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Isomerism
Isomerism
Isomerism
isomerism 2.19
Level 2
C CH3 CH3
H2C = C C – CH2
H H
(a) E (b) Z
(c) Does not show geometrical isomerism (d) None
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
NH–C Cl–
Cl
O
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
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
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isomerism 2.21
Me
Me
(c) and
O
C – O – Ph
O – C – Ph
O
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
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
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
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°
Me
(c) Me (d)
Me
Me
HOOC Cl
(a) (i)-R (ii)-S (b) (i)-S (ii)-R (c) (i)-S (ii)-S (d) (i)-R (ii)-S
Cl
(a) Different drawings of the same conformation of the same compound
(b) Stereoisomers
(c) Constitutional isomers
(d) Different conformations of the same compound
(a) (b)
(c) (d)
21. Calculate the total number of geometrical isomers for the following compound
• • •
Me
(a) Cl • (b)
H H
(c) (d)
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
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isomerism 2.25
28. Choose the total number of constitutional isomers with the formula C4H10O.
(a) 9 (b) 7 (c) 5 (d) 3
Br
30. In which structure Gauche form has less potential energy than antiform
(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
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
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
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2.28 chapter two
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
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
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
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
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2.30 chapter two
C2H5
Br
OH
CH2–OH
(c) and Positional isomers
CH3
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
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
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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
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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)
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
Cl Cl
(c) (d)
O O
(a) (b)
O O
Cl Cl
(c) (d)
O O
(a) (b)
O O
Cl Cl
(c) (d)
Br Cl Cl Br
(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)
(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
CH3 CH3
HO
H3C
C D
(c) (d)
T C
Br OH
Br D CH3
D
(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
(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
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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
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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
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.
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
Separation of enantiomers
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
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.
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
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
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
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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
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.
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
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
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:
Cl
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
(b) Fe (q) C6
Ferrocene (staggered)
(c) (r) S6
COOH H
H COOH
(t) C5
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
O
Cl
Br
(b) Cl (q) Optically active compound
Br
R
P
(c) R (r) Meso compound
R
P
R
F
C
CH3
C Cl
I CH3
Br
F Cl
(b) Cl F (q) Optically active compound
Br
Cl Cl
Br Br
F F
Cl Cl
Br
Cl
Cl
C
Br
C
(d) (s) Axis of symmetry present
C
Br
Cl
(t) Asymmetric compound
N N
(a) (p) Optically inactive
compound
H3C OH HO CH3
CH3 H3C
O O
Et Et
N N
N O O
(d) N (s) Axis of symmetry
MeO present
OMe
N N
(t) Dissymmetric
compound
CH HC
(b) C (q) Optically active compound
CH HC
HNC
H NH
3
CH3
C
(c) (r) Meso compound
Cl CH3
Cl
Cl
H3C
CH3
(d) (s) Axis of symmetry present
Cl
Br
(t) Asymmetric compound
Cl
(a) Cl (p) Optically inactive compound
Cl
Br
Cl
I
Cl
I
F
(t) Asymmetric compound
F F
Cl Br
F F
Cl Br
F F
Cl Cl
(t) Asymmetric compound
Br
Cl
(d) (s) Axis of symmetry present
Cl
Br (t) Asymmetric compound
N N
(b) (q) Optically active compound
Cl Cl
(a) (p) Optically inactive compound
Br
Br
(b) (q) Optically active compound
Br
Br
Br Br
Br
Cl
(d) (s) Axis of symmetry present
Cl
Br (t) Asymmetric compound
O
(b) (q) Optically active molecules with chiral
O centres.
O
(c) (r) Compounds have even number of chiral
centres
NH
O
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
H H
(a) (p) Molecule has chiral centre
Me N O
(b) Me (q) Molecule is asymmetric
Ph COOH
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.
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
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
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isomerism 2.59
COOH NO2 Cl Cl
(e) (f)
COOH Br Br O2N
O
(g) (h) (i)
O
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)
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
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
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
Workbook Exercises
Exercise 1
1. 2. 3.
4. 5. 6.
7. 8. 9.
OH
40. 41. 42.
N
NH
43. 44. 45.
OH
OH OH N
N N
46. 47. 48.
D D
55. T T 56. HN NH 57. HN NH
N OH
58. 59. 60.
O
64. 65. 66.
O
OH
N HN N
67. 68. 69.
N NH N
HO
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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
Cl Cl Cl Br F F
Br Br Cl Br F F
Cl
96. C C C C CH 97. C C C C CH
F F
Exercise 2
1. 2. 3. 4.
5. 6. 7. 8.
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
O
45. NH 46. 47. 48. O
O HN O O
HO HO
O
53. 54. 55. 56.
OH
Cl
Br Br 70. D D
68. Cl Cl 69.
O
71. 72. O 73.
O O
107. 108. O 109.
O O
O
O O
110. 111. 112.
122. 123.
124. 125.
126. 127.
128. 129.
130. 131.
Cl Br Br
132. Cl 133.
Cl Cl
HO Br
134.
F
Exercise 3
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.
Cl
Cl
25. 26.
27. 28.
29. 30.
31. 32.
33. C 34.
35. 36.
37. 38.
39. 40.
41. 42.
43. 44.
45. 46.
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
Exercise 4
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
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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
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2.76 chapter two
Exercise 5
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
16. 17.
N N N N
18. 19.
N
N
20. N N 21.
N
NO2 Cl Cl
22. 23.
Br Br O2N
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isomerism 2.77
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
Cl Br
F Cl
Br
Br Br
78. Br
Cl
Cl
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
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.