

(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile

(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile

2. The total number of cyclic isomers possible for a hydrocarbon molecular formula C4H6 is / are :

3. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [IIT-JEE 2012]
(A) sp and sp3 (B) sp and sp2 (C) only sp3 (D) sp2 and sp3

4. The carboxyl functional group (– COOH) is present in : [IIT-JEE 2012]

(A) picric acid (B) barbituric acid (C) ascorbic acid (D) aspirin

5. The IUPAC name(s) of the following compound is(are) : [JEE. Adv 2017]

H3 C Cl

(A) 4-methylchlorobenzene (B) 4-chlorotoluene

(C) 1-chloro-4-methylbenzene (D) 1-methyl-4-chlorobenzene

PART - II : JEE MAIN PROBLEMS (PREVIOUS YEARS)

1. The IUPAC name of is : [AIEEE-2007]

(1) 5, 5-Diethyl-4, 4-dimethylpentane (2) 3-Ethyl-4,4-dimethylheptane

(3) 1, 1-Diethyl-2, 2-dimethylpentane (4) 4, 4-Dimethyl-5, 5-diethylpentane

2. 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

3. The IUPAC name of neopentane is : [AIEEE-2009]

(1) 2, 2-dimethylpropane (2) 2-methylpropane
(3) 2, 2-dimethylbutane (4) 2-methylbutane
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
4. Aspirin is known as : [AIEEE 2012]
(1) Acetyl salicylic acid (2) Phenyl salicylate
(3) Acetyl salicylate (4) Methyl salicylic acid

5. The IUPAC name of the following compound is : [JEE Main 2018]

(1) 4-methyl-3-ethylhex-4-ene (2) 4,4-diethyl-3-methylbut-2-ene

(3) 3-ethyl-4-methylhex-4-ene (4) 4-ethyl-3-methylhex-2-ene

6. What is the IUPAC name of the following compound ? [JEE Main (Jan)-2019]

CH3 CH3
H
H
CH3 Br

(1) 3-Bromo-1,2-dimethylbut-1-ene (2) 4-Bromo-3-methylpent-2-ene

(3) 2-Bromo-3-methylpent-3-ene (4) 3-Bromo-3-methyl-1,2-dimethylprop-1-ene

7. The correct IUPAC name of the following compound is : [JEE Main (April)-2019]

(1) 5-chloro-4-methyl-1-nitrobenzene (2) 2-methyl-5-nitro-1-chlorobenzene

(3) 3-chloro-4-methyl-1-nitrobenzene (4) 2-chloro-1-methyl-4-nitrobenzene

8. The IUPAC name of the following compound is : [JEE Main (April)-2019]

CH3
H 3C CH

CH3
CH2

(1) 3,5-dimethyl-4-propylhept-6-en-1-yne (2) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

(3) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene (4) 3,5-dimethyl-4-propylhept-1-en-6-yne
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

ANSWER KEY
Exercise # 1

PART - I
A-1. (a) (1°, 2°, 3°) H atoms = (9, 4, 1) (b) (1°, 2°, 3°) H atoms = (3, 10, 1)
(c) (1°, 2°, 3°) H atoms = (6, 16, 0) (d) (1°, 2°, 3°) H atoms = (0, 18, 4)
A-2. (a) 2° (b) 3° (c) 1°
A-3. (a) 1° (b) 2° (c) 3° (d) 3°
A-4. (a) 3° carbon (b) 2° carbon (c) 4° carbon
A-5. 11
A-6. (a) 22 s bonds (b) 19 s bonds, 5p bonds
A-7. 7
2
sp sp sp2 3
sp sp sp sp 3 sp
2

A-8. CH 2= C = CH – CH2 – C º C – CH 2– COOH

A-9. H2C = C = CH2 ; M.W. = 40.

A-10. (a) Homocyclic, alicyclic, saturated (b) Homocyclic, aromatic, unsaturated
(c) Heterocyclic, alicyclic, saturated (d) unsaturated.
B-1. (a) 2-Methyl propane (b) 2, 2-Dimethyl propane
(c) 2-Methyl butane (d) 2, 2-Dimethyl butane
B-2. (a) isopropyl group (b) sec-butyl group (c) Tert-butyl group
(d) Ethyl group (e) n-propyl group
B-3. (a) 2,2,3-Trimethylpentane (b) 5-(1,2-Dimethylpropyl)nonane
(c) 5-Ethyl-3-methyloctane (d) 4-Ethyl-2,2,6-trimethylheptane
(e) 4-Ethyl-3, 7-dimethylnonane (f) 4-(1,1-Dimethylethyl)-5-(1-methylethyl) octane
B-4. (a) 1-methylethyl (b) 1-methylpropyl (c) 1, 2-dimethylpropyl (d) 2, 3-dimethylbutyl
B-5. (a) 1-Bromo-3-chloro-4-methylpentane (b) 1-Chloro-3-ethyl-4-iodopentane
(c) 4-Bromo-3-chloro-6-nitrooctane (d) 2-Bromo-2-chloro-5-fluoro-4-methylheptane
B-6. (a) s-Butylcyclohexane (b) t-Butylcyclohexane
(c) Isopropylcyclohexane (d) Neopentylcyclopentane
B-7. (a) ring (b) side chain (c) ring (d) ring (e) side chain (f) side chain
B-8. 7
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

B-9. (a) (b)

(c) (d)

C-1. (a) Pent-2-ene (b) But-1-yne

(c) 3-Methylbut-1-ene (d) 4–Ethyl–2–methylhex-1-ene
C-2. (a) ethenyl (b) ethynyl (c) 1-methylethenyl (d) prop-2-enyl
(e) ethylidene (f) 1-methylethylidene
C-3. General formula ® CnH2n
H2C = CH2 Ethylene Ethene
CH3–CH=CH2 Propylene Propene
CH3–CH2–CH=CH2 a-Butylene 1-Butene
C-4. General formula ® CnH2n–2
(A) CH º CH Acetylene Ethyne
(B) CH3–CºCH Methyl acetylene (Allylene) Propyne
(C) CH3–CºC–CH3 Dimethyl acetylene (Crotonylene) But-2-yne

1 2 3 4 5
C-5. (a) (b) (c) CH3 –C C–CH–CH3
CH3
4-Methylpent-2-yne
C-6. (a) 4-Methylpent-2-yne (b) 4-Propylhept-2-yne (c) 3,4,4-Trimethylhex-1-yne
C-7. (a) cyclohexylethene (b) 1-Ethylcyclohex-1-ene
(c) 1-Ethenylcyclohex-1-ene (d) 1-cyclohex-1-enylbuta-1,3-diene
C-8. 3
3-Bromo-6-ethylcyclohexa-1, 4-diene
C-9. 5
5-Ethyl-2,6-dimethyl-4-(3-methylbutyl)oct-2-ene

D-1. Seniority order of functional groups :

–COOH > –CN > –CHO > > –OH > –NH2

D-2. 6

–CHO , , –NH2 , , –COOH , are functional group present.

JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
D-3. (a) 4-Methylpent-2-en-1-ol (b) 4, 5–Dimethylhex–5–ene–2–thiol
(c) N,N-Dimethylpropan-2-amine (d) 1-Chloro - 4 - methylpentan - 2 - one
(e) Methoxyethane (f) Ethoxyethane

D-4. (a) (b) (c) (d)

D-5. (a) 3-Chlorobutan-2-ol

(e) 5-Oxoheptane-3-sulphonic acid.

E-1. (a) (b)

(c) (d)

E-2. (a) Methyl-2-ethylbutanoate

(b) Ethyl-3-methylpent-4-en-1-oate
(c) 3,3 Dimethyl –2 – (1–methylethyl)butanamide
E-3. 7
E-4. 9 + 6 = 15
X = 9, Y = 6
4-(But-2-enyl)non-6-enoic acid

F-1. (a) Methylbenzene (b) Isopropylbenzene

(c) Diphenylmethane (d) 1-Chloro-1-phenylethane.
F-2. (a) 5-Formyl-2-nitrobenzoic acid (b) 4-Ethoxycarbonylbenzoic acid
(c) 4-Nitroaniline (d) 3-Methylphenol
F-3. 3
(a) Cyclohexylbenzene (b) 4-Bromo-3, 6-diphenyloctane
(c) 1, 2-Dichloro-4-ethyl-5-nitrobenzene (d) 4-Chloro-1-nitro-2-propylbenzene
F-4. (a) Ethanoic-2-methylpropanoic anhydride (b) Benzenecarboxylic anhydride
(c) Pent-2-enedioic anhydride (d) Cyclohexane-1, 2-dicarboxylic anhydride
F-5. (a) Methyl methanoate (b) 2-Ethoxycarbonylethanoic acid
(c) Phenyl benzenecarboxylate (d) 2-Ethanoyloxybenzenecarboxylic acid
F-6. (a) 2-Methylpropanamide (b) N-Methylpropanamide
(c) N, N-Dimethyl-2-methylpropanamide (d) N-Phenylbenzenecarboxamide
F-7. 2
f and g are correct.
G-1. (a) Chain isomers (b) Functional isomers (c) Homologs.
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism
G-2. (a) I, II & III are functional isomers
(b) I, & II are position isomers, (I or II) & III are functional isomers.
(c) I, II & III are functional isomers
(d) I & II are chain isomers, I & III are chain isomers and II & III are position isomers
G-3. 1 & 2 are position isomers, 1 & 3 are position isomers, 2 & 3 are position isomers.
G-4. 6

(c) and Chain isomers

H-1. 9
H-2. 11
DU = Number of p-bond (unsaturation) + Number of cyclic ring present = 9 +2 = 11

O O
p bond of cyanide group R–CºN, aldehydic group R-C-H & ketonic group R-C-R are also considered.

H-3. 4, Metamers

H-4. or

H-5. (i) CH3–O–CH2–CH2–CH2–CH3 (ii)

(iii) (iv)

(v) CH3–CH2–O–CH2–CH2–CH3 (vi)

PART - II
A-1. (B) A-2. (B) A-3. (B) A-4. (A) A-5. (A)
A-6. (C) A-7. (C) A-8. (D) A-9. (C) A-10. (D)
B-1. (D) B-2. (D) B-3. (D) B-4. (A) B-5. (C)
B-6. (B) B-7. (A) B-8. (C) C-1. (A) C-2. (D)
C-3. (C) C-4. (B) C-5. (D) C-6. (B) C-7. (B)
C-8. (B) C-9. (B) D-1. (C) D-2. (B) D-3. (D)
D-4. (C) D-5. (B) D-6. (B) D-7. (B) E-1. (D)
E-2. (B) E-3. (B) E-4. (C) E-5. (C) E-6. (C)
E-7. (A) E-8. (D) E-9. (B) F-1. (C) F-2. (B)
F-3. (B) F-4. (C) F-5. (C) F-6. (A) G-1. (C)
G-2. (A) G-3. (C) G-4. (D) G-5. (A) G-6. (C)
G-7. (D) H-1. (C) H-2. (B) H-3. (B) H-4. (B)
H-5. (B) H-6. (D) H-7. (B) H-8. (D)
JEE (Adv.)-Chemistry IUPAC Nomenclature & structural Isomerism

PART - III
1. (A – p), (B – p,q), (C – p,r), (D – s)
2. (A – p), (B – p), (C – r), (D – q)

Exercise # 2

PART - I

1. (D) 2. (A) 3. (D) 4. (A) 5. (A)

6. (B) 7. (D) 8. (B) 9. (B) 10. (C)
11. (B) 12. (A) 13. (C) 14. (D) 15. (A)
16. (C) 17. (D)

PART - II

1. 6 2. 4 3. 5 4. 3 5. 6
6. 4 7. 6 8. 9 9. 6 10. 4
11. 5 12. 14 13. 8 14. 3 15. 3

PART - III

1. (AD) 2. (CD) 3. (AC) 4. (BD) 5. (ABD)

6. (BC) 7. (ACD) 8. (ACD) 9. (ABD) 10.
(ABCD)
11. (BCD)

PART - IV
1. (C) 2. (C) 3. (C) 4. (D) 5. (B)
6. (B)

Exercise # 3

PART - I
1. (B) 2. 5 3. (B) 4. (D) 5. (B,C)

PART - II

1. (B) 2. (D) 3. (A) 4. (A) 5. (D)

6. (B) 7. (D) 8. (D)