Resonance Iupac Ques Bank

IUPAC Nomenclature and Structural Isomerism
 Marked Questions may have for Revision Questions.


PART - I : SUBJECTIVE QUESTIONS

-I: SUBJECTIVE QUESTIONS
Section (A) : Fundamental of Organic Chemistry

(A) :
A-1. Write the number of  and  bonds in the following molecules ?
  ?
(a) (b) (c)
Sol. (a) 19  bonds, 6 bonds(b) 22  bonds (c) 20  bonds

(a) 19  , 6 (b) 22  (c) 20 
A-2. Find the number of 1°, 2° & 3° hydrogen atoms in the following compounds
1°, 2° 3°
(a) (b) CH3–CH2–CH3 (c) CH3–CH2–CH2–CH3
Sol. (a) 1° H  9, 3° H  1 (b) 1°H  6, 2°H  2 (c) 1°H  6, 2°H  4

A-3. Find the hybridization state of each carbon atoms in following compound ?
CH2 = C = CH – CH2 – C  C – CH2 – NH2

Ans.
A-4. Expand each the following condensed formulae into their complete structural and bond line formulae :
(1) HOCH2CH2NH2 (2) CH3(CH2)3OH (3) CH3CH2COCH2CH3 (4) CH3CH=CH(CH2)3CH3
Ans. (1) H2N–CH2–CH2–OH and
(2) CH3 – CH2 – CH2 – CH2 – OH and
(3) and
(4) CH3 – CH = CH – CH2 – CH2 – CH2 – CH3 and

A-5. Find DU of following compound :-
(D.U.)
(a) C5H10 (b)
Ans. (a) = 1, (b) = 5

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ADVIUPSI -1
A-6. Find DU of following compound :-
(a) C6H6O (b) C6H5I (c) C5H9N

Ans. (a) 4, (b) 4, (c) 2
A-7. Draw formulae for the first four members of each homologous series begining with the following.
(a) H–COOH (b) H–CH=CH2 (c)

Sol. (a) H–COOH, CH3–COOH, CH3–CH2–COOH , CH3–CH2–CH2–COOH
(b) CH2=CH2, CH3–CH=CH2, CH3–CH2–CH=CH2, CH3–CH2–CH2–CH = CH2
(c) CH3–CO–CH3, CH3–CO–C2H5, C2H5–CO–C2H5,C3H7–CO–C2H5
A-8. Classify the following compounds as homocyclic, heterocyclic, alicyclic, aromatic, saturated and
unsaturated.
(a) (b) (c) (d)
Ans. (a) Homocyclic, alicyclic, saturated (b) Homocyclic, aromatic, unsaturated

(c) Heterocyclic, alicyclic, saturated (d) unsaturated.
(a) (b)
(c) (d)
A-9. Indicate the following as 1°, 2° and 3° amines.
1°, 2° 3° ?
(a) (b) (c) N (d)
Sol. (a) 2° (b) 2° (c) 3° (d) 3°

A-10. Indicate the following as 1°, 2° and 3° alcohol.
1°, 2° 3° ?
(a) (b) (c)
Sol. (a) 2° (b) 3° (c) 1°
Section (B) : IUPAC-Nomenclature of Alkane & Cycloalkane

(B) : IUPAC-
B-1. Write IUPAC name of the following compounds :
IUPAC
(a) (b) (c)
Sol. (a) 2-Methyl propane (b) 2, 2-Dimethyl propane (c) 2, 2-Dimethyl butane
(a) 2- (b) 2, 2- (c) 2, 2-
ADVIUPSI -2
B-2. Write IUPAC name of the following compounds:-
IUPAC :
(a) (b)
Sol. (a) 5-Ethyl-3-methyloctane (b) 4-Ethyl-2,2,6-trimethylheptane

(a) 5- -3- (b) 4- -2,2,6-
B-3. Write correct IUPAC name of the following
IUPAC :
(i) (ii) (iii) (iv)
Sol. (i) (ii)
(iii) (iv)
1- 1- -2-
B-4. Write the correct IUPAC name of the following compounds. ( IUPAC )
CH3
|
(i) CH3 — CH2 — CH2 — CH2 — CH2 — CH — C — CH2CH3
| |
CH3 CH2 — CH2 — CH3
(ii)
Ans. (i) 4-Ethyl-4,5-dimethyldecane (4- -4,5-

(ii) 4-(1,1-Dimethylethyl)-5-(1-methylethyl) octane (4-(1,1- )-5-(1- )
B-5. Write structures of the following IUPAC name.
IUPAC
(i) 1, 3-Dicyclopentyl propane (ii) 1-Methyl-4-propylcyclohexane
(iii) 2-Ethyl-1,1-dimethylcyclopentane
(i) 1, 3- (ii) 1- -4-
(iii) 2- -1,1-
ADVIUPSI -3
Sol. (i) (ii) (iii)
B-6. Write IUPAC names of the following hydrocarbon (use common naming for hydrocarbon groups.)
IUPAC
(a) (b) (c) (d)
Sol. (a) s-Butylcyclohexane (b) t-Butylcyclohexane

(c) Isopropylcyclohexane (d) Neopentylcyclopentane
(a) s- (b) t-
(c) (d)
B-7. Identify the parent chain in the following compounds as ring or side chain.
(a) (b) (c)
(d) (e) (f)
Ans. (a) ring (b) side chain (c) ring (d) ring
(e) side chain (f) side chain
(a) (b) (c) (d)
(e) (f)
B-8. Write the common name of the following alkyl groups.
(a) (b) (c)
(d) –CH2–CH3 (e) CH3–CH2–CH2–

Sol. (a) Isopropyl group (b) Secondary–butyl group (c) Tertiary-butyl group (d) Ethyl group
(e) n-propyl group
(a) (b) (c) (d)
(e) n-
Section (C) : IUPAC-Nomenclature of Alkene, Cycloalkene, Polyenes & Alkyne

(C) : IUPAC-
C-1. Write the general formula of alkenes. Give IUPAC names of first three members.
IUPAC
ADVIUPSI -4
Sol. General formula  CnH2n
 CnH2n
H2C = CH2 Ethene
CH3–CH=CH2 Propene
CH3–CH2–CH=CH2 1-Butene 1-
C-2. Write IUPAC name of the following :
IUPAC
(i) (CH3)3 C – CH = CH2 (ii) CH2 = CH – CH = CH2
(iii) (iv)
Sol. (i) (ii)
(iii) (iv)
C-3. Draw the bond line structures of the following compounds.

(a) 2-Methylhept-3-ene (b) 2,6-Dimethylhepta-1, 5-diene
(a) 2- -3- (b) 2, 6– -1, 5-
Ans. (a) (b)
C-4. Write IUPAC name of the following

IUPAC
(i) (ii) (iii)
Ans. (i) 5-Methylhexyne (ii) 3-Methylbutyne (iii) 4-Methylpent-2-yne

(i) 5- (ii) 3- (iii) 4- -2-
C-5. Draw structure of following IUPAC names.
IUPAC
(i) Hexa-2,4-diyne ( –2,4– ) (ii) Pent-3-ene-1-yne ( -3- -1- )
(iii) Pent-1-en-4-yne ( -1- -4- ) (iv) Pent-1-en-3-yne ( -1- -3- )
ADVIUPSI -5
Sol. (i) (ii)
–2,4–
(iii) (iv)
C-6. Write the IUPAC name of the following ( IUPAC )
(i) (ii)
(iii) (iv)
Sol. (i) (ii) 1–(Hex–3–enyl)cyclohex–1–ene (1–( –3– ) –1–
1-
(iii) (iv)
3- -6-
Section (D) : IUPAC Nomenclature of non-chain terminating functional groups

(D) : IUPAC-
D-1. Write the IUPAC names of the following compounds.
IUPAC
(a) (b) (c) (d)
(e) (f) (g) (h)
Sol. (a) 3-Chlorobutan-2-ol (3- -2- )

(b) 2-Ethylbut-3-en-1-ol (2- -3- -1- )
(c) 5-Aminomethyl-3-ethylheptan-2-ol (5- -3- -2- )
(d) 3-Butylpentane-2,4-dione (3- -2,4- )
(e) 5-Oxoheptane-3-sulphonic acid. (5- -3- )
(f) 3-(2-Bromoethyl)hexan-2-ol (3-(2- ) -2- )
(g) 2,5-Dichloro-3-ethoxy-4-methoxyhexane (2,5- -3- -4- )
(h) 3-Bromo-4-methylpentane-2-sulphonic acid (3- -4- -2-
ADVIUPSI -6
D-2. Draw the structures of each of the followings.
(a) Butan-1-ol (b) Butane-2-thiol
(c) Pentan-2-amine (d) Pentan-2-one
(e) 3-Chloropentan-1-ol (f) Hexan-2,4-dione
(a) -1- (b) -2-

(c) -2- (d) -2-
(e) 3- -1- (f) -2,4-
Sol. (a) CH3–CH2–CH2–CH2–OH (b) CH3–CH(SH)–CH2–CH3
(c) CH3–CH(NH2)–CH2–CH2–CH3 (d) CH3–CO–CH2–CH2–CH3
(e) HO–CH2–CH2–CH(Cl)–CH2–CH3 (f) CH3–CO–CH2–CO–CH2–CH3
Section (E) : IUPAC Nomenclature of chain terminating functional groups

(E) : IUPAC-
E-1. Select the longest continous carbon chain in each of the following molecules.
(a) (b) (c) (d)
(e) (f) (g) (h)
Sol. (a) (b) (c) (d)
(e) (f) (g) (h)
E-2. Write the structure of the following compounds :

(a) 3-Hydroxypentane-2-sulphonic acid. (b) 3-Chloromethylpentanoic acid
(c) 3-Bromobutanoyl chloride (d) Cyclohexyl ethanoate
(e) Phenyl ethanoate (f) 2-Chloroethyl propanoate
(g) Diethyl pentanedioate
(a) 3- -2- (b) 3-

(c) 3- (d)
(e) (f) 2-
(g)
Ans. (a) CH3–CH(SO3H)–CH(OH)–CH2–CH3 (b)
(c) (d) (e)
(f) CH3–CH2–COOCH2–CH2–Cl (g)
ADVIUPSI -7
E-3. Write the structure of the following compounds :
(a) Butanamide (b) N-methylethanamide
(c) Cyclopropanecarboxylic anhydride (d) Cyclopropylbutanoate
(a) (b) N-
(c) (d)
Ans. (a) (b)
(c) (d)
E-4. Write IUPAC Name ( IUPAC ):
(a) (b) (c)
Sol. (a) Methyl-2-ethylbutanoate (b) Ethyl-3-methylpent-4-en-1-oate

( -2- ) ( -3- -4- -1-
(c) 3,3 Dimethyl –2 – (1–methylethyl)butanamide (3,3- -2-(1-
E-5. Write IUPAC names of following compounds.

IUPAC
(a) (b) (c) (d)
Ans. (a) Ethanoic 2-methylpropanoic anhydride (b) Benzenecarboxylic anhydride

(c) Pent-2-enedioic anhydride (d) Cyclohexane-1, 2-dicarboxylic anhydride
(a) -2- (b)
(c) -2- (d) -1, 2-
E-6. Write IUPAC names of following compounds.

IUPAC
(a) (b)
(c) (d)
Ans. (a) 2-Methylpropanamide (b) N-Methylpropanamide

(c) N, N-Dimethyl-2-methylpropanamide (d) N-Phenylbenzenecarboxamide
(a) 2- (b) N-
(c) N, N- -2- (d) N-
ADVIUPSI -8
Section (F) : IUPAC-Nomenclature of Aromatic compounds
(F) : IUPAC-
F-1. Write IUPAC name of the following :
IUPAC
(a) (b) (c) (d)
Ans. (a) Methylbenzene (b) Isopropylbenzene

(c) Diphenylmethane (d) 1-Chloro-1-phenylethane.
Ans. (a) (b)
(c) (d) 1- -1-
F-2. Write the correct IUPAC name of the following :
IUPAC
(a) (b) (c) (d)
Ans. (a) Cyclohexylbenzene (b) 4-Bromo-3, 6-diphenyloctane

(c) 1, 2-Dichloro-4-ethyl-5-nitrobenzene (d) 4-Chloro-1-nitro-2-propylbenzene
(a) (b) 4- -3, 6-
(c) 1, 2- -4- -5- (d) 4- -1- -2-
F-3. Write common & IUPAC name of following structure:

IUPAC :
(a) (b) (c) (d)
Ans. (a) 1,2–Dimethyl benzene (o–Xylene) (b) Phenylethene (Styrene)

(c) 4–Methyl phenol (p–cresol) (d) 2–Hydroxybenzenecarbaldehyde (Salicylaldehyde)
(a) 1,2– (o– ) (b) ( )
(c) 4– (p– ) (d) 2– ( )
Section (G) : Structural Isomerism

(G) :
G-1. Identify the relationship between the given compounds.
(a) and (b) and
(c) and
ADVIUPSI -9
(a)
(b)
(c)
Sol. (a) Chain Isomers (b) Functional isomers (c) Homologs.

(a) (b) (c)
G-2. Identify the relationship between the given compounds.
(a) & (b) &
(c) &
(d) &
(a) (b)
(c)
(d)
Sol. (a) Chain Isomers (b) Functional isomers (c) Metamers. (d) Position isomers
(a) (b) (c) (d)
Section (H) : Number of Structural Isomers

(H) :
H-1. Draw all structurally isomeric alkenes with molecular formula C4H8.
C4H8
H2C  C – CH3
Ans. H2C = CH – CH2 – CH3, H3C – CH = CH – CH3, |
CH3
H-2. Draw all structurally isomeric 2º chlorides with molecular formula C5H11Cl.
C5H11Cl 2º
ADVIUPSI - 10
Ans. , ,
H-3. Draw all structurally isomeric benzene containing isomers with molecular formula C7H8O.
C7H8O
Ans. , , , ,
H-4. Draw all structurally isomeric cyclic bromides with molecular formula C4H7Br.
C4H7Br2
Ans. , , ,
H-5. The ring chain functional isomer of compound But-2-ene are.

2
Ans. or
PART - II : ONLY ONE OPTION CORRECT TYPE

- II : (ONLY ONE OPTION CORRECT TYPE)
Section (A) : Fundamental of Organic Chemistry

(A) :
A-1. Molecular formula of naphthaquinone is
(A) C12H8O2 (B) C11H6O2 (C*) C10H6O2 (D) C10H8O2
A-2.
ADVIUPSI - 11
Incorrect statement for the above structure :
(A) I, II & III have CnH2n-2 general formula
(B) I , II & III have same empirical formula
(C*) I , II are identical and homologue of compound III.
(D) I, II & III have same molecular formula
(A) I, II III CnH2n-2 (B) I , II III

(C*) I , II III (D) I, II III
A-3. Which of the following is not an alicyclic compound ?
(A) (B) (C) (D*)
A-4. The saturated heterocyclic compound is :
(A) (B) (C*) (D)
A-5. Which of the following compound is unsaturated hydrocarbon ?
(A) (B) CH3–C  N (C) (D*)
Section (B) : IUPAC-Nomenclature of Alkane & Cyclo alkane

(B) : IUPAC-
B-1. The correct IUPAC name of the alkane is :
(A) 2-Ethyl-4-methylhexane (B) 5-Ethyl-3-methylhexane

(C*) 3,5-Dimethylheptane (D) 3,5-Dimethylhexane
IUPAC
(A) 2- -4- (B) 5- -3-

(C*) 3,5- (D) 3,5-
B-2. The correct structure of 6-Ethyl-2,3,5-trimethylnonane is :
6- -2,3,5-
(A*) (B)
(C) (D)
ADVIUPSI - 12
B-3. The correct IUPAC name of the following compound is :
IUPAC
(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.
(A) 1- -1- -2- -2- -1- (B) 3- -4- -4- -3-
(C*) 2- -1- -1- -2- (D) 1- -1- -2- -2- -2-
B-4. A student named a certain compound as 2, 3-diethylbutane. Its correct IUPAC names is
(A) 2, 3-Dimethylhexane (B*) 3, 4-Dimethylhexane
(C) 2-Ethyl-3-methylpentane (D) 2-Ethylbutane
2, 3- IUPAC
(A) 2, 3- (B*) 3, 4-
(C) 2- -3- (D) 2-
B-5. In which of the following compound IUPAC numbering is correct ?

IUPAC ?
(A) (B) (C*) (D)
Section (C) : IUPAC-Nomenclature of Alkene, Alkyne, Cyclo alkene & polyenes

(C) : IUPAC-
C-1. Select the structure with correct numbering in the chain :
(A) (B)
(C) (D*)
C-2. The correct IUPAC name of the compound

(A) 4-Ethylpent-1-ene (B) 2-Ethylpent-4-ene (C*) 4-Methylhex-1-ene (D) 3-Methylhex-1-ene
IUPAC
(A) 4- -1- (B) 2- -4- (C*) 4- -1- (D) 3- -1-
C-3. The correct structure of 2-Ethyl-3-methylhexa-1,4-diene :

2- -3- -1,4- :
(A) (B) (C*) (D)
ADVIUPSI - 13
C-4. The correct IUPAC name of the compound
(A) 1-Ethenylcyclohexa-2, 4-diene (B*) 5-Ethenylcyclohexa-1, 3-diene

(C) 6-Ethenylcyclohexa-1, 3-diene (D) Cyclohexa-2, 4-dienylethene
IUPAC
(A) 1- -2, 4- (B*) 5- -1, 3-

(C) 6- -1, 3- (D) -2, 4-
Section (D) : IUPAC Nomenclature of non-chain terminating functional groups

(D) : IUPAC-
D-1. Which of the following is a correct priority order of functional groups?
(A)
(B*)
(C)
(D)
D-2. The IUPAC name of
Br
|
CH3  CH  CH2  CH2  CH2  C  CH3 is :
| |
OH Br
(A*) 6, 6-Dibromoheptan-2-ol (B) 2, 2-Dibromoheptan-6-ol
(C) 6, 6-Dibromoheptan-2-al (D) None of these
Br
|
CH3  CH  CH2  CH2  CH2  C  CH3 IUPAC
| |
OH Br
(A*) 6, 6- -2- (B) 2, 2- -6-

(C) 6, 6- -2- (D)
ADVIUPSI - 14
D-3. The correct structure of 6-Amino-4-hydroxycylohex-2-ene-1-sulphonic acid.
6- -4- -2- -1-
(A) (B*) (C) (D)
D-4. The correct IUPAC name of the given compound is

IUPAC
(A) 3–Chloro–1–fluoro–1–iodo–4–methoxybut–1–en–3–yne
(B) 4–Methoxy–2–chloro–1–fluoro–1–iodobutenyne
(C) 3–Chloro–4–fluoro–4–iodo–1–methoxybutenyne
(D*) 2–Chloro–1–fluoro–1–iodo–4–methoxybutenyne
(A) 3– –1– –1– –4– –1– –3–

(B) 4– –2– –1– –1–
(C) 3– –4– –4– –1–
(D*) 2– –1– –1– –4–
Section (E) : IUPAC-Nomenclature of chain terminating Functional groups

(E) : IUPAC-
E-1. The IUPAC name of the following is :
CH3 CH  CH  CH 2  CH  CH2COOH
|
NH 2
(A*) 3-Aminohept-5-enoic acid (B) 5-Aminohex-2-enecarboxylic acid
(C) 3-Aminohept-4-enoic acid (D) 5-Aminohept-2-enoic acid
IUPAC
CH3 CH  CH  CH2  CH  CH2COOH
|
NH2
(A*) 3- -5- (B) 5- -2-
(C) 3- -4- (D) 5- -2-
E-2. 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
(A) 2, 3- (B) 3- -2- -3-

(C*) 3- -2- -3- (D) 2, 3-
ADVIUPSI - 15
E-3. The correct IUPAC name of compound is :
(A) 1-Chloropentane-1, 4-dione (B) 4-Chlorocarbonylbutan-2-one

(C*) 4-Oxopentanoyl chloride (D) 3-Oxobutanecarbonyl chloride
IUPAC
(A) 1- -1, 4- (B) 4- -2-

(C*) 4- (D) 3-
E-4. The correct IUPAC name of following compound is
IUPAC
(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
(A) 4- -3- -5- -1-
(B) 2- -5- -3- -1-
(C*) 4- -5- -2- -1-
(D) 3- -4- -5- -1-
E-5. IUPAC name of given compound is :

IUPAC
(A) 3- Carbonitrile-3-methyl butanal (B) 3-Formyl-2-methyl propne nitrile

(C) 3-Cyanobutanal (D*) 2-Methyl-4-oxobutane nitrile]
(A) 3- -3- (B) 3- -2-
(C) 3- (D*) 2- -4-
E-6.
The IUPAC name of the compound is :

(A*) Propanoic anhydride (B) Dipropanoic anhydride
(C) Ethoxy propanoic acid (D) 1-Oxopropyl propanoate
ADVIUPSI - 16
IUPAC
(A*) (B)
(C) (D) 1-
E-7. The IUPAC name of the compound is :
(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride

(C) Cyclobutanedicarboxylic anhydride (D*) Butanedioic anhydride
IUPAC
(A) (B)
(C) (D*)
E-8. The correct IUPAC name of following compound is :
IUPAC
(A) Methyl -2-ethylpropanoate (B) Methyl butane-2-carboxylate

(C*) Methyl- 2-methylbutanoate (D) Methoxypentanone
(A) -2- (B) -2-
(C*) -2- (D)
E-9. IUPAC name of the compound BrCH2  CH  CO  CH2  CH2CH3 is

|
CONH2
(A*) 2-Bromomethyl-3-oxohexanamide (B) 1-Bromo-2-amido-3-oxohexane
(C) 1-Bromo-2-amido-n-propylketone (D) 3-Bromo-2-proponyl-propanamide
BrCH2  CH  CO  CH2  CH 2CH3 IUPAC
|
CONH2
(A*) 2- -3- (B) 1- -2- -3-
(C) 1- -2-- -n-- (D) 3- -2- -
Section (F) : IUPAC-Nomenclature of Aromatic compounds

(F) : IUPAC-
ADVIUPSI - 17
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
IUPAC
(A) 5- -3- (B) 3- -5-

(C*) 3- -5- (D) 1- -3- -5-
F-2. IUPAC name of
(A) 4-Chlorophenyl benzoate. (B*) Phenyl-4-chlorobenzenecarboxylate.
(C) Benzyl-4-chlorobenzenecarboxylate. (D) 4-Chloro diphenylcarboxylate.
IUPAC
(A) 4- (B*) -4-

(C) -4- . (D) 4-
F-3. The correct IUPAC name of the compound.

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

(C*) N–(4-chlorophenyl)methanamide (D) N–(Parachlorophenyl)–N–formylaniline
(A) N– -4- (B) N– -4-

(C*) N–(4- ) (D) N–( )–N–
F-4. IUPAC name of the compound is
(A) 2-Chlorocarbonyl ethylbenzenecarboxylate (B) 2-Carboxyethylbenzoyl chloride

(C*) Ethyl 2-(chlorocarbonyl)benzenecarboxylate (D) Ethyl 1-(chlorocarbonyl)benzenecarboxylate
IUPAC
(A) 2- (B) 2-
(C*) 2-( ) (D) 1-( )
ADVIUPSI - 18
F-5. The correct IUPAC name of the compound
(A*) 2-Phenoxycarbonylbenzenecarboxylic acid (B) Phenyl-2-carboxybenzenecarboxylate

(C) 2-Benzoyloxybenzenecarboxylic acid (D) 2-Benzyloxycarbonylbenzenecarboxylic acid
IUPAC
(A*) 2- (B) 2-
(C) 2- (D) 2-
Section (G) : Structural Isomerism

(G) :
G-1. Isomers have essentially identical.
(A) Structural formula (B) Chemical properties (C*) Molecular formula (D) Physical properties
(A) (B) (C*) (D)

G-2. Compound with same molecular formula but different structural formula are called.
(A*) Isomers (B) Isotopes (C) Isobars (D) Isoelectric
(A*) (B) (C) (D)
G-3. What is the correct relationship between the following compounds ?
CH3  CH2  CH  CH2  CH3 , CH3  CH2  CH2  CH2  CH2

| |
CH3 CH3
(A*) Chain isomers (B) Position isomers (C) Functional isomers (D) Identical
(A*) (B) (C) (D)
G-4. What is the relation between 3-Ethylpentane and 3-Methylhexane ?

(A*) Chain isomers (B) Position isomers (C) Functional isomers (D) Relation
3- 3-
(A*) (B) (C) (D)
G-5. CH3 – CH2 – NH – CHO ; CH3  CH  CHO

|
NH2
Which type of isomerism is observed between and .

(A) Chain isomers (B) Position isomers (C*) Functional isomers (D) Metamers
CH3 – CH2 – NH – CHO ; CH3  CH  CHO
|
NH2
(A) (B) (C*) (D)

G-6. Molecular formula C4H10O represent
(A) Two primary alcohol (B) One secondary alcohol
(C) One tertiary alcohol (D*) All of these
ADVIUPSI - 19
C4H10O
(A) (B)
(C) (D*)
Section (H) : Number of Structural Isomers

(H) :
H-1. How many positional isomers are possible for dimethylcyclohexane ?
(A) 3 (B*) 4 (C) 5 (D) 6

H-2. How many aromatic isomers are possible for trichlorobenzene (C6H3Cl3) ?
(C6H3Cl3)
(A) 2 (B*) 3 (C) 4 (D) 5
H-3. The number of ether isomers represented by formula C4H10O is (only structural)
C4H10O ( )
(A) 4 (B*) 3 (C) 2 (D) 1
H-4. Total number of 2° amine isomers of C4H11N would be (only structural)
C4H11N 2° ( )
(A) 4 (B*) 3 (C) 5 (D) 2
H-5. How many structural isomers of all the tertiary alcohols with molecular formula C6H14O.
C6H14O
(A) 2 (B*) 3 (C) 4 (D) 5
H-6. The number of structural isomers for C5H10 are :
C5H10
(A) 8 (B) 6 (C) 9 (D*) 10
H-7. The number of acyclic isomers of C3H5Cl are :
C3H5Cl
(A) 1 (B) 2 (C*) 3 (D) 4
H-8. The number of cyclic ketones of molecular formula C3H4O are :
C3H4O
(A) 2 (B*) 1 (C) 3 (D) 4
H-9. The number of cyclic isomers of molecular formula C3H4Cl2 are :
C3H4Cl2
(A) 1 (B*) 2 (C) 3 (D) 4
H-10. The number of structural isomers of for C4H9Cl are :
C4H9Cl
(A) 1 (B) 2 (C) 3 (D*) 4
ADVIUPSI - 20
PART - III : MATCH THE COLUMN

- III : (MATCH THE COLUMN )
1. Match the following :

Column-I Column-II
(A) and (p) Homologs
(B) and (q) Functional isomers.
(C) and (r) Chain isomers.
(D) and (s) Have same general formula
(t) Have same empirical formula.
-I -II
(A) (p)
(B) (q)
(C) (r)
(D) (s)
(t)
Ans. (A  p,s) ; (B  q,s,t) ; (C  r,s,t) ; (D  q,s,t)
ADVIUPSI - 21
2._ Match the following :
Column-I (Benzene derivative molecular formula) Column-II (No. of aromatic structural Isomers)
(Here  X, Y, Z monovalent substituents)
-I ( ) -II ( )
(  X, Y, Z )
(A) C6H4X2 (p) 5

(B) C6H4XY (q) 3
(C) C6H4X3 (r) 4
(D) C6H3X2Y (s) 6
(E) C6H3XYZ (t) 10
Ans. (A  q) ; (B  q) ; (C  q) ; (D  p) ; (E  t)
ADVIUPSI - 22
PART - I : ONLY ONE OPTION CORRECT TYPE

-I: (ONLY ONE OPTION CORRECT TYPE)
1. 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, 6-Dimethyl-4-(1-methylene tertiary butyl) nonane
(D) 6, 6-Dimethyl-2-propyl-4-(1-methylpropyl) heptane
IUPAC
(A*) 2, 2, 5- -4-(1- )
(B) 4, 8, 8- -6-(1- )
(C) 3, 6- -4-(1- )
(D) 6, 6- -2- -4-(1- )
2. In the structure of 4-Isopropyl-2,4,5-trimethylheptane, number of 10, 20 & 30 H’s are respectively.

4- -2,4,5- 10, 20 30
(A) 18, 5, 4 (B*) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4
3. 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
IUPAC
(A*) 1, 4- -2- -5- (B) 1, 4- -5- -2-

(C) 2, 5- -1- -4- (D) 2, 5- -4- -1-
ADVIUPSI - 26
4. IUPAC nomenclature of the given organic compound will be : (CH3)2C(CH2CH3)CH2CH(Cl)CH3 :
(A) 5-Chloro 3, 3-dimethyl hexane (B) 4-Chloro-2-ethyl-2-methyl pentane
(C) 2-Chloro-4-ethyl-4-methyl pentane (D*) 2-Chloro-4, 4-dimethyl hexane
IUPAC (CH3)2C(CH2CH3)CH2CH(Cl)CH3
(A) 5- 3, 3- (B) 4- -2- -2-
(C) 2- -4- -4- (D*) 2- -4, 4-
5. The correct IUPAC numbering in the compound is :
IUPAC
(A) (B) (C) (D*)
6. 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
IUPAC
(A) 1- -2- (B*) 3- -1-

(C) 2- -1- (D) 3- -1-
7. Correct IUPAC name of the following compound is
(A*) 2-Amino-3-Formyl butane-1,4-dioic acid (B) 2-formyl-3-amino butane-1,4-dioic acid

(C) 3-Amino-2-formyl butane-1,4-dioic acid (D) 2-Amino-3-carboxy-4-oxo butanoic acid
IUPAC
(A*) 2- -3- -1,4- (B) 2- -3- -1,4-

(C) 3- -2- -1,4- (D) 2- -3- -4-
ADVIUPSI - 27
8. 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
IUPAC
(A) 1, 2, 3- -1, 3- (B*) 2, 4- -3-

(C) 1, 3- -1, 2, 4- (D) 1, 3, 4- -2, 4-
9. IUPAC name of the following molecule is
IUPAC
(A) 2-Bromobenzene-1,4-dioic acid (2- -1,4- )

(B) 3-Bromobenzene-1,4-dicarboxylic acid (3- -1,4- )
(C*) 2-Bromobenzene-1,4-dicarboxylic acid (2- -1,4- )
(D) 3-Bromobenzene-1,6-dicarboxylic acid (3- -1,6- )
10. IUPAC name of picric acid is
(A) 2,4,6-Trinitrobenzene carboxylic acid (B) 2,4-Dinitrobenzene carboxylic acid
(C*) 2,4,6-Trinitrophenol (D) 2,4-Dinitrophenol
IUPAC
(A) 2,4,6- (B) 2,4-
(C*) 2,4,6- (D) 2,4-
11. Which one of the compound is not isomer of others ?
(A) (B) (C) (D*)
12. What is the number of all (structurally isomeric) alkynes with molecular formula C6H10.
C6H10
(A) 6 (B*) 7 (C) 8 (D) 9
13. Number of structurally isomeric ethers with molecular formula C5H12O.

C5H12O
(A) 4 (B) 5 (C*) 6 (D) 7
14. How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom in
anthracene ?
(A*) 3 (B) 7 (C) 4 (D) 6

ADVIUPSI - 28
15. The number of structurally isomerc tribromo derivatives possible for benzene are :
(A) 2 (B*) 3 (C) 4 (D) 5
PART - II : SINGLE OR DOUBLE INTEGER TYPE

- II : (SINGLE OR DOUBLE INTEGER TYPE)
1. A hydrocarbon (R) has six membered ring in which there is no unsaturation. Two alkyl groups are attached to
the ring adjacent to each other. One group has 3 carbon atoms with branching at 1st carbon atom of chain and
another has 4 carbon atoms. The larger alkyl group has main chain of three carbon atoms of which second
carbon is substituted. Number of 2° carbons in R are :
(R) 6 (unsaturation)
3 1st 4
3 (R) 2°
:
Ans. 5
2. 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 CH (h) –CH2–CH=CH2 (i) –CH2–C CH
Ethynyl 2-Propenyl Prop-1-ynyl
(a) (b) (c)
1- 2,3-
(d) (e) = CH–CH3 (f)
2,3- 2-
(g) –C CH (h) –CH2–CH=CH2 (i) –CH2–C CH
2- -1-
Ans. 5
3. The number of compound(s) in which carbon atom of functional group can be counted in main chain is/
are :
(a) (b) (c)
(d) (e) (f)
Ans. 1
ADVIUPSI - 29
4. What is the degree of unsaturation in a compound with molecular formula C9H6N4 ?
C9H6N4
Ans. 9
5. The no. of isomeric pairs with correct relationship specified are :
(a) & position isomers
(b) & Metamers
(c) & Functional isomere
(d) & Position isomers
(e) & Position isomers
(f) & Functional isomers
(g) & Functional isomers
(a)
(b)
(c)
(d)
(e)
ADVIUPSI - 30
(f)
(g)
Ans. 4
6. How many structurally isomeric dibromo butanes are possible.
Ans. 6
7. How many number of all structurally isomeric dienes with molecular formula C5H8 are possible :
C5H8
Ans. 6
8. How many structural alkenes of formula C2FClBrI are possible :
C2FClBrI
Ans. 3
9. How many aromatic benzene ring containing isomers of formula C8H10 are possible :
C8H10
Ans. 4
10. How many tetramethyl benzene are possible :
Ans. 3
11. How many structurally isomeric cyclic isomers of molecular formula C3H7N are possible :
C3H7N
Ans. 4
12. The number of structurally isomeric ketones with molecular formula C6H12O are :
C6H12O
Ans. 6
(i) (ii) (iii) (iv)
(v) (vi)
13. The number of structurally isomeric esters with molecular formula C5H10O2 are.
C5H10O2
Ans. 9
ADVIUPSI - 31
PART - III : ONE OR MORE THAN ONE OPTION CORRECT TYPE
- III : (ONE OR MORE THAN ONE OPTION CORRECT TYPE)
1. All the members of a homologus series have same

(A*) Functional group (B) Empirical formula
(C*) General formula (D) All of these
(A*) (B) (C*) (D)
2. The pair of compounds having the same general formula.
(A*) and (B*) and
(C) and (D*) and H—CC—CC—H
(A*) (B*)
(C) (D*) H—CC—CC—H
3. Which of the following IUPAC names are correct.
(A*) (B*)
3-Ethyl-1, 1-dimethylcyclohexane 1-Ethyl-3-methyl-5-propylcyclohexane
(C*) (D)
2-Bromo-1-chloro-4-fluorocyclohexane 1-Bromo-4-chloro-3-fluorocyclohexane
ADVIUPSI - 32
IUPAC
(A*) (B*)
3- -1, 1- 1- -3- -5-
(C*) (D)
2- -1- -4- 1- -4- -3-
4. The compound with only primary hydrogen atoms is/are :

(A*) Hexamethylcyclopropane (B) Neohexane
(C*) Tetramethylbutane (D*) Hexamethylbenzene
(A*) (B)
(C*) (D*)
5. Which of the following is/ are incorrect IUPAC name/ (s) :

(A*) 2-Methylbutan -3-one
(B*) 3-Ethenylpent-1-en-4-yne
(C) 3- (2-Aminoethyl)-2-methylcyclohexan-1-ol
(D*) 4-Methyl-3-oxopentan-2-ol
IUPAC
(A*) 2- -3-
(B*) 3- -1- -4-
(C) 3-(2- )-2- -1-
(D*) 4- -3- -2-
ADVIUPSI - 33
6. Which of the following IUPAC names are correct.
(A*) 2-Methylcyclopentanecarboxamide.
(B) Cyclohexanoyl chloride.
(C*) 2-Methylcyclobutanecarbonitrile
(D*) Methyl 2-bromocyclohexanecarboxylate
IUPAC
(A*) 2-
(B)
(C*) 2-
(D*) 2-
7. Which of the following IUPAC names are incorrect.
(A) (B)
Methyl-3-nitrobenzenecarboxylate Ethyl 3-phenylbenzene-1-carboxylate
(C*) (D*)
Ethyl 2–methyl-2-(3–nitrophenyl)ethanoate 1, 1, 1-Trichloro-2, 2-di(4-chlorophenyl) ethane
ADVIUPSI - 34
IUPAC
(A) (B)
-3- -3- -1-
(C*) (D*)
-2– -2-(3– ) 1, 1, 1- -2, 2- (4- )

8. Which of the following is the correct relationship ?
(A*) I & II are functional isomers. (B*) II & IV are metamers.

(C) I & IV are position isomers. (D*) I & III are chain isomers.
(A*) I II (B*) II IV
(C) I IV (D*) I III
9. Which of the following are functional isomers of methyl ethanoate ?
(A*) CH3 – CH2 – COOH (B*) (C*) (D*)
10. Which of the following can be the isomer(s) of C8H8O :

C8H8O
(A) (B*) (C*) (D*)
ADVIUPSI - 35
PART - IV : COMPREHENSION
- IV : (COMPREHENSION)
Comprehension # 1 (Questions 1 to 2)
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.
#1( 1 2)
P, Q, R C4H6O3 P Q
R
1. Which of the following is P ?

P
(A) (B) (C) (D*)
2. Which of the following is the metamer of Q ?

Q
(A) (B*)
(C) (D)
ADVIUPSI - 36
PART - I : JEE (ADVANCED) / IIT-JEE PROBLEMS (PREVIOUS YEARS)

- I : JEE (ADVANCED) / IIT-JEE
* Marked Questions may have more than one correct option.
* -
1. Write IUPAC name of the following [IIT-JEE 2004]
IUPAC
Ans. 3–Aminobenzoic acid (3- )

2. Write IUPAC name of the following [IIT-JEE 2005]
IUPAC
Ans. 4–Methylbenzenesulphonic acid (4- )

3._ The IUPAC name of C6H5COCI is : [IIT-JEE-2006]
(A) Benzoyl chloride (B) Benzene chloro ketone
(C*) Benzene carbonyl chloride (D) Chloro phenyl ketone
C6H5COCI IUPAC [IIT-JEE-2006]
(A) (B)
(C*) (D)
4. The number of structural isomers for C6H14 is : [IIT- JEE 2007]
C6H14 [IIT- JEE 2007]
(A) 3 (B) 4 (C*) 5 (D) 6
5. The IUPAC name of the following compound is : [IIT-JEE-2009]
IUPAC
(A) 4-Bromo-3-cyanophenol (B*) 2-Bromo-5-hydroxybenzonitrile

(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile
(A) 4- -3- (B*) 2- -5-
(C) 2- -4- (D) 6- -3-
ADVIUPSI - 41
6. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is / are :
C4H6 [IIT-JEE 2010]
Ans. 5
7. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [IIT-JEE 2012]
3 2 3 2 3
(A) sp and sp (B*) sp and sp (C) only sp (D) sp and sp
(allene ; C3H4) [IIT-JEE 2012]
3 2 3 2 3
(A) sp sp (B*) sp sp (C) sp (D) sp sp
8. The carboxyl functional group (– COOH) is present in : [IIT-JEE 2012]
(A) picric acid (B) barbituric acid (C) ascorbic acid (D*) aspirin
(–COOH) [IIT-JEE 2012]
(A) (picric acid) (B) (barbituric acid)
(C) (ascorbic acid) (D*) (aspirin)
PART - II : JEE (MAIN) / AIEEE PROBLEMS (PREVIOUS YEARS)

- II : JEE (MAIN) / AIEEE
* Marked Questions are more than one correct options.
*
1. Which of the following compounds has wrong IUPAC name: [AIEEE- 2002, 3/225]
(1) CH3 – CH2 – CH2 – COO – CH2CH3  Ethyl butanoate
(2)  3-Methylbutanal
(3*)  2-Methyl-3-butanol
(4)  2-Methyl-3-pentanone
IUPAC : [AIEEE- 2002, 3/225]

(1) CH3 – CH2 – CH2 – COO – CH2CH3 
(2)  3–
(3*)  2– –3–
(4)  2– –3–
2. The general formula CnH2nO2 could be for open chain [AIEEE- 2003, 3/225]
(1) diketones (2*) carboxylic acids (3) diols (4) dialdehydes.
CnH2nO2 – [AIEEE- 2003, 3/225]
(1) (2*) (3) (4)
ADVIUPSI - 42
3. The IUPAC name of the compound is [AIEEE- 2004, 3/225]
(1) 3, 3-dimethyl-1-hydroxycyclohexane (2) 1, 1-dimethyl-3-hydroxycyclohexane

(3*) 3, 3-dimethyl-1-cyclohexanol (4) 1, 1-dimethyl-3-cyclohexanol
IUPAC [AIEEE- 2004, 3/225]

HO
(1) 3, 3– –1– (2) 1, 1– –3–
(3*) 3, 3– –1– (4) 1, 1– –3–
4. The IUPAC name of the compound shown below is [AIEEE- 2006, 3/165]
IUPAC [AIEEE- 2006, 3/165]
(1) 2 - Bromo-6-chlorocyclohex-1-ene (2) 6-Bromo-2-chlorocyclohexene

(3*) 3-Bromo-1-chlorocyclohex-1-ene (4) 1-Bromo-3-chlorocyclohexene
(1) 2- -6- -1- (2) 6- -2-
(3*) 3- -1- -1- (4) 1- -3-
5. The IUPAC name of is : [AIEEE-2007, 3/120]

(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
IUPAC [AIEEE-2007, 3/120]
(1) 5, 5- -4, 4- (2*) 3- -4,4-

(3) 1, 1- -2, 2- (4) 4, 4- -5, 5-
6. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system
of nomenclature is [AIEEE-2008, 3/105]
IUPAC
(1) –SO3H, –COOH, –CONH2, –CHO (2) –CHO, –COOH, –SO3H, –CONH2
(3) –CONH2, –CHO, –SO3H, –COOH (4*) –COOH, –SO3H, –CONH2, –CHO
7. The IUPAC name of neopentane is : [AIEEE-2009, 4/144]
(1*) 2, 2-dimethylpropane (2) 2-methylpropane
(3) 2, 2-dimethylbutane (4) 2-methylbutane
IUPAC : [AIEEE-2009, 4/144]
(1*) 2, 2- (2) 2-
(3) 2, 2- (4) 2-
8. Aspirin is known as : [AIEEE 2012, 4/120]

(1*) Acetyl salicylic acid (2) Phenyl salicylate
(3) Acetyl salicylate (4) Methyl salicylic acid
[AIEEE 2012, 4/120]
(1*) (2)
(3) (4)
ADVIUPSI - 43
 Marked Questions may have for Revision Questions.


This Section is not meant for classroom discussion. It is being given to promote self-study and self
testing amongst the Resonance students.
PART - I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))

- I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))
Max. Marks : 120 Max. Time : 1 Hr.
Important Instructions
1. The test is of 1 hour duration.

1
2. The Test Booklet consists of 30 questions. The maximum marks are 120.
30 120
3. Each question is allotted 4 (four) marks for correct response.
4
4. Candidates will be awarded marks as stated above in Instructions No. 3 for correct response of each question.
¼ (one fourth) marks will be deducted for indicating incorrect response of each question. No deduction from the
total score will be made if no response is indicated for an item in the answer sheet.
3
¼
5. There is only one correct response for each question. Filling up more than one response in any question will be
treated as wrong response and marks for wrong response will be deducted accordingly as per instructions 4
above.
4
1. How many  and  bonds are in the given compound ?

HC  C — CH = CH2
(1) 3 and 6 bonds (2*) 3 and 7 bonds (3) 2 and 7 bonds (4) 4 and 8 bonds
 
HC  C — CH = CH2
(1) 3 6 (2*) 3 7 (3) 2 7 (4) 4 8
2. How many 2º and 3° carbon atoms are present in the given compound respectively ?
2º 3°
(1*) 9 & 4 (2) 10 & 3 (3) 9 & 3 (4) 6 & 1
ADVIUPSI - 46
3. In the organic compound , the pair of hybridised orbitals involved in the formation
of : C2 – C3 bond is :
C2 – C3
(1) sp – sp2 (2) sp – sp3 (3*) sp2 – sp3 (4) sp3 – sp3
4. Which of the following is unsaturated hydrocarbon ?
(1) (2) (3) (4*)
5. The correct IUPAC name of the following compound is
(1) 4-Ethyl-3,5-dimethylhexane (2) 2,4-Dimethyl-3-ethylhexane

(3) 3-Ethyl-2,4-dimethylhexane (4*) 3-sopropyl-4-methylhexane
IUPAC
(1) 4- -3,5- (2) 2,4- -3-

(3) 3- -2,4- (4*) 3- -4-
6. Which is the structure of Pyrrole ?
(1*) (2) (3) (4)
7. Which IUPAC name is incorrect among the following compounds ?

(1) CH3–CH=CH–CH2–Cl 1-Chlorobut-2-ene
(2*) HCC–CH2–CH2–Br 1-Bromobut-3-yne
(3) CH3–CH=CH–CH=CH2 Penta-1,3-diene
(4) 4-Bromo-2,2-dichloropentane
IUPAC
(1) CH3–CH=CH–CH2–Cl 1- -2-
(2*) CHC–CH2–CH2–Br 1- -3-
(3) CH3–CH=CH–CH=CH2 -1,3-
(4) 4- -2,2-
ADVIUPSI - 47
8. Which of the following represent incorrect numbering.
(1) (2*) (3) (4)
9. The IUPAC name of the compound shown below is

IUPAC
(1) 2 - Bromo-6-chlorocyclohex-1-ene (2) 6-Bromo-2-chlorocyclohexene

(3*) 3-Bromo-1-chlorocyclohex-1-ene (4) 1-Bromo-3-chlorocyclohexene
(1) 2- -6- -1- (2) 6- -2-
(3*) 3- -1- -1- (4) 1- -3-
10. The IUPAC name of compound CH3–C(CH3)2 – CH2–CH=CH2 is
(1) 2, 2-Dimethylpent-4-ene (2) 2, 2-Dimethyl-2-pentene
(3) 1,1,1-Trimethylbut-3-ene (4*) 4,4-Dimethylpent-1-ene
CH3–C(CH3)2 – CH2–CH=CH2 IUPAC
(1) 2, 2- -4- (2) 2, 2- -2-
(3) 1,1,1- -3- (4*) 4, 4- -1-
11. What is the structure of 4-Methylhex-5-en-3-ol.

4- -5- -3-
(1) (2*)
(3) (4)
12. A compound having straight chain of five carbon atoms has one ketone group and two methyl groups on
different-different carbon atoms. The IUPAC name of the compound is :
(1) 2,4-Dimethyl-3-oxopentane (2*) 2,4-Dimethylpentan-3-one
(3) 3,4-Dimethyl-2-oxopentane (4) 3,3-Dimethylpentan-2-one
A compound having straight chain of five carbon atoms, It has one ketone group and two methyl groups on
IUPAC
(1) 2,4- -3- (2*) 2,4- -3-
(3) 3,4- -2- (4) 3,3- -2-
13. What is the IUPAC name of
(1) 5-Chloro-3-hydroxybenzenecarbonyl chloride. (2) 3-Hydroxy-5-chlorobenzenecarbonyl chloride.

(3*) 3-Chloro-5-hydroxybenzenecarbonyl chloride. (4) 1-Chlorocarbonyl-3-chlorobenzen-1-ol
ADVIUPSI - 48
IUPAC
(1) 5- -3- (2) 3- -5-

(3*) 3- -5- (4) 1- -3- -1-
14. The correct IUPAC name of compound is :
IUPAC
COOH
Br
NH2
(1) 3-Amino-6-bromocyclohexane-1-carboxylic acid
(2) 2-Bromo-5-aminocyclohexane-1-carboxylic acid
(3*) 5-Amino-2-bromocyclohexane-1-carboxylic acid
(4) 4-Bromo-5-carboxycyclohexanamine
(1) 3- -6- -1- (2) 2- -5- -1-
(3*) 5- -2- -1- (4) 4- -5-
15. The IUPAC name of is :
(1) N-Methyl-N-ethyl ethanamine (2) Diethyl methanamine

(3*) N-Ethyl-N-methyl ethanamine (4) Methyl diethyl ethanamine
IUPAC
(1) N- -N- (2)

(3*) N- -N- (4)
16. In the given formula G is an unknown group.

G
What will be the group G, which can change the word root (parent carbon chain length) of above structure?
G
(1) –CH=CH2 (2) –Cl (3) –CH2–CH2–CH3 (4*) –COOH
17. IUPAC name of is
(1) N-Deutero-N-formylbenzenamine (2) N-Phenylamino-N-deuteromethanal

(3*) N-Deutero-N-phenylmethanamide (4) N-Deuterobenzene carboxamide
IUPAC
(1) N- -N- (2) N- -N-

(3*) N- -N- (4) N-
ADVIUPSI - 49
18. Correct IUPAC name of given ester is :
IUPAC
CH3 – CH– C – O – C2H5
| ||
Br O
(1*) Ethyl 2–bromopropanoate (2) 2–Bromoethylpropanoate
(3) Ethyl 1–bromoethanoate (4) 2–Bromo ethoxyethanecarboxylate
(1*) 2– (2) 2–
(3) 1– (4) 2–
19. Relation between Ethyl benzenecarboxylate and phenyl propanoate is :
(1*) Metamers (2) Functional isomers
(3) Chain isomers (4) Homologues
:
(1*) (2)
(3) (4)
20. The correct IUPAC name of the compound :
is :
(1*) 4-Methoxy-2-nitrobenzaldehyde (2) 4-Formyl-3-nitro anisole

(3) 4-Methoxy-6-nitrobenzaldehyde (4) 2-Formyl-5-methoxy nitrobenzene
IUPAC
(1*) 4- -2- (2) 4- -3-

(3) 4- -6- (4) 2- -5-
21. Which of the following pair of compounds is not functional isomers ?
(1) and (2) and
(3) and (4*) and
(1) (2)
(3) (4*)
ADVIUPSI - 50
22. and are related as :
(1*) Functional Isomers (2) Position Isomers (3) Chain Isomers (4) Metamers
(1*) (2) (3) (4)

23. Which of the following is correctly matched.
(1) & chain somer (2*) & Identical
(3) & Positional isomer (4) & Metamer
(1) (2*)
(3) (4)
24. Which of the following pairs of structures do not represent isomers ?
(1) & (2) &
(3) & (4*) &
ADVIUPSI - 51
25. Total number of structural isomers possible from molecular formula C8H18 that contain 7 carbons in the parent
chain are :
7 C8H18
(1*) 3 (2) 4 (3) 5 (4) 6
26. Total number of position isomers of trimethyl cyclohexane are :
(1) 5 (2*) 6 (3) 7 (4) 8

27. How many 1 amines are possible with molecular formula C4H11N (only structural isomers)
C4H11N 1
(1) 3 (2*) 4 (3) 5 (4) 6
28. Hybridisation of carbon atoms present in the smallest ester are :

(1) All sp3 (2) All sp2 (3*) sp2 and sp3 (4) sp2 and sp
(1) sp3 (2) sp2 (3*) sp2 sp3 (4) sp2 sp

29. The number of metamers of the compound with molecular formula C5H12O is/are :
C5H12O
(1) 1 (2) 3 (3) 8 (4*) 6
30. How many tertiary alcohols is/are possible with molecular formula C5H12O ?
C5H12O
(1*) 1 (2) 2 (3) 3 (4) 4
PART - II : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))

- II : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))
Max. Time : 1 Hr. Max. Marks : 69
Important Instructions
A. General
1. The test is of 1 hour duration.
1
2. The Test Booklet consists of 23 questions. The maximum marks are 69.
23 69
B. Question Paper Format
3. Each part consists of five sections.
4. Section 1 contains 8 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE is correct.
1 8 (A), (B), (C) (D)
5. Section 2 contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE OR MORE THAN ONE are correct.
2 6 (A), (B), (C) (D)
6. Section 3 contains 6 questions. The answer to each of the questions is a single-digit integer, ranging from
0 to 9 (both inclusive).
3 6 0 9
7. Section 4 contains 1 paragraphs each describing theory, experiment and data etc. 2 questions relate to
paragraph. Each question pertaining to a partcular passage should have only one correct answer among
the four given choices (A), (B), (C) and (D).
ADVIUPSI - 52
4 1
(A), (B), (C) (D)
8. Section 5 contains 1 multiple choice questions. Question has two lists (list-1 : P, Q, R and S; List-2 : 1,
2, 3 and 4). The options for the correct match are provided as (A), (B), (C) and (D) out of which ONLY ONE
is correct.
5 1 ( -1 : P, Q, R S; -2 : 1, 2, 3 4)
(A), (B), (C) (D)
C. Marking Scheme
9. For each question in Section 1, 4 and 5 you will be awarded 3 marks if you darken the bubble corresponding
to the correct answer and zero mark if no bubble is darkened. In all other cases, minus one (– 1) mark will
be awarded.
1, 4 5 3
(0) (– 1)
10. For each question in Section 2, you will be awarded 3 marks. If you darken all the bubble(s) corresponding
to the correct answer(s) and zero mark. If no bubbles are darkened. No negative marks will be answered
for incorrect answer in this section.
2 3
11. For each question in Section 3, you will be awarded 3 marks if you darken only the bubble corresponding
to the correct answer and zero mark if no bubble is darkened. No negative marks will be awarded for
incorrect answer in this section.
3 3
SECTION-1 : (Only One option correct Type)

This section contains 8 multiple choice questions. Each questions has four choices (A), (B), (C) and
(D) out of which Only ONE option is correct.
–1 : ( )
8 (A),(B),(C) (D)
1. How many position isomers are possible for chlorophenol ?

?
(A) 2 (B*) 3 (C) 4 (D) 5
2. IUPAC name of is
(A*) 5-ethenylcyclopenta-1,3-diene (B) 3-ethenylcyclopenta-1,4-diene

(C) 1-ethenylcyclopenta-2,4-diene (D) 2-ethenylcyclopenta-1,3-diene
IUPAC
(A*) 5- -1,3- (B) 3- -1,4-

(C) 1- -2,4- (D) 2- -1,3-
3. How many carboxylic acid structure isomers are possible with C5H10O2 ?
C5H10O2 ?
(A) 3 (B*) 4 (C) 5 (D) 8
ADVIUPSI - 53
4. Which of the following is correct IUPAC name
(A) 2-Bromo cyclohex-5-ene carbaldehyde (B) Ethyl-2-vinyl pentanoate
(C*) 5-Bromo-3-chlorohept-3-ene (D) 2-Ethenylhexa-1,5-diene
IUPAC
(A) 2- -5- (B) -2-
(C*) 5- -3- -3- (D) 2- -1,5-
5. When X group is replaced by –CN, then the IUPAC name of the compound below is :
X –CN IUPAC
(A) 2-Methylpentane-3-nitrile (B) 3-Cyano-2-methylpentane

(C*) 2-Ethyl-3-methylbutanenitrile (D) 2-Methylpentane-3-carbonitrile
(A) 2- -3- (B) 3- -2-
(C*) 2- -3- (D) 2- -3-
6. Correct IUPAC name of following compound is
(A*) 2-Amino-3-formyl butane-1, 4-dioic anhydride

(B) 3-Amino-2-formyl butane-1, 4-dioic anhydride
(C) 3-Amino-2-oxobutane-1, 4-dioic anhydride
(D) 2-Formyl-3-amino butane-1, 4-dioic anhydride
IUPAC
(A*) 2- -3- -1, 4-

(B) 3- -2- -1, 4-
(C) 3- -2- -1, 4-
(D) 2- -3- -1, 4-
O
||
7. Me – O – C – Me and Et – O – CH = O are :
(A) Functional isomers (B*) Metamers (C) Positional isomers (D) Chain isomers
O
||
Me – O – C – Me Et – O – CH = O
(A) (B*) (C) (D)
ADVIUPSI - 54
8. Number of structurally isomeric carbonyl compounds possible with molecular formula C5H10O are :
C5H10O
(A) 5 (B) 6 (C*) 7 (D) 8
Section-2 : (One or More than one options correct Type)

This section contains 6 multiple choice questions. Each questions has four choices (A), (B), (C) and
(D) out of which ONE or MORE THAN ONE are correct.
-2 : ( )
6 (A), (B), (C) (D)
9. Which of the following statements are incorrect for aniline.

(A*) Compound is heterocyclic hydrocarbon.
(B*) Number of  bonds are 8.
(C*) Degree of unsaturation of the compound is 3
(D) It contains functional group amine
(A*) (B*)  8
(C*) 3 (D)
10. Select 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
IUPAC
(A*) -1,1,1,1- (B) 5- - -1,7-
(C*) 2- (D) 1- -3- -4-
11. 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
IUPAC
(A*) 4- -3- (B*) 1- -3- -1-
(C) 4- -3- (D*) 3- -1- -1-
12. Which of the following represent correct pair of homologous ?
(A) & (B*) Me–OH & MeCH2CH2OH
(C*) & (D) CH3–CH2–NH2 &
13. Which of the following is/are correct statement(s) :
(A*) & are functional isomers to each other
(B*) & are position isomers to each other
ADVIUPSI - 55
(C) & are chain isomers to each other
(D*) & are metamers of each other..
(A*)
(B*)
(C)
(D*)
14. Which of the following is/are correct statement(s) :

(A) The number of structural isomers for molecular formula C3H8 are 2
(B*) The number of structural isomers for molecular formula C5H12 are 3
(C*) The number of structural isomers for molecular formula C6H14 are 5
(D) The number of benzene ring containing structural isomers for molecular formula C6H4BrCl are 4
(A) C3H8 2
(B*) C5H12 3
(C*) C6H14 5
(D) C6H4BrCl 4
Section-3 : (Single/ Double Integer Value Correct Type.)

This section contains 6 questions. Each question, when worked out will result in one integer from
0 to 9 (both inclusive)
-3: ( )
6 0 9( )
15. Number of functional groups present in the following compounds are :
Ans. 6
ADVIUPSI - 56
16. The no. of amine(s) with correct IUPAC name is/are
(a) (b) (c)
N,N-Dimethyl-2-methylethanamine 2-Methylpropanamine N-Ethyl-N-Phenylbenzenamine
(d) (e)
3,4,4-Trimethylpentane-3-amine N-Propyl-2-methylethanamine
(f) (g)
3-Ethylamino-2-methylcyclohexan-1-ol (2-Methyl) N-ethyl-N-isopropyl propanamine

IUPAC
(a) (b) (c)
N,N- -2- 2- N- -N-
(d) (e)
3,4,4- -3- N- -2-
(f) (g)
3- -2- -1- (2- ) N- -N-

Ans. 4
17. The no. of compound 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
ADVIUPSI - 57
(e) (f) (g)
4-Amino-1-nitrobenzene 3-Methylphenol 2,4,6-Trimethylbenzenecarbonlychloride

IUPAC
(a) (b)
2- 3- -4- -5-
(c) (d)
3- -5- 1- -3- -4-
(e) (f) (g)
4- -1- 3- 2,4,6-
Ans. 2
18. How many alkynes isomers are formed with molecular formula C4H6 ?
C4H6
Ans. 2
19. Then number of structurally isomeric compound(s) possible with molecular formula C8H18 containing 5 carbons
in main chain having methyl group(s) as side chain are
C8H18
Ans. 4
20. The number of possible alkynes (strucutral only) for the compound having molecular formula C3FClBrI is :
C3FClBrI
Ans. 4
SECTION-4 : Comprehension Type (Only One options correct)

This section contains 1 paragraphs, each describing theory, experiments, data etc. 2 questions
relate to the paragraph. Each question has only one correct answer among the four given options
(A), (B), (C) and (D)
–4 : ( )
1
(A), (B), (C) (D)
ADVIUPSI - 58
Paragraph For Questions 21 to 22

Compounds having same molecular formula but different connectivity of atoms or groups are called structure
isomers. Structrue isomers are further classify according to their dissimilarities.
21 22
connectivity
21. Which is not the isomer of butanoic acid?

(A) 3-Hydroxybutanal (B) Ethyl ethanoate
(C) 2-Methylpropanoic acid (D*) Butane-2,3-diol
(A) 3- (B)
(C) 2- (D*) -2,3-
22. In the following skelton Z can be, if the molecular formula is C5H10O2 :
CH3 – CH2 – CH – CH3
|
Z
(i) A carboxylic acid (ii) An ester
(iii) Hydroxyaldehyde (iv) Alkanediol
(A*) i & ii (B) iii & iv (C) i & iv (D) ii & iii
Z C5H10O2
CH3 – CH2 – CH – CH3
|
Z
(i) (ii)
(iii) (iv)
(A*) i & ii (B) iii & iv (C) i & iv (D) ii & iii
SECTION-5 : Matching List Type (Only One options correct)

This section contains 1 questions, each having two matching lists. Choices for the correct combination
of elements from List-I and List-II are given as options (A), (B), (C) and (D) out of which one is correct
-5 :
1 (A), (B), (C)
(D)
23. List-I -I List-II -II
(P) Ph–CH2–O–CH=O & Ph–O–CH2–CH=O (1) Chain isomers
(Q) & (2) Position isomers
(R) & (3) Functional isomers
(S) & (4) Metamers
ADVIUPSI - 59
Code :
P Q R S P Q R S
(A) 3 1 2 4 (B) 4 1 2 3
(C) 4 2 2 3 (D*) 3 1 1 3
PART - III : OLYMPIAD (PREVIOUS YEARS)

- III : OLYMPIAD
STAGE - I (NATIONAL STANDARD EXAMINATION IN CHEMISTRY (NSEC))

1. How many structural isomers can be obtained by the replacement of one hydrogen atom of propene with
chlorine ? (INChO-2001)
(A) 4 (B*) 3 (C) 2 (D) 5

2. The IUPAC name of CH2 = CHCN is : (INChO-2001)
(A) Cyanoethene (B) Vinyl cyanide. (C) Ethenenitrile (D*) 2-Propenitrile
CH2 = CHCN IUPAC
(A) (B) (C) (D*) 2-
3. The number of isomers of C6H14 is : (INChO-2001)

C6H14
(A) 6 (B*) 5 (C) 4 (D) 7
4. The compound which represents an unsaturated hydrocarbon is : (INChO-2002)
(A) CH3 – C  N (B*) CH3 – CH = CH2 (C) CH3 – CH = O (D) all of these
5. The number of possible primary alcohols with the molecular formula C4H10O is : (INChO-2002)
C4H10O
(A) 1 (B*) 2 (C) 3 (D) 4
6. The IUPAC name of HOCH2CH = C(CH3)2 (INChO-2002)
(A) 2-Methyl-2-buten 4-ol (B*) 3-Methyl-2-buten-1-ol
(C) 2-Methyl-2-butenol (D) 3-Methyl-2-butenol.
HOCH2CH = C(CH3)2 IUPAC
(A) 2- -2- -4- (B*) 3- -2- -1-
(C) 2- -2- (D) 3- -2-
7. The compound 2-Chloro-3-methyl-1-butanol has the following formula (INChO-2006)
2- -3- -1-
(A*) CH3CH(CH3)CHCICH2OH (B) CH3CHOHCH(CH3)CH2CI
(C) CH2CIC(CH3)2CH2OH (D) CH3CHCICH(CH3)CH2OH.
8. How many different alcohols (not including optical isomers) are possible with the molecular formula : C4H10O?
(INChO-2006)
C4H10O ( ) ?
(A) 3 (B*) 4 (C) 5 (D) 6
9. The C–C–H bond angle in ethylene is : (INChO-2007)
C–C–H
0
(A) 180 (B) 1090280 (C*) 1200 (D) 900
ADVIUPSI - 60
10. The IUPAC name of is : (INChO-2007)
(A) 2–Chlorocarbonylethyl benzoate (B) 2–Carboxyethylbenzoylchloride

(C*) Ethyl–2–(chlorocarbonyl) benzoate (D) Ethyl–1–(chlorocarbonyl) benzoate
IUPAC
(A) 2– (B) 2–
(C*) –2–( ) (D) –1–( )
11. How many sigma bonds and pi bonds are present in CH2=C=CH2 ? (INChO-2007)
(A) 6 sigma and 1pi (B) 8 sigma and 0 pi
(C) 4 sigma and 4 pi (D*) 6 sigma and 2 pi
CH2=C=CH2  
(A) 6 1 (B) 8 0
(C) 4 4 (D*) 6 2
12. The number of ether metamers represented by the molecular formula C4H10O is : (INChO-2009)
C4H10O
(A) 1 (B) 2 (C*) 3 (D) 4
13. The IUPAC name of is : (INChO-2009)
(A) 2-Bromo-3-methylbut-3-ene (B*) 4-Bromo-3-methylpent-2-ene

(C) 2-Bromo-3-methylpent-3-ene (D) 4-Bromo-2,3-dimethylbut-2-ene
IUPAC :
(A) 2- -3- -3- (B*) 4- -3- -2-

(C) 2- -3- -3- (D) 4- -2,3- -2-
14. The IUPAC name of the following compound is : (INChO-2010)
IUPAC
(A) n-Propyl ethanoate (B) Ethyl propanoate

(C) Pentanoic anhydride (D*) n-Propyl propanoate
(A) n- (B)
(C) (D*) n-
15. The number of isomers of dibromobiphenyl (Biphenyl - C 6H5) is (INChO-2011)
( - C 6H5)
(A) 8 (B) 10 (C*) 12 (D) 4
ADVIUPSI - 61
16. The IUPAC name of the following compound is : (INChO-2011)
(A) 3-Methoxy ethylpropanoate (B*) Ethyl 4-methoxybutanoate

(C) 1,4-Diethoxybutane (D) Ethoxy 3-methoxybutyrate
IUPAC :
(A) 3- (B*) 4-
(C) 1,4- (D) 3-
17. The correct IUPAC name of the following compound is : (INChO-2012)
IUPAC
(A) 2-Bromo-5-methylbicyclo[5:4:0]heptanes (B) 3-Bromo-7-methylbicyclo[3.2.0]heptanes

(C*) 3-Bromo-6-methylbicyclo[3.2.0]heptanes (D) 2-Methyl-6-bromobicyclo[2.3.0]heptane
(A) 2- -5- [5:4:0] (B) 3- -7- [3.2.0]
(C*) 3- -6- [3.2.0] (D) 2- -6- [2.3.0]
18. The IUPAC name of the following compounds is (INChO-2014)
IUPAC
(A*) 5-Bromo-3-(bromomethyl) pent-1-ene (B) 3-(1-Bromomethyl)-4-bromobut-1-ene

(C) 1,4-Dibromo-3-ethenylbutane (D) 1-Bromo-3-(bromomethyl) but-4-ene
(A) 5- -3-( ) -1- (B) 3-(1- )-4- -1-

(C) 1,4- -3- (D) 1- -3-( ) -4-
STAGE - V (INTERNATIONAL CHEMISTRY OLYMPIAD (IChO))

PROBLEM # 1
There is only one correct answer to each question
1.1 What is the correct systematic name (IUPAC name) for the compound below?
(CH3)2CHCH(CH2CH3)(CH2CH2CH3)
3-Isopropylhexane 2-Methyl-3-propylpentane
Ethyl isopropyl propyl methane 3-Hexylpropane
3-Ethyl-2-methylhexane
ADVIUPSI - 62
IUPAC
(CH3)2CHCH(CH2CH3)(CH2CH2CH3)
3- 2- -3-
3-
3- -2-
Ans. 5
1.2 Which of the following is a pair of structural isomers?
(i) and (ii) and
(iii) and (iv) and
Ans. (iii)
ADVIUPSI - 63

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IUPAC Nomenclature and Structural Isomerism

 Marked Questions may have for Revision Questions.

PART - I : SUBJECTIVE QUESTIONS

Section (A) : Fundamental of Organic Chemistry

(a) (b) (c)

Sol. (a) 19  bonds, 6 bonds(b) 22  bonds (c) 20  bonds

Sol. (a) 1° H  9, 3° H  1 (b) 1°H  6, 2°H  2 (c) 1°H  6, 2°H  4

CH2 = C = CH – CH2 – C  C – CH2 – NH2

(1) HOCH2CH2NH2 (2) CH3(CH2)3OH (3) CH3CH2COCH2CH3 (4) CH3CH=CH(CH2)3CH3

Ans. (1) H2N–CH2–CH2–OH and

(2) CH3 – CH2 – CH2 – CH2 – OH and

(4) CH3 – CH = CH – CH2 – CH2 – CH2 – CH3 and

(a) C5H10 (b)

Ans. (a) = 1, (b) = 5

(a) C6H6O (b) C6H5I (c) C5H9N

(a) H–COOH (b) H–CH=CH2 (c)

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

Ans. (a) Homocyclic, alicyclic, saturated (b) Homocyclic, aromatic, unsaturated

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

Sol. (a) 2° (b) 2° (c) 3° (d) 3°

(a) (b) (c)

Sol. (a) 2° (b) 3° (c) 1°

Section (B) : IUPAC-Nomenclature of Alkane & Cycloalkane

(a) (b) (c)

Sol. (a) 5-Ethyl-3-methyloctane (b) 4-Ethyl-2,2,6-trimethylheptane

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

Sol. (i) (ii)

Ans. (i) 4-Ethyl-4,5-dimethyldecane (4- -4,5-

Sol. (i) (ii) (iii)

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

Sol. (a) s-Butylcyclohexane (b) t-Butylcyclohexane

(a) (b) (c)

(d) (e) (f)

(a) (b) (c)

(d) –CH2–CH3 (e) CH3–CH2–CH2–

Section (C) : IUPAC-Nomenclature of Alkene, Cycloalkene, Polyenes & Alkyne

Sol. (i) (ii)

C-3. Draw the bond line structures of the following compounds.

(a) 2- -3- (b) 2, 6– -1, 5-

Ans. (a) (b)

C-4. Write IUPAC name of the following

(i) (ii) (iii)

Ans. (i) 5-Methylhexyne (ii) 3-Methylbutyne (iii) 4-Methylpent-2-yne

Sol. (i) (ii)

C-6. Write the IUPAC name of the following ( IUPAC )

Sol. (i) (ii) 1–(Hex–3–enyl)cyclohex–1–ene (1–( –3– ) –1–

Section (D) : IUPAC Nomenclature of non-chain terminating functional groups

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

(e) (f) (g) (h)

Sol. (a) 3-Chlorobutan-2-ol (3- -2- )

(a) -1- (b) -2-

Section (E) : IUPAC Nomenclature of chain terminating functional groups

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

(e) (f) (g) (h)

Sol. (a) (b) (c) (d)

(e) (f) (g) (h)

E-2. Write the structure of the following compounds :

(a) 3- -2- (b) 3-

Ans. (a) CH3–CH(SO3H)–CH(OH)–CH2–CH3 (b)

(c) (d) (e)

(f) CH3–CH2–COOCH2–CH2–Cl (g)

Ans. (a) (b)

E-4. Write IUPAC Name ( IUPAC ):

(a) (b) (c)