ISOMERISM

1. The number of structural isomers for chlorobutane is :

(A) 2 (B) 4 (C) 6 (D) 5

M
Cl
1. (B) Cl
(1)
(2) Cl (3) Cl (4)

A
2. How man dibromobenzenes are possible?

R
(A) 1 (B) 2 (C) 3

O
G
O
U
3. CH3 CH2 C H and CH3 C CH3 are
R
(A) Positional isomers (B) Functional isomers
(C) Chain isomers (D) Metamers
U

3. (B)
G

4. Which of the following pairs of structure does not represent isomers?

EN

(A) and (B) and

O O
O
OH
OH
LL

O O
(C) and (D) and
O
4. (D)
A

5. How many distinct terminal alkynes are possible for a compound having molecular formula C5H8?
(A) 1 (B) 2 (C) 3 (D) 4

5. (B)

6. How many distinct terminal alkenes are possible having molecular C6H12?
(A) 3 (B) 4 (C) 5 (D) 6

-1 -
7. How many structural isomers are possible when one of the hydrogen is replaced by a chlorie atom is

(A) 4 (B) 6 (C) 7 (D) 8

7. (A)

8. The number of ether metamers represented by the molecular formula C4H10O is :

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

8. (C)

9. CH3 CH2 CH2 CO2H CH3 CH CH3

M
(A) CO2H
A and B are :

A
(A) Chain isomers (B) Positional isomers
(C) Functional isomers (D) Metamers

R
9. (A)

G
10. How many positional isomers are possible for the compound given :
(A) 2 (B) 3 U (C) 4 (D) 5

10. (B)
R
11. How many cyclic structural isomers are possible for C5H10 ?
(A) 4 (B) 5 (C) 6 (D) 7
U

11. (B)

12. How many structural isomers are possible for molecular formula C3H6 BrCl?
G

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

12. (B)
EN

CH2 NH2
13. How many position isomers are possible for ?
LL

(A) 3 (B) 5 (C) 6 (D) 8

13. (A)
A

14. There are 8 isomers that have the molecular formula C5H11Br. How many of them are tertiary alkyl bromides?
(A) 0 (B) 1 (C) 2 (D) 3

14. (B)

15. How many structural isomers of C4H8 contains one  bond?

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

-2 -
16. What is DBE of Cubane?
(A) 5 (B) 6 (C) 4 (D) 3

16. (A)

17. Degree of unsaturation present in

(A) 2 (B) 5 (C) 7 (D) 6

17. (C)

M
OH
18. OH and are :

A
(A) Chain isomers (B) Functional isomers

R
(C) Metamers (D) Positional isomers

18. (D)

19.

G
CH3 – O – CH2 – CH2 – CH3 and CH3 – CH2 – O – CH2 – CH3
(A) Positional isomers
(C) Metamers
U
(B) Chain isomers
(D) Functional isomers
R
19. (C)
U

20. How many ring chain isomers for C5H10.

(A) 5 (B) 2 (C) 3 (D) 6
G

20. (A)

21. Which of the following pairs of compounds are not position isomers ?
EN

OH
(A) OH and (B) O and
O

COOH O
O O
LL

(C) COOH and (D) and

O

21. (C)
A

22. Which of the following compounds is isomeric with methyl vinyl ether ?
(A) Propanal (B) 1-propanol (C) Ethylmethyl ether (D) Ether

22. (A)

23. 2-butyne and 1, 3-butadiene are :

(A) Chain isomer (B) Position isomer (C) Functional isomer (D) Tautomers

-3 -
 24. Compound which is not isomeric with diethyl ether is :
(A) Methyl-n-propyl ether (B) 1-butanol
(C) 2-methyl-2-propanol (D) Butanone

24. (D)

25. Which of the following pairs of compounds may be regarded both as functional isomer and position isomer ?
(A) Benzyl alcohol and methoxy benzene (B) o-cresol and p-cresol
(C) Benzyl alcohol and o-cresol (D) Benzyl alcohol and benzyl methyl ether
25. (C)

26. Which of the following will not show tautomerism.

M
OH O O O

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

A
26. (D)

R
27. Which of the following have negligible enol content?

G
O O
O
U O O O O
(A) O O
(B) (C) (D)
CH3 C CH2 C CH3
27. (A)
R
O
D2O/OD
U

28. Prolonged treatment gives :

O
D D
G

O O O
D D D D D D D
(A) (B) (C) (D)
D D D D D
28. (B) D D
EN

29. How many hydrogen in the compound given below are replaced by deuterium when it is shaken in D2O containing
traces of hydroxide?
LL

H
A

H
O

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

-4 -
30. Which of the following Hydrogen will not participate in tautomerism

1
O
H H5

H CH2 H4
2
H3

(A) 1, 2 (B) 1, 3 (C) 3, 5 (D) 2, 5

30. (D)
31. How many tautomers can be drawn for the following -dicarbonyl ?

M
O O

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

R
31. (C)
32. How many enolisable hydrogen are there in the following compound?

G
O U
R
(A) 2 (B) 4 (C) 5 (D) 7
32. (B)
U

33. How many of them have stable enol form than keto
G

O O CH3 CH2 CH3 O O

O C C C
C C
CH3 C CH3 O O C6H5 CH2 C6H5
EN

O
LL

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

33. (A)
A

34. Nitro and acetonitro are

(A) Functional isomers (B) Positional isomers
(C) Metamers (D) Tautomers

-5 -
35. Which of the following will show tautomerism :

O O
O
O
(A) (B) (C) (D)
N
O
H
35. (D)
36. Order of stability of enol form of the following keto form is :

O O O

M
O O
CH3 C CH3 CH3 C CH2 C CH3 CH3 C CH2 C OEt

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

R
36. (C)
37. Order of stability of mol form of the following keto is :

G
x O O
y
O O
z
O
U
(A) x>y>z (B) y>x>z (C) y>z>x (D) z>x>y
R
37. (B)
U

38. Stability order of enol of following keto is :

O O O
G

X Y Z
EN

(A) x>y>z (B) y>z>x (C) y>x>z (D) x>z>y

38. (D)
39. Enol content of which of them greater
LL

O O

O
A

O O
A B

(A) B>A (B) A>B (C) A= B (D) unpredictable

-6 -
40. Which of the following is most stable enol form of cyclohexane - 1,3 - dione?
O O

OH OH OH OH OH OH OH O
(A) (B) (C) (D)

40. (D)
41. Which of the following have highest enol content?

M
O O O O O O
O O
(A) (B) (C) (D)
Ph Ph Ph Ph OC2H5

A
41. (C)

R
42. Which of the following will not form an enolate?

G
O O
O
O
(A) (B) (C) (D)
U
R
42. (C)
43. Increasing order of percentage of following are :
U

OH OH
G

x
EN

y z

(A) x>y>z (B) y >z>x (C) y> x>z (D) z > y > x
43. (B)
LL

H C N H N C
44. A B
A and B are :
A

(A) Functional isomers (B) Constitutional isomers

(C) Tautomers (D) Positional isomers

-7 -
45. Which is most stable enol of following :

O
H CH3
D H

OH OH OD OH
D CH3 H CH3 CH3 CH3
(A) (B) D (C) (D)

45. (B)

M
46. Which of the following pairs of structures does not represent tautomers ?
O O

A
OH O
(A) and (B) OH and O
H

R
CHO CHOH
H OH
O

G

O O
O OH U 
(C) and (D) and
N N
R
H
46. (D)
U

47. The compound which may exhibit tautomerism :

O
G

(A) HO NO (B) HN O (C) (D) All of these

CHO
EN

47. (D)
48. Which of the following compounds show tautomerism ?
O S
(A) NH2  C NH2 (B) NH2  C NH2 (C) HO N=O (D) All of these
LL

48. (D)
49. Tautomerism is not exhibited by :
A

(A) CH = CH −OH (B) O O (C) O (D) O

O O

50. (B)
50. In which of the following enol content is maximum ?
(A) Ph2CHCHO (B) NCCH2COOEt (C) CH3COCH2COCH3 (D) PhCOCH3

-8 -
51. Geometrical isomerism is possible in :

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

51. (D)
52. Which of the following will not exhibit geometrical isomerism?

(A) (B)
O O

M
(C) (D)

A
R
52. (C)
53. Write IUPAC name of the following compounds?

G
H H
C C H U
H3C C C
H CH2 CH3
R
(A) Cis, trans -2-,4-hepta diene
(B) 2Z, 4E - 2,4 -hepta diene
U

(C) Cis, Cis - 2,4 - hepta diene

(D) 2E, 4E - 2,4 - hepta diene
G

53. (A)
54. Which of the following will form two isomers with NH2OH?
(A) Benzaldehyde (B) Acetone
EN

(C) Benzoquinone (D) Benzophenone

54. (A)
55. How many geometrical isomers are possible for
LL

CH3 – CH = C = CH – CH = CH – CH3
(A) 0 (B) 1 (C) 2 (D) 3
55. (C)
A

Cl

56. How many geometrical isomers possible for

Cl Cl

(A) 0 (B) 1 (C) 2 (D) 3

-9 -
57. How many geometrical isomers possible for
CH3 – CH = C = C = C = CH – CH =CH – CH = CH – CH3
(A) 0 (B) 8 (C) 3 (D) 4
57. (D)
58. How many geometrical isomers possible for given compound ?
(A) 0 (B) 2 (C) 3 (D) 4
58. (B)
59. Which of the following compound will not show geometrical isomerism ?

Cl Cl
(A) (B) (C) (D) All of these
Cl

M
Cl
59. (D)

A
60. How many geometrical isomers are possible
Ph – CH = CH – CH = CH – Ph?

R
(A) 2 (B) 3 (C) 4 (D) 5
60. (B)

G
61. Which of the following compound will not show geometrical isomer?

(A)
H3C
C C C
CH3
U (B) CH3 – C  C – CH3
H H
R
CH3 H
U

(C) C C (D) All of these

H H
G

61. (D)
EN

62. How many geometrical isomers possible for ?

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

62. (B)
LL

63. Which of the following have geater boiling points/ Melting point

CH3 Cl CH3 CH3

C C C C
A

Cl CH3 Cl Cl
A B
(A) M.P : A > B, B.P : A > B (B) M.P : B > A, B.P : A > B
(C) M.P : B > A, B.P : B > A (D) M.P : A > B, B.P : B > A

-10 -
64. Determine double bond stereochemistry (E or Z) for the following molecule.

F CH3 F Br
C C C C
CH3 H H I
[A] [B]
(A) A:E,B:E (B) A :Z , B : Z (C) A : E, B : Z (D) A:Z,B:E
64. (D)
65. What is the relationship between trans- 2- butene and cis -2- butene?
(A) Constitutional isomers (B) Enantiomers
(C) Diastereomers (D) Conformational isomers

M
65. (C)
66. Which of the following doesnot represent syn-anti ?

A
Ph
(A) Ph – N = N – Ph (B) C N OH
Ph

R
(C) Ph – CH = N – OH (D) Both (A) and (B)
66. (B)

G
67. Geometrical isomers is possible for U
CH3 CH3 CH3
(A) (B) C
H H CH3
R
U

(C) CH3 CH2 C CH2CH3 (D)

NOH
G

67. (A)
68. Assign double bond configuration to the following I, II respectively
EN

COOH
II C
CH2OH

NC I
LL

H2N CH2 CN

(A) E, E (B) Z, E (C) E, Z (D) Z, Z

A

-11 -
69. Which of the following pairs of compound are the correct notations given?

Ph Ph Ph
(A) N N and N N
anti syn Ph

CH3 OH
(B) C N CH3
and C N
H OH
syn H
anti

CH3 CH2CH3

M
H3C Cl H2C CH3
C C
and C C
(C) H CH3 BrCH2

A
Z CH3
E

R
H COOH
C C NH2 H

G
H H
C C
(D) and COOH
NH2
Z
U
E
R
69. (B)
70. Which of following compound will show geometrical isomerism ?
U

(A) Ph – C  C – Me (B) (C6H5)2N2 (C) (D) CH3 C CH3

G

Cl Cl
N
OH
70. (B)
EN

71. Which of the following compounds will not exhibit geometrical isomerism ?
F
CH3 Cl
(A) H Br (B) CH=NNH
LL

Me Me
H H
A

(C) H H (D) NN Cl

Me Me

71. (D)
72. The geometrical isomerism is shown by
CH2 CH2 CHCl
(A) (B) (C) (D)
CHCl

-12 -
73. Which will show geometrical isomerism ?

CHCH3
CHCH3 CHCH3

(A) (B) (C) (D) A and C both

CH3 CH3

73. (D)
74. What, if anything, can be said about the magnitude of the equilibrium constant K for the following equilibrium ?

H H
H CH(CH3)2 H3 C

M
CH3 H

CH(CH3)2

A
(A) K=1 (B) K<1 (C) K>1 (D) No estimate of K can be made

R
74. (B)

G
75. Which of the following does not contain plane of symmetry?

Cl
Cl Cl
U Cl
Cl H CH3
R
(A) (B) (C) (D)
Cl
U

75. (C)
G

76. Which of the following is Homomer of :

O
EN

?
Cl
H3C
LL

CH3 Cl CH3 Cl

(A) (B)
A

O O

O O

(C) (D)
H 3C Cl H 3C Cl

-13 -
77. How many stereoisomers are possible for following molecule?
Cl
Br

(A) 4 (B) 8 (C) 12 (D) 16

77. (D)

CH3 Cl
H Cl CH3 is :
78. If optical rotation produced by Cl is 36° than that produced by H
H Cl H
CH3 CH3

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

A
78. (C)
79. How are the following compounds related ?

R
CH3 Br
CH3
Br

G
Br
H Br H
U CH3

(A) Diastereomers (B) Enantiomers (C) Meso form (D) Identical

R
79. (A)
80. Which of the following pairs of compound is a pair of enantiomer?
U

Br Br
G

(A) (B)
Cl Cl
EN

Cl Cl

(C) (D)
LL

Cl Cl Cl Cl

80. (B)
81. Which of the following compounds can be optically active?
A

H3C Cl CH3
H H
C C C
H3C H H H3C CH3
(3)
(1) (2)

Select correct answer given :

(A) 1 and 3 (B) 1 and 2 (C) 2 and 3 (D) 1, 2 and 3

-14 -
82. Which of the following statements about the relationship of the structure (P), (Q), (R) and (S) is incorrect?

H Br H H Br H Br
Br

P Q R S

(A) P and R are enantiomers (B) P and R are identical

(C) Q and S are identical (D) P and Q are enantiomers
82. (A)
83. The observed rotation of 2 gm of a compound in 10 ml solution in a 25 cm long polarimeter tube is +13.4°. The

M
specific rotation of compound is :
(A) +30.2° (B) – 26.8° (C) + 26.8° (D) + 40.2°

A
83. (C)
84. How many geometrical isomers are possible for

R
Cl

G
Cl Cl U
(A) 0 (B) 1 (C) 2 (D) 3
84. (C)
R
85. Which of the following molecule is resolvable?
U

NO2 SO3H NO2 SO3H

(A) (B)
G

NO2 SO3H SO3H NO2

(C) (D)
EN

85. (B)
86. If sample of 2 - butanol have an enantiomeric excess of 60% of 1, 2 - butanol then percent of each isomer in the
mixture is :
LL

(A) 60% l and 40% d (B) 80% l and 20% d

(C) 70% l and 30% d (D) 60% l and 34% d
86. (B)
A

87. What is relation between the structure shown below ?

CH2Br CH3

H and Br

(A) Not isomers (B) Constitutional isomers

(C) Conformational isomers (D) Configrational isomers

-15 -
88. Number of assymetric centres present in the compound below are ?

H
CH(CH3)2

H3C

CH3
H

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

NH2

M
89. OH
(A) (B)

A
Total number of stereoisomers (a + b = 7)
(A) 5 (B) 6 (C) 7 (D) 8

R
89. (C) 4 + 3 = a + b.

G
90. What is configuration of following compound ?
CH3 U
H Cl
Cl H
R
CH2CH3
(A) 2S, 3R (B) 3R, 3S (C) 2S, 3S (D) 2R, 3R
U

90. (C)
G

91. Number of chiral carbon centre in the following molecule?

CH3
OH CH3
EN

N H
O
(A) 0 (B) 1 (C) 2 (D) 3
LL

91. (C)
92. Which of the following molecule have (2R, 3 - Z) configuration?
H3C H CH3 H
A

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

H H H H
C C CH3 C C CH3
H3C C H3C C
(C) (D)
H OH
HO H

-16 -
93. Assign the configuration of C-2 and C-4 of following molecule.

H OH H OH

OHC CHO
(A) S, R (B) R, R (C) S, S (D) R, S
93. (A)
94. Which of the following structures is chiral?

Br Cl
Br Cl
Br Cl Br

M
(A) Cl Br (B) (C) Br Cl (D)

A
Cl
Cl Br
Br Cl

R
94. (D)
95. C8H16 that can form cis-trans isomerism and also have chiral center is :

G
H H
(A) (B) U (C) Both of these (D) None of these

95. (A)
R
96. The number of enantiomers of the compound CH3 CH CH  COOH is :
Br Br
U

(A) 2 (B) 3 (C) 4 (D) 6

96. (C)
G

97. Which of the following compounds are meso forms ?

CH3
EN

CH3 CH3
H OH H Cl
H OH Cl H CH3
C2H5 CH3 3
1 2
LL

(A) 1 only (B) (3 only) (C) 1 and 2 (D) 2 and 3

97. (B)
98. Which of the following compound is achiral ?
H HO H
A

HO H HO H HO

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

-17 -
99. Which of the following compunds is optically active ?
CH3
CH3 Cl
H Cl Br Br
(A) H3C OH (B) (C) (D)
H Cl Cl
CH3
CH3
99. (C)
100. Which New man projection formula does not represent the following compound ?

Cl

M
A
H H Cl
Me MeCl Me H
Me H Me

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

G
H Me Me H

100. (D)
U
101. Number of conformational isomers for n-butane are ?
(A) 5 (B) 4 (C) 6 (D) infinite
R
U

102. Stability order of conformers of n-butane is :

(A) Skew > anti > eclipsed > Partially eclipsed
G

(B) Anti > Skew > partially eclipsed > eclipsed

(C) Partially eclipsed > anti > Skew > eclipsed
(D) anti > partially eclipsed > Skew > eclipsed
102. (B)
EN

103. Identify conformer of 2-methyl pentane:

CH3 H CH3
H CH3
LL

H H H H H
Et

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

H H3C H
H
A

H3C H
CH2CH3 CH3 H H

-18 -
 OH
H Z

104.
H H
H

Above gauche form is stable when Z is :

O
(A) – CH3 (B) – Et (C) (D) Ph
C OEt

M
+
NMe3

A
H Z

R
105.
H H

G
H

Above gauche form is stable when Z is : U

(A) – F (B) – OH (C) – OCH3 (D) All of these
105. ( )
R
106. Which of the following is most stable stable conformer of cyclobutane -1,4 -diol.
U

OH
OH OH
G

(A) (B)
EN

OH

HO
HO
LL

(C) (D)
OH
OH
A

106. (B)
107. Among conformers of butane which occur at energy minima on a graph of potential energy versus dihedral angle?
(A) Gauche (B) Eclipsed and partially elipsed
(C) Anti (D) Gauche and anti

-19 -
108. Most stable conformer of is :

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

M
H
H

A
109.
H H

R
G
(A) (B) (C) (D)

109. (A)
110. Which is least stable conformer of cyclohexane?
U
R
(A) (B) (C) (D)
U
G

CH3 CH3
H H H H
EN

111. and
CH3 H3C H
H3C
H CH3
LL

(A) Conformational isomers (B) Stereoisomers

(C) Constitutional isomers (D) Identical
111. (C)
A

Br CH3 H CH3
112. and are :
H H Br H

(A) enantiomers (B) diastereomers (C) conformers (D) homologues

-20 -
113. Which of the following is most stable ?

OH OH OH
HO
(A) (B)

OH
HO
HO
(C) (D)
OH

M
113. (A)

A
114. Stereo isomers possible for following compound

CH CH CH2 CH3

R
CH CH2

G
(A) 8 (B) 16 (C) 32 (D) 64
114. (A)
115. Which of the following is optically inactive?
U
R
Br
OHC CH3
U

CH3 CHClBr
(A) C C (B)
CH2Cl R CN
H
G

Cl Br I Cl CH3O
EN

CH3
(C) (D) C
Br CH2 Br
CH3Br I CH3
LL

115. (C)
116. Which of the following is chiral :
A

Cl Cl
CH3 CH CH3 H +
(A) C C (B) C N
H3C CH3 H3C

H3C H
(C) (D) All of these
H CH3

-21 -
117. How many gauche conformation of n -butane are possible?
(A) 2 (B) 3 (C) 4 (D) 1
117. (A)
118. Which of the following have D - configuration ?

OH COOH
OH CH2OH
H CHO
(A) (B) H C2H5 (C) H OH (D) H3C OH
CH2OH
CH3 CHO H
118. (B)

M
119. Which of the following diene is chiral?
(A) CH3 – CH = C = CH2 (B) CH3 – CH = CH – CH = CH2
(C) CH3 – CH = C = CH – CH3 (D) CH2 – CH – CH2– CH = CH2

A
R
Br CH3 H CH3
120. and are
H H Br H

G
(A) Identical (B) Diasteromers (C) Conformers (D) Homologs
120. (B)
121. Which of the following statements is true ?
U
(A) A mixture of enantiomers can be separated on the basis of difference in their boiling points (by a method
R
called fractional distillation)
(B) A mixture of enantiomers can be separated on the basis of difference in their solubility in any solvent
U

(C) A mixture of enantiomers can be separated by converting them into diastereomers by reacting them with an
optically active reagent
G

(D) A mixture of enantiomers can be separated by passing plane polarised through their solution
121. (C)
122. Well known pain killer Nurofen is an ibuprofen. How many stereoisomers it would have
EN

OH
O
If we have a racemic mixture of ibuprofen which one of the following can be used to resolve the isomers ?
LL

Ph
(A) 4, CH3 – CH2 – OH (B) 8,CH3COH
A

Ph

D
(C) 4,CH3COH (D) 8, CH3 – CH2 – OH
Ph

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123. How many spatial orientations are possible in the following compound ?

I CH=CHCH3

CHClCH3 Br

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

H Me
Me Me Me H
124. and

M
Me Me Me H
H Me

A
(A) Conformational isomers (B) Configurational isomers
(C) Constitutional isomers (D) Identical

R
G
U
R
U
G
EN
LL
A

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