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EXERCISE

Isomerism
ENGLISH MEDIUM
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® Chemistry : Isomerism
Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

STRUCTURAL ISOMERISM HC≡C–CH2–CH–CH3 & CH3–C≡C–CH–CH3
7.
1. CH3CHOHCH2CHO and CH3CH2CH2COOH CH3 CH3
constitute a pair of :- are
(1) Position isomers (2) Metamers
(1) Chain isomer (2) Homologous
(3) Optical isomers (4) Functional isomers
(3) Position isomer (4) None
SR0001
SR0093
2. The minimum number of carbon atoms present
8. How many structural isomer are possible for
in an organic compound to show chain
C5H8 having one triple bond ?
isomerism is
(1) 4 (2) 3 (3) 5 (4) 1
(1) 2 (2) 3 (3) 5 (4) 4
SR0094
SR0002

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GEOMETRICAL AND OPTICAL ISOMERISM
3. CH3–NH–C2H5 and (CH3)3N show which type of
H3C H
isomerism :- 9. C C H Exhibits :-
H3C C
(1) Position (2) Functional H3C COOH

(3) Chain (4) None (1) Tautomerism

(2) Optical isomerism
SR0005
(3) Geometrical isomerism
4. CH3–CH–CH2–C=O and CH3–CH2–CH2–C–Cl (4) Geometrical and optical isomerism
SE0011
Cl H O
are constitute a pair of :- COOH
(1) Position isomers H OH
10. Meso–tartaric acid H OH is optically
(2) Metamers
COOH
(3) Optical isomers
(4) Functional group isomers inactive due to the presence of :-
(1) Molecular symmetry
SR0006
(2) Molecular asymmetry
5. Which are metamers :- (3) External compensation

(1)CH3–O–CH2CH2CH3, CH3–CH2–O–CH2–CH3 (4) Two asymmetric carbon atoms

SE0019
(2) C2H5–O–C2H5, CH3CH2CH2CH2OH
(3) CH3–O–C2H5, CH3–CH2–O–CH3 11. Identify R configuration :
COOH CN
(4) CH3–C–CH3, CH3–CH2–C–H
O O (1) H (2) CH3 C≡CH
SR0008 CH3 CH2OH

6. Which similarity is necessary for isomerism– CHO COOH

(1) Molecular formula
(3) H OH (4) H2N H
(2) Structure formula
(3) Physical formula CH2OH CH3
(4) Chemical formula
SE0023
SR0009
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
Chemistry : Isomerism ®
Pre-Medical
12. Among the following structure I to III CONFORMATIONAL ISOMERISM
C2H5–CH–C3H7, CH3–C–CH–C2H5, C2H5–CH–C2H5 15. Which conformation of butane will have the
minimum energy :-
CH3 O CH3 CH3
(1) Gauche
(I) (II) (III) (2) Anti/staggered
(3) Eclipsed
It is true that :- (4) None
(1) All three are chiral compounds SE0035
(2) Only I and II are chiral compounds 16. Which of the following are true statements.
(3) Only II is chiral compound
(a) Alkanes have infinite no. of conformation
(4) Only I and III are chiral compounds
SE0026 (b) The rotation is hindered due to repulsive
interaction between electron clouds, called
13. Which one of the following is a meso–compound. torsional strain
COOH CH3 (c) The barrier is about 50 kJ/mole
H OH H OH (d) The barrier is about 1-20 kJ/mole

®
(1) H (2) HO (1) a, b, d (2) a, b, c
OH H
(3) only b (4) only a, d
CH2OH CH3 SE0095
COOH CH2OH 17. Which of the following has minimum steric
strain?
HO H H Cl
H CH3
(3) HO H (4) H Cl H H H H
CH3 CH2OH (1) (2)
H CH3 H H
SE0028
CH3 CH3
14. Which compound is optical active – H H
H OH
H H H H
(1) CH3 C COOH (2) CH3 C COOH (3) (4)
H H H H H
H
CH3 CH3 CH3 H
SE0096
(3) CH3 C COOH (4) CH3 C COOH
OH Cl
SE0032

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 4 4 2 4 1 1 3 2 2 1 3 2 4 2 2
Que. 16 17
Ans. 1 4

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
® Chemistry : Isomerism
Pre-Medical

EXERCISE-II (Previous Year Questions) AIPMT/NEET

AIPMT-2006 6. Which of the following conformers for ethylene

1. Which of the following is not chiral :- glycol is most stable :-

(1) 2–Butanol OH OH
(2) 2,3–Dibromo pentane OH H
(3) 3–Bromo pentane (1) H (2) HO
(4) 2–Hydroxy propanoic acid H H H H
H H
SE0036
OH OH
AIPMT-2007
H OH H H
2. CH3—CHCl—CH2—CH3 has a chiral centre
(3) H H (4) H H
which one of the following represents its R
configuration H OH
C2H5 C2H5 SE0043

®
(1) H CH3 (2) Cl CH3
AIPMT Pre.-2012
Cl H
7. Which of the following acids does not exhibit
CH3 C2H5
optical isomerism?
(3) H Cl (4) H3C Cl
(1) Lactic acid
C2H5 H
(2) Tartaric acid
SE0039
(3) Maleic acid
AIPMT-2008
(4) α-amino acids
3. How many stereoisomer does this molecule have
CH3CH=CHCH2CHBrCH3 SE0046
(1) 8 (2) 2 (3) 4 (4) 6 AIPMT Mains-2011
SE0040
8. The IUPAC name of the following compound
AIPMT-2009
Cl CH2CH3
4. Which of the following compounds will exhibit
cis-trans (geometrical) isomerism ? is :-
(1) 1-Butanol (2) 2-Butene CH3 I
(3) 2-Butanol (4) 2-Butyne
(1) cis-2-chloro-3-iodo-2-pentene
SE0041
(2) trans-2-chloro-3-iodo-2-pentene
AIPMT-2010
(3) cis-3-iodo-4-chloro-3-pentene
5. In the following the most stable conformation of (4) trans-3-iodo-4-chloro-3-pentene
n–butane is :- SE0047
CH3 CH3
H H CH3 Re-AIPMT-2015

(1) (2) 9. Two possible stereo-structures of

H H H
H H3C H CH3CHOH.COOH, which are optically active,
H
CH3 are called :-
CH3
H H CH3 (1) Enantiomers
(2) Mesomers
(3) (4) (3) Diastereomers
H H H
H H H
CH3 (4) Atropisomers
SE0042 SE0048
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
Chemistry : Isomerism ®
Pre-Medical
10. The number of structural isomers possible from NEET-II 2016
the molecular formula C3H9N is : 13. The correct corresponding order names of four
(1) 2 (2) 3 (3) 4 (4) 5 aldoses with configuration given below
NC0049 CHO CHO
NEET-I 2016 H OH HO H

11. Which of the following biphenyls is optically H OH H OH

CH2OH CH2OH
active?
O2N CHO CHO
HO H H OH
(1)
HO H HO H
I CH2OH CH2OH
Br Br
respectively, is :-

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(2) (1) L-erythrose, L-threose, D-erythrose, D-threose
(2) D-erythrose, D-threose, L-erythrose, L-threose
I I
(3) L-erythrose, L-threose, L-erythrose, D-threose
I
(4) D-threose, D-erythrose, L-threose, L-erythrose
(3)
SE0052

I NEET(UG) 2017
CH3 14. With respect to the conformers of ethane, which
of the following statements is true ?
(4)
(1) Bond angle changes but bond length remains
CH3
same
SE0050
(2) Both bond angle and bond length change
12. The correct statement regarding the
(3) Both bond angles and bond length remains
comparison of staggered and eclipsed
same
conformation of ethane, is :-
(4) Bond angle remains same but bond length
(1) The staggered conformation of ethane is less
changes
stable than eclipsed conformation, because
SE0056
staggered conformation has torsional strain
(2) The eclipsed conformation of ethane is more NEET(UG) 2021
stable than staggered conformation, because 15. Dihedral angle of least stable conformer of
eclipsed conformation has no torsional strain ethane is :
(3) The eclipsed conformation of ethane is more (1) 120° (2) 180°
stable than staggered conformation even (3) 60° (4) 0°
through the eclipsed conformation has SE0109
torsional strain
(4) The staggered conformation of ethane is 16. The compound which shows metamerism is:
more stable than eclipsed conformation, (1) C5H12 (2) C3H8O
because staggered conformation has no (3) C3H6O (4) C4H10O
torsional strain. SR0110
SE0051
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
® Chemistry : Isomerism
Pre-Medical
NEET(UG) 2021 (Paper-2) NEET(UG) 2022 (OVERSEAS)
17. The correct configuration assigned for 18. Which one is not a D-sugar ?
compounds (I) and (II) respectively is CHO

COOH H OH
Cl CH3 (1)
H OH C OH H
Br CH2CH3 CH2OH
CH3
I II CHO
H OH
(1) R, R (2) S, S
(2)
H OH
(3) R, S (4) S, R
SE0115 CH2OH
CH2OH

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(3) C=O
H OH
CH2OH

CHO
HO H
(4)
H OH
CH2OH
SE0116

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 2 3 2 3 3 3 2 1 3 2 4 2 3 4
Que. 16 17 18
Ans. 4 1 1

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
Chemistry : Isomerism ®
Pre-Medical
EXERCISE-III (Analytical Questions) Master Your Understanding
1. Which of the following does not contain any 5. How many isomers of C5H11OH will be primary
asymmetric carbon but can show alcohols (exclude stereoisomers) :–
enantiomerism:- (1) 2 (2) 3 (3) 4 (4) 6
(1) Lactic acid (2) 1, 3-pentadiene NC0069
(3) Tartaric acid (4) 2, 3-pentadiene 6. The minimum number of carbon atoms in ketone
SE0063 to show metamerism :–
2. Which of the following represents the structure (1) 3 (2) 4 (3) 5 (4) 6
having cis arrangement around each double SR0070
bond :-
7. The total number of configurational isomers of
H
(1) the given compound are :-
CH3–CH=CHCHOHCHOHCH3
H
(1) 2 (2) 4 (3) 6 (4) 8
(2)
SE0073

®
(3)
COOH COOH
H OH H3C OH
8. HO CH3 and HO H are :-
(4)
COOH COOH
H H
(1) Enantiomers (2) Position isomers
SE0064
(3) Geometrical isomers (4) Homomers
3. The complete IUPAC name of the compound :- SE0075
CH3 H
9. Which of the following is not a metamer of
Br C4H10O
(1) Diethyl ether
(1) (R)-1-Bromo-1-phenyl ethane (2) Methyl n-propyl ether
(2) (S)-1-Bromo-1-phenyl ethane (3) 2–Methoxy propane
(3) (E)-1-Bromo-1-phenyl ethane (4) Isobutyl alcohol
(4) (Z)-1-Bromo-1-phenyl ethane SE0076
SE0066
10. How many compounds among the following are
4. Which one of the following is the most stable chiral ?
conformation of 2, 3–butanediol :- H HO H
H3C H3C
OH OH
H OH H CH3 OH Br
Br Br
(1) (2)
H CH3 H CH3
CH3 OH Br
H OH Br
OH OH
HO CH3 HO CH3 (1) 1 (2) 2
(3) (4) (3) 3 (4) 4
CH3 H H CH3 SE0097
H H
SE0067

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10
Ans. 4 2 1 3 3 3 4 4 4 3

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