GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 115

EXERCISE – 1: Basic Objective Questions

F  COOCH3  COCl 6. Which of the following is aromatic compound?
1.
I II III
Which of these groups has –I effect ?
(a) I (b) II (a) (b)
(c) III (d) all of these
2. The arrangement of (CH3)3C—, (CH3)2CH—,
CH3CH2 — when attached to benzene or unsaturated (c) (d)
group in increasing order of inductive effect is
7. Which of the following is Aromatic?
(a) (CH3)3 C — < (CH3)2 CH— < CH3CH2—
(b) CH3CH2 — < (CH3)2 CH — < (CH3)3 C — (a) (b)
(c) (CH3)2CH — < (CH3)3 C— < CH3CH2 —
(d) (CH3)3C — < CH3CH2 — < (CH3)2 CH — (c) (d) All of these
3. In which of the following molecule the resonance effect 8. Which of the following is non-Aromatic ?
is not present?
(a) (b)
(a) (b) (c) (d) All of these
9. Which of the following is aromatic?
(c) (d)
4. The most unlikely representation of resonance structure
of p–nitrophenoxide ion is :
(a) (b)

(c) (d)
10. Which of the following is Anti-aromatic?
(a) (b)

(a) (b)
(c) (d) All of these
11. Which of the structures below would be aromatic ?

(c) (d)
5. Aniline is weaker base than ethyl amine. This is due to
(i) (ii)
(a) – I effect of NH2 in aniline
(b) – R effect of NH2 in aniline
(c) + I effect of NH2 in aniline
(iii) (iv)
(d) + R effect of NH2 in aniline (a) i and iv (b) i, iii and iv
(c) iii and iv (d) ii
116 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

12. Which one of the following, is more acidic? (c) iii > i > ii > iv > v (d) ii > i > iii > iv > v

17. Which of the following is strongest base?

(a) (b)

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

13.

(c) (d)
18. Ease of ionization to produce carbocation and bromide
ion under the treatment of Ag  will be maximum in
Compare acidic strength:
which of the following compounds?
(a) a > b > c (b) b > c > a
(c) b > a > c (d) a > c > b
14.

Br
(a) Br
Br (b)
Br
O

Compare acidic strength:

Br Br
(a) a > c > d > b (b) d > a > c > b (c) (d)
(c) d > c > a > b (d) d > c > b > a 19. Among the following alkenes
15. Compare acidic strength: (I) 1–Butene (II) cis–2–Butene
(i) Ph — CO2H (ii) Ph — OH (III) trans–2–Butene
(iii) Ph — C CH (iv) Ph — CH2 – OH the decreasing order of stability is
(a) III > I > II (b) I > II > III
(a) i > ii > iii > iv (b) i > ii > iv > iii
(c) II > I > III (d) III > II > I
(c) i > iv > iii > ii (d) ii > i > iv > iii
20. Which of the following carbocation is most stable?
16. Compare acidic strength:

(i) (ii)
(a) (b)

(iii) (iv)
(c) (d)

(v)
(a) i > ii > iii > iv > v (b) i > iii > ii > iv > v
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 117

21. Consider the following structures (a) I > II > III (b) III > II > I
(c) III > I > II (d) II > I > III
25. Which of the carbanion is most stable?

The correct sequence of these carbocations in the

decreasing order of their stability is
(a) IV, III, II, I (b) I, II, III, IV
(c) IV, II, III, I (d) I, III, II, IV (a) (b)
22. Most stable carbocation among the following is

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

26.

(c) (d) All are equally stable

23. What is the correct order of stability of the given cations:
Which of the following orders is correct for no-bond-
resonance energy of these radicals ?
(a) I > II > III (b) III > II > I
(c) I > III > II (d) II > I > III
27. Which among the following free radicals is most stable?

(a) (b)

CH2 CH2

(c) C H 3 (d)

(a) III > II > IV > I (b) I > II > III > IV Structural Isomerism
(c) III > I > II > IV (d) IV > II > III > I
28. Isomers of a substance must have the same
(a) Structural formula (b) Physical properties
24. (c) Chemical properties (d) Molecular formula
29. The molecular formula of a saturated compound is
C2H4Cl2. The formula permits the existence of two
(a) functional isomers (b) position isomers
(c) optical isomers (d) cis-trans isomers

Which of the following orders is correct for the stability

of these carbanions?
118 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

30. 37. Which of the following is an example of functional

isomerism?
(a) Isopentane and Neopentane
(b) Glucose and Fructose
(c) Diethyl Ether and 2–Methoxy Propane
(d) –Naphthol and –Naphthol
38. The number of isomers of C6H14 is
Among these, positional isomers are (a) 4 (b) 5
(a) I and II (b) I and III (c) 6 (d) 7
(c) II and III (d) all of these 39. The possible number of alkynes with the formula C5H8
31. The compound which is not isomeric with diethyl ether is
is (a) 2 (b) 3
(a) n-Propyl Methyl Ether (b) Butan–1–ol (c) 4 (d) 5
(c) 2–Methyl Propan–2–ol (d) Butanone 40. The number of isomers for the aromatic compound
32. A functional isomer of 1-butyne is C7H8O (containing benzene ring) are
(a) 2-Butyne (b) 1-Butene
(a) 2 (b) 3
(c) 2-Butene (d) 1, 3-Butadiene
(c) 4 (d) 5
33.
41. How many isomers are possible with trisubstituted
benzene with all the three groups same?
OH (a) 3 (b) 4
(c) 5 (d) 6
42. The number of structural isomers possible from the
molecular formula C7H16 is
(a) 5 (b) 7
(c) 9 (d) 10
43. The total number of isomers for C4H8 is
(a) 5 (b) 6
(c) 7 (d) 8
Among these functional isomers are
44. The number of aromatic isomers possible for C7H8O is
(a) I and II (b) I and III
(c) II and III (d) Both (a) and (c) (a) 2 (b) 3
34. C3H9N cannot represent (c) 4 (d) 5
(a) 1° Amines (b) 2° Amines 45. The number of structural isomers possible from the
(c) 3° Amines (d) Quaternary salt molecular formula C3H9N is
35. An isomer of ethanol is
(a) 4 (b) 6
(a) methanol (b) diethyl ether
(c) acetone (d) dimethyl ether (c) 3 (d) 5
46. How many possible carboxylic acids and esters are for
a compound with molecular formula C4H8O2?
36. (a) four (b) six
(c) five (d) eight
47. Isomers of propionic acid are
(a) HCOOC2H5 and CH3COOCH3
(b) HCOOC2H5 and C3H7COOH
(c) CH3COOCH3 and C3H7OH
II is the functional isomer of
(a) I only (b) III only (d) C3H7OH and CH3COCH3
(c) both I and III (d) none of these
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 119

48. Tautomers have Geometrical Isomerism

(a) same physical properties but different chemical
properties 53. The restricted rotation about carbon-carbon double
(b) same chemical properties but different physical bond in 2-butene is due to
properties (a) Overlap of one s- and sp2-hybridized orbitals
(c) different physical and chemical properties 2
(d) same physical and chemical properties (b) Overlap of two sp -hybridized orbitals
49. Identify the compound that exhibits tautomerism 2
(c) Overlap of one p- and one sp -hybridized orbitals
(a) 2-butene (b) lactic acid (d) Sideways overlap of two p-orbitals.
(c) 2-pentanone (d) methyl alcohol 54. The simplest alkene which is capable of exhibiting
50. Tautomerism will be exhibited by geometrical isomerism has
(a) (CH3)3CNO (b) (CH3)2NH (a) 3 carbon atoms (b) 5 carbon atoms
(c) R3CNO2 (d) RCH2NO2 (c) 6 carbon atoms (d) 4 carbon atoms
55. Cis-trans nomenclature of geometrical isomers is
51. (I)
OH possible only if
(a) at least one group present at one Carbon of the C=C
bond is same as one at the other carbon of the C=C
O
bond.
(II)
O (b) C=C bond bears three identical groups or atoms.
(c) C=C bond bears four different group or atoms.
(d) none of these
56. Which of the following can exist as cis and trans
isomers?
OH (a) CH2  CH  Cl
(III) (b) CH2  CH  CH  CH2
(c) CH3CH2 CH  CHCl
(d) CHCl  CCl2
57. Geometrical isomerism is not shown by
(a) 1, 1–Dichloropent–1–ene
Which among these can exhibit tautomerism?
(b) 1, 2–Dichloropent–1–ene
(a) I only (b) II only
(c) 1, 3–Dichloropent–2–ene
(c) III only (d) all of these
(d) 1, 4–Dichloropent–2–ene
52. 58. Which of the following compounds will exhibit cis-
trans (geometrical) isomerism?
(a) But–2–ene (b) But–2–yne
(c) Butan–2–ol (d) Butanal
59. Which one of the following compound will show
geometrical isomerism ?

(a) (b)

Stability order among these tautomers is

(a) I > II > III (b) III > II > I (c) (d)
(c) II > I > III (d) II > III > I
120 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

60. But-2-ene exhibits cis-trans-isomerism due to 70. Which of the following compounds does not exhibit
(a) rotation around C3 – C4 sigma bond geometrical isomerism?
(b) restricted rotation around bond (a) 1, 1–Dichlorobut–2–ene
(c) rotation around C1 – C2 bond (b) 1, 2–Dichlorobut–2–ene
(d) rotation around C2 – C3 double bond (c) 1, 1–Dichlorobut–1–ene
61. Which of the following compounds will exhibit (d) 2, 3–Dichlorobut–2–ene
geometrical isomerism? 71. Maleic acid and fumaric acid are
(a) 1–phenyl–2–butene (a) Position isomers (b) Geometrical isomers
(b) 3–phenyl–1–butene (c) Enantiomers (d) Functional isomers
(c) 2–phenyl–1–butene 72. Which of the following has zero dipole moment?
(d) 1,1–diphenyl–1–propene (a) cis-2-Butene (b) trans-2-Butene
62. Which of the following compounds will not show (c) 1-Butene (d) 2-Methyl-1-propene
geometrical isomerism? 73. Of the following compounds, which will have zero
(a) 3-Phenyl-2-propenoic acid dipole moment?
(b) 2-Butene (a) 1, 1-Dichloroethylene
(c) 3-Methyl-2-butenoic acid (b) cis-1, 2-Dichloroethylene
(d) 3-Methyl-2-pentenoic acid (c) trans-1, 2-Dichloroethylene
63. Which one of the following can exhibit cis-trans (d) None of these compounds
isomerism? 74.
(a) CH3 –– CHCl –– COOH (b) H  C  C  Cl
(c) ClCH  CHCl (d) ClCH2 –– CH2Cl
64. Which of the following compounds exhibits
geometrical isomerism ? How many geometrical isomers of this bromonium ion
(a) C2H5Br (b) (CH)2(COOH)2 are possible?
(a) 0 (b) 2
(c) CH3CHO (d) (CH2)2(COOH)2
(c) 3 (d) 4
65. Which of the following would exhibit cis-trans 75. –CH3 –CD3 –OH –NH2
isomerism?
I II III IV
(a) CH3CH2CH=CH2 (b) ClCH=CHCl
Among these groups, which of the following orders is
(c) ClCH=CCl2 (d) CH2=CH–COOH the correct priority order according to sequence rule?
66. Which of the following will show geometrical (a) II > I > IV > III (b) III > IV > II > I
isomerism? (c) II > III > IV > I (d) IV > III > II > I
(a) 1-Butene (b) 1, 2-Dibromobutene 76. The E-isomer among the following is:
(c) Propene (d) Isobutylene (a)
67. Which of the following compounds can exhibit Cl Br
geometrical isomerism? C C
(a) Hex–1–ene (b) 2–Methylpent–2–ene H3C C2H5
(c) 3–Methylpent–1–ene (d) Hex–2–ene (b)
Cl C2H5
68. Each of the following compounds show geometrical
C C
isomerism except H3C CHO
(a) But–2–ene–1,4–dioic acid (c)
(b) But–2–yne–1,4–dioic acid H3C CH CH2
(c) But–2–ene C C
(d) 3–Chlorohex–2–ene H CH3
69. Which of the following compounds can show (d)
geometrical isomerism? H CHCl2
(a) Vinyl chloride (b) 1, 1–Dichloroethene C C
(c) 1, 2–Dichloroethene (d) Trichloroethene H3 C CHCl2
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 121

77. Which is a pair of geometrical isomers? CH3 H

I.
C C H
Cl Br
H CH2 C
C C
C CH3
H Br
COOCH3
II.
(a) (2E, 5E) (b) (2Z, 5Z)
Cl Br
(c) (2E, 5Z) (d) (2Z, 5E)
C C 80. What is the configuration of the given molecule?

H CH3

III. (a) (1E,5Z) (b) (1E,3E)

Cl CH3 (c) (1Z,5Z) (d) (1Z,5E)
81.
C C

Br H

IV.
This compound can be named as
H Br
(a) only trans-3-methyl-2-pentene
C C (b) only 3-methyl-(2Z)-pentene
(c) trans-3-methyl-2-pentene as well as 3-methyl-(2Z)-
Cl CH3 pentene
(a) I and II (b) I and III (d) trans-3-methyl-2-pentene as well as 3-methyl-(2E)-
(c) II and IV (d) III and IV pentene
78. Which is a pair of geometrical isomers? 82. What is the IUPAC name of the following compound?
I. COOH
Cl Br
C C
H Br
(a) (Z)-2-Methylpent-2-enoic acid
II.
Cl Br (b) (E)-2-Methylpent-2-enoic acid
C C (c) (Z)-2-Methylpent-2-ene carboxylic acid
H CH3
(d) (E)-2-Methylpent-2-ene carboxylic acid
83. What is the IUPAC name of the following compound?
III.
Cl CH3 Br
C C
I
Br H
F
IV.
H Br
C C Cl
Cl CH3
(a) (1Z,3E)-4-Bromo-1-chloro-4-fluoro-1-iodobuta-1,3-
(a) I and II (b) I and III diene
(c) II and IV (d) III and IV (b) (1E,3Z)-4-Bromo-1-chloro-4-fluoro-1-iodobuta-1,3-
79. The correct configuration name of diene
122 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

(c) (1Z,3E)-1-Bromo-4-chloro-1-fluoro-4-iodobuta-1,3- (a) Polarimeter (b) Refractometer

diene (c) Spectrograph (d) Tracer technique
(d) (1E,3Z)-1-Bromo-4-chloro-1-fluoro-4-iodobuta-1,3- 91. When an optically active compound is placed in a 10
diene dm tube, is present 20 g in a 200 mL solution rotates
84. The prefixes syn and anti are used to denote the plane polarized light by 30o. Calculate the angle of
(a) Structural isomers rotation and specific angle of rotation if above solution
(b) Conformational isomers is diluted to 1 L.
(c) Geometrical isomers
(a) 16o and 36o (b) 6o and 30o
(d) Optical isomers
85. Which of the following compound will not exhibit (c) 3o and 30o (d) 6o and 36o
geometrical isomerism? 92. The compound has:
(a) CH3  CH = CH  COOH Br F

(b) Br  CH  CH  Br
(c) C6 H5  CH = NOH
H CH3
O H3C H

(d)
86. Geometrical isomers are possible for: F Br
(a) (a) plane of symmetry (b) axis of symmetry
(c) center of symmetry (d) no symmetry
93. Optical isomerism arises from the presence of
(b) (a) An asymmetric carbon atom
CH3CH2 C CH3 (b) A centre of symmetry
O (c) A line of symmetry
(c) (d) Any of the above
CH3CH2 C CH3 94. Which of the following structures is chiral?
NOH Br Cl
(d)
Br
C6H5 C C6H5

O
87. The number of geometrical isomers of the given Cl Br
Cl
compound CH3  CH  CH  CH  CH  C2 H5 is (a) (b)
Cl Br

(a) 2 (b) 3 Cl
Br
(c) 4 (d) 5
88. The number of isomers of dibromo derivative of an Cl Br
alkene (molar mass 186 g mol-1) is
(a) two (b) three
(c) four (d) six Br Cl
Br Cl
(c) (d)
Optical Isomerism 95. A stereo-center is
(a) An atom in which an interchange of any two group
89. Rotation of polarised light can be measured by will result in a new stereoisomer
(b) A chiral carbon atom
(a) Monometer (b) Galvanometer
(c) Both of these
(c) Polarimeter (d) Viscometer (d) none of these
96. Which of the following compound is not chiral
90. Optical activity is measured by
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 123

(a) DCH2CH2CH2Cl (b) CH3CHDCH2Cl (i) 1, 2–dimethyl cyclohexane

(c) CH3CHClCH2D (d) CH3CH2CHDCl (ii) 3–methyl cyclopentene
97. Which of the following compounds is not chiral? (iii) 3–methyl cyclohexene
(a) 1–Chloropentane (a) two, one, one (b) one, one, one
(b) 2–Chloropentane (c) two, none, two (d) two, none, one
(c) 1–Chloro–2–Methyl Pentane 102. Which of the following compounds has asymmetric
(d) 3–Chloro–2–Methyl Pentane centre?
98. Which of the following compounds possesses chiral (a)
carbon?
CH 2  CH  CH  CH==CH 2
(a)
|
Br
(b)
(b)

(c) Br

(c)

(d) Br

(d)
O
99. Among the following four structures I to IV.
CH3 O CH3

C2H5 CH C3H7 CH3 C CH C2H5

(I) (II) Br
H 103. Which of the following compounds has asymmetric

CH3
H C centre?
C2H5 CH C2H5 O
H Br
(III) (IV)
It is true that
(a) all four are chiral compounds
(b) only I and II are chiral compounds (a) (b) Br
(c) only III is a chiral compound
(d) only II and IV are chiral compounds
100. Which of following have asymmetric carbon atom? Br
(a) CH2Cl–CH2Br (b) CH3CHCl2 (c) (d) both (b) and (c)
(c) CH3CH2Cl (d) CH2Br–CHOH–CH3

104. Which of the following compounds has asymmetric

101. How many asymmetric carbon atoms are present in:
centre?
124 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

1 2 3 4 5 6 7
O O
O C H3  C H2  C H2  C H2  C H2  C H2  C H3
To make it a chiral compound, the attack should be on
carbon
O

OH OH (a) 1 (b) 3
(a) (b) (c) 4 (d) 7
110. The following compound can exhibit:
H3C H

C C H

Br C
Br H3C
(c) (d)
H3C COOH
105. Which of the following amines have a stereogenic
centre? (a) geometrical isomerism
(b) geometrical and optical isomerism
(c) optical isomerism
(d) tautomerism
(I) (II) 111.
Cl Cl

(III) (IV) And

(a) I, II, III (b) III, IV, V
(c) I, III, IV (d) II, III, IV Cl Cl
are_______ isomer.
106. Count the number of stereocentres in the molecule (a) Position (b) Optical
below (c) Geometrical (d) Diastereomers
112. Consider following structures and write correct
statements
R1 R1
(a) three (b) five
R4 Si R4 Ge
(c) six (d) seven
107. The number of chiral centers present in 3,4-dibromo-2- R2 R2
R3 R3
pentanol is: (a) (b)
(a) 1 (b) 2 R1 R1
(c) 3 (d) 4
108. Number of chiral carbon atom in R4 N R4 C
Br R2 R2
R3 R3
(c) (d)
CH2CH3 where R1 R2 R3 R4
(a) 2 (b) 4 (a) Only 4 shows optical isomerism
(c) 3 (d) 1 (b) 1 and 2 show optical isomerism
(c) 1, 2 and 4 show optical isomerism
(d) All show optical isomerism

109. Consider the following organic compound.

GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 125

113. Which of the following compound may exhibit optical (c) CH3CH2CH2CH2OH
activity? (d)
CH3 CH 3  CH 2  CH  CH 3
|
OH
H2N Cl
(a) (b) (CH3)2C(OH)CN 119. Which of the following is optically active?
(a)

 CH 3  Me
 
 | 
H OH
(c) (d) C3 H 7  N  C2 H5 
  H H
 |  Et
 
 H 
114. An organic compound C4H8O, is found to be optically
active. Which of the following could it be? COOH COOH
(a) CH3 –– CH2 –– CH2 –– CHO (b)
(b) CH2 –– CO –– CH2 –– CH3 Et

(c) CH 2  CH  CH (OH )  CH3

(d) (CH3)2CH –– CHO
H Me H
115. Which of the following is an optically active
compound?
(a) 1-Butanol (b) 1-Propanol
(c) 2-Chlorobutane (d) 4-Hydroxyheptane COOH COOH
116. A compound with molecular formula, C7H16 shows (c)
optical isomerism, the compound will be Et
(a) 2, 3-dimethylpentane (b) 2, 2-dimethylpentane
(c) 2-methylhexane (d) none of these
117. The optically inactive compound from the following is COOH H
CH3
(a) 2-chloropropanal
(b) 2-chloropentane
(c) 2-chlorobutane
(d) 2-chloro-2-methylbutane H COOH
118. Which of the following will not show optical activity? (d) All of these
(a) 120. Which of the following is optically active?
C2 H5
Cl Cl H
|
CH3  C  CH 2  CH  CH 2
|
H
(b) Cl H Cl
(a) (b)
H

Cl Cl
C

Cl Cl
(c) (d)
126 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

121. Which of the following shows optical isomerism? H CH3

(a) cis–1, 2–Dimethyl cyclohexane
(b) trans–1, 3–Dimethyl cyclohexane C F F H
(c) trans–1, 4–Dimethyl cyclohexane H3C
(d) All of the above CH2 CH3 CH2 CH3
122. – CHO – COOH – CN – NO2
I II III IV 126. The absolute configurations of the two centres in the
Among these groups, which of the following orders is following molecules are:
the correct priority order in accordance with sequence 1
COOH
rule?
(a) IV > III > II > I (b) IV > II > I > III 2
H Br
(c) II > I > III > IV (d) III > IV > II > I 3 CN
H
123. Rank of the following groups in order of R, S
precedence (iv is highest): OH
–CH(CH3)2 –CH2CH2Br –CH2Br –C(CH3)3
(a) 2(R), 3(S) (b) 2(R), 3(R)
1 2 3 4 (c) 2(S), 3(S) (d) 2(S), 3(R)
I II III IV 127. The configuration at C-2 and C-3 of the compound
(a) 3 2 4 1 given:
(b) 1 4 2 3 CH3
(c) 3 4 1 2
(d) 3 4 2 1 H Cl
124. The two structures (I) and (II) represented below are Cl H
CH3 CH3
C2H5
H COOH HO H (a) 2R, 3S (b) 2S, 3R
(c) 2S, 3S (d) 2R, 3R
128. Correct configuration of the following molecule is:
OH COOH
CH3
(I) (II)
H OH
(a) enantiomers
(b) diastereomers CH3 OH
(c) two representations of the same molecule
(d) functional isomers H
125. The structure of (S)-2-fluorobutane is best represented (a) 1S, 2S (b) 1S, 2R
by: (c) 1R, 2S (d) 1R, 2R
129. Determine the absolute configurations of the chiral
(a) (b) centres in the following compound.
CH3CHCH 2 CH3 F a
|
O
F C H
H3C
CH2 CH3 b

(c) (d) Br

(a) a = R; b = S (b) a = R; b = R
(c) a = S; b = S (d) a = S; b = R
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 127

130. 133.
CH3 CH3 CH3 CH3 COOH COOH
Br  1 1
H Br H Br
2 0 2

180

H Cl Cl H
Br 3 3
H H H H
I II CH3 CH3
4 4
H H 4I 4II
H
Br  CH3 Br 
Holding C–2 unit of I in hand, rotation of C–3 unit
about C2–C3 bond by 180° seems to produce II.
CH3 CH3 Which of the following statements is correct?
CH3 H
III IV (a) I and II are a pair of enantiomers
(b) I and II are a pair of diastereomers
Which of the following statements is true about these
molecules? (c) I and II are a pair of conformers
(a) I is a mesomer (d) I and II are identical
(b) I and II are identical 134. The correct statement about the compound A, B and C
(c) III and IV are a pair of enantiomers COOCH3 COOH
(d) all of these
131. The (R)- and (S)- enantiomers of an optically active H OH H OH
compound differ in H OH H OH
(a) their reactivity with achiral reagents
COOH COOCH3
(b) their optical rotation of plane polarized light (A) (B)
(c) their melting points COOH
(d) their solubility in achiral reagents
132. Which of the following pairs of compounds are H OH

enantiomers? HO H
(a)
CH3 CH3 3 COOCH
(C)
H OH HO H (a) A and B are identical
and
HO H H OH (b) A and B are diastereomers
CH3 CH3
(c) A and C are enantiomers
(b) (d) A and B are enantiomers
CH3 CH3 135. Optical rotation produced by
H OH HO H CH3
and
HO H HO H H Cl
CH3 CH3
Cl H
(c)
CH3 CH3
CH3
H OH H OH
and is 36°, then that produced by
HO H H OH
CH3
CH3 CH3
(d) H Cl
CH3 CH3
H Cl
HO H HO H
and
H OH HO H CH3
is
CH3 CH3 (a) – 36° (b) 0°
(c) + 36° (d) unpredictable
128 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

136. From the structure of the three stereoisomers of tartaric 143. Racemic mixture is formed by mixing two
acid, which statement should be true? (a) isomeric compounds
COOH COOH (b) chiral compounds
(c) meso compounds
H OH HO H
(d) enantiomers with chiral carbon
HO H H OH 144. The conversion of dextro- or laevo- form into racemic
COOH COOH mixture is called
(1) (2) (a) Resolution (b) Racemisation
COOH (c) Dehydration (d) Revolution
H OH
145. In the reaction,
CH3CHO + HCN  CH3CH(OH)CN,
H OH
a chiral centre is produced. This product would be
COOH (a) Laevorotatory (b) Meso-compound
(3)
(a) 1 is (+), 2 is (–), and 3 is optically inactive (c) Dextrorotatory (d) Racemic mixture
(b) 1 is (–), 2 is (+), and 3 is optically inactive H
(c) 1 is (+), 2 is (–), and 3 is meso
(d) 3 is optically inactive, but nothing can be said about 146. C6H5CHO + HCN  C6H5 C CN
1 and 2. OH
137. Which of the following will have a meso-isomer also? The product would be
(a) 2–Chlorobutane (b) 2, 3–Dichlorobutane (a) a racemate
(c) 2, 3–Dichloropentane (b) optically active
(d) 2–Hydroxypropanoic Acid
(c) a meso compound
138. meso-Tartaric acid is optically inactive due to the
presence of (d) a mixture of diastereomers
(a) Molecular symmetry 147. Statement–1: Molecules that are non-superimposable
(b) Molecular asymmetry on their mirror images are chiral.
(c) External compensation Statement–2: All chiral molecules have chiral centres.
(d) Two asymmetric carbon atoms (a) Statement–1 is True, Statement–2 is True;
139. Meso form of tartaric acid is: Statement–2 is a correct explanation for Statement–1.
(a) Dextorotatory
(b) Statement–1 is True, Statement–2 is True; Statement–
(b) Laevorotarory
(c) Neither Laevo nor dextro rotatory due to internal 2 is not a correct explanation for Statement–1.
compensation (c) Statement–1 is True, Statement–2 is False.
(d) A mixture of equal quantities of dextro and levo (d) Statement–1 is False, Statement–2 is True.
rotatory forms 148. Which one of the following alkene, when reacted with
140. A pair of optically active compounds which are not the HCl produces racemic mixture?
mirror images are called
CH3 CH3
(a) Mesomers (b) Anomers
(c) Epimers (d) Diastereomers
141. An important chemical method to resolve a racemic C C
mixture makes use of the formation of
(a) a meso compound (b) enantiomers CH3 CH3
(a)
(c) diastereomers (d) racemates
CH3
142. An enantiomerically pure acid is treated with racemic
mixture of an alcohol having one chiral carbon. The
ester formed will be C CH2
(a) Optically active mixture
(b) Pure enantiomer CH
3
(b)
(c) Meso compound
(d) Racemic mixture (c) CH3CH2 CH  CH2
(d) CH3CH  CH2
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 129

149. The process of separation of racemic mixture into d and 158.

l- enantiomers is called
(a) resolution (b) racemisation
(c) filtration (d) distillation How many optical isomers are possible in this
150. The process of separation of a racemic modification compound?
(a) 2 (b) 3
into d- and l-enantiomers is called
(c) 4 (d) 5
(a) Resolution (b) Dehydration 159. The number of enantiomers of the compound
(c) Revolution (d) Dehydrohalogenation CH3CHBrCHClCOOH is
151. The number of optical active isomers possible for (a) 0 (b) 1
CH3CH  C  CHCH3 is (c) 3 (d) 4
(a) 2 (b) 3 160. The number of stereoisomers for pent-3-en-2-ol is
(a) 2 (b) 3
(c) 6 (d) 8
(c) 4 (d) 5
152. Number of stereoisomers of the compound, 2-chloro-4-
methylhex-2-ene is
(a) 2 (b) 4 Conformers
(c) 8 (d) 16
153. The number of enantiomers of the compound 161. Which of the following will have least hindered rotation
CH3CHBrCHBrCOOH is
about carbon-carbon bond ?
(a) 1 (b) 2
(c) 3 (d) 4 (a) Ethane (b) Ethylene
154. Number of Stereoisomers for CHO – CHOH – CHOH (c) Acetylene (d) Hexachloroethane
– CH2OH is 162. Isomers which can be interconverted through rotation
(a) 2 (b) 4 around a single bond are
(c) 6 (d) 8 (a) conformers (b) diastereomers
155. The compound, whose stereochemical formula is (c) enantiomers (d) positional isomers
written below, exhibits x geometrical isomers and y 163. The isomers which can be converted into another form
optical isomers by rotation of the molecule around single bond are
CH3 H (a) Geometrical isomers (b) Conformers
OH (c) Enantiomers (d) Diastereomers
C C 164. The Newman projection below represents
H CH2 CH2 C CH3 H

H H CH3

The values of x and y are:

(a) 4 and 4 (b) 2 and 2
(c) 2 and 4 (d) 4 and 2 H H
156. How many geometrical and optical isomers are CH3
possible in this compound?
(a) A staggered form of 2-methyl propane
(b) A gauche form of butane
(c) An eclipsed form of 2-methyl propane
(a) 0, 2 (b) 0, 3
(c) 2, 0 (d) 2, 2 (d) A most stable conformation of 2-methyl butane
157.

How many optical isomers are possible in this

compound?
(a) 2 (b) 3
(c) 4 (d) 5
130 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

165. In the following structures, which two forms are H3C CH3 CH3
staggered conformation of ethane ?
H CH3

H H H H
H H
(c) (d)

169. The most stable conformation of ethylene glycol is

(a) anti (b) gauche
(c) fully eclipsed (d) partially eclipsed
170. The most stable conformation of 1,2-diphenylethane is
(a)
H

(a) 1 and 4 (b) 2 and 3 H5C6 H

(c) 1 and 2 (d) 1 and 3

166. Which of the following is a conformer of isobutane?
CH3 H5C6 H
H CH3
H
H H
(b)
H H5C6
H H
H CH3
H5C6 H
CH3 H
(a) (b)
CH3 H H
H H H H
H
H
H CH3 (c)
H CH3
H5C6
H H
(c) (d)
H H
167. The most stable conformation of n-butane is
(a) skew-boat (b) Eclipsed
(c) Gauche (d) Staggered-anti
H H
168. Which conformation of the alkane has the highest
potential energy? C6H5

CH3 CH3 (d)

H H
H CH3 H

H C6H5

H H H H

H CH3
(a) (b) H C6H5
H
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 131

171. Which of the following statements is true about these

two structures?
Cl
Cl
CH3 D
H Br

173. Which one of the following is the most stable structure

of cyclohexatriene?
CH3
H CH3 (a) Chair form (b) Boat form
D
Br (c) Half chair form (d) Planar form
CH3
I
II 174. Which of the following is the most stable form of
(a) I and II are a pair of enantiomers cyclohexane?
(b) I and II are a pair of diastereomers (a) Boat (b) Planar
(c) I and II are a pair of conformers (c) Twist boat (d) Chair
(d) I and II are a pair of structural isomers 175. Which of the following is the most energetic
172. The Baeyer’s angle strain is expected to be maximum conformation of cyclohexane?
in (a) Boat (b) Twisted boat
(a) cyclopentane (b) cyclodecane (c) Chair (d) Half chair
(c) cyclooctane (d) cyclohexane
132 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

EXERCISE – 2: Previous Year Questions

1. Which is the strongest acid? 8. α-hydroxypropanoic acid has ……. asymmetric carbon
(CPMT 2009) (MHT CET-2010)
(a) C6H6 (b) C3H6 (a) 4 (b) 3
(c) CH  CH (d) CH3OH (c) 2 (d) 1
9. Which of the following is optically active?
2. The number of metamers of the compound with (Manipal-2010)
molecular formula C4H10O is (a)
(AFMC 2009)
(a) 1 (b) 3
(c) 8 (d) 6
3. Which of the following compounds will exhibit
cis-trans (geometrical) isomerism?
(b)
(AIPMT 2009)
(a) 2-butene (b) Butanol
(c) 2-butyne (d) 2-butenol (c)
4. Which will not show geometrical isomerism?
(AIIMS 2009)

(a) CH3CH = NOH (b) (d)

(c) HO—N = N—OH (d) (CH3)2C = NOH
5. Which of the following is an aromatic compound?
(AFMC 2009) 10. In the following the most stable conformation of n-
butane is: (AIPMT 2010)
(a) (b)
(a) (b)

(c) (d)
6. Assertion: A compound with delocalised electrons is
more stable than that compound would be if all its
electrons were localised.
Reason: The extra stability, a compound gains as a
result of having delocalised electrons, is called
delocalisation energy. (c) (d)
(AIIMS 2009)
(a) Both Assertion and Reason are true and Reason is
the correct explanation of Assertion.
(b) Both Assertion and Reason are true but Reason is
not the correct explanation of Assertion.
(c) Assertion is true but Reason is false.
(d) Both Assertion and Reason are false.
7. The number of isomers for the compound with the
molecular formula C2BrCl.FI is
(Manipal-2010)
(a) 3 (b) 4
(c) 5 (d) 6
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 133

11. Which of the following conformers for ethylene glycol (c) RCOOH > ROH > C2H2> H2O
is most stable?
(d) RCOOH > H2O > ROH > C2H2
(AIPMT 2010)
(a) 14. Which of the following is the most stable carbocation?
(CPMT 2010)
(a) C6 H 5CH 2 (b) CH 3CH 2

(c)  CH 3 2 C H (d)  CH 3 3 C 
15. Which of the following species is paramagnetic in
nature?
(CMC 2010)
(b)
(a) Carbonium ion (b) Free radical
(c) Carbene (d) Nitrene
16. The total number of isomers of C4H7OH is
(CPMT 2010)
(a) 3 (b) 4
(c) 6 (d) 7
17. At room temperature, the eclipsed and staggered forms
of ethane cannot be isolated because.
(c) (AFMC 2010)
(a) they interconvert rapidly.
(b) both the conformers are equally stable.
(c) the energy difference between the conformers is
large.
(d) there is a large energy barrier of rotation about the s
- bond.
18. Which one of the following exhibits geometrical
isomerism?
(d)
(Kerala CEE-2011)
(a) 1,2-dibromopropene
(b) 2,3-dimethylbut-2-ene
(c) 2,3-dibromobut-2-ene
(d) 2-methylbut-2-ene
19. Among the following, the oxime of which shows
geometrical isomerism, is
(DUMET-2011)
(a) acetone
12. Given are cyclohexanol (I), acetic acid (II), 2, 4, 6- (b) diethylketone
trinitrophenol (III) and phenol (IV). In these the order (c) formaldehyde
of decreasing acidic character will be (AIPMT 2010) (d) oxime of benzaldehyde
(a) III > IV > II > I (b) III > II > IV > I 20. Among the following, the optically active compound is
(c) II > III > I > IV (d) II > III > IV > I (Kerala CEE-2011)
13. The correct order of acidity of the following (a) CH3CH2OH
compounds is. (b) CH3CH—CHCH3
(CPMT 2010) (c) CH3CHDOH
(a) RCOOH > C2H2> H2O > ROH (d) CH3CH2COCH3

(b) RCOOH > ROH > H2O > C2H2

134 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

21. The maximum number of possible optical isomers in 1- 29. Given

bromo-2-methyl cyclobutane is
(Guj CET-2011)
(a) 4 (b) 2
(c) 8 (d) 16
22. Geometrical isomerism is shown by
(UP CPMT-2012) I and II are
(a) C  C  (b)  C  C  (NEET Kar. 2013)
(c) C  C  (d) None of these (a) A pair of optical isomers
23. Which of the following acids does not exhibit option (b) Identical
isomerism? (c) A pair of conformers
(CBSE AF-2012) (d) A pair of geometrical isomers
(a) Maleic acid (b) α-amino acid 30. Geometrical isomerism is not possible in
(c) Lactic acid (d) Tartaric acid (Kerala CEE-2014)
24. In which of the following compound, one of the (a) 2, 4-hexadiene
structure isomers is also capable of showing (b) benzophenone oxime
enantiomorphism. (c) but 2-ene
(AIPMT 2012) (d) 1, 2-dichloroethene
(a) C3H8 (b) C3H6Br2 31. The organic compound with two asymmetric carbon
(c) C3H12 (d) C6H14 atoms is
25. The amino acid which is not optically active is (Kerala CEE-2014)
(UPCPMT-2012) (a) 3,4-dimethylheptane
(a) lactic acid (b) serine (b) 3-methyl-1-pentene
(c) alanine (d) glycine (c) 2-chlorophexane
26. Which of the following reagents will be able to (d) 5-ethyl-2,3-dimethylheptane
distinguish between 1-butyne and 2-butyne? 32. The correct statement regarding a carbonyl compound
(AIPMT 2012) with a hydrogen atom on its alpha-carbon-carbon, is
(a) NaNH2 (b) HCl (AIPMT-2015)
(c) O2 (d) Br2 (a) a carbonyl compound with a hydrogen atom on its
alpha carbon rapidly equilibrates with its corresponding
27. The order of stability of the following tautomeric
enol and this process is known as aldehyde-ketone
compound is (NEET-2013)
equilibration
(b) a carbonyl compound with a hydrogen atom on its
alpha carbon rapidly equilibrates with its corresponding
enol and this process is known as carbonylation
(c) a carbonyl compound with a hydrogen atom on its
alpha-carbon rapidly equilibrates with its keto-enol
tautomerism
(d) a carbonyl compound with a hydrogen atom on its
corresponding enol
(a) I > II > III (b) III > II > I
(c) II > I > III (d) II > III > I
28. The cis and trans isomers are represented by
(UP CPMT-2013)
(a) pent-1-ene (b) but-2-ene
(c) prop-1-ene (d) but-1-ene
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 135

33. Given

37. Which of the following biphenyls is optically active?

(NEET 2016)
Which of the given compounds can exhibit
tautomerism?
(NEET 2015)
(a) I and III
(b) II and III (a)
(c) I, II and III
(d) I and II
34. Two possible stereo structures of CH3CH(OH)COOH,
which are optically active, are called
(AIPMT 2015) (b)
(a) enantiomers (b) mesomers
(c) diastereomers (d) atropisomers
35. Which among the given molecules can exhibit
tautomerism?
(NEET-2016) (c)

(a) III only (b) Both I and III (d)

(c) Both I and II (d) Both II and III 38. The correct statement regarding the comparison of
36. Which of the following biphenyls is optically active? staggered and eclipsed conformation of ethane, is
(NEET 2016) (NEET 2016)
(a) (a) The staggered conformation of ethane is less stable
than eclipsed conformation because staggered
conformation has torsional strain
(b) The eclipsed conformation of ethane is more stable
than staggered conformation, because eclipsed
conformation has no torsional strain
(b)
(c) The eclipsed conformation of ethane is more stable
than staggered conformation even though the eclipsed
conformation has torsional strain
(d) The staggered conformation of ethane is more stable
than eclipsed conformation, because staggered
(c) conformation has no torsional strain.

(d)
136 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

39. The pair of electron in the given carbanion, CH 3 C  C  43. The correct statement regarding electrophile is
, is present in which of the following orbitals? (NEET 2017)
(NEET 2016) (a) electrophile is negatively charged species and can
from a bond by accepting a pair of electrons from
(a) sp2 (b) sp
another electrophile.
(c) 2p (d) sp3 (b) electrophiles are generally neutral species and can
40. Assertion (A) The configuration of given compound is form a bond by accepting a pair of electrons from a
Z. nucleophile.
(c) electrophile can be either neutral or positively
charged species and can form a bond by accepting a
pair of electrons from a nucleophile.
(d) electrophile is a negatively charged species and can
Reason (R) Z-configuration shows the presence of form a bond by accepting a pair of electrons from a
bulkier groups as the opposite side of double bond. nucleophile.
(AIIMS-2017) 44. Which of the following compound can exhibit
(a) Both A and R are correct but R is the correct tautomerism?
explanation of A (JIPMER-2018)
(b) Both A and R are correct but R is not the correct (a)
explanation of A
(c) A is correct but R is incorrect
(d) Both A and R are incorrect
41. Assertion (A) The following molecule is non-
superimposable on its mirror image, hence it is chiral. (b)

(c)
Reason (R) All chiral molecules have chiral centres.
(AIIMS 2017)
(a) Both A and R are correct and R is the correct
explanation of A (d)
(b) Both A and R are correct but R is not the correct
explanation of A
(c) A is correct but R is incorrect
(d) Both A and R are incorrect 45. The pair of structures given below represents
42. Which one is the correct order of acidity? (JIPMER-2018)
(NEET 2017)
(a)
CH  CH  CH3  C  CH  CH2  CH2  CH3  CH3
(a) Chain isomers (b) Position isomers
(b) (c) Tautomers (d) Metamers
CH  CH  CH2  CH2  CH3  C  CH  CH3  CH3
(c)
CH3  CH3  CH2  CH2  CH3  C  CH  CH  CH
(d)
CH2  CH2  CH3  CH  CH2  CH3  C  CH  CH  CH
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 137

46. Which one is the most acidic compound? 48. The most stable carbocation, among the following is
(NEET 2018) (NEET 2019)

(a) (CH 3 )3 C  CH  CH 3

(b) CH3  CH 2  CH  CH2  CH 3

(a) (b (c) CH3  CH  CH2  CH2  CH 3

(d) CH3  CH2  CH2
49. Tertiary butyl carbocation is more stable than a
secondary butyl carbocation because of which of the
following?
(c) (d) (NEET 2020)
47. The number of sigma (  ) and pi (  ) bonds in (a) –I effect of –CH3 groups
pent-2-en-4-yne is (b) +R effect of –CH3 groups
(NEET 2019) (c) –R effect of –CH3 groups
(a) 13 bonds and no  bond (d) Hyperconjugation
(b) 10 bonds and 3  bonds 50. Dihedral angle of least stable conformer of ethane is:
(c) 8 bonds and 5  bonds (NEET 2021)
(d) 11 bonds and 2  bonds (a) 0 (b) 120
(c) 180 (d) 60
138 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

EXERCISE – 3: Achiever’s Section

Single choice questions
4. Which of the following, has the most acidic hydrogen ?
1. Among the following, the least stable resonance (a) 3-hexanone
structure is (b) 2, 4-hexanedione
(a) (c) 2, 5-hexanedione
(d) 2, 3-hexanedione
5. Which one of the following compounds cannot show
tautomerism?

(b)

(a)

(c)

(b)

(d)

(c)

(d)
2. Which of the following resonating structures of 6. The enolic form of acetone contains
1-methoxy-1, 3-butadiene is least stable? (a) 9 sigma bonds, 1 pi bond and 2 lone pairs
 (b) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(a) C H 2  CH  CH  CH  O  CH 3 (c) 10 sigma bonds, 1 pi bond and 1 lone pair
 (d) 9 sigma bonds, 2 pi bonds and 1 lone pair
(b) CH 2  CH  C H  CH  O  CH 3
7. The number of isomers for the compound with

(c) C H 2  C H  CH  CH  O  CH 3 molecular formula C2BrClFI is
 (a) 3
(d) CH 2  CH  C H  C H  O  CH 3 (b) 4
3. In the following carbocation ; H/CH3 that is most (c) 5
likely to migrate to the positively charged carbon is (d) 6

(a) CH3 at C-4

(b) H at C-4
(c) CH3 at C-2
(d) H at C-2
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 139

8. Which of the Fischer projection formula correspond to 12. The absolute configuration of
the following stereo structure? HO2C CO2H

HO OH
H H

(a) S, S (b) R, R
(c) R, S (d) S, R
CHO CHO
13. Which of the following molecule have (2R, 3-Z)
configuration?
H OH HO H
(a) (b)
H3C H H 3C H
H OH HO H C C C C
H C CH3 H C CH3
HO H H OH
CH2OH CH2OH
(a) (b) (c) (d)
CHO CHO
H H H H
H OH C C C C
HO H
H3C C CH3 H3C C CH3

HO H HO H H OH
H OH
14. Which of the following molecules is expected to rotate
the plane of polarised light?
CH2OH CH2OH (a)
(c) (d)
9. Following types of compounds (as I, II) CHO
(I) CH3CH  CHCH3
HO H
(II) CH3 CH OH

CH2CH3 CH2OH

are studied in terms of isomerism in (b)

(a) chain isomerism (b) position isomerism
(c) conformers (d) stereoisomerism
10. Which one of the following acids does not exhibit SH
optical isomerism? (c)
(a) Lactic acid (b) Tartaric acid
H2N NH2
(c) Maleic acid (d) -amino acids
11. The absolute configuration of the following compound H H
is
CH3 Ph Ph
2
H Cl (d)
3
Cl H COOH

CH3
(a) 2S, 3R (b) 2S, 3S H2N H
(c) 2R, 3S (d) 2R, 3R
H
140 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

15. The number of stereoisomers possible for a 21. Increasing order of stability among the three main
compound of the molecular formula conformations (Eclipse, Anti, Gauche) of 2–
CH3  CH  CH  CH  OH   Me is fluoroethanol is
(a) Eclipse, Gauche, Anti (b) Gauche, Eclipse, Anti
(a) 3 (b) 2 (c) Eclipse, Anti, Gauche (d) Anti, Gauche, Eclipse
(c) 4 (d) 6
16. How many optically active stereoisomers are possible
Assertion-Reason Type Questions
for butane–2, 3–diol?
(a) 1 (b) 2
While answering these questions, you are required to
(c) 3 (d) 4
choose any one of the following four response
17. Number of stereoisomers of the given compound
(A) If both assertion and reason are correct and reason
OH
is the correct explanation of assertion.
(B) If both assertion and reason are true but reason is
CH3 CH CH CH CH3
is not the correct explanation of assertion.
(a) 2 (b) 4 (C) If assertion is true but reason is false.
(c) 3 (d) 6 (D) If reason is true but assertion is false.
18. The total number of stereoisomers possible for (A) is: 22. Assertion: 1,2-dichloro cyclopropane show
geometrical isomerism
Me
Reason: It has restricted rotation of atoms about a
Me covalent bond
(a) A (b) B
Me (c) C (d) D
Me 23. Assertion: Both cis-1,3-Dimethyl cyclobutane and
(a) 8 (b) 7 trans-1,3-dimethyl cyclobutane are optically inactive.
(c) 6 (d) 4 Reason: cis-1,3-dimethyl cyclobutane has the plane of
symmetry, whereas trans form has the centre of
19. If the stereochemistry about the double bond in (A) is
symmetry.
cis, the total number of stereoisomers for (A) is: (a) A (b) B
Me (c) C (d) D
Me 24. Assertion 1,3-dichloro propadiene rotate plane
polarized light.
Me Reason The molecules of 1,3-dichloro propadiene are
Me
dissymmetric
(a) 2 (b) 3 (a) A (b) B
(c) 4 (d) 5 (c) C (d) D
20. 25. Assertion: Enantiomers differ in their chemical action
CH3 with another enantiomer.
H H
Reason: A pair of enantiomers have different
orientation of collision with another enantiomer
3
2 forming different transition state.
H H (a) A (b) B
(c) C (d) D
CH3 26. Assertion Enantiomers have same enthalpy of
formation.
C2 is rotated clockwise 120° about C2––C3 bond. The
Reason Pair of enantiomers have same connectivity
resulting conformer is
and similar bonding environment.
(a) partially eclipsed (b) eclipsed
(a) A (b) B
(c) gauche (d) staggered
(c) C (d) D
GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM 141

27. Assertion: Meso–tartaric acid is optically active.

Reason: Optically active molecule is a molecule that
cannot be superimposed on its mirror image
(a) A (b) B
(c) C (d) D
28. Assertion: Meso form of 2, 3-butanediol has
permanent optical inactivity.
Reason: It has internal enantiomerism
(a) A (b) B
(c) C (d) D
29. Assertion: Conformers are impractical to separate.
Reason: Conformers have negligibly small difference
in their potential energy.
(a) A (b) B
(c) C (d) D
30. Assertion: Cyclobutane is less stable than
cyclopentane.
Reason: Presence of ‘bent bond’ causes loss of orbital
overlap.
(a) A (b) B
(c) C (d) D
142 GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM

Notes:

Find Answer Key and Detailed Solutions at the end of this book

General Organic Chemistry (Revision)

& ISOMERISM
ANSWER KEY 241
CHAPTER - 3 : GENERAL ORGANIC CHEMISTRY (REVISION) & ISOMERISM
Exercise - 1: Basic Objective Questions

DIRECTIONS FOR USE-

Scan the QR code and check detailed solutions.

1. (d) 2. (b) 3. (b) 4. (c) 101. (a) 102. (c) 103. (d) 104. (b)
5. (d) 6. (b) 7. (d) 8. (d) 105. (a) 106. (c) 107. (c) 108. (a)
9. (c) 10. (c) 11. (c) 12. (c) 109. (b) 110. (c) 111. (b) 112. (d)
13. (c) 14. (c) 15. (b) 16. (a) 113. (d) 114. (c) 115. (c) 116. (a)
17. (d) 18. (c) 19. (d) 20. (c) 117. (d) 118. (c) 119. (c) 120. (b)
21. (a) 22. (a) 23. (a) 24. (d) 121. (b) 122. (b) 123. (c) 124. (c)
25. (d) 26. (c) 27. (a) 28. (d) 125. (c) 126. (a) 127. (c) 128. (a)
29. (b) 30. (d) 31. (d) 32. (d) 129. (c) 130. (d) 131. (b) 132. (a)
33. (d) 34. (d) 35. (d) 36. (b) 133. (b) 134. (d) 135. (b) 136. (d)
37. (b) 38. (b) 39. (b) 40. (d) 137. (b) 138. (a) 139. (c) 140. (d)
41. (a) 42. (c) 43. (b) 44. (d) 141. (c) 142. (a) 143. (d) 144. (b)
45. (a) 46. (b) 47. (a) 48. (c) 145. (d) 146. (a) 147. (c) 148. (c)
49. (c) 50. (d) 51. (d) 52. (c) 149. (a) 150. (a) 151. (a) 152. (b)
53. (d) 54. (d) 55. (a) 56. (c) 153. (d) 154. (b) 155. (b) 156. (a)
57. (a) 58. (a) 59. (b) 60. (b) 157. (c) 158. (a) 159. (d) 160. (c)
61. (a) 62. (c) 63. (c) 64. (b) 161. (a) 162. (a) 163. (b) 164. (a)
65. (b) 66. (b) 67. (d) 68. (b) 165. (c) 166. (c) 167. (d) 168. (c)
69. (c) 70. (c) 71. (b) 72. (b) 169. (b) 170. (c) 171. (d) 172. (b)
73. (c) 74. (b) 75. (b) 76. (b) 173. (d) 174. (d) 175. (d)
77. (c) 78. (d) 79. (d) 80. (b)
81. (c) 82. (a) 83. (d) 84. (c)
85. (d) 86. (c) 87. (c) 88. (b)
89. (c) 90. (a) 91. (b) 92. (c)
93. (a) 94. (d) 95. (c) 96. (a)
97. (a) 98. (d) 99. (b) 100. (d)
242 ANSWER KEY

Exercise - 2: Previous Year Questions Exercise - 3: Achiever’s section

DIRECTIONS FOR USE- DIRECTIONS FOR USE-

Scan the QR code and check detailed solutions. Scan the QR code and check detailed solutions.

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

5. (a) 6. (b) 7. (d) 8. (d) 5. (a) 6. (a) 7. (d) 8. (b)
9. (a) 10. (b) 11. (d) 12. (b) 9. (d) 10. (c) 11. (b) 12. (b)
13. (d) 14. (d) 15. (b) 16. (d) 13. (c) 14. (a) 15. (c) 16. (b)
17. (a) 18. (c) 19. (d) 20. (c) 17. (b) 18. (a) 19. (b) 20. (c)
21. (a) 22. (b) 23. (a) 24. (b) 21. (c) 22. (b) 23. (a) 24. (a)
25. (d) 26. (a) 27. (b) 28. (b)
25. (a) 26. (a) 27. (d) 28. (a)
29. (c) 30. (b) 31. (a) 32. (c)
29. (a) 30. (a)
33. (c) 34. (a) 35. (a) 36. (a)
37. (b) 38. (d) 39. (b) 40. (c)
41. (c) 42. (a) 43. (c) 44. (b)
45. (b) 46. (b) 47. (b) 48. (c)
49. (d) 50. (a)