CHAPTER

2 Isomerism

Question Bank

Level 1

1. How many stereocenters does latomoxef (an oxacephem antibiotic) have?

HO O
N N O
S N O
N N NH OH
O
O
O

OH
(a) 2 (b) 3 (c) 4 (d) 5

2. Which molecule is (R, Z)-7-methoxy-2, 7-dimethyl-4-propylnona-1, 4-diene?

H3CO OCH3

(a) (b)

H3CO OCH3

(c) (d)
2.2 chapter two

3. Choose the correct order that has the following compounds correctly arranged with respect
tothermodynamic stability.
CH3
CH3
(i) (ii) H3C CH3 (iii)
CH3
CH3
(a) ii < i < iii (b) i < ii < ii (c) i < iii < i (d) iii < i < ii

4. Which of the structures below is a diastereomer of A?

H H
HO

CH3
CH3 CH3 H H
OH
(i) (ii) (iii)
OH HO
H H H H CH3
CH3 H H
HO
(iv) (v)
OH
H H CH3

(a) i (b) iii (c) ii and iv (d) iv

5. The total number of structural isomers of C4H11N would be

(a) 4 (b) 8 (c) 5 (d) 10

6. Which of the following pair is the chain isomer?

(a) , (b) ,

(c) , (d) ,

7. How many geminal dichloride with different formula are possible for C3H6Cl2?
(a) only one (b) two (c) three (d) four

8. What is the relation between 3-ethylpentane and 3-methylhexane?

(a) Chain isomers (b) Position isomers
(c) Functional isomers (d) Metamers

9. How many isomers are possible for methyl anthracene?

(a) 2 (b) 3 (c) 4 (d) 5

10. The compounds (CH3)3N and CH3CH2CH2NH2 represent

(a) chain isomerism (b) position isomerism
(c) functional isomerism (d) all of the above
 isomerism 2.3

11. An isomer of ethanol is

(a) methanol (b) acetone
(c) diethyl ether (d) dimethyl ether

12. The number of primary, secondary and tertiary amines possible with the molecular
­formula C3H9N respectively
(a) 1, 2, 2 (b) 1, 2, 1 (c) 2, 1, 1 (d) 3, 0, 1

13. Examine the relation between the following pairs of compounds

Cl OH
Cl Cl and OH
(i) (ii) OH
and
Cl OH
COOH COOH
(iii) and
HOOC
COOH
(a) All i, ii, iii are identical
(b) All i, ii, iii are isomers
(c) i, ii are identical, iii is isomer
(d) i is identical and ii, iii are isomers

Br COOH Br
COOH
14. and are

HOOC Br Br COOH
(a) Positional (b) Chain (c) Geometrical (d) Functional

15. 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
COOH
OCOH
16. and Functional isomers

OEt
OMe
Et
and Metamers
Me

CH2 – CH2 – OH CH2 – O – CH3

and Metamers
2.4 chapter two

Me – N – Me CH2 – NH – CH3

and Functional isomers

(a) TFTF (b) FTTF (c) TTFT (d) TFFT

17. Which compound is not the isomer of 3-ethyl-2-methylpentane?

(a) (b) |

|
(c) (d)
|
18. Which of the following is not the correct relationship?
Me
Me Me
(i) (ii)
Me Me
O – Me
OH
Me Me

(iii) (iv)

OH O – Me
(a) ii and iv are metamers (b) i and ii are functional isomers
(c) i and iii are chain isomers (d) i and iv are positional isomers

19. 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

20. Which one of the compound is not isomer of others?

(a) (b)

(c) (d)

21. CH3 – CH2 – NH – CHO; CH3 – CH – CHO

NH2
i ii
Which type of isomerism is observed between i and ii?
(a) Chain isomers (b) Position isomers
(c) Functional isomers (d) Metamers
 isomerism 2.5

22. The correct relationship among the following pairs of given compounds is
O
O O ||
(i) || || (ii) O
|| O
O O
O
(a) Chain isomer (b) Positional isomer
(c) Metamer (d) Functional isomer

23. Which of the following is a pair of metamers?

O
(a)
O
O
O
(b) O
O

(c)
NH2 H2N
Br
Cl
(d) I
Br Cl
I
24. Which of the following can show tautomerism?
O

(a) O O (b)

O
O O

(c) (d)

O O

25. Which of the following can show tautomerism?

O
O O
H3C C
(a) (b)
C CH3

O
H
C
H C CH – CH2
(c) (d) all of these
H C CH – CH2
C
H
2.6 chapter two

26. Which of the following can show tautomerism?

(a) (CH3)3CNO (b) (CH3)2NH (c) R3CNO2 (d) RCH2NO2

27. Which will not show tautomerism?

(a) O O (b) CH NOH

(c) O (d) O O

O
28. Which will not show tautomerism?
(a) CH3CH2CH2CH2NO2 (b) (CH3)2CH–CH2NO2
(c) CH3CH–CH2CH3 (d) (CH3)3C–NO2
|
NO2
29. Which of the following compound show tautomerism?

C=O
(a) (H3C)2CCl–CH=CH2 (b)
H
(c) (H3C)2C(NO2)­–CH=CH–CHO (d) None of these

30. Which of the following will not show tautomerism?

H3C (H3C)3C N=O
(a) C=N (b) C=C
H OH H3C CH3

(H3C)3C N=O H3C

(c) C=C (d) H3C C=N
(H3C)3C C(CH3)3 C=C OH
H H
31. Tautomerism will be exhibited by
(a) (CH3)2NH (b) (CH3)3CNO
(c) R3CNO2 (d) RCH2NO2

32. Which of the following is not an example of tautomeric equilibrium?

+ 
(a) H2C = CH – C = O CH2 – CH = C – O

H H
(b) –N = N – NH NH – N = N
(c) > CH – N = O > C = N – OH
(d) –NH – C = O – N = C – OH

O
O
NO2
33. i O ii iii
 isomerism 2.7

Among these compounds, which of following is the correct order of % enol content?
(a) i > ii > iii (b) iii > ii > i (c) ii > iii > i (d) i > iii > ii

34. Which of the following will have highest percentage of enol content?
O O O
(a) C6H5 – C – CH2 – C – OC2H5 (b) CH3 – C – O – C2H5

O O O O
(c) CH3 – C – CH2 – C – OCH3 (d) CH3 – C – CH2 – C – CH3

35. Which of the following compounds have less enol content?

i N ii
O N
| | O
H H
(a) i (b) ii
(c) Both (a) and (b) (d) None of these

36. Which of the following compounds have higher enol content?

O O

i ii

NO2 OCH3
(a) i (b) ii
(c) i = ii (d) None of these

37. Geometrical isomers differ in

(a) position of functional group (b) spatial arrangement of atoms
(c) position of atoms (d) length of carbon chain

38. Stereoisomers have different

(a) Molecular formula (b) Structural formula
(c) Configuration (d) Molecular mass

39. Which of the following compounds has restricted rotation?

H3C CH3 CH3

(a) C C (b) C
||

H3C CH3 H

(c) C C (d) All of these

2.8 chapter two

40. Which of the following compounds does not have restricted rotation?
CH3

(a) CH3 (b)

CH3 CH3
Br CH3
(c) C=C (d) H C C H
Cl H
Br Br
41. Which compound can show geometrical isomerism?
(a) CH3CH = C(CH3)2 (b) CH3CH = CH2
(c) CH3CH = CHCH3 (d) (CH3)2C = C(CH3)2

42. Which of the following will not show cis-trans isomerism?

(a) CH3 – C = CH – CH2 – CH3 (b) CH3 – CH – CH = CH – CH2 – CH3

CH3 CH3
(c) CH3 – CH = CH – CH3 (d) CH3 – CH2 – CH = CH – CH2 – CH3

43. Geometrical isomerism is shown by

H I H I
(a) C=C (b) C=C
H Br CH3 Br
H3C Cl H Cl
(c) C=C (d) CH3 C=C
H3C Br Cl

44. The “E”-isomer is

F H H3C CH3
(a) C=C (b) C=C
Cl Br H H
H3C C2H5
(c) C=C (d) none of the above
H CH(CH3)2
45. The compounds X and Y shown in the below reaction can be
P+Q
– H2O
Ph – NH.NH2 + (X) + (Y) Organic
products
(a) CH3 – CH2 – C – CH3 + CH3 – C – Ph (b) Ph – C – CH3 + CH3CHO

O O O
(c) CH2 = O + CH3CHO(d) CH2 = O + CH3 – C – CH3

O
46. The “Z”-isomer is
Cl H Cl CH3
(a) C C (b) C C
||
||

F Br F C2H5
CH3 Cl HOOC COOH
(c) C C (d) C C
||

||

C2H5 COOH H H
 isomerism 2.9

47. Which of the following compounds cannot show geometrical isomerism?

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

H3C CH3 H3C CH3

48. The total number of geometrical isomers possible in following compound is

Ph – HC = HC CH = CH – CH3
(a) 2 (b) 1 (c) 6 (d) 8

49. The total number of geometrical isomers possible in following compound is

CH = CH – CH = CH

(a) 4 (b) 6 (c) 3 (d) 2

50. The number of geometrical isomers in the following compound is

CH3 – CH = CH – CH = CH – C2H5
(a) 4 (b) 3 (c) 2 (d) 5

51. The number of cis-trans isomer possible for the following compound is

(a) 2 (b) 4 (c) 6 (d) 8

52. What characteristic is the best common to both cis-2-butene and trans-2-butene?
(a) B.P. (b) Dipole moment
(c) Heat of hydrogenation (d) Product of hydrogenation

53. Number of chiral carbon atoms in the compound x, y and z respectively would be
Me Me
Me Me

Y
X Z
(a) 0, 2, 1 (b) 1, 0, 1 (c) 1, 2, 1 (d) 1, 2, 0
2.10 chapter two

54. Number of chiral carbon persent in the following compound is

CH3 – CH – CH2 – CH – CH – CH3

OH Br C2H5
(a) 2 (b) 3 (c) 4 (d) 5

55. Which of the following have asymmetric carbon atom?

Cl Br H Cl
(a) H – C – C – H (b) H – C – C – Cl
H H H H
H Cl H H
(c) H – C – C – H (d) H – C – C – CH3
H H Br OH
56. Meso‑tartaric acid and d‑tartaric acid are
(a) positional isomers (b) enantiomers
(c) diastereomers (d) racemic mixture

57. observe the following structures (i) to (iii)

(i) C2H5 – CH – C2H5 (ii) (CH3)2CH – CH – CH – CH3

CH3 OH CH3

(iii) CH3 – CH – CH – CH3

OH CH3
Correct statement is
(a) All three are chiral compounds
(b) i and ii are chiral
(c) Only ii is chiral
(d) Only iii is chiral

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

(a) 1 (b) 2 (c) 3 (d) 4

59. Which of the following compound has “S” configuration?

CH3 OH
(a) H OH (b) Br CH3

Br H
CH3 CH3
(c) Br OH (d) HO Br
H H
60. The number of optically active isomers observed in 2,3‑dichlorobutane is
(a) 0 (b) 2 (c) 3 (d) 4
 isomerism 2.11

61. The correct configuration assigned for compound (i) and (ii) respectively is
COOH CH3

(i) H CH3 (ii) C

COOCH3
COOCH3 HOOC
H
(a) R, R (b) S, S (c) S, R (d) R, S

62. The R/S configurations of these compounds are respectively

HO H
CF3 H NH2 H CH3
HS CHO
   COOH   
(a) R, R, R (b) R, S, R (c) R, S, S (d) S, S, S

63. Which of the following compound has plane of symmetry (Pos) but not centre of ­symmetry
(Cos)?
H Br
H CH3
(a) (b) H Cl
Cl H
CH3 H
F H
Br Cl F

(c) H Br (d)
H H

Br H F
64. The instrument which can be used to measure optical activity, i.e., specific rotation
(a) Refractometer (b) Photometer
(c) Voltmeter (d) Polarimeter

65. The two compounds given below are

D Cl
H Br I H
H Cl D H
I      Br

(a) Enantiomer (b) Identical

(c) Meso compound (d) Diastereomers

66. Which of the following compounds do not possess a C2 axis of symmetry?

D

(a) (b) H3C CH3

D

H3C CH3
2.12 chapter two

CH3 D

(c) H3C CH3 (d) H3C H

H D

H H H CH3
67. How many stereoisomers can exist for the following acid?
H – C(OH).CO2H

H – C.CO2H
H – C(OH).CO2H
(a) Two (b) Four (c) Eight (d) Sixteen

68. CH3 – CH – CH – CH – CH3

Br Br Br
Total number of stereoisomers in the above compound is
(a) 6 (b) 4 (c) 8 (d) 16

69. Total number of stereoisomers of the compound is given below

CH3 – CH – CH – CH3

OH Br
(a) 2 (b) 4 (c) 6 (d) 8

70. 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

71. Total number of stereoisomer of compound is given below

CH3 – CH = CH – CH – CH = CH – C2H5

Cl
(a) 2 (b) 4 (c) 6 (d) 8

72. CH3 – CH – CH – CH – CH3

Cl Br OH
Total number of stereoisomers in the above compound is
(a) 6 (b) 4 (c) 8 (d) 16

73. The enantiomeric excess and observed specific rotation of a mixture containing 6 g of
(+)-2-butanol and 4 (g) of (–)-2-butanol are respectively (If the specific rotation of
­enantiomerically pure (+)-2-butanol is +13.5 units)
(a) 80%, +2.7 unit (b) 20%, –27 unit
(c) 20%, +2.7 unit (d) 80%, –27 unit
 isomerism 2.13

74. Which of the following pair of isomers cannot be separated by fractional crystallisation or
fractional distillation?
(a) Maleic acid and fumaric acid
(b) (+)-Tartaric acid and meso-tartaric acid
(c) CH3 – CH – COOH and H2N – CH2 – CH2 – COOH

NH2
(d) (+)-lactic acid and (–)-lactic acid

75. Increasing order of stability among the three main conformation (i.e., eclipse, anti, gauche)
of ethylene glycol is
(a) Eclipse, gauche, anti (b) Gauche, eclipse, anti
(c) Eclipse, anti, gauche (d) Anti, gauche, eclipse

76. Which of the following pairs of compound is/are identical?

Cl CH3 CH3 I

H Cl H I H H
(a) CH3 (b) Cl CH3
H CH3 Cl H Cl I

Cl CH3 I H H
Br H Br
H
F Br H H H Cl
(c) F H (d)
Br H F Br I H I
Br
H Cl H
F
77. The two structures (i) and (ii) represent
CH3 CH3
H H H H
(i) (ii)
H3C CH3 H3C H
H CH3
(a) Conformational isomers (b) Stereoisomers
(c) Constitutional isomers (d) Identical
78. In which of the following has minimum torsional strain and minimum Vander waal strain?
CH3
CH3
H CH 3 H

(i) (ii)
CH3 H
H CH CH3
CH3 3 CH3
CH3
CH3
CH3 H CH3

(iii) (iv)
H H
H CH3 CH3
CH3 CH3
(a) i (b) ii (c) iii (d) iv
2.14 chapter two

79. In the Newman projection formula of the least stable staggered form of n
­ -butane, which of
the following reasons is the causes of its unstability?
(a) Van der Waal’s strain (b) Torsional strain
(c) Combination of both (d) None of these

80. Which of the following represent the staggered conformation with dihedral angle f = 60?
CH3 CH3
H H H CH3
(a) (b)
H H H H
CH3 H

CH3 CH3
CH3 H
(c) (d)

H H H H
H H H CH3
81. The dihedral angle between two methyl groups in partially eclipsed conformation of
n-butane is
(a) 180° (b) 120° (c) 90° (d) 109°28’

82. Which of the following is an achiral molecule?

CH3 CH3
H3C Cl Br H
(a) (b)
H Cl H Cl
H CH3
CH3 COOH
H OH H OH
(c) (d)
H3C H H OH
CH3 COOH

83. Which of the following is most stable?

CHO CHO
H NH2 H H
(a) (b)
H H H H
H NH2
CHO CHO
NH2 H
(c) (d)
H H H
H H
H H NH2
 isomerism 2.15

84. Evaporation of an aqueous solution of ammonium cyanate gives urea. This reaction
­follows the class of
(a) Polymerisation (b) Isomerisation
(c) Association (d) Dissociation

85. The possible number of alkynes with the formula C5H8 is

(a) 2 (b) 3 (c) 4 (d) 5

86. How many isomers of C5H11OH will be primary alcohols

(a) 2 (b) 3 (c) 4 (d) 5

87. Number of isomeric forms of C7H9N having benzene ring will be

(a) 7 (b) 6 (c) 5 (d) 4

88. Which of the following is an isomer of diethyl ether

(a) (CH3)3COH (b) CH3CHO
(c) C3H7OH (d) (C2H5)2CHOH

89. Total number of isomeric alcohols with the formula C4H10O is

(a) 1 (b) 2 (c) 3 (d) 4

90. The molecular formula of a saturated compound is C2H4Cl2. The formula permits the exist-
ence of two
(a) functional isomers (b) position isomers
(c) optical isomers (d) cis-trans isomers

91. The type of isomerism found in urea molecule is

(a) Chain (b) Position
(c) Tautomerism (d) None of these

92. An alkane can show structural isomerism if it has ......... number of minimum ­carbon atoms
(a) 1 (b) 2 (c) 3 (d) 4

93. How many chain isomers can be obtained from the alkane C6H14?
(a) 4 (b) 5 (c) 6 (d) 7

94. Keto-enol tautomerism is observed in

O O
(a) C6H5 C H (b) C6H5 C CH3

O O CH3
(c) C6H5 C C6H5 (d) C6H5 C C C6H5
CH3

95. The number of geometrical isomers in case of a compound with the structure
CH3–CH=CH–CH=CH–C2H5 is
(a) 4 (b) 3 (c) 2 (d) 5
2.16 chapter two

96. Which one of the following will show geometrical isomerism?

(a) CH2Cl CH3 (b) CH3 H
C C
H CH C(CH3)2 CH2Cl CH C(CH3)2
(c) CH2 CH CH2Cl (d) CH3CH2CH=CHCH2CH3
C
H CH CH2
97. In the reaction: CH3CHO + HCN ⎯→ CH3CH(OH)CN
a chiral centre is produced. The number of stereoisomers of the product is
(a) 3 (b) 2
(c) 4 (d) none of these

98. The molecule 3-penten-2-ol can exhibit

(a) Optical isomerism (b) Geometrical isomerism
(c) Metamerism (d) Tautomerism
The correct answer is
(a) (a) and (b) (b) (a) and (c) (c) (b) and (c) (d) (a) and (d)

99. Find the total number of isomers (including stereo isomers) in dimethyl cyclopropane and
dimethyl cyclobutane
(a) 6, 8 (b) 5, 6 (c) 4, 5 (d) 4, 6
Cl
H5C2
H H
100. has
H H
C2H5
Cl
(a) plane of symmetry (b) centre of symmetry
(c) C3 axis of symmetry (d) C4 axis of symmetry

101. How many optically active cycloalkanones are possible with the molecular f­ormula
C5H8O?
(a) 8 (b) 6 (c) 5 (d) 4

H3C CH3 H3C H

102. and is/are
H H H CH3
(a) Geometrical isomers (b) Position isomers
(c) Chain isomers (d) Enantiomers
CH3
103. For the given compound which of the CH3 – C = CH – C – CH = C – CH3 ­following state-
ment(s) are correct? D D D
(a) It has 4 stereoisomers
(b) It has 3 stereoisomers
(c) It has 2 chiral centres
(d) The compound does not show G.I.
 isomerism 2.17

104. Racemic mixture is formed by mixing two

(a) Isomeric compounds (b) Chiral compounds
(c) Meso compounds (d) Enantiomers

105. Which of the following does not show geometrical isomerism?

(a) 1,2-dichloro-1-pentene (b) 1,3-dichloro-2-pentene
(c) 1,1-dichloro-1-pentene (d) 1,4-dichloro-2-pentene

106. The general formula CnH2nO2 could be for open chain

(a) Diketones (b) Carboxylic acids
(c) Diols (d) Dialdehydes

107. Among the following four structures i to iv

CH3 O CH3
| || |
(i) C2H5 – CH – C3H7 (ii) CH3 – C – CH – C2H5
H CH3
| |
(iii) H – C⊕ (iv) C2H5 – CH – C2H5
|
H
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

108. Amongst the following compounds, the optically active alkane having lowest ­molecular
mass is CH3
|
(a) CH3–CH2–CH2–CH3 (b) CH3 – CH2 – CH – CH3
H
|
(c) CH3–C– (d) CH3–CH2–C≡CH
|
C2H5
109. Which of the following compounds is not chiral?
(a) 1-chloropentane (b) 2-chloropentane
(c) 1-chloro-2-methylpentane (d) 3-chloro-2-methylpentane

110. Which of the following molecules is expected to rotate the plane of polarised light?
COOH
H2N NH2
(a) H H (b) H2N H
Ph Ph H
CHO

(c) HO H (d)

CH2OH SH
2.18 chapter two

111. The correct decreasing order of priority for the functional groups of organic compounds in
the IUPAC system of nomenclature is
(a) –SO3H, –COOH, –CONH2, –CHO
(b) –CHO, –COOH, –SO3H, –CONH2
(c) –CONH2, –CHO, –SO3H, –COOH
(d) –COOH, –SO3H, –CONH2, –CHO
HO2C CO2H
112. The absolute configuration of OH is
HO H H
(a) R, R (b) R, S (c) S, R (d) S, S

113. The alkene that exhibits geometrical isomerism is

(a) 2-methyl propene (b) 2-butene
(c) 2-methyl-2-butene (d) propene

114. The number of stereoisomers possible for a compound of the molecular formula
CH3–CH=CH–CH(OH)–Me is
(a) 2 (b) 4 (c) 6 (d) 3

115. Out of the following, the alkene that exhibits optical isomerism is
(a) 3-methyl-2pentene (b) 4-methyl-1-pentene
(c) 3-methyl-1-pentene (d) 2-methyl-2-pentene

116. Identify the compound that exhibits tautomerism

(a) 2-butene (b) Lactic acid (c) 2-pentanone (d) Phenol
 isomerism 2.19

Level 2

Single and Multiple-choice Type

1. The value of equilibrium constant (K) for the following equilibria
H H
H3C e a H CH3
C H 3 C
eH C CH3
CH 3 C
H3C CH3 a
H 3 C CH3
C CH3
H3C
CH3
Chair Twist boat
(a) K = 1 (b) K > 1
(c) K < 1 (d) Cannot relate

2. E/Z nomenclature of the following compound is

CH3
H–C≡C C CH3
C CH3

C CH3 CH3
H2C = C C – CH2
H H
(a) E (b) Z
(c) Does not show geometrical isomerism (d) None

3. Correct order of stability of the following carbocations is

⊕ ⊕ ⊕
CH2 CH2 CH2 ⊕
CH2

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

CH3 CD3
CH3 CD3 H
(a) i > ii > iii > iv (b) i > ii > iv > iii
(c) ii > i > iv > iii (d) i > iv > ii > ii

4. Which of the following compounds are chiral?

O
H3C– –Cl
C–NH
C=C=C
(i) (ii)

NH–C Cl–
Cl
O
2.20 chapter two

Cl H
Cl H O
Cl
C
(iii) (iv) (v)
NH
O O C
H CH3
O
(a) i, ii, iii, v (b) ii, iii, v (c) i, ii, iii, v (d) i, iv, v

5. The conformation of the following compound is

Et
Me

CMe3
Me3C
Me3C Me
(a) (b)
Me
Et
Et
Me3C Et
(c) Me (d)
Et CMe3
Me
6. Which of the following represent the meso compound?
Cl
H5C2
C2H5 H
(a) H5C2 (b)
H
C2H5 CH3
H
Cl
H Cl
Cl H3C CH3
(c) (d)
H Cl Cl
N
H
7. Among the following pair of compounds functional isomer is

and
(a)

N≡C Me N≡C Me
Me
Me

(b) and

N=O
O–NO
O
 isomerism 2.21

Me
Me

(c) and
O
C – O – Ph
O – C – Ph
O

O – CH2 – CH3 and CH2 – O – CH3

(d)

8. Identify equilibrium which has maximum K (equilibrium constant)

Me
(a) K
Me

OH
(b) K H
O
O O

Me
Me K
(c)
Me
Me

OMe
(d) O K O
O
O OMe

9. The most stable Newmann projection of the 2,3-dichlorobutane, whose Fischer projection
is given below is
CH3 – CH – CH – CH3
Cl Cl
CH3 CH3
Cl H H CH3
(a) (b)
H Cl H Cl
CH3 Cl

CH3 CH3
H3C H
(c) (d)
Cl CH3
H Cl H Cl
H Cl
2.22 chapter two

10. The correct stereochemical descriptions for the structure given below are
OH
Me CH2 – CH2 –
H
D
(a) 1S, 4E (b) 1R, 4E (c) 1R, 4Z (d) 1S, 4Z

11. The number of optical isomers possible for the compound is

Cl
HO
CH(OCOCH3)2
NC
(a) 2 (b) 4 (c) 8 (d) 6

12. Which one of the following compounds will not rotate the plane of plane p
­ olarised light?
HOOC NO2
Cl Cl
(a) (b) C=C=C
H H
NO2 COOH
OH
H H
(c) C (d) HOOC H
H5C2 C2H5 H OH
COOH
13. The correct Fischer projection formula of the Newman projection representation is
H
Me COOH

Ph OH
H
H H
(a) Ph OH (b) HO Ph
Me COOH Me COOH
H H
H H
Ph OH HO Ph
(c) (d)
HOOC Me HOOC Me
H H
14. Which one of the following statements regarding the projections shown below (i and ii) is
correct?
Cl Cl
H C H
6 5 H
(i) (ii) Cl C6H5
C6H5 H
Cl H5C6 H
(a) Both the projections represent the same configuration
(b) Both (i) and (ii) are optically active
(c) Only (i) is optically active
(d) Only (ii) is optically active
 isomerism 2.23

15. Among the following compounds which is used for resolution of racemic mixture?
Me Me
N Me Me
(a) (b)
Cl Cl
Et Me
Cl Br Me Cl
(c) (d)
I H H Cl
16. Identify specific rotation of a mixture have 5 g of (+)2-butanol and 7 g of (–)2-butanol
(If specific rotation of 100% pure compound is 13.5°)
(a) –2.25° (b) –1.6° (c) 12.2° (d) 4.45°

17. Identify compound having highest heat of combustion

tBu Me
(a) Me (b) tBu

Me
(c) Me (d)
Me
Me

18. Identify R and S configurations of chiral centres in the following compound

HOOC Cl
(a) (i)-R (ii)-S (b) (i)-S (ii)-R (c) (i)-S (ii)-S (d) (i)-R (ii)-S

19. What is the relationship between the two structures shown?

H3C Cl
CH3

Cl
(a) Different drawings of the same conformation of the same compound
(b) Stereoisomers
(c) Constitutional isomers
(d) Different conformations of the same compound

20. C8H12 has 3° of unsaturation. Thus, it can have the structure

(a) (b)

(c) (d)

21. Calculate the total number of geometrical isomers for the following compound

• • •

(a) 2 (b) 4 (c) 8 (d) 16

2.24 chapter two

22. Identify the value of KC for the following equilibrium

Me
Me Me Et
Me
Me
Et Me
(a) KC > 1 (b) KC < 1 (c) KC = 1 (d) None of these

23. Identify the relationship between the following pairs of compound

H H H
H H
and
H H
H H H
(a) Positional isomers (b) Geometrical isomers
(c) Functional isomers (d) Identical compounds

24. Identify compounds that give geometrical isomerisation

Me
(a) Cl • (b)
H H

(c) (d)

25. Which conformation has a C3 axis of symmetry?

(a) Boat (b) Twist boat (c) Chair (d) Enveloped

26. Which of following represent (E)-3, 6-dibromo-6-methyl-3-heptene?

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

Br
27. Which of the following represent a pair of enantiomers?
Me Me

(i) HO H (ii) H Cl
H Cl HO H
Et Et
Et Me

Cl H HO H
(iii) (iv)
HO H Cl H
Me Et
(a) i and ii (b) iii and iv (c) i and iv (d) ii and iii
 isomerism 2.25

28. Choose the total number of constitutional isomers with the formula C4H10O.
(a) 9 (b) 7 (c) 5 (d) 3

29. Identify optically active molecules

Br Cl
•
•
NH •
(a) • (b) • • • NH
• •
•
Cl Br
•
Cl •
(c) (d) Cl
•
Cl
•
Br

30. In which structure Gauche form has less potential energy than antiform

(a) CH3 – CH2 – CH2 – Cl (b) HO – CH2 – CH2 – F

(c) CH2 — CH2 (d) HO – CH2 – CH2 – OH

Br Br
31. Which of the following molecule/s show the plane of symmetry as well as axis of
symmetry?
Me Cl
Br H
(a) (b)
Me
Me Cl
H Br
D D
Cl

(c) • • (d)

Cl
Cl
32. The C3 axis of symmetry is present in which of the following compounds?
H
H B H
N N
(a) (b)
B B
H N H
H
2.26 chapter two

Cl

(c) (d)

Cl Cl
33. Which of the following compounds are chiral?
H ⊕ H
Br H N
(a) (b) C2H5 – O – C C6H5

H Br O

H H
C
O C C C C
(c) C (d)

C
NO2 NO2
H CH3
34. Which of the following molecule(s) has C3 axis of symmetry and plane of symmetry?
Me Cl

(a) (b)

Me Me Cl
H

Me H B H
N N
(c) (d)

Me B B
Me H N H

H
35. In which of the following case correct relationship is given?

H3C Br Br CH3

(a)
Enantiomers

H Br Br H
(b)
Br Enantiomers
H H Br
H Br Br H
 isomerism 2.27

Br I Br I
(c)
Diastereomers
OH CH3 OH CH3

(d) Cl Cl Enantiomers
Br Br
36. Which of the following is an optically active compound?

H CH3
C C H
(a) (b)
H H3C
H
H5C2 C2H5 H Cl Cl
C=C
(c) CH3 (d)
C2H5
Br
37. Which of the following options is correct?
(a) pk1 Cis but-2-ene dioic acid < Trans but-2-ene dioic acid
NC CH3 H CH3
(b) Dipole moment C=C C=C
H H NC H
Cl Cl H Cl
(c) Stability C=C C=C
H H Cl H
H NH2 H CH2 – NH2
(d) Basicity C=C C=C
Cl H Cl H
38. Which of the following are optically active?
Me
Me
(a) (b)
Cl
Me Me
H
OH
Me
(c) (d)
Me
Cl
H
39. For the given compounds, correct statement is/are
O O O
(i) H3C – C – O – (ii) – C – OH (iii) H3C – O – C –

CH3
2.28 chapter two

(a) i and ii are positional isomers

(b) ii and iii are functional group isomers
(c) i and iii are metamers
(d) i and iii are positional isomers

40. Among the following pair of compounds or conformers, identify pair(s) in which the
Ist compound has more stability than the IInd
Me Me
HO H H Me
(a) and
H OH H OH
Me O–H

(b)
and

tBu tBu
tBu H H OH
(c) and
HO H HO H
OH tBu

(d) and tBu

tBu Me
Me

41. Among the following pair of compounds identify metamers

O O
(a) and
Me O–C–Me Me C–OMe

O O
(b) CH2–C–OMe and CH2–CH2–C–OH

CH2–CH3 CH2–CH2–CH3
(c) and H–N
Me–N–CH2–CH3 CH2–CH3

(d) CH3–CH2–NH and CH3–NH–CH2–Ph

42. Which of the following pairs show functional group isomerism?

O O
(a)
Cl and
Cl
(b) CH3COOCOC6H5 and C6H5COOCOCH3
(c) HCOOCH3 and CH3COOH
O
(d) CH3COCH3 and
 isomerism 2.29

43. Identify compound(s) in which gauche conformer is more stable than staggered
(a) Ethylene diamine (b) Succinic acid
(c) Ethylene glycol (d) n-butane

44. Identify the compound which has axial conformer more stable than equatorial
OH Et
O Me H
(a) (b) OH (c) (d) Me
H H
OH H Me
H H

45. Among the following compounds, C3 axis is present in

Cl

(a) (b) PCl5 (c) (d) Cl Cl

46. Identify among the following compounds having plane of symmetry, centre of
­symmetry and axis of symmetry
Cl
H Cl
(a) (b)
Cl H
Cl
Me Cl Cl H

(c) Cl H Me H (d) Ph H H Ph

H H H Cl
47. Identify diastereo isomeric pairs
COOH
COOH
(a)
and

OH OH
(b)
and

Cl Cl

(c) HO OH and HO OH

Cl Cl
Cl Cl
Cl Cl

(d) and

H Me
Me H
2.30 chapter two

48. Identify the optically active compound

Cl
H H
H H
(a) H Me (b)
Me H H H
H Br H
Ph Cl
(c) (d) Br Cl
Ph H
Cl OH

49. Which of the following statements is correct?

NH2 H3C O
C
HO Br
(i) C (ii) C (iii)
H CH2–OCH3 H
C2H5 CH2–OCH3
OH
(a) i and ii have R-configuration
(b) i and iii have R-configuration
(c) Only iii has R-configuration
(d) i and iii have S-configuration

50. Which of the following relationships are correctly matched?

O
(a) and Positional isomers
O
Br
C2H5
(b) and Identical

C2H5
Br
OH
CH2–OH
(c) and Positional isomers

CH3

(d) and Chain isomers

51. Which of the following molecules is/are optically active?

H3C H3C
H H
H H
(a) H OH (b) H OH
CH3 H
H H
H CH3
 isomerism 2.31

H
(c) (d) H Br
Br Me
OH
Me
52. Identify compound(s) in which gauche conformer is more stable than staggered
(a) 1, 2-difluoroethane (b) Chloropropane
(c) Ethylene glycol (d) Succinic acid

53. Identify the structure of Erythro

D
D

H CH3
(a) (b) H CH3
CH3
H D

CH3 D H

Cl D

D CH3 H Br
(c) (d)
Cl
H D

D CH3
Br
54. Identify the structure of Erythro
D
CH3
H OH H CH3
(a) (b)
H OH CH3
CH3

D H
CH3CH3
HO
H3C D
(c) (d)
T OH
Br CH3
Br D
D
55. Identify the structure of Threo
CH3
H3C CH3
H OH
(a) (b)
HO H D Cl D
T
CH3
2.32 chapter two

CH3CH3
HO
H3C
(c) (d) D
T
Br OH
Br D CH3
D
56. Identify the structure of meso compounds
D
D

H CH3 CH3
H
(a) (b)
CH3
H D

D H
CH3
Cl
H3C OH
D CH3 D
(c) (d)
Cl T
H3C OH
D Me
57. Identify the structure of meso compounds
D
OH

H CH3 H CH3
(a) (b)
H3C OH CH3

CH3
D H
CH3
CH3CH3
H OH
(c) (d)
HO H
Br
Br D
CH3 D
58. Identify the structure of optically inactive compounds
D

H CH3 HO OH
(a) (b)
H D

CH3
 isomerism 2.33

Cl

D CH3 HO OH
(c) (d)
Cl

D H
59. Identify the structure of Meso

HO OH
(a) (b)

(c) (d)

60. Identify the structure of identical compounds

OH
CH3
H OH H CH3
(a) (b)
H OH CH3

CH3
HO H
CH3 CH3
HO
H3C
D
(c) (d)
T
HO OH
HO H CH3
H
61. Identify the structure of identical compounds

(a) (b)
Cl Cl Cl Cl
H
H

(c) (d)
CH2
Cl Cl
CI
CI
2.34 chapter two

62. Identify the geometrical isomers

H H CN CN
H CN H H
(a) (b)
CN H H H
H H H H
H CN H CN
CN H H H
(c) (d)
H H H CN
H H H H
63. Identify the pair of chain isomers
H Me H Me
Me Me H H Me Me H H
(a) (b)
Me H Me Me Me Me Me Me
H H H Me
H H
H Me H H
(c) (d)
H H H H Cl Cl Cl Cl
COOH COOMe
64. Identify the pair of diastereoisomers
Cl Cl
(a) (b)
Cl Cl Cl Cl

Cl Cl
(c) (d)

65. Identify the pair of diastereoisomers

O O
(a) (b)
O O

Cl Cl
(c) (d)

66. Identify the pair of diastereomers

O O
(a) (b)

O O
 isomerism 2.35

Cl Cl
(c) (d)
Br Cl Cl Br

67. Identify the pair of diastereoisomers

(a) (b)

Cl Cl
(c) (d)

Cl Cl
68. Identify the pair of enantiomers

Cl
(a) (b)

Cl
Cl Cl
(c) (d)
Cl Cl Cl Cl
Br Br
69. Identify the optically active shape

(a) (b)

(c) (planner) (d) (planner)

2.36 chapter two

70. Identify the structures having centre of symmetry

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

71. Identify the pair of enantiomers

(a)

(b)

HO HO OH
O O
(c)
OH
OH OH

Cl Cl
(d)
Br Br
72. Identify the structure of Erythro-butane-2, 3-diol
OH
CH3
H OH H CH3
(a) (b)
H OH CH3

CH3
HO H
CH3 CH3
HO
H3C
C D
(c) (d) C
T
OH
HO
HO D CH3
D
73. Identify the structure of Threobutane-2,3-diol
CH3
H3C CH3
H C OH
(a) (b) C C
HO C H
HO H
H OH
CH3
 isomerism 2.37

CH3 CH3
HO
H3C
C D
(c) (d)
T C
Br OH
Br D CH3
D

74. Identify the structure of identical compounds

(a) (b)
Cl Cl Cl Cl
H H
CI H

(c) (d)
CH2 CH2

CI H CI
CI
75. Identify the structure of identical compounds
CH3
H
(a) (b)
H Cl
Cl
CH3
H H
CI H
(c) (d)
CI CI
H CI
76. Identify the structure of enantiomeric compounds
H H
H CI
(a) (b) Cl
Cl
H CI
H H

Cl
Cl
(c) (d)
Cl Cl
2.38 chapter two

77. Identify the structure of transdecaline

H H
H H H H H
H H
(a) H (b)
H
H H H
H H H H H
H

(c) (d)

78. Identify the compounds that give trans product on reaction with Zn dust and heat
CI
CH3
H Cl H CH3
(a) (b)
H Cl CH3

CH3
CI H
CH3 CH3
Cl
H3C
D
(c) (d)
T
Cl
CI
H CH3
CI H
79. Identify the compounds that give cis product on reaction with Zn dust and heat
H
CH3
H Cl CI CH3
(a) (b)
Cl H CH3

CH3
CI H
CH3CH3
Cl
H3C
D
(c) (d)
T
Cl
H
H CH3
CI
CI
80. Identify the compounds that give cis product on reaction with Zn dust and heat
CH3 CH3
H Cl H Cl
(a) (b)
Cl H H Cl
CH3 CH3
 isomerism 2.39

CH3 CH3
Et Cl Et Cl
(c) (d)
Et Cl H3C Cl
CH3 Et
81. Identify the compounds that give cis product on reaction with Zn dust and heat
Et H

CI CH3 CI CH3
(a) (b)
CH3 CH3

CI Et CI H
CI CI

H CH3 Ph CH3
(c) (d)
CH3 CH3

CI H CI Ph
82. Identify the compounds that give trans product on reaction with Zn dust and heat
Cl
H3C CH3
H3C
Et
(a) Et (b)
Cl Cl H Cl H
CH3
Cl
H3C CH3 H3C
D
(c) (d)
T
Cl
H Cl Cl H
CH3
83. Identify the compounds that give trans product on reaction with Zn dust and heat
CH3
CH3 CH3
Cl Et
(a) (b)
H Cl Et
CI H
CI CH3
CH3
CH3 CH3
Cl Et
(c) (d)
CI Et Cl
CI H
H
CH3
2.40 chapter two

84. Identify the compounds that give trans product on reaction with alcoholic KOH and heat
Et
CH3
Et Cl H CH3
(a) (b)
H Et CH3

CH3
CI Et
CH3 CH3
Cl
H3C
(c) (d) H
T
Et CH3
CI Et Et
H
85. Identify the compounds that give trans product on reaction with alcoholic KOH and heat
CH3 CH3
H Ph Ph Cl
(a) (b)
Cl Ph H Et

CH3 CH3
CH3 CH3
Et Cl Et H
(c) (d)
Et H H3C Cl

CH3 Et
86. Identify the compounds that give trans product on reaction with alcoholic KOH and heat
Et Ph

CI CH3 CI CH3
(a) (b)
CH3 CH3

H Et H Ph
Et H

H CH3 Ph CH3
(c) (d)
CH3 CH3

CI Ph CI Ph
 isomerism 2.41

87. Identify the compounds that give trans product on reaction with alcoholic KOH and heat
Cl
H3C CH3
H3C Et
(a) (b)
Et
H Ph H Cl Ph
CH3
Cl
H3C CH3 H3C
H
(c) (d) Ph
H Et Cl Ph Pr
CH3
88. Identify the compounds that give trans product on reaction with alcoholic KOH and heat
CH3
CH3CH3
Cl Et
(a) (b)

Pr H Et
Pr H
CI CH3

CH3
CH3CH3
Cl Et
(c) (d)
CI Et H
Pr H
Pr CH3

Comprehension Type
Passage 1
Different spatial arrangements of the atom that result from restricted rotation about a single
bond are conformers. The general stability order of these conformer are as follows.
Anti > Gauch > Partially eclipsed > Fully eclipsed
Although anti is more stable than gauch but in some cases gauch is more stable than anti.

89. Which one of the following is the most stable conformer?

CH3 CH3
HO H H OH
(a) (b)
H OH H OH
CH3 CH3
OH CH3
H CH3 H CH3
(c) (d)
H CH3 H OH
OH OH
2.42 chapter two

90. Number of possible stable conformers of butane is

(a) 2 (b) 4 (c) 6 (d) Infinite

91. Which of the following are more stable conformers?

Cl Cl Cl Cl
Cl CH3 H3C H
(a) (b) (c) (d) All of them
H
H CH3 H CH3 H CH
H CH3 3
Cl
Passage 2
With few exceptions, enantiomers cannot be separated through physical means. When in racemic
mixtures, they have the same physical properties. Enantiomers have similar chemical properties as
well. The only chemical difference between a pair of enantiomers occurs in reactions with other chi-
ral compounds. Thus resolution of a racemic mixture typically takes place through a reaction with
another optically active reagent. Since living organisms usually produce only one of two possible
enantiomers, many optically active reagents can be obtained from natural sources. For instance,
(S)-(+)-lactic acid can be obtained from animal muscle tissue and (S)-(–)-2-methyl-1-butanol from
yeast fermentation.

CO–2 CO–2
+ +
CO2H CO2H NH2 NH3 NH3
H Cl Cl H H CH3 H Cl H CH3 Cl H H CH3

+ Reaction 1

Racemic mixture of (R)-phenylethylamine salt salt

phenylchloroacetic acid HCl HCl
CO2H CO2H
H Cl Cl H

Separation of enantiomers

In the resolution of a racemic acid, a solution of (R)-phenylethylamine is reacted with a racemic

mixture of phenylchloroacetic acid to form the corresponding salts. The salts are then separated
by careful fractional crystallisation. Hydrochloric acid is added to the separated salts, and the
respective acids are precipitated from their solutions.
Resolution of a racemic base can be accomplished in the same manner with tartaric acid.

92. Quinine, a natural antimalarial, is commonly used as an optically active reagent to resolve
acidic enantiomers. How many chiral carbons exist in the quinine molecule drawn below?
OCH3
N

OH

Quinine

(a) 5 (b) 2 (c) 3 (d) 4

 isomerism 2.43

93. Which of the following compounds might be used to resolve a racemic mixture of acidic
enantiomers?
Cl Cl
(a) C C C C (b) CH3–CH2–CH3
H H
Et
(c) CH3–CH2–CH2–CH3 (d) Me – C – NH2
Ph
94. Which of the following amines could in principle be used as a resolving agent for a race-
mic carboxylic acid?
CH3 CH3
(a) CH3 – CH – NH – CH3 (b) (±) C6H5 – CH – NH2
(c) (–) C6H5 – CH – NH2 (d) CH3NH2
CH3
Passage 3
Stereoisomers are compounds that have same sequence of covalent bonds but differ in the rela-
tive dispositions of their atoms in space. Geometrical and optical isomers are the two important
types of configurational isomers.
The compound with double bonds or ring structure has restricted rotation, so exists in two
geometrical forms. The double bonds in larger rings can also cause geometrical isomerism. The
optical isomers rotate the plane of plane-polarised light. A sp3-hybridised carbon atom bearing
four different types of substituents is called an asymmetric centre of chiral centre. A chiral object
or molecule cannot be superimposed on its mirror image. Stereoisomers that are mirror images
of each other are called enantiomers. The stereoisomers that are not mirror images of each other
are called diastereomers. Diastereomers have different physical properties.
A racemic mixture is optically inactive and contains equal amounts of both the enantiomers.
Resolution refers to method of separating a racemic mixture into two pure enantiomers. A meso
compound is an optically inactive stereoisomer, which is achiral due to the presence of an inter-
nal plane of symmetry of centre of symmetry within the molecule.

95. The pair showing identical species is

CH3 CH3
Br CH3 H CH3
(a) and
H Br Br Br
H H
Me Br
D Et
(b) H OH and
D Br H OH
Et Me
H COOH
H COOH HO
(c) and
H
HOOC OH H OH
OH COOH

(d) None of these

2.44 chapter two

96. Which of the following pairs are diastereomers?

Me Me Br Br
Cl Cl H
(a) H and (b) and
H Br H Br
Et Et Br Br
OH OH
H3C OH HO H
(c) and (d) All of them
H CH3 H CH3
H CH3
97. The following two compounds are
O
(i) (ii)
O
(a) Identical (b) Diastereomers
(c) Positional isomers (d) Enantiomers

Passage 4
Isomers that have the same skeletons (that is, with component atoms attached in the same
sequence) but differ from each other with relative positions of some atoms in three-dimensional
space by virtue of rotation about σ bonds are called conformational isomers or conformers.
A quantitative description that relates relative atomic positions to the changes in potential energy
during rotation about a σ bond describes the energetics of conformational interconversion, a
­process known as conformational analysis.
Rotation about (C −σ C) bond in ethane can give various conformers:
In structure A1 or B1, C–H flagpoles at C-1 completely overlap each other at C-2. This form is
called eclipsed conformation.
H H H H
1 H 1 H H
H H
H H H H
2 H H
H H H H
H 2
H H H
(A1) (B1) H (A2) (B2)
           
In structure A2 or B2, C—H flagpoles at C-1 is fixed at 60° dihedral angle so that it is exactly
between two C–H flagpoles at C–2. This is called staggered conformation.
• Various other structures in between eclipsed and staggered conformations are called
skew conformation.
• Structures B1 and B2 show the orientations of the hydrogens on the front carbon relative
to those on the back carbon, these are called Newman projections.
• Structures A1 and A2 are called Sawhorse projections.

98. Among the following conformers, which has highest potential energy for n
­ -butane (along
C2–C3 bond rotation)?
(a) Skew (b) Fully eclipsed
(c) Staggered (d) Partially eclipsed
 isomerism 2.45

99. In the following chair conformer correct orientation of –OH groups is/are
OH 6
4 CH2OH
O
5 2
HO
3 OH 1
OH
(a) OH groups at C1, C2 and C4 are axial
(b) OH groups at C1 and C2 are axial
(c) OH groups at C1 and C4 are axial
(d) OH groups at C1, C2 and C4 are equatorial

100. In the following equilibrium, the value of “K” is

CH3
H K
CH3
H
(a) K < 1 (b) K > 1 (c) K = 1 (d) None of these

Passage 5
Consider the following pairs of compounds
OH CH3
H OH
(i) and
H OH
CH3
OH

Me Me
(ii) and

Me Me
Me Me
Me Me

(iii)
and
Me Me

Me Me
Cl

Cl
(iv) and

Cl

Cl
2.46 chapter two

(v)
OH HO
and
OH
HO
101. Identical pair of compounds is/are
(a) i and ii (b) ii and iii (c) iv and v (d) i and v

102. Both compounds in above pair are meso

(a) 1st pair (b) 2nd pair (c) 5th pair (d) 4th pair

103. Diastereoisomeric pair is

(a) 1st pair (b) 2nd pair (c) 3rd pair (d) 4th pair

Passage 6
Presence of chiral carbon in organic compound is neither a necessary nor a sufficient condition
showing optical activity. The chirality, i.e., dissymmetry of a molecule as a whole is the necessary
condition for optical activity.

104. Which of these compounds will NOT show optical activity?

H5C6 C6H5
(a) CH3–CHOH–CH2–CH3 (b) C=C=C
H7C10 C10H7
NO2 COOH
H2N H
(c) O2N (d)
H2N NH2
HOOC NO2
105. Which of the following pairs is correctly matched?
(a) CH 3 − CH = C = CH 2; optically active
allene

H3C COOH
(b) C ; optically active
H3C H
Alkylidene
CH3 C4H9
(c) C=C=C ; optically active
H5C6 allene C7H15

HOOC NO2
(d) ; optically active

HOOC NO2
106. Which one of the following is an achiral molecule?
COOH CH2OH C6H5 C6H5
H – C – OH H – C – OH H – C – Br H – C – Br
(a) (b) (c) (d)
H – C – OH HO – C – H H – C – Br H – C – Br
C6H5 CH2OH C6H13 C6H5
 isomerism 2.47

Passage 7
Observe the given molecule/s

OH H
H OH H OPh
(i) (ii) (iii)
H Br H Ph
Br Br

Ph Ph H
HO H OH
H
(iv) H Br (v) (vi) Br
OH H Br
Ph
Ph Ph
107. Correct statement is
(a) i and ii are enantiomers (b) iii and v are diastereomers
(c) i and iv are identical (d) i and vi are diastereomers

108. Diastereomeric pair is

(a) i and ii (b) i and vi (c) ii and v (d) iii and vi

109. If Br is attatched in place of –OH group in structure “V” (with same s­ tereochemistry) then
resultant structure is
(a) Meso
(b) Threo
(c) Structure has odd degree of unstaturation
(d) Structure is identical to (i) compound

Matrix Type
Match the columns:

110. Column I Column II

H O H
H H
(a) (p) Compounds give positional isomerisation with
H H 1,2-dichloro benzene.
H O H
Ph
Cl H
(b) (q) Degree of unsaturation in the given compound is
H Cl even [excluding zero value]
Ph
2.48 chapter two

Cl

(c) (r) Given compound or conformer has zero dipole

moment.
Cl
Cl
H
(d) (s) Net dipole of one mole of compound is nonzero.
H
H H
Cl (t) Compound has ketone functional group.

111. Column I (Compound) Column II (Isomerism)

D H D CH2OH
(a) C=C and C=C (p) Functional isomers
H OCH3 H H
O O
(b) (q) Geometrical isomers
and

H H Cl H
(c) C=C and C=C (r) Position isomers
Cl CH2CN H CH2NC
CN H CN
(d) and (s) Chain isomers
H
(t) Metamer

112. Column I (Structure) Column II (Configuration)

H3C CH2CH3
(a) C C (p) E
H CH3
CHO
(b) HO – C – H (q) Z
CH2OH
Br F
(c) C C (r) R
Cl I
CHO
(d) HO – C – CH2OH (s) S
H
(t) Plane of symmetry

113. Column I Column II

(a) (p) Plane of symmetry absent

 isomerism 2.49

(b) Fe (q) C6

Ferrocene (staggered)

(c) (r) S6

COOH H

(d) Ph H H Ph (s) Ci/COS

H COOH
(t) C5

114. Column I Column II

(Compounds) (Type of isomerism)
O O
(a) CH3–CH2–CH2–C–CH3 and CH3–CH2–C–CH2–CH3 (p) Positional

CH2–OH CH3
(b) OH (q) Conformational
and

CH3 CH3
CH3
(c) (r) Metamerism
and
CH3

CH3 CH3
Br CH3 Br H
(d) and (s) Functional
H Br Br H
H CH3 (t) Optical isomerism
2.50 chapter two

115. Column I Column II

Me
S O

(a) (p) Optically inactive compound

O S
S–

O
Cl
Br
(b) Cl (q) Optically active compound

Br
R

P
(c) R (r) Meso compound
R
P

R
F

(d) Br Cl (s) Axis of symmetry present

I (t) Asymmetric compound

116. Column I Column II

Cl CH3

C
CH3

(a) Cl C (p) Optically inactive compound

C Cl

I CH3

Br
F Cl
(b) Cl F (q) Optically active compound
Br

I
 isomerism 2.51

Cl Cl

Br Br

(c) (r) Meso compound

F F

Cl Cl

Br
Cl
Cl
C
Br
C
(d) (s) Axis of symmetry present

C
Br

Cl
(t) Asymmetric compound

117. Column I Column II

N N
(a) (p) Optically inactive
compound
H3C OH HO CH3

CH3 H3C

O O

(b) (q) Optically active

compound
H3C CH3
Cl
(c) Cl CH3 (r) Meso compound
H3C
2.52 chapter two

Et Et

N N
N O O
(d) N (s) Axis of symmetry
MeO present
OMe

N N
(t) Dissymmetric
compound

118. Column I Column II

O
Cl
CH
(a) (p) Optically inactive compound
CH
CH3
HN
O O

CH HC
(b) C (q) Optically active compound
CH HC

HNC
H NH
3
CH3

C
(c) (r) Meso compound

(d) (s) Axis of symmetry present

(t) Asymmetric compound

119. Column I Column II

(a) (p) Optically inactive compound

 isomerism 2.53

Cl CH3

(b) I (q) Optically active compound

Cl CH3
I

Cl

(c) (r) Meso compound

Cl

H3C
CH3
(d) (s) Axis of symmetry present
Cl

Br
(t) Asymmetric compound

120. Column I Column II

Cl
(a) Cl (p) Optically inactive compound

Cl
Br

(b) (q) Optically active compound

Cl
Br

Cl
I

(c) (r) Dissymmetric compound

Cl
Br

Cl
I

(d) (s) Axis of symmetry present

Cl
Br

F
(t) Asymmetric compound
2.54 chapter two

121. Column I Column II

H3C
CH3
(a) (p) Optically inactive compound
Cl Br

F F

(b) (q) Optically active compound

Cl Br
F F

(c) (r) Degree of unsaturation is odd

H3C CH3

Cl Br
F F

(d) CH3 (s) Axis of symmetry present

H3C

Cl Cl
(t) Asymmetric compound

122. Column I Column II

(a) (p) Optically inactive compound

(b) (q) Optically active compound

Cr3+

(c) (r) Dissymmetric compound

 isomerism 2.55

Br

Cl
(d) (s) Axis of symmetry present
Cl
Br (t) Asymmetric compound

123. Column I Column II

(a) (p) Optically inactive compound

N N
(b) (q) Optically active compound

(c) (r) Dissymmetric compound

(d) (s) Axis of symmetry present

(t) Asymmetric compound

124. Column I Column II

Cl Cl
(a) (p) Optically inactive compound

Br
Br
(b) (q) Optically active compound

Br
Br
Br Br

(c) C (r) Dissymmetric compound

C
C
Cl Cl
2.56 chapter two

Br

Cl
(d) (s) Axis of symmetry present
Cl
Br (t) Asymmetric compound

125. Column I Column II

(a) OH (p) Optically active molecules without chiral

centres
NH2

O
(b) (q) Optically active molecules with chiral
O centres.

O
(c) (r) Compounds have even number of ­chiral
centres
NH
O

(d) Me Me (s) Optically inactive molecules

H H

126. Column I Column II

Me
(a) (p) Optically active
Me

Me
(b) (q) Optically inactive
Me

Me Me
(c) (r) Compounds show geometrical isomerism
H H
Me
(d) (s) Plane of symmetry

Me
 isomerism 2.57

127. Column I Column II

H H
(a) (p) Molecule has chiral centre

Me N O
(b) Me (q) Molecule is asymmetric

Ph COOH

(c) HOOC H Ph H (r) Molecule is dissymmetric

H H

Me n-butyl
(d) C=C=C (s) Molecule is optically inactive
H COOH

Integer Type
128. µ obs = ∑ µ i x i; where µi is the dipole moment of stable conformer and xi is the mole ­fraction
of that conformer of Z–CH2–CH2–Z in Newmann’s projection. If µsolution or µnet = 1 D and
mole fraction of antiform = 0.82, find µGauche.

129. Number of primary amine possible for C4H11N is

130. How many chiral centres are present in the following compound?
CH3
Br
Br

CH3
131. How many chiral centres are present in the following compound?
CH3

H3C CH3
H3C

H3C

HO
2.58 chapter two

132. How many stereoisomers are possible for the following compound?
CH3
O OH

H3C O O O

O
O OH
OH CH3
133. How many stereoisomers are possible for the following compound?
CH3 CH3
NH
H3C CH3
CH3
O
134. How many stereoisomers are possible for the following compound?
OH CH2

H2C N
O H O
H2N CH2 NH2
N N
H O H

CH3 CH2
135. How many stereoisomers are possible for the following compound?
O

N
NH

HO N N NH2
O

O
HO P O

OH
136. How many compounds are optically active?

N N N N
(a) (b)
N

Br
Br
(c) (d)
Br
C Br
 isomerism 2.59

COOH NO2 Cl Cl

(e) (f)

COOH Br Br O2N

O
(g) (h) (i)
O

(j) (k) (l)

Br
I

Cl
137. How many stereocentres are possible for the following compound?
CH3
H3C
O H3C
O CH2

H3C CH3
138. How many compounds are optically inactive?

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

O O NH
(e) (f) (g) (h)
HN O O

O
HN
(i) (j) (k) (l)
O NH

Cl Cl
(m) (n) (o) (p)

Cl Cl
O
(q)
2.60 chapter two

139. How many geometrical isomers are possible for the following compound?
H3C CH3

H3C CH3

140. How many geometrical isomers are possible for the following compound?
CH3
H3C CH3

H3C CH3
CH3
141. How many geometrical isomers are possible for the following compound?

Ph COOH

HOOC Ph
142. How many steroisomers are possible for the following compound?
CH3
Cl Br
Cl Br
H3C CH3
Br Cl
Cl Br
CH3
 isomerism 2.61

Answer Keys
Level 1
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
b a d d b b b a b c d c c a c
16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
c b d a d c ac ab d d d d d a c
31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
d a b d b a b c d d c a b c d
46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
d a d c a a d a b d c d b c b
61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
c a c d a c b b b a d c c d c
76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
a c b a b b a a b b d c a d b
91 92 93 94 95 96 97 98 99 100 101 102 103 104 105
c d b b a d b a d b a a a d c
106 107 108 109 110 111 112 113 114 115 116
b b c a c a a b b c c

Level 2
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
b a b b b c b b a d b d c d a
16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
a b c c d b b b abd c b b b bc abd
31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
bd abcd abc acd bcd acd abd ad bc bd ad acd abc ab abcd
46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
ab abcd cd a abd acd abcd abcd abcd ab abc bd abd abc abc
61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
cd ac a a cd a a d ab bc ad ab ab bc bc
76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
ab bc abcd abc acd ab abd cd d ac d acd ad b a
91 92 93 94 95 96 97 98 99 100 101 102 103 104 105
b d d c d ab b b c b c c a d c
106 107 108 109 110(a) 110(b) 110(c) 110(d) 111(a) 111(b) 111(c) 111(d) 112(a) 112(b) 112(c)
d c a a rst qrs pqr s p rt p s qt s pt
2.62 chapter two

112(d) 113(a) 113(b) 113(c) 113(d) 114(a) 114(b) 114(c) 114(d) 115(a) 115(b) 115(c) 115(d) 116(a) 116(b)
r rs st qrs ps pr s p t qs pr qs qt pr pr
116(c) 116(d) 117(a) 117(b) 117(c) 117(d) 118(a) 118(b) 118(c) 118(d) 119(a) 119(b) 119(c) 119(d) 120(a)
ps qt qst qst qst pr qt qt pr prs prs pr qs qt ps
120(b) 120(c) 120(d) 121(a) 121(b) 121(c) 121(d) 122(a) 122(b) 122(c) 122(d) 123(a) 123(b) 123(c) 123(d)
ps p qt qrt qrt qrt pr ps ps qrs qrs p ps qt qt
124(a) 124(b) 124(c) 124(d) 125(a) 125(b) 125(c) 125(d) 126(a) 126(b) 126(c) 126(d) 127(a) 127(b) 127(c)
qrs qrs ps qrs qr qr rs p qrs qs qsr qrs pr pq s
127(d) 128 129 130 131 132 133 134 135 136 137 138 139 140 141
q 5.55 5 2 8 64 1024 32 8 9 8 7 4 8 5
142
5
 isomerism 2.63

Workbook Exercises
Exercise 1

Identify molecules that show Geometrical Isomerism

1. 2. 3.

4. 5. 6.

7. 8. 9.

10. 11. 12.

13. 14. 15.

16. 17. 18.

19. 20. 21.

22. 23. 24.

25. 26. 27.

28. 29. 30.

31. 32. 33.

34. 35. 36.

2.64 chapter two

37. 38. 39.

OH
40. 41. 42.
N

NH
43. 44. 45.

OH
OH OH N
N N
46. 47. 48.

49. 50. 51. HN NH

52. HN 53. N N 54. N

NH N

D D
55. T T 56. HN NH 57. HN NH

N OH
58. 59. 60.

61. HN NH 62. O O 63. N N

O
64. 65. 66.
O

OH
N HN N
67. 68. 69.
N NH N
HO
 isomerism 2.65

OH Cl
O
N
70. 71. 72.
O
NH

Cl F Cl F Cl F
73. C C C C 74. C C C C 75. C C C C
Br Cl Cl Cl F F

F F
76. C C C C 77. C C C C 78. C C C C
F Cl F Cl Cl

Cl Cl Cl Cl Cl
79. C C C C CH2 80. C C C C CH 81. C C C C C
F F F F

COOH
Cl Cl Cl F
82. C C C C C CH 83. C C C C CH 84.
F F
COOH

N N
85. 86.

N N
87. 88. N N
N

Cl Cl Cl Cl
N
89. 90.
N
Br Br

Br Br COOH COOH

91. 92.

Br Br
2.66 chapter two

Cl Cl Cl Br F F

93. 94. 95.

Br Br Cl Br F F

Cl
96. C C C C CH 97. C C C C CH
F F
 isomerism 2.67

Exercise 2

Identify molecules that show Geometrical Isomerism

1. 2. 3. 4.

5. 6. 7. 8.

9. 10. 11. 12.

O NH

13. 14. 15. 16.

17. 18. 19. 20.

21. 22. 23. 24.

25. 26. 27. 28.

Cl Br Cl
29. 30. 31. 32.
Br Br Br
Cl O HO
Cl
33. 34. 35. 36.
F

HO
37. 38. 39. 40.

O
41. 42. 43. 44.
O O
F
2.68 chapter two

O
45. NH 46. 47. 48. O
O HN O O

49. 50. 51. 52.

O

HO HO
O
53. 54. 55. 56.
OH

57. 58. 59. 60.

61. 62. 63. 64.

65. 66. 67.

Cl
Br Br 70. D D
68. Cl Cl 69.

O
71. 72. O 73.

74. 75. 76.

77. 78. 79.

80. 81. 82.

83. 84. 85.

 isomerism 2.69

86. 87. 88.

89. 90. 91.

92. 93. 94.

95. 96. 97.

98. 99. 100.

101. 102. 103.

104. 105. 106.

O O
107. 108. O 109.
O O
O
O O
110. 111. 112.

113. 114. 115.

116. 117. 118.

119. 120. 121.

2.70 chapter two

122. 123.

124. 125.

126. 127.

128. 129.

130. 131.

Cl Br Br
132. Cl 133.
Cl Cl

HO Br
134.
F
 isomerism 2.71

Exercise 3

Identify molecule give G.I.

O O O
O O
1. 2. 3.
O N N
H H
H
N
4. HN NH 5. 6. N
N
N H H
H

7. 8. 9.

10. 11. 12. Cl Cl

Cl

13. Cl Cl 14. 15.

Cl

16. 17. 18.

19. 20. 21.

22. 23. 24.

25. 26.

27. 28.

29. 30.
2.72 chapter two

31. 32.

33. C 34.

35. 36.

37. 38.

39. 40.

41. 42.

43. 44.

45. 46.

Identify stable conformer

Me Me NMe+3 NMe+3
H Cl H H H F H H
47. H H H H 48. H
H H H
H Cl
H F
i ii i ii

NMe+3 NMe+3 NMe+3 NMe+3

H CHO H H H I H H
49. H 50. H H
H H H H H
H CHO H I
i ii i ii
 isomerism 2.73

Me Me Me Me
: H : H : : : H
N N O O
51. 52.
H Me Me H H Me Me H
H H H :
i ii i ii

NO2 NO2 F F
H COOH H H H F H H
53. H H H H 54. H H H H
H COOH H F
i ii i ii

Cl Cl NO2 NO2
H Cl H H H OH H H
55. H H H H 56. H H H H
H Cl H OH
i ii i ii
2.74 chapter two

Exercise 4

Identify Isomeric Relationship between pair of Compounds

CN CN H H Me Me Me H
H H H CN H H H H
1. 2.
H H H H H H H
CN
H H H H H H Me H
CN H Me H Me OH H OMe
H Me H NC H H H H
3. 4.
H H H H H H H H
H H H H H H H H
Me H H H H H H Me
H H H H H H H H
5. 6.
H OMe H OEt Et Et Et Me
H H H H H H H H
Me H Me H H H Me Me
H Et H Me Et Me Me H
7. 8.
H H H Me Me Et Me Me
H H H H H H Me Me
H H H H
Me Me Me Et
9.
Me Me H Me
H H H H

CN CN H H
H H H NC
10.
H H NC H
H H H H
COOH Me H COOMe
H H H H
11.
H H H H
H H H H
H H H H
H O H H OH
12.
H H H H
H H H H
Me OMe H OMe
H H H H
13.
H H H H
H H Me H
 isomerism 2.75

Et H H H
H H H H
14.
H OMe H OPr
H H H H
H H Me Me
H H H H
15.
Et Et Me Me
H H H H
Me H Me H
H OPr H Me
16.
H H Me
OMe
H H H H
H H Me Me
Et i-Pr Me Me
17.
Me Et Me Me
H H Me Me
H H H H
Me Me Me Et
18.
Me Me H OMe
H OH H H
H Me H Me
Me Me H H Me Me H H
19. 20.
Me H Me Me Me Me Me Me
H H H Me
H H NO2 ONO
H Me H H H H H H
21. 22.
H H H H H H H H
COOH COOMe H H
Cl Cl Cl Cl
H Cl H H H H H F
23. 24.
H H H Cl F Br Br H
H H H H
i-Pr Bu COMe COEt
H H H H H H H H
25. 26.
H H H H H H H H
i-Pr Et Et Me
CHO COEt
H H H H
27.
H Me H H
Me H
2.76 chapter two

Exercise 5

Identify optically active compounds

1. 2. 3.

Cl Cl Cl Br F F

4. 5. 6.

Br Br Cl Br F F
COOH NO2

7. 8. 9.

COOH NO2
CN
N N
10. 11. 12.

NC

13. 14. 15.

16. 17.

N N N N
18. 19.
N

N
20. N N 21.
N

NO2 Cl Cl

22. 23.

Br Br O2N
 isomerism 2.77

24. 25. 26.

27. 28. 29.

30. 31. 32.

33. 34. 35.

36. 37. 38.

39. 40. 41.

42. 43. 44.

45. 46. 47.

48. 49. 50.

51. 52. 53.

2.78 chapter two

54. 55. 56.

Br
Cl Br
57. 58. 59.

Cl Br
Br
Cl Cl
60. 61. Cl Cl 62. Cl Cl
Cl
Cl
Cl Cl
Br Br
63. 64. 65.
Cl Cl Cl Cl Cl Cl
Cl

66. O Br 67. 68. N

Cl Br
F Cl

69. 70. Br 71.

Br Br Br
I Cl
Br
Cl Br
Cl Br
Cl O
72. 73. 74.
Cl O
Br
Cl

75. 76. 77. Cl

Cl Cl
Cl

Br
Br Br
78. Br
Cl
Cl
 isomerism 2.79

Solution for Workbook Exercises

Exercise 1
Molecules that show Geometrical Isomerism
4, 6, 9, 11, 13, 16, 23, 24, 25, 26, 27, 30, 31, 33, 34, 35, 36, 38, 39, 40, 41, 44, 47, 50, 51, 52, 53, 54, 55, 56, 58, 59, 60,
61, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 76, 77, 82, 86, 89, 90, 92.

Exercise 2
Molecules that show Geometrical Isomerism
6, 9, 11, 12, 13, 14, 17, 18, 19, 20, 21, 22, 23, 25, 26, 28, 29, 30, 31, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47,
48, 49, 50, 51, 52, 53, 54, 59, 61, 62, 63, 67, 68, 69, 70, 73, 78, 79, 83, 77, 86, 87, 90, 92, 93, 94, 95, 97, 98, 99, 100, 101,
102, 103, 106, 107, 109, 110, 111, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134.

Exercise 3
Molecules that show Geometrical Isomerism
1, 3, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 23, 25, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, 41,
42, 43, 45, 46.
Stable Conformer
47(I), 48(I), 49(I), 50(II), 51(II), 52(I = II), 53(I), 54(I), 55(II), 56(I).

Exercise 4
Isomeric Relationship between pair of compounds
1. Positional Isomers 2. Positional Isomers
3. Functional Isomers 4. Functional Isomers
5. Metamers Isomers 6. Chain Isomers
7. Chain Isomers 8. Chain Isomers
9. Chain Isomers 10. Functional Isomers
11. Functional Isomers 12. Not Isomers
13. Positional Isomers 14. Metamers Isomers
15. Chain Isomers 16. Metamers Isomers
17. Chain Isomers 18. Functional Isomers
19. Chain Isomers 20. Positional Isomers
21. Functional Isomers 22. Functional Isomers
23. Positional Isomers 24. Positional Isomers
25. Chain Isomers 26. Metamers Isomers
27. Functional Isomers
 2.80 chapter two

Exercise 5
Optically active compounds
4, 7, 8, 10, 12, 14, 15, 22, 23, 24, 25, 27, 28, 30, 34, 36, 37, 38, 39, 41, 43, 44, 45, 46, 48, 49, 50, 51, 52, 53, 55, 56, 58,
59, 62, 63, 64, 65, 66, 67, 69, 73.