(@NEETxNOAH) Isomerism Ex

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PRE-MEDICAL
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CHEMISTRY
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EXERCISE

Isomerism
ENGLISH MEDIUM
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Chemistry : Isomerism ®
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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

®
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
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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 ®
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EXERCISE-II (Previous Year Questions) AIPMT/NEET
Re-AIPMT-2015 (2) The eclipsed conformation of ethane is more
stable than staggered conformation, because
1. Two possible stereo-structures of
eclipsed conformation has no torsional strain
CH3CHOH.COOH, which are optically active,
(3) The eclipsed conformation of ethane is more
are called :-
stable than staggered conformation even
(1) Enantiomers
through the eclipsed conformation has
(2) Mesomers
(3) Diastereomers torsional strain
(4) Atropisomers (4) The staggered conformation of ethane is
SE0048 more stable than eclipsed conformation,

2. The number of structural isomers possible from because staggered conformation has no
the molecular formula C3H9N is : torsional strain.

®
(1) 2 (2) 3 (3) 4 (4) 5 SE0051
NC0049 NEET-II 2016

NEET-I 2016 5. The correct corresponding order names of four


aldoses with configuration given below
3. Which of the following biphenyls is optically
CHO CHO
active?
H OH HO H
O2N
H OH H OH
(1) CH2OH CH2OH

I CHO CHO
Br Br HO H H OH
HO H HO H
(2) CH2OH CH2OH

I I respectively, is :-
I (1) L-erythrose, L-threose, D-erythrose, D-threose

(3) (2) D-erythrose, D-threose, L-erythrose, L-threose


(3) L-erythrose, L-threose, L-erythrose, D-threose
I
(4) D-threose, D-erythrose, L-threose, L-erythrose
CH3
SE0052
(4) NEET(UG) 2017

CH3 6. With respect to the conformers of ethane, which


of the following statements is true ?
SE0050
(1) Bond angle changes but bond length remains
4. The correct statement regarding the
same
comparison of staggered and eclipsed
(2) Both bond angle and bond length change
conformation of ethane, is :-
(3) Both bond angles and bond length remains
(1) The staggered conformation of ethane is less
same
stable than eclipsed conformation, because
(4) Bond angle remains same but bond length
staggered conformation has torsional strain
changes
SE0056
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7. Dihedral angle of least stable conformer of 10. Which one is not a D-sugar ?
ethane is : CHO CHO
(1) 120° (2) 180° (3) 60° (4) 0° H OH H OH
SE0109 (1) (2)
OH H H OH
8. The compound which shows metamerism is:
CH2OH CH2OH
(1) C5H12 (2) C3H8O
CH2OH CHO
(3) C3H6O (4) C4H10O
HO H
SR0110 (3) C=O (4)
H OH
NEET(UG) 2021 (Paper-2) H OH
CH2OH
9. The correct configuration assigned for CH2OH
compounds (I) and (II) respectively is

®
SE0116
COOH NEET(UG) 2023 (Manipur)
Cl CH3
H OH C 11. Which amongst the following compounds will
Br CH2CH3
CH3 show geometrical isomerism ?
I II (1) Pent-1-ene
(1) R, R (2) S, S (3) R, S (4) S, R (2) 2,3-Dimethylbut-2-ene

SE0115 (3) 2-Methylprop-1-ene


(4) 3,4-Dimethylhex-3-ene
SE0117

EXERCISE-II (Previous Year Questions) ANSWER KEY


Que. 1 2 3 4 5 6 7 8 9 10 11
Ans. 1 3 2 4 2 3 4 4 1 1 4
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Chemistry : Isomerism ®
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EXERCISE-III (Analytical Questions) Master Your Understanding
1. Which of the following does not contain any 6. The minimum number of carbon atoms in ketone
asymmetric carbon but can show to show metamerism :–
enantiomerism:- (1) 3 (2) 4 (3) 5 (4) 6
(1) Lactic acid (2) 1, 3-pentadiene SR0070
(3) Tartaric acid (4) 2, 3-pentadiene 7. The total number of configurational isomers of
SE0063 the given compound are :-
2. Which of the following represents the structure CH3–CH=CHCHOHCHOHCH3
having cis arrangement around each double
(1) 2 (2) 4 (3) 6 (4) 8
bond :-
SE0073
H
(1) COOH COOH
H H OH H3C OH
8. CH3 and HO are :-

®
HO H
(2)
COOH COOH
(3) (1) Enantiomers
(2) Position isomers
(3) Geometrical isomers
(4)
(4) Homomers
H H
SE0075
SE0064
3. The complete IUPAC name of the compound :- 9. Which of the following is not a metamer of
CH3 H C4H10O
Br (1) Diethyl ether
(2) Methyl n-propyl ether
(1) (R)-1-Bromo-1-phenyl ethane (3) 2–Methoxy propane
(2) (S)-1-Bromo-1-phenyl ethane (4) Isobutyl alcohol
(3) (E)-1-Bromo-1-phenyl ethane SE0076
(4) (Z)-1-Bromo-1-phenyl ethane
10. How many compounds among the following are
SE0066
chiral ?
4. Which one of the following is the most stable H HO H
H3C H3C
conformation of 2, 3–butanediol :-
OH Br
OH OH Br Br
H OH H CH3
(1) (2)
H CH3 H CH3 Br
H OH Br
CH3 OH
OH OH
(1) 1 (2) 2
HO CH3 HO CH3 (3) 3 (4) 4
(3) (4) SE0097
CH3 H H CH3
H H 11. Which of the following is not chiral :-

SE0067 (1) 2–Butanol


(2) 2,3–Dibromo pentane
5. How many isomers of C5H11OH will be primary
(3) 3–Bromo pentane
alcohols (exclude stereoisomers) :–
(4) 2–Hydroxy propanoic acid
(1) 2 (2) 3 (3) 4 (4) 6
SE0036
NC0069
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® Chemistry : Isomerism
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12. CH3—CHCl—CH2—CH3 has a chiral centre 16. Which of the following conformers for ethylene
which one of the following represents its R glycol is most stable :-
configuration
OH OH
C2H5 C2H5 OH H
(1) H CH3 (2) Cl CH3
(1) H (2) HO
Cl H H H H H
H H
CH3 C2H5
OH OH
(3) H Cl (4) H3C Cl H OH H H
C2H5 H
(3) H H (4) H H
SE0039
H OH
13. How many stereoisomer does this molecule have
SE0043
CH3CH=CHCH2CHBrCH3
17. Which of the following acids does not exhibit
(1) 8 (2) 2 (3) 4 (4) 6

®
SE0040 optical isomerism?

14. Which of the following compounds will exhibit (1) Lactic acid
cis-trans (geometrical) isomerism ? (2) Tartaric acid
(1) 1-Butanol (2) 2-Butene
(3) Maleic acid
(3) 2-Butanol (4) 2-Butyne
SE0041 (4) α-amino acids

15. In the following the most stable conformation of SE0046


n–butane is :-
18. The IUPAC name of the following compound
CH3 CH3
H H CH3 CH2CH3
Cl

(1) (2) is :-
H H H CH3 I
H H3C H
H
CH3 (1) cis-2-chloro-3-iodo-2-pentene
CH3
H H CH3 (2) trans-2-chloro-3-iodo-2-pentene
(3) cis-3-iodo-4-chloro-3-pentene
(3) (4)
(4) trans-3-iodo-4-chloro-3-pentene
H H H
H H H
CH3 SE0047
SE0042

EXERCISE-III (Analytical Questions) ANSWER KEY


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