TARGET IIT-JEE

ISOMERISM

INDEX
EXERCISE-I ............................................ 2-11
EXERCISE-II.........................................12-16
EXERCISE-III .......................................17-36
EXERCISE-IV .......................................37-42
 EXERCISE - I
1. Which of following will exhibit geometrical isomerism?
(A) 1-phenyl-2-butene (B) 3-phenyl-1-butene
(C) 2-phenyl-1-butene (D) 1,1-diphenyl-1-propene

2. Which of the following heptanols are chiral 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol.
(A) All are chiral (B) 2-heptanol and 3-heptanol
(C) 2-heptanol, 3-heptanol & 4-heptanol (D) 3-heptanol and 4-heptanol

3. Examine the compound on the right. How many stereoisomers having this constitution are possible ?
CH3
H3C
O
H3C
CH3
Br
CH3
CH3
(A) 2 (B) 4 (C) 6 (D) 8

4. How many stereoisomers of (CH3)2 CHCH=CHCH2CH(OH)CH2Br are possible ?

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

5. Which two of the following compounds represents a pair of enantiomers ?

HO OH HO OH

HO OH HO OH
I II III IV

(A) I & II (B) II & III (C) III & IV (D) II & IV

6. Which two of the following compounds are diastereomers ?

OH OH OH
OH HO OH OH
OH
O
OH O O O OH
OH
OH
I III IV
II
(A) I & II (B) II & IV (C) III & IV (D) I & III

7. Among the following, a pair of resolvable configurational enantiomers is given by

(A) cis-1, 2-dimethylcyclohexane (B) cis-1, 3-dimethylcyclohexane
(C) cis-1, 4-dimethylcyclohexane (D) trans-1, 3-dimethylcyclohexane

8. In the given following compound find out the pair of enantiomers and diastereomers
OH O

R R
R
(A) 2, 2 (B) 2, 4 (C) 4, 4 (D) 4, 2

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9. Compound having meso stereoisomer?
(A) 2,3-dimethyl butane (B) 1,3-dichloropentane
(C) 2,4-pentane-diol (D) 2,3-dichloro heptane

10. What kind of reagent would be needed to resolve a racemic amine, such as 2-aminobutane ?
(A) the pure optically active amine to serve as a template for crystallization.
(B) an achiral carboxylic acid to give a recemic mixture of amine salts.
(C) an enantiomerically pure chiral carboxylic acid to give a diastereomeric mixture of amine salts ?
(D) a racemic chiral carboxylic acid to give a complete mixutre of isomeric amine salts.

O OH O
|| | ||
11. S – CH = CH – CH – C – CH3
..

Number of chiral centers are :

(A) 1 (B) 2 (C) 3 (D) 4

12. The molecule(s) that exist as meso structure(s)

(K) (L) (M)

(A) only M (B) both K and L (C) only L (D) only K

13. Which two of the following compounds are identical ?

OH OH OH
OH HO OH OH
OH
O
OH O O O OH
OH
OH
I III IV
II
(A) I & II (B) II & IV (C) III & IV (D) I & III

14. Which of the folllowing is properly classified as a meso compound ?

C2H5
CH3 H C2H5
OH CH3 H OH
H OH HO H
H H
(A) HO H (B) OH (C) H OH (D) H OH
CH3 H CH3 C2H5 CH3

15. Which of the following compounds is (S)–4–chloro–1–methylcyclohexene ?

CH3 CH3
CH3 CH3

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

Cl Cl Cl Cl

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16. How many stereoisomers are possible for the following molecule.

Cl
Br CH = CH
CH3

(A) 4 (B) 8 (C) 16 (D) 32

17. How many stereoisomers are possible for the following compound?

NO2 CHBrMe

CH=CHMe I
(A) 2 (B) 4 (C) 6 (D) 8

18. For the following Newman projection

Cl
H Cl

H H
H
H H H Cl Cl H H Cl

Cl Cl Cl H H H H H
(A) (B) (C) (D)

H H H H H Cl Cl H
19. Relationship in between

CH3 CH3
CH3 Cl H Cl
&
H Cl Cl H
H CH3
(A) diastereomer (B) Identical (C) Enantiomer (D) None of these

20. Which conformer is responsible for dipole moment.

(A) Anti (B) gauche (C) Partial Eclipsed (D) Fully eclipsed

21. Which of the following compound represent R–2–butanol ?

Me Et Et OH

(A) OH (B) Me H (C) Me OH (D) Me Et

Et
H OH H H
22. How many meso stereisomers exist for 2, 3, 4, 5-tetrachloro hexane?
(A) 1 (B) 2 (C) 3 (D) 4

23. Compound X and Y are constitutional isomers with molecular formula C5H10. Compound X possesses a
carbon-carbon double bond in the TRANS configuration, while compound Y possesses a carbon-carbon
double bond that is not stereoisomeric. Total different possible structures for compound Y are :
(A) 2 (B) 3 (C) 4 (D) 5

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24. Total number of optically active alkyne possible from molecular formula C3FCl BrI

(A) 2 (B) 4 (C) 6 (D) 8

CH3
C2H5 CH3
CH3 CH3
25. CH3 CH3 H C2H5
N N
H H
H CH3
CH3 CH3 N
H C2H5
(I) (II)
(III)
Which of the following statement is correct?

(A) I & II are conformational isomers while II & III are functional isomers

(B) I & II are functional isomers while II & III are conformational isomers
(C) I & II are functional isomers while I & III are conformational isomers

(D) None of the above

Me
Me
26. H
H
Incorrect statement about this compound is:
(A) It shows geometrical isomerism (B) It posses centre of symmetry
(C) It posses plane of symmetry (D) It shows optical isomerism

27. Sum of stereoisomer in the given compound (a) and (b) are
Cl
Cl Cl = a (stereoisomer) ; = b (stereoisomer)
Cl
a+b=?
(A) 3 (B) 4 (C) 5 (D) 6

28. Shows which type of isomersim

O O
Cl C—O C—O Cl
H CH3
C=C and
C=C
H CH3 H H
(A) Functional group isomerism (B) Geometrical isomerism
(C) Metamerism (D) Position isomerism

29. Which of the following will not show optical isomerism.

(A) Cl – CH = C = C = CH – Cl (B) Cl – CH = C = C = C = CH – Cl
H
Cl H

(C) (D)
Me Cl
Me
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30. On chlorination of propane number of products of the formula C3H6Cl2 is
(A) 3 (B) 4 (C) 5 (D) 6

31. The number of optically active isomers observed in 2,3-dichlorobutane is:

(A) 0 (B) 2 (C) 3 (D) 4

32. Which of the following, compounds displays geometrical isomerism?

(A) CH2 = CHBr (B) CH2 = CBr2 (C) ClCH=CHBr (D) Br2C=CCl2

33. Number of possible 3D-isomers (Stereoisomer) of glucose are

(A) 10 (B) 14 (C) 16 (D) 20

34.

The above compounds differ in

(A) configuration (B) conformation (C) structure (D) chirality

35.

Which of the above formula represent identical compounds?

(A) I and II (B) I and IV (C) II and IV (D) III and IV

36. The structures shown here are related as being:

(A) conformers (B) enantiomorphs

(C) geometrical isomers (D) diastereoisomers

37. The prefered conformation of trans-1,2-dibromocyclohexane is:

(A) diaxial (B) diequatorial (C) axial/ equatorial (D) neither A,B, nor C

38. The number of optically active compounds in the isomers of C4H9Br is

(A) 1 (B) 2 (C) 3 (D) 4

39. Meso tartaric acid and d-tartaric acid are

(A) Position isomers (B) Enantiomers (C) Diastereomers (D) Racemic mixture

40. Molecular formula C3H6Br2 can have (including stereoisomers) :

(A) Two gem dibromide (B) One vic dibromide
(C) Two tertiary dibromo alkane (D) Two secondary dibromo alkane
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41. How many stereoisomer may have this natural occuring compound.

O
HO CH2 – OH

HO CH=CH–CH=CH–CH2–CH2–CH3
(A) 8 (B) 16 (C) 64 (D) 128

42. Which of the following statements must be true for two pure chiral isomers ?
(A) they must be enantiomers (B) they must be diastereomers
(C) they must be stereoisomers (D) they must be optically active

43. Stereoisomers differ from each other in what respect ?

(A) Composition (B) constitution (C) configuration (D) seric hindrance

OH OH
| |
44. CH3  CH2  CH2  CH2 and CH3  C  CH3 are
|
CH3
(A) chain isomers (B) positional isomers (C) both (D) none

45.

Relation between given pair is

(A) Enantiomer (B) Diastereomer (C) Identical (D) Structural Isomer

46. The number of isomers of C5H10 is

(A) 10 (B) 11 (C) 12 (D) 13

47. The number of isomers of C3H5Br3 is (including stereoisomers)

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

CH3
H Cl
48. HO H
C2H5
The compound with the above configuration is called:
(A) (2S, 3S)-2-chloro-3-pentanol (B) (2S, 3R)-2-chloro-3-pentanol
(C) (2R, 3R)-2-chloro-3-pentanol (D) (2R, 3S)-2-chloro-3-pentanol

CH3 CH3
H Cl H Cl is
49. Optical rotation produced by Cl H is 36° then that product by H Cl
CH3 CH3

(A) – 36° (B) 0° (C) +36° (D) unpredictable

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50. Following eclipsed form of propane is repeated after rotation of
OH

O = – CH3
H H
H H
(A) 45° (B) 90° (C) 120° (D) 180°

51. Which of the following sugars has the configuration (2S, 3R, 4R) ?

CHO CHO CHO CHO

H OH H OH HO H HO H
H OH HO H H OH HO H
(A) (B) (C) (D)
H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH

52. Which of the following statements is true for a pair of diastereomers ?

(A) they will have identical physical properties.
(B) they will have specific rotations of opposite sign
(C) they will have identical chemical properties (e.g. reactivity)
(D) they will have different physical properties.

53. Match List I with List II and select the correct answer from the codes given below the lists:
List I

O O
|| ||
(A) CH 3  C  O  CH 2  CH 2  CH 3 and CH 3  CH 2  C  O  CH 2  CH 3

(B) and

(C) and

(D) and

List II
(1) Enantiomer (2) Position isomers (3) Metamers (4) Tautomers
Codes :
(A) (B) (C) (D) (A) (B) (C) (D)
(A) 3 2 4 1 (B) 3 2 1 4
(C) 1 2 3 4 (D) 2 3 4 1

54. How many total isomers are possible by replacing one hydrogens atoms of propane with chlorine
(A) 2 (B) 3 (C) 4 (D) 5
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55. The two compounds given below are

(A) enantiomers (B) identical (C) optically inactive (D) diastereomers

56. Given compound shows which type of isomerism

O O
S—O and S—O
O O
(A) Chain isomerism (B) Positional isomerism
(C) Metamerism (D) Functional group isomerism

57. Which of following pair is Diastereomers:

CO2H
H OH CO2H CH3 H CH3
H OH
H
CH3 C C H
(A) H OH (B) C=C Br Br C=C
HO H
CO2H CO2H H H H CH3
CH3 Et Cl Cl
H OH HO H Cl Cl
(C) H SH HS H (D)
Et CH3 Cl Cl

58. How many stereoisomers of the following molecule are possible?

HOOC.CH = C = CH.COOH
(A) two optical isomers (B) two geometrical isomers
(C) two optical and two geometrical isomers (D) None

59. Which of the following cannot be written in an isomeric form?

(A) CH3–CH(OH)–CH2–CH3 (B) CH3 – CHO
(C) CH2 = CH – Cl (D) Cl – CH2CH2 – Cl

60.

Which of the above compounds are enantiomers?

(A) II and III (B) III and IV (C) III and V (D) I and V

61. Which species exhibits a plane of symmetry?

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

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62. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are
(A) enantiomers (B) geometrical isomers
(C) metamers (D) conformational isomers

Et
Keq. Et
63.
Me Me
equilibrium constant for above reaction is :
(A) K = 1 (B) K > 1 (C) K < 1 (D) K = 0

64. Minimum C atoms required for a compound to show geometrical isomerims:

(A) 2 (B) 3 (C) 4 (D) None of these

65. How many plane of symmetry are present in nepthalene

Naphthalene
(A) 1 (B) 2 (C) 3 (D) 6

66. On chlorination of propane number of products of the formula C3H6Cl2 is

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

67. The relationship among the following pairs of isomers is

O Br Br Br H CHO CHO
O H OH HO H
H H H Br CH2OH CH2OH
I II III IV

I A : Constitutional
II B : Configurational
III C : Conformational
IV D : Optical

(A) I-A, II-B, III-B, IV-D (B) I-A, II-A, III-B, IV-D
(C) I-B, II-A, III-B, IV-D (D) I-B, II-B, III-A, IV-B

68. Which of the following compound has centre of symmetry but not plane of symmetry.

Br Cl Br Cl Br Cl Br Cl

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

Cl Br Cl Br Cl Br Cl Br

69. Total number of geometric diastereomers exist for 1, 3-dichloro-2, 4-dimethyl cydobutane?
(A) 3 (B) 4 (C) 5 (D) 6

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70. Which conformer of n-butane is chiral
(A) anti (B) gauche (C) fully-ecllipsed (D) none of these

71. Most stable conformer of CH3 – O – O – CH3 is (when rotated between oxygens)

.. ..
CH3
.. .. .. .. .. .. .. .. .. .. CH3

(A) .. .. (B) (C) .. CH3 (D) ..

CH3 CH3 CH 3 CH3 CH3

ANSWER KEY
1. A 2. B 3. D 4. C 5. C 6. D 7. D
8. B 9. C 10. C 11. B 12. B 13. B 14. A
15. A 16. C 17. D 18. B 19. B 20. B 21. C
22. B 23. C 24. D 25. D 26. B 27. C 28. C
29. A 30. C 31. B 32. C 33. C 34. C 35. B
36. D 37. B 38. B 39. C 40. A 41. C 42. D
43. C 44. A 45. C 46. C 47. D 48. A 49. B
50. C 51. C 52. D 53. A 54. A 55. A 56. C
57. B 58. A 59. C 60. C 61. D 62. C 63. B
64. D 65. C 66. C 67. B 68. A 69. C 70. B
71. A

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 EXERCISE - II
1. The number os isomers for the compound with molecular formula C2BrClFI is [AIEEE-2001]
(A) 3 (B) 4 (C) 5 (D) 6

2. Which of the following compounds exhibits, stereoisomerism? [AIEEE-2002]

(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid

3. A similarity between optical and geometrical isomerism is that [AIEEE-2002]

(A) each forms equal number of isomers for a given compound
(B) If in a compound one is present then so is the other
(C) both are included in stereoisomerism
(D) they have no similarity
4. Which of the following does not show geometrical isomerism ? [AIEEE-2002]
(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1,4-dichloro-2-pentene
5. Racemic mixture is formed by mixing two [AIEEE-2002]
(A) isomeric compounds (B) chiral compounds
(C) meso compounds (D) optical isomers
6. Among the following four structures I to IV [AIEEE-2003]

CH3 O CH3 H CH3

| || | | |
C2H5 — CH — C3H7 CH3 — C — CH — C2H5 H—C C2H5 — CH — C2H5
|
H
(I) (II) (III) (IV)
it is true that :
(A) all four are chiral compounds (B) only I and II are chiral compounds
(C) only III is a chiral compound (D) only II and IV are chiral compounds

7. On mixing a certain alkane with chlorine and irradiating it with ultraviolet light, it forms only one
monochloroalkane. This alkane could be [AIEEE-2003]
(A) propane (B) pentane (C) isopentane (D) neopentane

8. Which of the following will have meso-isomer also ? [AIEEE-2004]

(A) 2- chlorobutane (B) 2- hydroxy propanoic acid
(C) 2,3 – dichloropentane (D) 2-3- dichlorobutane

9. Amongst the following compound, the optically active alkane having lowest molecular mass is
[AIEEE-2004]

(A) H3C CH3 (B) H3C

CH
CH3 CH3
CH3
H3C
(C) (D)
C 2H 5 H3C CH3

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10. Which of the following compound is not chiral ? [AIEEE-2004]
(A) 1- chloropentane (B) 3-chloro-2- methyl pentane
(C) 1-chloro -2- methyl pentane (D) 2- chloropentane

1
CH3
H
H H
3
2
11. H H
CH3

C2 is rotated anti-clockwise 120° about C2-C3 bond. The resulting conformer is [AIEEE-2004]
(A) partially eclipsed (B) eclipsed (C) gauche (D) staggered

12. Due to the presence of an unpaired electron, free radicals are: [AIEEE-2005]
(A) Chemically reactive (B) Chemically inactive
(C) Anions (D) Cations
13. 2 methylbutane on reacting with bromine in the presence of sunlight gives mainly [AIEEE-2005]
(A) 1 – bromo -2- methylbutane (B) 2–bromo-2-methylbutane
(C) 2 – bromo -3- methylbutane (D) 1–bromo-3-methylbutane

14. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is [AIEEE-2005]
(A) n-hexane (B) 2, 3-dimethylbutane
(C) 2,2-dimethylbutane (D) 2-methylpentane

15. Which types of isomerism is shown by 2,3-dichlorobutane? [AIEEE-2005]

(A) Tautomerism (B) Optical (C) Geometric (D) Structural
16. Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of 2-fluoroethanol
is [AIEEE-2006]
(A) Eclipse, Gauche, Anti (B) Gauche, Eclipse, Anti
(C) Eclipse, Anti, Gauche (D) Anti, Gauche, Eclipse
17. The IUPAC name of C6H5COCl is [AIEEE-2006]
(A) benzoyl chloride (B) benzene chloro ketone
(C) benzene carbonyl chloride (D) chloro phenyl ketone

18. Which of the following molecules is expected to rotate the plane of plane polarized light ? [AIEEE-2007]

CHO COOH
H2N NH2
(A) HO H (B) (C) H H (D) H2N H
SH
Ph Ph H
CH2OH

19. Which one of the following conformation of cyclohexane is chiral? [AIEEE-2007]

(A) Twist boat (B) Rigid (C) Chair (D) Boat

20. The number of stereoisomers obtained by bromination of trans-2-butene is [AIEEE-2007]

(A) 1 (B) 2 (C) 3 (D) 4

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21. Read the following questions and answer as per the direction given below: [AIEEE-2007]
Statement-I : Molecules that are non-superimposable on their mirror images are chiral. Statement II All
chiral molecules have chiral centres.
Statement-II : All chiral molecules have chiral centers.
(A) Statement I is correct; Statement II is correct; Statement II is the correct explanation of Statement I.
(B) Statement I is correct; Statement II is correct; Statement II is not the correct explanation of Statement I.
(C) Statement I is correct; Statement II is incorrect.
(D) Statement I is incorrect; Statement II is correct.

HO2C CO2H
22. The absolute configuration of is [AIEEE-2008]
HO H OH
H
(A) S, S (B) R, R (C) R, S (D) S, R

23. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]

(A) 2-butene (B) 2-methyl-2-butene (C) propene (D) 2-methyl propene

24. The number of stereoisomers possible for a compound of the molecular formula [AIEEE-2009]
CH3 – CH = CH – CH(OH) – Me is :
(A) 4 (B) 6 (C) 3 (D) 2

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

(A) 2-methylpropane (B) 2, 2-dimethylbutane
(C) 2-methylbutane (D) 2, 2-dimethylpropane

26. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular mass
of 44 u. The alkene is [AIEEE-2010]
(A) 2-butene (B) ethene (C) propene (D) 1-butene

27. Identify the compound that exhibits tautomerism. [AIEEE-2011]

(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol

28. Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the presence
of : [AIEEE-2011]
(A) two ethylenic double bonds (B) a vinyl group
(C) an isopropyl group (D) an acetylenic triple bond
29. How many chiral compounds are possible on monochlorination of 2- methyl butane? [AIEEE-2012]
(A) 8 (B) 2 (C) 4 (D) 6

30. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono
substituted alkyl halide ? [AIEEE-2012]
(A) Tertiary butyl chloride (B) Neopentane
(C) Isohexane (D) Neohexane

31. The absolute configuration of [JEE Mains-2016]

CO2H
H OH
H Cl
CH3
is :
(A) (2R, 3S) (B) (2S, 3R) (C) (2S, 3S) (D) (2R, 3R)

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32. In the following structure, the double bonds are marked as I, II, III and IV [JEE Mains Online-2017]

II

III
I IV

Geometrical isomerism is not possible at site (s) :

(A) III (B) I (C) I and III (D) III and IV

33. The total number of optically active compounds formed inthet following reaction is :
[JEE Mains Online, 2018]

O
HBr

(A) Two (B) Four (C) Six (D) Zero

34. The IUPAC name of the following compound is [JEE Mains Online, 2019]

CH3
H3C CH

CH3
CH2

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

(C) 3-methyl-4-(1-methylporop-2-ynyl)-1-heptene (D) 3, 5-dimethyl-4-propylhept-1-en-6-yne
35. The correct IUPAC name of the following compound is [JEE Mains Online, 2019]

NO2

Cl
CH3

(A) 2-methyl-5-nitro-1-chlorobenzene (B) 3-chloro-1-methyl-1-nitrobenzene

(C) 2-chloro-1-methyl-4-nitrobenzene (D) 5-chloro-1-methyl-1, 1-nitrobenzene

36. Which of the following compounds will show the maximum ‘enol’ content? [JEE Mains Online, 2019]
(A) CH3COOCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2

37. The IUPAC name of the following compound is [JEE Mains Online, 2019]

CH3 OH
H3C CH CH CH2 COOH

(A) 4,4-dimethy-1-hydroxybutanoic acid (B) 2-methyl-3-hydroxypentan-5-oic acid

(C) 3-hydroxy-4-methylpentanoic acid (D) 4-methyl-3-hydroxypetanoic acid
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38. What is the IUPAC name of teh following compound ? [JEE Mains Online, 2019]

H3C CH3

H
H
H3C Br

(A) 3-bromo-3-methyl-1, 2-dimethylprop-1-ene (B) 3-bromo-1, 2-dimethylbut-1-ene

(C) 2-bromo-3-methylpent-3-ene (D) 4-bromo-3-methylpent-2-ene
39. The IUPAC name of the follwoing compound is [JEE Mains Online, 2019]
OH

CN
Br
(A) 4-bromo-3-cyanophenol (B) 2-bromo-5-hydroxybenzonitrile
(C) 2-cyano-4-hydroxybromobenzene (D) 6-bromo-3-hydroxybenzonitrile
40. In the following skew conformation of ethane, H' – C – C H' dihedral angle is : [JEE Mains Online, 2019]
H
H' 29º
H
H

H''

H
(A) 58º (B) 120º (C) 149º (D) 151º
41. The number of chiral carbons in chloramphenicol is ____________. [JEE Mains Online-2020]

42. The number of chiral centres in penicillin is____________. [JEE Mains Online-2020]

43. The number of chiral carbons present in the molecule given below is ... [JEE Mains Online-2020]

N
O
H
C
H3C CH3
OH
N

ANSWER KEY
1. D 2. D 3. C 4. C 5. D 6. B 7. D
8. D 9. D 10. A 11. 12. A 13. B 14. B
15. B 16. C 17. C 18. A 19. A 20. A 21. C
22. B 23. A 24. A 25. D 26. A 27. C 28. B
29. C 30. B 31. B 32. B 33. B 34. D 35. C
36. B 37. C 38. D 39. B 40. C 41. 2 42. 3
43. 5
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 EXERCISE - III
One or more than one correct questions :
1. In which of the following molecule show chirality.

Me Me
COOMe Cl
(I) (II)
(A) I is trans & chiral (B) II is trans & chiral (C) I is cis & chiral (D) II is trans & achiral

2. Total number of stereoisomer is odd number for

CO2H CHO
H OH H OH
(A) (B) (C) (D) H OH
H OH H OH
CO2H CH2 – OH

3. Statement-1 : This compound will show geometrical isomerism

Statement-2 : Terminal carbon groups are perpendicular to each other

(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True

4. Which of the following compounds is optically active?

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

5. C4H6O2 does represent:

(A) A diketone (B) A compound with two aldehyde
(C) An alkenoic acid (D) An alkanoic acid

6. Which of the following compounds is optically active?

(A) 1-Bromobutane (B) 2-Bromobutane
(C) 1-Bromo-2-methylpropane (D) 2-Bromo-2-methylpropane
CH3
7. Which of the following operations on the Fischer formula H OH does not change its absolute
C2H5
configuration?
(A) Exchanging groups across the horizontal bond
(B) Exchanging groups across the vertical bond
(C) Exchanging groups across the horizontal bond and also across the vertical bond
(D) Exchanging a vertical and horizontal group

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8. Which of the following combinations amongst the four Fischer projections represents the same absolute
configurations?

(A) (II) and (III) (B) (I) and (IV) (C) (II) and (IV) (D) (III) and (IV)

9. Which of the following compounds are optically active?

(A) CH3.CHOH.CH2.CH3 (B) H2C=CH.CH2.CH=CH2 (C) (D)

10. Which of the following will show optical isomerism as well as geometrical isomerism.

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

11. Which of the following are correct representation of L–amino acids

(A) (B)

(C) (D)

12. Which of the following are D sugars:

CHO
H OH
HO H
(A) (B) (C) (D)
H OH
HO–CH2 H
OH

13. The Fischer projection of the molecule as represented in the wedge dash.

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

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14. Given compound shows which type of isomersim

and

(A) Chain isomerism (B) Positional isomerism

(C) Constitutional isomerism (D) None

15. Which of following compound having plane of symmetry.

CO2H CH2–Br
H H Cl H
H OH
(A) (B) (C) C=C (D)
H OH H
HO OH Cl
CO2H
16. Among options (A – D), identify that combination which is capable of making below compound a chiral
compound.

R H
H P

H H

H Q S H
P Q R S
(A) (CH3)3C– –H –H –H
(B) (CH3)3C– –CH3 –H –H
(C) (CH3)3C– –H (CH3)3C– –H
(D) (CH3)3C– (CH3)3C– (CH3)3C– –H

17. Among the following pairs, which pairs are enantiomers of each other?

Vinyl
H Cl
Cl H
(A) (B)
AcO Cl H Cl H

Vinyl
OAc

Et Et
O O O
Et
(C) (D)
O Me Me
Et
18. The number of stereoisomers possible for the below compound (do not change cis/trans configurations of the
olefins) are
O CO2H

OH
OH
(A) 8 (B) 16 (C) 32 (D) 12

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19. Which of the following represent distereoisomeric pair

Me Me
H OH HO H
(A) (B) H OH H OH
HO H H OH
Me Me

Me F
Me Me Me H
(C) H F H Cl (D) C=C=C C=C=C
H Me
Cl Me H H

20. Determine the position of substituents in the most stable conformation according to IUPAC nomencalture:

Me

Me
Me
(A) 1e, 2a, 4e (B) 1e, 3a, 4e (C) 1a, 2e, 4a (D) 1a, 3e, 4a

21. Compound-I Compound-II

CH3 CH3

Compound I and II are ?

(A) Identical (B) Position Isomers (C) Enantiomers (D) Geometrical Isomers

CH3

22. H OH
HO H

CH3

Correct statement(s) about given compound.

(A) POS is absent but COS is present.
(B) If POS is absent in fisher projection formula following the golden rule then COS will also be absent in
same compound in it's any conformation.
(C) It is optically inactive compound.
(D) It's anti staggered form is more stable than gauche form

23. Which of the following compound has C2-axis of symmetry.

Cl Cl Cl H
(A) (B) (C) C C (D) All
H H H Cl

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24. Which of the following is/are D-carbohydrate
CHO CH2OH
(A) H OH (B) H OH
HO H HO H
CH2OH CHO

OH CHO
HO H
(C) H CHO (D)
H OH
CH2OH CH2OH

25. (R)-Limonene is found in many citrus fruits, induding oranges and lemons :

Which of the following compounds are enantiomers of the above compound ?

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

26. Which of the following molecules has axis of symmetry and a coaxial plane of symmetry ?

Cl Cl H H
O
(A) (B) (C) C (D)
H H Cl Cl

27. Which of the following pair of compound are diastereomers ?

CH3 CH3 Cl I

(A) Cl Cl Cl I H
H H Cl H H (B) Cl H H Cl I Cl

CH3 CH3 I H

Br H H Br
F Br H H H Cl
(C) Br F H H (D)
F Br Br I H I
F H Cl H
28. Which of the following compound/s can show optical isomerism ?

COOH Cl
H OH
(A) (B)
H OH
Cl
COOH

(C) Me–CH=C=CH–Me (D)

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Assersion & Reasion :
O
Me NH H

29. Statement-1 is opticallyactive.

H NH Me
O
Statement-2 Optically active compound do not have plane of symmetry.
(A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1
(B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1
(C) Statement-1 is true, Statement-2 is false
(D) Statement-1 is false, Statement-2 is true

30. Statement-1 Configuration does not change with change in conformation.

Statement-2 Two different configuration are restricted towards rotation across  bond.
(A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1
(B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1
(C) Statement-1 is true, Statement-2 is false
(D) Statement-1 is false, Statement-2 is true

Comprehension :
Comprehension (Q.31 to Q.33) :
If a molecule contains one carbon atom carrying four different groups it will not have a plane of symmetry and
must therefore be chiral. A carbon atom carrying four different groups is a stereogenic or chiral centre.
A structure with a plane of symmetry is achiral and superimposable on its mirror image and cannot exist as
two enantiomer. A structure without a plane of symmetry and centre of symmetry is chiral and not
superimposable on its mirror image and can exist as two enantiomer.

CH3
H Br
H Cl
31.
H F
CH3

Number of enantiomeric pairs are

(A) 2 (B) 4 (C) 8 (D) 10

Cl Cl

32.
Cl Cl Cl Cl
(a) (b)

Relation between (a) & (b) is

(A) Enantiomer (B) Diastereomer (C) Identical (D) Structural isomer

33. Compound has both center of symmetry and P.O.S

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

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Comprehension (Q.34 to Q.36) :
The antibiotic cephalosporin C has a specific rotation of +103º in water.

O
||
H2N NH S
HO2C N O
O ||
O
Cephalosporin C

34. Total number of chiral centres present are

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

35. What is the maximum number of stereoisomers for the above structure?
(A) (B) 8 (C) 16 (D) 32

36. If a synthetic sample of cephalosporin C has an optical rotation of +82º, what percent of the enantiomers is
levorotatory ?
(A) 90% (B) 80% (C) 10% (D) 20%

Comprehension (Q.37 to Q.38) :

If plane-polarized light is passed through one enantiomer of a chiral substance (either the pure enantiomer or
a solution of it), the plane of polarization of the emergent light is rotated. A substance that rotates the plane
of polarized light is said to be optically active. Individual enantiomers of chiral substances are optically
active.

37. HO

Total stereoisomer of given compound will be

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

38. Which of the following compound show optical isomerism (Assuming cyclobutane ring is planar)

F
F
(A) F (B)
F

(C) (D)
F

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Match the Column :
39. Match the column:
Column I Column II

(A) Compound show geometrical isomerism (P)

(B) Compound shows optical isomerism (Q)

(C) Compound having plane of symmetry (R)

(D) Compound having centre of symmetry (S)

40. Match the column :

Column I Column II

(A) (P) Chiral

(B) (Q) Plane of symmetry

(C) (R) S

(D) (S) E (Entegen)

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41. Match the column :
Column-I Column II

(A) (P) Meso compound

Me2N
Me OH
CC–Me

(B) (Q) Compound having even no. of chiral

O centres.

(RO-486/mifepristone)

(C) (R) Optically active compound.

(D) (S) Compound having odd no. of chiral

42. Match the column :

(I) (II)

(III) (IV)

Column I Column II
(A) Plane of symmetry (P) I
(B) Centre of symmetry (Q) II
(C) Show geometrical isomerism (R) III
(D) Show optical isomerism (S) IV

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43. Match the column :
Compound Relationship

(A) (P) Identical

OH
OH

(B) (Q) Enantiomeric pair

OH
OH
H COOH COOH H
(C) (R) Epimeric pair
Me H H Me

HO
(D) HO (S) Diastereomeric pair
OH
OH
(T) One of the compound is meso

44. Match the column :

Column-I Column-II
Me Me
(A) (P) Plane of symmetry
H H
Me H
(B) (Q) Centre of symmetry
H Me
H
Me
(C) Me (R) Axis of symmetry
H
(D) Gauche form of n-butane across (S) Chiral
C2 – C3 bond (T) Can show geometrical isomerism

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45. Match the column :
Column I Column II

(A) (P) Total number of stereoisomers is odd

for the structure

(B) (Q) Total number of stereoisomers is even

for the structure

(C) (R) Odd number of chiral centre

(D) (S) Even number of chiral centre

centres.

46. Match the column :

Column I Column II

Cl Cl
Cl Cl

(A) (P) Position isomers

Cl Cl
Cl
Cl
Cl

(B) (Q) Enantiomers

Cl Cl Cl

Cl Cl

(C) (R) Diastereomers

Cl Cl Cl Cl
Cl Cl
Cl
(D) (S) Identical
Cl
Cl Cl
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47. Match the column :
Column I Column II

Cl O

Me
(A) (P) Total number of stereo isomers are odd.
Me Cl
Br

(B) (Q) Total number of stereocenter are even or

Br
have centre of symmetry.
H Cl
C
(C) (R) Compounds having plane of symmetry
C
Cl H
or axis of symmetry
COOH
H OH
(D) HO H (S) Compounds have zero dipole in given form.
COOH

48. Match the column :

Column I Column II

CH3 H
H H3C
CH2OH CH2NH2
(A) and (P) Structural isomer
NH2 OH

CH3 Cl
H H
Cl CH3
(B) and (Q) Identical
Et Et

CH3 H
H H3C
OH Et
(C) and (R) Enantiomers
Et OH

H 5C 2 H5C2
(D) and (S) Diastereomers
OH H H OH

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Subjective :
49. Determine if the following pairs are identical, isomers, enanatiomers, or diastereomers.
OH OH HO OH
(i) _________________

OH
OH
(ii) _________________

CHO CH2OH
H OH HO H
(iii) H OH HO H _________________
CH2OH CHO

50. Determine if the following pairs are identical, isomers, enanatiomers, or diastereomers.
HO
H NH2 OH
H2N H
(i) HO COOH _________________
HOOC OH
L-DOPA

CH2OH CH2OH
H OH H OH
H CH3 H3C H
(ii) _________________

(iii) _________________

51. Classify each of the following pairs of structures as :

I. Identical E. Enantiomers D. Diastereomers
CH = O CH = O
(a) H OH & HO H
CH3 CH3

CH = O CH = O
H OH HO H
(b) &
H OH H OH
CH3 CH3

Br Br
Br Br Br Br
(c) Br & Br

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52. Classify each of the following pairs of structures (a)–(e) as
I. Identical E. Enantiomers D. Diastereomers
CH3 CH3 CH3 CH2CH3
(a) H Br & Br H (b) H Cl & H CH 3
CH2CH3 CH2CH3 CH2CH3 Cl

CH3 CH3 CH3 CH3

H Br H Br H Br Br H
(c) & (d) &
H Br Br H H Br Br H
CH3 CH3 CH3 CH3

Br Br
Br Br
(e) &
Br Br

53. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, different compounds that are not isomeric).
OH OH
H H
CH3 CH3
(a) _________________

OH OH CH3
H H
CH3
(b) _________________

OH OH
H H
CH3 CH3
(c) _________________

OH OH
H H
CH3 CH3
(d) _________________

OH OH
H H
CH3 CH3
(e) _________________

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54. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, conformational isomers, different compounds that are not isomeric).
O O
CH3 CH3
(a) _________________
H3C H3C

O O
CH3 CH3
(b) _________________
H3C H3C

O O
CH3 CH3
(c) _________________
H3C H3C

O O
CH3 CH3
H3C
(d) _________________
H3C

O O
CH3 H3C
(e) _________________
H3C CH3

55. Select chiral molecule out of the following list compound.

(i) (ii)

(iii) (iv)

(v)

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56. Discuss the optical activity of the following two compounds and also label them as polar and non polar.

(I) (II)

Circle the word(s) in this Circle one word in this column

57. Column A column that describe the Column B that best describes the relationship
molecule in column A. of the molecules in columns A and B.
Br CH 3
chiral achiral enantiomers diastereomers
(a) (a)
H3C H meso none of these Br H identical none of these

H3C H H3C H

chiral achiral enantiomer s diastereom ers

(b) OH (b) HO
meso none of these identical none of these

CH3 CH3

chiral achiral enantiomers diastereomers

(c) (c)
meso none of these identical none of these
CH3 CH3

HO HO

HO OH chiral achiral HO OH enantiomer s diastereom ers

(d) (d)
meso none of these identical none of these

58. A cyclobutandicarboxylic acid exist in two stereo-isomeric forms in which one is polar but non-resolvable
while other is non-polar but resolvable into enantiomers. Deduce structures of all these compounds.

59. How many isomers are possible for nitrophenol?

60. A compound with molecular formula C4H10O, can show metamerism, functional isomerism and positional
isomerism. Justify the statement.

61. Calculate the total number of stereoisomers in the following compounds.

(I) (II) (III)

62. With reasons, state whether each of the following compounds I to VII is chiral.

(I) (II) (III)

(IV) (V) (VI)

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63. Considering rotation about the C-3 – C-4 bond of 2-methylhexane:
(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.

64. Determine whether each of the following compounds is a cis isomer or a trans isomer.

(a) (b) (c)

(d) (e) (f)

65. Mark each chiral center in the following molecules with an asterisk. How many stereoisomers are possible
for each molecule ?

OH
CH2 – COOH
(a) CH 3CHCHCOOH (b) CH – COOH (c) (d)

HO OH HO–CH–COOH

O OH
(e) O COOH (f) (g)
OH O

66. Mevacor is used clinically to lower serum cholesterol levels. How many chirality centers does Mevacor have?
HO O

O
O

O
CH3
CH3

H3C
Mevacor

67. Among the following How many compounds are chiral ?

H3C H3C

H3C CH3 CH3 H3C CH3 CH3

(a) (b) (c) (d)
H3C Cl H3C Cl Cl CH3 H3C Cl

CH3 Cl CH3 H3C Cl Cl CH3

(e) (f) (g) (h)
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68. Are the following structures chiral as drawn? When placed in a solution at 298 K, which structure will show
an optical rotation ? Explain.

(a) (b) (c) (d) (e) (f)

69. Which of the following compounds are chiral ? Which, if any, are meso?

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

70. Among of the following how many are meso compounds ?

Br Br Br H
CH3
C C C C
(i) H H (ii) H
CH3 CH3 Br
CH3

CH3
CH3 HO
HO OH
CH3
(iii) (iv) (v)
OH OH
OH

CHO CH2OH CH2OH

CH2OH
H OH HO H H OH
H OH
(vi) H OH (vii) (viii) (ix)
H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH

71. Among the following compounds how many has a stereoisomer that is a meso compound ?
(a) (i) 2,3-dimethylbutane (ii) 2-bromo-3-methylpentane (iii) 1-bromo-2-methylcyclohexane
(b) (i) 3,4-dimethylhexane (ii) 3,4-diethylhexane
(c) (i) 1,3-dimethylcyclohexane (ii) 1,4-dimethylcyclohexane (iii) 1,2-dimethylcyclohexane

72. Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers ?

CH3 CH3 Cl Cl
(A) and (B) and

CH3 CH3 CH3 CH3

Cl

Cl Cl Cl
(C) and (D) and

CH3 CH3 CH3 CH3

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73. Is the following compound optically active ?

Cl Br

Br Cl

74. Total number of chiral centers in amoxicillin, which belongs to the family of semisynthetic penicillins.

O
||
HO CH—C—HN
| S CH3
NH2
N CH3
O
C
HO O
Amoxicillin

75. Sum of stereocenter is/are ;

H H

(1) (a)
Cl Cl

O
||
(2) S—CH=CH—CH—CH3 (b)
|
Cl
Sum of (a + b = ?)

ANSWER KEY
1. AD 2. ABC 3. D 4. BC 5. ABC 6. B 7. C
8. C 9. ACD 10. ACD 11. ACD 12. ACD 13. AC 14. BC
15. ABCD 16. C 17. CD 18. B 19. A 20. A 21. D
22. B 23. D 24. D 25. AC 26. ABCD 27. BC 28. ABCD
29. D 30. C 31. B 32. B 33. D 34. A 35. B
36. C 37. B 38. B 39. (A) P, Q, R; (B) P, Q, S; (C) R ; (D) R
40. (A) P,R,S (B) P, R, (C) P, S, (D) P 41. (A) Q, R ; (B) R,S; (C) Q, R; (D) P, Q
42. (A) Q; (B) P; (C) P,Q,S; (D) R,S 43. A – R, S ; B – Q ; C – Q ; D – S, T
44. A – P, T ; B – S,T,R ; C – P,Q,T,R ; D – S,R 45. (A) Q, S ; (B) Q, S ; (C) P, S ; (D) Q, R
46. (A) R, (B) P, (C) S, (D) S 47. (A) P,Q,R ; (B) Q,R,S ; (C) Q,R,S ; (D) P,Q,R
48. (A) P ; (B) R ; (C) Q ; (D) R 49. (i) Diastereomers (ii) Enantiomers (iii) Identical
50. (i) Identical (ii) Diastereomers (iii) Diastereomers
51. (a) E (b) D (c) I 52. (a) E (b) I (c) D (d) I (e) E
53. (a) Diastereomer (b) Diastereomer (c) Not isomer (d) Structural (e) Enantiomer
54. (a) Diastereomer (b) Not isomer (c) Enantiomers (d) Structural isomers (e) Identical
55. (i) achiral (ii) achiral (iii) chiral (iv) chiral (v) achiral
56. Compound I is optically inactive since it contain a plane of symmetry. Compound II is enantiomeric since it does
not contain plane of symmetry, hence chiral. Also compound I is polar while II is non polar]

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57. (A) Column (a) chiral (b) chiral (c) meso/achiral (d) chiral
(B) Column (a) enantiomers (b) enantiomers (c) diastereomers (d) diastereomers
58. The compound must be 1,2-cyclobutan-dicarboxylic acid since all other constitutional isomers are non-resovable.

59. 3

60. (i) Et – O – Et, (ii) CH3 – O – CH2 – CH2 – CH3, (iii) CH3 – CH2 – CH2 – CH2 – OH, (iv) CH3 – CH2 – CH – CH3
|
I & II metamers, I & III functional isomers, III & IV position isomers OH
61. (I) 4, (II) 3, (III) 4 62. achiral : I, III ; chiral : II, IV, V, VI

Et
Et
H H
63. (a) (b)
H H
H
H H
H
64. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans

65. (a) 4 (b) 4 (c) 2 (d) 8 (e) 4 (f) 4 (g) 4 66. 8 67. 2 (c, e)
68. 2(a, d) 69. chiral  a, b ; meso  c 70. 5(i, iii, iv, vi, viii)
71. (a) 0 (b) 1 (c) 2
72. (A) Diastereoisomer, (B) Identical, (C) Diastereoisomer, (D) Constitutional isomers
73. Not optically active 74. 4 75. 7

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 EXERCISE - IV
1. Write structural formulae for all the isomeric alcohols having the molecular formula C4H10O. [JEE 1984]
2. True or False :
m-chlorobromobenzene is an isomer of m-bromochlorobenzene. [JEE 1985]

3. True or False:
2, 3, 4-Trichloropentane has three asymmetric carbon atoms. [JEE 1990]

4. Isomers which can be interconverted through rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers

5. The shows: [JEE 1995(Scr.)]

(A) geometrical isomerism (B) optical isomerism

(C) geometrical & optical isomerism (D) tautomerism

6. How many optically active stereoisomers are possible for butane-2,3-diol? [JEE 1997]
(A) 1 (B) 2 (C) 3 (D) 4

7. When cyclohexane is poured on water, it floats, because: [JEE 1997]

(A) cyclohexane is in 'boat' form (B) cyclohexane is in 'chair' form
(C) cyclohexane is in 'crown' form (D) cyclohexane is less dense than water

8. Which of the following compounds will show geometrical isomerism? [JEE 1998]
(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene

9. Which of the following compounds will exhibit geometrical isomerism? [JEE 2000 (Scr.)]
(A) 1-Phenyl-2-butene (B) 3-Phenyl-1-butene
(C) 2-Phenyl-1-butene (D) 1,1-Diphenyl-1-propene

10. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III. [JEE 2000]

11. The number of isomers for the compound with molecular formula C2BrClFI is
(A) 3 (B) 4 (C) 5 (D) 6 [JEE 2001 (Scr.)]

12. Which of the following compounds exhibits stereoisomerism? [JEE 2002 (Scr.)]
(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid

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13. In the given conformation, if C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then the
conformation obtained is [JEE 2004 (Scr.)]
4
CH3
H H
3
2
H H
1CH3
(A) fully eclisped conformation (B) partially eclipsed conformation
(C) gauche conformation (D) staggered conformation

14. (i) obs =  i x i

i
where i is the dipole moment of a stable conformer of the molecule, Z–CH2–CH2–Z and xi is the mole
fraction of the stable conformer.
Given : obs = 1.0 D and x (Anti) = 0.82
Draw all the stable conformers of Z–CH2–CH2–Z and calculate the value of (Gauche).
(ii) Draw the stable conformer of Y–CHD–CHD–Y(meso form), when Y= CH3 (rotation about C2–C3)
and Y = OH (rotation about C1 – C2 ) in Newmann projection. [JEE 2005]
15. The number of structural isomers for C6H14 is [JEE 2007]
(A) 3 (B) 4 (C) 5 (D) 6

16. Statement-1 : Molecules that are not superimposable on their mirror images are chiral.
because
Statement-2 : All chiral molecules have chiral centres.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True. [JEE 2007]

17. The correct statement(s) about the compound given below is (are) [JEE 2008]
Cl H

CH3
H3C

Cl H
(A) The compound is optically active (B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry (D) The compound possesses axis of symmetry

18. The correct statement(s) concerning the structures E, F and G is (are) [JEE 2008]

H3C O H3C OH H3C CH3

H3C CH3 H3C CH3 H3C OH

(E) (F) (G)
(A) E, F and G are resonance structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers

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19. The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3(X) is (are)
(A) The total number of stereoisomers possible for X is 6 [JEE 2009]
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2
20. The total number of cyclic structural as well as stereo isomers possible for compound with the molecular
formula C5H10 is [JEE 2009]

21. In the Newman projection for 2,2-dimethylbutane [JEE 2010]

X
H3C CH3

H H
Y
X and Y can respectively be
(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3

22. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is
[JEE 2010]

23. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is (are) [JEE 2011]

H H H
C—C
(A) (B) H — C C—C
H2C CH2 CH2
(C) H2C = C = O (D) H2C = C = CH2
24. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [JEE 2012]
(A) sp and sp3 (B) sp and sp2 (C) only sp2 (D) sp2 and sp3
25. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ? [JEE 2012]

HO HO Cl
H H CH3 CH3
H OH H OH HO H
Cl CH3
HO H H OH HO H
HO H HO H
CH3 Cl CH3 Cl Cl
M N O P Q

(A) M and N are non-mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical

26. The correct combination of names for isomeric alcohols with molecualr formula C4H10O is/are
[JEE Adv. 2014]
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1, 1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) iso-butyl alcohol and 2-methylpropan-1-ol

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27. The total number(s) of stable conformers with non-zero dipole moment for the following compound is/are
[JEE Adv. 2014]
Cl
Br CH3
Br Cl
CH3
28. The total number of stereoisomers that can exist for M is [JEE Adv. 2015]

H3C CH3

H3C
(M) O

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

H3C Cl

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

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

30. For the given compound X, the total number of optically active stereoisomers is_____.
[JEE Advance 2018]

HO
HO
This type of bond indicates that the configuration at the specific
carbon and the geometry of the double bond is fixed
This type of bond indicates that the configuration at the specific
HO carbon and the geometry of the double bond is NOT fixed
HO
X
31. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______. [JEE Advance 2019]

32. Newman projection P, Q, R and S are shown below: [JEE Advance 2020]

Which one of the following options represent identical molecules?

(A) P asnd Q (B) Q and S (C) Q and R (D) R and S

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33. Which one of the following structures has the IUPAC name 3-Ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic
acid? [JEE Advance 2020]

OH

CO2H
HO2C
(A) (B)

OH
OH OH

CO2H CO2H
(C) (D)

34. The Fishcer projection of D-erythrose is shown below:

CHO
H OH
H OH
CH2OH
D-erythrose

D-erythrose and its isomers are listed as P, Q, R and S in Column-I. Choose the correct relationship of P, Q,
R and S with D-erythrose from Column-II. [JEE Adv. 2020]
Column-I Column-II

OHC HO H
(P) H (1) Diastereomer
HO OH

OHC OH

(Q) HO H (2) Identical

H OH

H
OHC OH
(R) H (3) Enantiomer
HO OH

OHC OH

HO
(S) OH
H
H
P Q R S P Q R S
(A) 2 3 2 2 (B) 3 1 1 2
(C) 2 1 1 3 (D) 2 3 3 1

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 ANSWER KEY
1. 4 2. False 3. True 4. A 5. B 6. B 7. D
8. A, C 9. A 10. enantiomers–I & III; diastereomers – I & II and II & III 11. D

1
12. D 13. C 14. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = – OH
0.18

15. C 16. C 17. AD 18. BCD 19. AD 20. 7 21. BD

22. 5 23. BC 24. B 25. ABC 26. ACD 27. 3 28. 2
29. BC 30. 7 31. 10 32. C 33. D 34. 3

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