JEE (Adv.

)-Chemistry Stereoisomerism

Marked Questions may have for Revision Questions.

PART - I : SUBJECTIVE QUESTIONS
Section (A) : Geometrical isomerism
A-1. Write the essential conditions for geometrical isomerism.

A-2. Define restricted rotation and give one example each of acyclic and cyclic compound, which can show
geometrical isomersm.

B]
A-3. Which of the following can show geometrical isomerism?
H OH
(i) (ii) (iii) (iv) C=N

T
CH3

[II
Cl
H H
C C
(v) (vi) CH3 (vii) CH3 (viii) CH2= CH – CH = CH – Ph
Cl
NA Cl

A-4. Which of the following carbonyl compound will give two products after reaction with NH2OH ?

O
RA

(i) (ii) CH3–CHO (iii)

CHO
(iv) DCHO (v) (vi)
IN

Section (B) : CIP Rules (E/Z Naming) & Physical Properties of G.I
CH

B-1. Assign E or Z to the following compounds-

CN I
CN Br OMe
SA

D H
(a) (b) (c) (d)
CH2–NH2 Me Cl
Br
F

B-2. Give the IUPAC names with stereochemical descriptors (E/Z) for each of the following compounds.

(a) (b)

B-3. (a) BrHC = CHBr exists as two diastereomers draw them and compare their dipole moment.
(b) trans-Butenedioic acid has higher melting point than cis-butenedioic acid. Why ?
(c) Draw the cis and trans structures of hex-2-ene. Which isomer will have higher b.p. and why ?

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JEE (Adv.)-Chemistry Stereoisomerism
Section (C) : Chiral carbon and Projection Formula

CH3
C-1. O
CH3
CH3
CH3 O
Progesterone
Several step
Human female Hormone
HO
Diosgenin

What is number of chiral centres present in Diosgenen is ?

C-2. The total number of chiral centres present in the artificial sweetener Aspartam are

T B]
[II
C-3. How many number of chiral centres present in the following compounds ?
NA
CH2OH
O
H OH
H
OH H
RA

HO

(i) H OH D(+)-Sucrose (ii)

O
HO H2C O

H H HO
IN

CH2OH
OH H
CH

Section (D) : R/S & D/L naming

D-1. Find R/S configuration of following compounds.
SA

(I) (II) (III) (IV)

D-2. Find D/L configuration in the following molecules.

(I) (II) (III)

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JEE (Adv.)-Chemistry Stereoisomerism
D-3. The R/S configuration of following compounds are :

(a) (b)

(c) (d)

Section (E) : Element of Symmetries (POS, COS, AOS)

B]
E-1. Find plane of symmetry and centre of symmetry (if possible) in the following compounds.

(I) (II) (III)

T
[II
(IV) (V)
NA
E-2. Find plane of symmerty, centre of symmerty and axis of symmetry (if possible) in the following molecules.

Cl Cl
RA

(i) (ii) (iii)

H H

Br H
IN

(iv) (v) (vi)

H Br
CH

Section (F) : Definition and Properties of Enantiomers, Diastereomers, Mesocompounds

F-1. Find relationship between the given pairs.
SA

(I) and (II) and

(III) and (IV) and

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JEE (Adv.)-Chemistry Stereoisomerism

H CH3 CH3 H H CH3

C C C

F-2.

Cl Br Br Cl Cl Br
I II III
(i) Total number of fractions on fractional distillation of I, II and III. (ii) Optical active compounds.
(iii) Relation between I and II. (iv) Relation between I and III.
F-3. State the relationship among the following pairs of compounds.

B]
(i) and (ii) and

T
[II
(iii) and NA
Section (G) : Specific rotation, optical purity, enantiomeric excess and Optical Resolution
G-1. What does D/L & d/ represent?

G-2. Write the definition of specific rotation.

RA

G-3. Write the formula for optical purity & enantiomeric excess.

G-4. The total number of fractions (n) obtained in the following reaction is ..........
CH3 CH3 CH3 CH3
IN

H
R–COOH + H OH + H OH H OCOR + H OCOR
(±)
D C2H5 D C2H5
CH
SA

Section (H) : Optical active compounds without chiral carbon and amine inversion
H-1. Which of the following are chiral compound?
O CH3
O || Cl |+ H
(i) S (ii) P (iii) N
Me Et C2H5O Br Et D

Me CH3
| |+
H
(iv) Si (v) C (vi)
Et Ph C2H5 H

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JEE (Adv.)-Chemistry Stereoisomerism
H-2. Which of the following are chiral molecules?
H Br
(i) Ph–CH=C=C=CH–Cl (ii) CH3–CH=C=C=C=CH–CH3 (iii)
Br H

Br
(iv) (v) (vi)

Cl Cl

Section (I) : Calculation of number of Stereoisomers

I-1. How many n-octene can show geometrical isomerism ?

B]
I-2. For the given compound CH3 – CH – CH CH – CH3 .
|
OH

T
(I) Total number of stereoisomers.

[II
(II) Number of optically active stereoisomers.
(III)Total number of fractions on fractional distillation of all stereoisomers.

I-3. The total number of possible isomers with molecular formula C6H12 that contain a cyclobutane ring.
NA
I-4. Trimethylene cyclopropane (A) is another isomer of benzene. It can be prepared from (X) as follows.

(i) LiAlH4
(ii) HBr NaOEt ,EtOH
RA

Draw the structures of the stereoisomers of X.

I-5. The number of isomers for the compound with molecular formula C2BrClFI are :
IN

Section (J) : Conformational Isomerism

J-1. Draw the most stable conformation of meso-CH3CHD – CHDCH3
CH

J-2. Write the most polar and most stable conformer of 1-nitropropane.
J-3. Write the newman projection formula of the following compounds
(I) Cl–CH2–CH2–CH3 in its most polar form.
(II) HO–CH2–CH2–OH in its most stable form.
SA

(III) HOOC–CH2–CH2–COOH in its least stable staggered form.

J-4. Draw the most stable newman projection formula along C1–C2 bonds of following compounds.

(i) (ii) (iii)

(iv) (v) (vi)

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JEE (Adv.)-Chemistry Stereoisomerism
Section (K) : Cyclohexane

K-1. Determine whether each of the following compounds is a cis isomer or a trans isomer.

H Br H H
H
Cl H CH3 Br
Br H
(a) (b) (c) (d)
CH3 CH3
Br H
H

H H
Cl CH3

B]
(e) CH3
CH3 (f)
H H

T
K-2. Which of the following combination of axial & equitorial bonds show Cis or Trans orientation in Dimethyl

[II
cyclohexane?
(i) 1e, 2e (ii) 1e, 3e (iii) 1e, 4e (iv) 1e, 2a (v) 1e, 3a (vi) 1e, 4a (vii) 1a, 3a
K-3. Which one is more stable and why ?
NA
RA
IN

PART-II : OBJECTIVE QUESTIONS

CH

Section (A) : Geometrical isomerism

A-1. In the given haloalkene M, atoms X, Y and Z represents hydrogen or bromine or chlorine.
To show cis-trans isomerism, what could be the identities of atoms X, Y and Z?
SA

Z H
H C=C
C=C H X Y Z
CH3
Y CH – CH 2 – C = C 1 Cl H Cl
CH 3 2 H Br Cl
CH3 X
3 H Br H
(M)

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

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JEE (Adv.)-Chemistry Stereoisomerism
A-2. Which of the following will not show geometrical isomerism ?

(1) CH3 – N N – CH = CH2 (2)

(3) CH3 – CH = N – OH (4) Cl–CH=C=CH–Cl
A-3. Which of the following compounds will not show geometrical isomerism ?
(A) Azomethane (B) 1-Bromo-2-chloroethene
(C) 1-Phenylpropene (D) 2-Methyl-2-butene
A-4. Which of the following compound can not show geometrical isomerism ?

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

T
A-5. Which among the following will show geometrical isomerism ?

[II
H3C CH3 H OH
(A) (B) H CH3 (C) C6H5–CH=N–OH (D) All of these
H D
NA
Section (B) : CIP Rules (E/Z Naming) & Physical Properties of G.I
B-1. Which one of the following is Z isomer ?
CH 3 C=C Br CH3 C=C Cl CH3 C=C Cl CH3 C=C H
(A) (B) (C) (D) H
H H Br CH3
RA

Cl Br H
B-2. The correct order/s for the given pair of isomers is

(A) > (Melting point)

IN

(B) < (Dipole moment)

CH

(C) > (Boiling point)

(D) > (Water solubility)

SA

Section (C) : Chiral carbon and Projection Formula

C-1. Number of chiral centres in [X] & [Y] is a & b respectively. The value of (a–b) is :
O

Me
OH
[X] = O [Y] =
Cl Br
Cl

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

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I H

:
N OH
C-2. has ‘x’ chiral centre then find the value of x :
D
Cl
S
O

(A) 7 (B) 8 (C) 6 (D) 5

C-3. Chiral molecules are :
(A) Superimposable on their mirror image (B) Not superimposable on their mirror image

B]
(C) unstable molecules (D) capable of showing geometrical isomerism

Section (D) : R/S & D/L Naming.

T
D-1. Configuration of I & II respectively will be :

[II
CH2OH
COOH
H OH
H3C H OH
NH2
H CHO
NA
(A) D, D (B) L , D (C) D , L (D) L, L

D-2. The S-ibuprofen is responsible for its pain relveing property. Which one of the structure shown is S-ibuprofen :
RA

O
Me C–OH Me H
(A) Me C (B) Me C
CH3 C–OH
H CH3 O
IN

CH3 O
Me Me C–OH
CH

(C) Me C H (D) Me C H
C–OH
O CH3

D-3. Which of the following combinations amongst the four Fischer projections represents the same absolute
SA

configurations ?

CH3 OH CH=CH2 H
H OH H CH3 CH3 OH HO CH=CH2
CH=CH2 CH=CH2 H CH3
(I) (II) (III) (IV)

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

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D-4.. The correct IUPAC name of D-Glucose is :

(D-Glucose)

(1) (2D, 3D, 4L, 5D)-2, 3, 4, 5, 6-pentahydroxyhexanal

(2) D-2, 3, 4, 5, 6-pentahydroxyhexanal

B]
(3) 6-oxo-(2D, 3L, 4D, 5D)-2, 3, 4, 5, 6-pentahydroxohexane
(4) (2D, 3L, 4D, 5D)-2, 3, 4, 5, 6-pentahydroxyhexanal

D-5. Which of the following is the structure of (S)-Pentan-2-ol is ?

T
[II
(A) (B) (C) (D)
NA
D-6. Which Fisher projection represents the given wedge dash structure?
RA
IN

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

CH

D-7. Which of the following have same configuration?

F Br H
SA

C H C Cl C Br
Cl Br H F F Cl
I II III
(A) I & II (B) II & III (C) I & III (D) All

D-8. Which has D configuration?

CH3 OH CH3 COOH

H COOH H OH H2N H
(A) HO H (B) (C) (D)
COOH CH3 CHO CH3

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Section (E) : Element of Symmetries (POS, COS, AOS)
E-1. Compound have :
CH3
H H
H
Cl
H Cl
CH3
(A) Plane of symmetry (B) Centre of symmetry
(C) Axis of symmetry (D) None
E-2. Which of the following compound posses plane of symmetry ?

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

T
[II
E-3. Which of the following are chiral ?

(1) (2)
NA (3) (4)

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

Section (F) : Definition and Properties of Enantiomers, Diastereomers, Meso compounds
RA

F-1. Identify meso compound.

CO2H
Cl CH3
CO2H Me Me CO2H
(A) HO2C (B) (C) HO2C (D)
IN

Cl Cl
CO2H
CH

CH3 C2H5
H SH HS H
F-2. H OH & H OH are :
SA

C2H5 CH3
(A) Diastereomers (B) Enantiomers (C) Identical (D) Constitutional isomers

F-3. The two compounds (I) and (II) are related as :

COOH COOH
HO H OH H
H
H OH OH
and
COOH COOH
(I) (II)
(A) Enantiomers (B) Anomers (C) Diastereomers (D) Identical
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F-4. Stereoisomers which are not mirror image of each other, are called :
(A) Enantiomers (B) Tautomers (C) Meso (D) Diastereomers
F-5. Which one among the following is not diastereomeric pair?

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

B]
F-6. What is the relationship between (I) & (II) ?

T
[II
(A) Enantiomer (B) Diastereomers (C) Constitutional isomer (D) Identical molecules
NA
Section (G) : Specific rotation, optical purity, enantiomeric excess and Optical Resolution
G-1. When an optically active compound is placed in a 10 dm tube is present 20 gm in a 200 ml solution rotates
the PPL by 30°. Calculate the angle of rotation & specific angle of rotation if above solution is diluted to 1
RA

Litre?
(A) 16° & 36° (B) 6° & 30° (C) 3° & 30° (D) 6° & 36°

G-2. (+) tartaric acid has a specific rotation of + 12 unit when measured in 12 cm polarimeter tube and 2g/ml
concentration at given temperature and light. When it is diluted to half the concentration, length of tube and
other parameters being same, then the specific rotation will be :
IN

(A) + 6 unit (B) + 12 unit (C) – 6 unit (D) + 24 unit

CH

G-3. If optical rotation produced by is + 36º then that produced by is

SA

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

G-4. The enantiomeric excess and observed rotation of a mixture containing 6 gm of (+)-2-butanol and 4 (gm) of
(–)-2-butanol are respectively (If the specific rotation of enantiomerically pure (+)-2-butanol is + 13.5 unit).
(A) 80%, + 2.7 unit (B) 20%, – 27 unit (C) 20%, + 2.7 unit (D) 80%, – 27unit

G-5. The racemic mixture of Alanine can be resolved by using -

(1) (+)-2-Butanol (2) ( )-2-Chlorobutanoic acid

(3) (±) -2-Butanol (4) (d mix)-2-Chlorobutanoic acid
(A) 1 & 2 only (B) 1 & 3 only (C) 2 & 4 only (D) 3 & 4 only
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G-6. The major product (ester) of the following reaction is

H2SO 4
+

(A) A single stereoisomer (optically active) (B) A mixture of diastereomers (both optically active)
(C) A racemic mixture (optically inactive) (D) A mixture of four stereoisomers (two racemic mixtures)
G-7. Which of the following pair of isomers can not 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 (D) (+)-lactic acid and (–)-lactic acid

B]
|
NH2

Section (H) : Optical active compounds without chiral carbon and Amine inversion

T
H-1*. Which of the following compounds will show optical activity ?

[II
(A) (B) (C) (D)
NA
H-2. Which of the following amine is optically active ?

(A) CH3NH2 (B) CH3NHC2H5 (C) CH3CH2CH2– (D) sec-Butylamine

RA

H-3. The following molecules are :

H CH3
C=C=C
H3C H
IN

(A) Enantiomers (B) Diastereomers (C) Identical (D) Conformers

H-4.* Which of the following is/are chiral ?

CH

(A) (B)
SA

H Br
(C) (D)
Br H

Section (I) : Calculation of no. of Stereoisomers

I-1. 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

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I-2. How many geometrical isomers are possible for the given compound?
Ph – CH = CH – CH = CH – COOH
(A) 2 (B) 4 (C) 6 (D) 8
I-3. How many geometrical isomers are possible for the given compound?

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

I-4. Total number of optically active stereoisomers of tartaric acid is

(A) 2 (B) 4 (C) 3 (D) 0
I-5. Number of fractions on fractional distillation of mixture of :

T B]
[II
(A) 2 (B) 3 (C) 4 (D) 1

I-6.
NA
Total number of optically active stereoisomers of CH3 – CH – CH – CH – CH3
| | |
Cl Cl Cl
(A) 2 (B) 4 (C) 6 (D) 8
RA

I-7. The total number of ketones (including stereo isomers) with the molecular formula C6H12O is :
(A) 4 (B) 5 (C) 6 (D) 7
I-8. Total number of optical active stereoisomers of the following compound is :
CH3 – CH = CH – CHCl – CH = C = CH – CH = CH – CH3
(A) 8 (B) 6 (C) 16 (D) 10
IN
CH

I-9. is a Fischer projection of one of______stereoisomers?

SA

(A) 2 (B) 4 (C) 8 (D) 12

Section (J) : Conformational Isomerism

J-1. What is the value of p & q of following conformer of 2,3-dimethyl butane ?
p
H3C CH 3

H CH3
q
(A) p = H, q = H (B) p = CH3, q = CH3 (C) p = CH3, q = H (D) p = H, q = CH3

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J-2. Which of the following pairs of compound is/are identical ?

Br H CH3 I
F H F Br I H
(A) Br (B) Cl H CH3
H Cl I
F Br I
F H H
H

Cl CH3 H Br
H H H Cl
H CH3 Cl H
(C) Cl (D)
H CH3 H Br H
I I
Cl CH3 Cl H

B]
J-3. Which of the following is associated with Torsional strain ?
(A) Repulsion between bond pair of electrons (B) Size of the groups present at adjacent atoms

T
(C) Bond angle strain (D) Attraction of opposite charges

[II
J-4. The Baeyer’s angle strain is expected to be maximum in
(A) Cyclodecane (B) Cyclopentane (C) Cyclobutane (D) Cyclopropane

J-5. Newman projection of Butane is given,C-2 is rotated by 120º along C2-C3 bond in anticlockwise direction the
NA
conformation formed is :
RA

(A) anti (B) fully eclipsed (C) gauche (D) partially eclipsed
IN

J-6. Which of the following is an achiral molecule?

CH

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

SA

J-7. The true statement about the following corformation is :

(A) It has maximum angle strain.

(B) It does not have eclipsing strain (tortional strain).
(C) It does not have any intramolecular hydrogen bonding.
(D) It has maximum vander waal strain.

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J-8. and are

(A) Enantiomers (B) diastereomers (C) Identical compounds (D) Conformers

Section (K) : Cyclohexane

K-1. When cyclohexane is poured on water, it floats, because :

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

T
K-2. The least stable conformation of cyclohexane is

[II
(A) Boat (B) Chair (C) Twist boat (D) Half chair

K-3. Flagpole interaction is present in :

(A) Boat form of cyclohexane (B) Chair form of cyclohexane
NA
(C) Anti form of n-butane (D) Fully eclipsed form of n-butane

K-4. Chair form of cyclohexane is more stable than boat form because :
(A) In chair form carbons are in staggered form and in boat form carbons are in eclipsed form
(B) In chair form carbons are in eclipsed form and in boat form all the carbons are in staggered form
RA

(C) Bond angle in chair form is 111° and bond angle in boat form is 109.5°
(D) Bond angle in chair form is 109.5° and in boat form 111°

K-5. The most stable form of trans-1,4-dimethylcyclohexane is represented as :

IN

CH3

(A) (B)
CH3
CH

H3C
(C) (D)
CH3
SA

K-6. The most stable form of cis cyclohexane-1,3-diol is represented as :

(A) (B)

OH OH
(C) (D)

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PART - III : MATCH THE COLUMN

1. Column I Column II

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

CH3 Cl
H Cl H CH3
(B) & (Q) Identical

B]
Et Et

CH3

T
H
H OH H3C Et
(C) & (R) Enantiomers

[II
Et OH
H5C2 H5C2
(D) & (S) Diastereomers
NA
HO H H OH

2. Match the column–I

RA

Column-I Column-II
(Compounds) (Total number of stereoisomers)

Cl
(1) (P) 8
IN

(2) Cl Cl (Q) 4
CH

(3) Cl Cl (R) 3
SA

Cl

(4) Cl Cl (S) 2

Cl

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3. Match the compounds of Column-I with their relationship with mentioned in Column-II.

Column-I Column-II

B]
P. 1. Geometrical isomer

T
[II
NA
Q. 2. Conformation
RA

R. 3. Positional isomer
IN
CH
SA

S. 4. Identical

Code :
P Q R S
(A) 4 2 3 1
(B) 1 2 4 3
(C) 2 1 3 4
(D) 1 2 3 4

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4. Match the column-I with column-II
Column-I Column-II

(A) (P) Chiral Molecule

B]
(B) (Q) Achiral Molecule

T
[II
NA
(C) (R) Plane or centre of symmetry present
RA

(D) (S) Axis of symmetry present (except C1).

IN
CH
SA

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Marked Questions may have for Revision Questions.

PART - I : OBJECTIVE QUESTIONS

1. Which two of the following compounds are diastereomers?

OH OH OH
OH
OH OH OH
HO
(I)
O (II) (III) (IV)
OH

B]
O O O
OH OH OH

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

[II
2. Which two of the following compounds represents a pair of enantiomers?

HO OH HO OH
(I) (II) (III) (IV)
NA
HO OH OH OH

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

3. Which one of the following is resolvable ?

H H
H CH3 H H
H
COOH (D) HOOC
IN

(A) (B) (C) COOH

CH3 H CH3 CH3
COOH H
CH

4. The correct statement for the given compound is

O
S
SA

S
O
(A) It can shows geometrical isomerism (B) It can show optical isomerism
(C) It contain chiral centre (D) None of these

5. Compound CH2Cl2 contain :

(A) Plane of symmetry (B) Centre of symmetry

(C) Axis of symmetry (D) Both (A) & (C)

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6. Which of the following can not show geometrical isomerism :

H Cl

Cl
(A) (B) (C) (D)
Cl Cl Cl
7. Which one of the following compounds will show enantiomerism ?

(A) CH3 –– –– CH3 (B) H3C – – CH3

O O

B]
(C) –– OH (D) –– OH
O
––

HO – H2C

T
8. Number of conformational isomers of ethane

[II
(A) 7 (B) 3 (C) 4 (D) Infinite

9. Which of the following statement regarding the projections shown below is true ?
NA
RA

(A) ‘a’ and ‘b’ both represent the same configuration

(B) Both ‘a’ and ‘b’ are optically active
(C) ‘b’ alone is optically active
IN

(D) ‘a’ alone is optically active

10. The given compound (X) has :

CH
SA

(A) chirality (B) superimposability on its mirror image isomer

(C) plane of symmetry (D) C2 axis of symmetry
11. The compounds X and Y in below reaction can be

Ph – NH . NH2 + (X) + (Y)

(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
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12. No. of Geometrical isomers for following compound is :

(A) 8 (B) 16 (C) 32 (D) 10

13. How many stereoisomers are possible for ?

B]
(A) 128 (B) 64 (C) 32 (D) 16
14. How many spatial orientations are possible in the following compound ?

T
[II
(A) 2 (B) 8 (C) 6 (D) 4
NA
15. A pure sample of 2-chlorobutane shows rotation of PPL by 30° in standard conditions. When above sample
is made impure by mixing its opposite form, so that the composition of the mixture becomes 87.5% d-form
and 12.5% -form, then what will be the observed rotation for mixture.
(A) – 22.5° (B) + 22.5° (C) + 7.5° (D) – 7.5°
RA

PART - II : NUMERICAL TYPE QUESTIONS

1. Identify total number of stereoisomers for the following compound ?

IN

CH2-CH-CH-CH=CH-CH3
OH Cl
CH

2. Identify number of molecules which usually can show geometrical isomerism (at room temperature)?

Cl Cl
Br
SA

(1) (2) N (3) (4)

Cl
H D HO
Cl
H H

(5) (6) (7) (8)

Me Me

(9) (10)

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3. How many cyclic and acyclic structural isomers of C5H10 can show geometrical isomerism?

4. In given compounds how many can show geometrical isomerism-

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

5. How many of the following carbonyl compound will give two products after reaction with NH2OH :

B]
(i) (ii) (iii)

T
[II
NA
(iv) (v) (vi)
RA

(vii) (viii) (ix) CH3–CH=O

6. Total number of stereoisomers of truxillic acid are :

IN

7. In given compounds how many have Z configuration along double bond ?

CH

(i) (ii)
SA

(iii) (iv)

8. Sum of C2 & C3 axis of symmetry is

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9. How many of the following are cis dichlorocyclohexane.

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

(v) (vi) (vii) (viii)

10. How many of the following are (configurational) enantionmers of (A) ?

T B]
[II
(A) =
NA
(p) (q) (r) (s) (t)
RA

11. Pure cholesterol has a specific rotation of –32. A sample of cholesterol prepared in the lab has a specific
rotation of –8. The enatiomeric excess of the sample of chloresterol is x%. x is :
IN
CH

12. Pure (R) Mandelic acid has specific rotation of –150. If a smaple contains 60% of the R

and 40% of its enantiomer, then [ ] of this solution is.

SA

13. Total number of geometrical isomers in the given compound are

C = CH – DC = CD – HC = C

14. Total number of geometrical isomers in the given compound are :

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15. Total number of stereoisomers of compound CH3 CH CH CH CH CH CH3 are :
|
Cl

16. Total number of optically active stereoisomers of CH3 – CH – CH CH – CH – CH3 are :

| |
Cl Cl

17. For the compound A–CH2–CH27–A draw the newmann projection formula of all the stable conformational
isomers if obs
= 2D and Xanti = 0.75 then find gauche
.(If A = NO2)

B]
18. Observ e the com pound 'M'

T
M=

[II
If in this compound
X = Total number of asymmetric C* atoms
Y = Number of similar asymmetric C* atoms
NA
Z = Number of optically active stereoisomers
W = Number of opticaly inactive isomers
R = Number of geometrical orientations in space
Report your answer as :
X+Y+Z+W+R
RA

PART - III : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. Re-orient the molecule at the left to match the partially drawn perspective at the right. Find the two missing
substituents at their correct positions.
IN

(A) CH2CH 3 M
CH

F F
H3C N
H H
(B) H
SA

CH3 X Y
F
CH2CH3 H CH2CH 3

(A) M CH 3CH 2 (B) X CH 3 (C) M CH 3 (D) X F

N CH 3– Y F N CH 3CH 2 Y CH 3

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2. Among the following the non- resolvable compound is/are :

CH3
H3C CH3
Br
(A) C C (B) (C) P (D) N
Cl Br H CH3 H Br
H3C H 3C
Br H

3. Which of the following statements for a meso compound is/are correct ?

(A) The meso compound has either a plane or centre of symmetry
(B) The meso compound is optically inactive due to internal compensation.
(C) The meso compound is achiral
(D) The meso compound is formed when equal amounts of two enantiomers are mixed

B]
4. Compounds which can show both optical as well as geometrical isomerism?

T
(A) (B)

[II
(C) (D)
NA
5. What should be the minimum conditions to show geometrical isomerism ?
(A) Restricted rotation about double bond or ring.
(B) Groups which are responsible to show geometrical isomerism differ in their relative distance.
(C) Free rotation about single bond.
RA

(D) Two different groups at both restricted atoms.

6. Which of the following compounds can show optical isomerism as well as geometrical isomerism?
IN

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

CH

7. Which of the following statement(s) is/are true about the following compounds ?
SA

(A) ( ) and ( ) are identical (B) ( ) and ( ) are geometrical diastereomers

(C) ( ) and ( ) are structural isomers. (D) ( ) and ( ) are structural isomers.
8. Which of the following compounds has cis configuration at each double bond ?
(A) (B)

(C) (D)

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9. Which of the following is true for maleic acid and fumaric acid.
(A) Configurational isomers (B) Stereo isomers
(C) Z and E isomers (D) Constitutional isomers
10. Which of the following is correct statement :
(A) Geometrical isomers are not mirror image isomer.
(B) A compound having double bond (restricted bond) always show geometrical isomerism.
(C) Acyclic compoubd having single bond does not show geometrical isomerism.
(D) Cyclodecene can show cis & trans form.
11. Which of the following statement(s) is/are correct for given compound :

T B]
(A) It is a optically active compound
(B) It can show geometrical isomerism

[II
(C) It posses centre of symmetry but not plane of symmetry.
(D) It is a meso compound
12. Find out correct statement/s.
(A) All chiral centers are stereogenic centers.
NA
(B) All stereogenic centers are not chiral center.
(C) A compound may be chiral without chiral center.
(D) A compound will be chiral only if it has at least one chiral center.

H
RA

OH
C2H5 C
13. H C
OH
CH3
IN

Fischer projection formula of this compound can be represented as :

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

CH

14. Which of the following compounds will have C2 axis of symmetry ?

SA

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

15. is :

(A) optically active molecule. (B) having plane of symmetry.

(C) having axis of symmetry. (D) having centre of symmetry

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PART - IV : COMPREHENSION
Comprehension # 1
Tartaric acid [HO2CCH(OH)CH(OH)CO2H] was an important compound in history of stereochemistry. Two
naturally occuring forms of tartaric acid are optically inactive. One optically inactive form (P) has a melting
point of 210-212°C and can be separated into two optically acitve forms, whereas other optically inactive form
(Q) cannot be resolved further.
1. Optically inactive form Q is

(A) (B) (C) (D) none of these

B]
2. A optically inactive form P is :

T
(A) Optically inactive due to internal compensation.
(B) Optically inactive due to presence of plane of symmetry.

[II
(C) Optically inactive due to external compensation.
(D) Optically inactive due to intramoleuclar hydrogen bonding.
Comprehension # 2
Carbohydrates are biomolecules which perform diverse functions such as being energy sources and
NA
constituents of nucleic acids.In solution, monosaccharides, the simplest unit of carohydrates, exist in cyclic
hemicacetal form. The cyclic form is in equilibrium with small quantity of the open chain form.
In a trivial system of naming (D,L-system), the carbohydrates having the configuration at the asymmetric
carbon of highest number same as that of R-glyceraldehyde (shown below) are called D forms while those
having opposite configuration at the same carbon are called L-forms.
RA

R-Glyceraldehyde

Monosacharides X , Y and Z have the following structures.

IN

H OH H OH
CH
SA

3 Classify sugars X ,Y and Z into D or L forms.

(A) L,L,L (B)L,L,D (C) L,D,D (D) D,L,L

4 Which is the correct term to describe the relationship of each of the following structure with X ?

(a) (b) (c)

(A) Compound a is diastereomers of X. (B) Compound b is identical of X.

(C) Compound c is enantiomers of X. (D) All are correct.
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PART - I : JEE (ADVANCED) / IIT-JEE PROBLEMS (PREVIOUS YEARS)

* Marked Questions may have more than one correct option.

1. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The
ester formed will be : [IIT-JEE-2003(S), 2/84]
(A) Optically active mixture (B) Pure enantiomer (C) Meso compound (D) Racemic mixture

2. A racemic mixture of (±) 2-phenylpropanoic acid on esterification with (+) 2-butanol gives two ester. Mention

B]
the stereochemistry of the two esters produced. [IIT-JEE-2003(M), 2/60]

3. Give the Newman projection formula of the least stable staggered form of n–butane. Which of the following

T
reasons is the causes of its unstability ? [IIT-JEE-2004, 2/60]
(i) Vander–Waal’s strain (ii) Torsional strain (iii) Combination of both.

[II
4. It is given that for conformational isomers, the net dipole moment is [IIT-JEE-2005, 6/60]
obs
= x
i i
where obs
= observed dipole moment of the compound
NA
i
= dipole moment of the stable conformational isomers
xi = mole fraction of stable conformers
for the compound Z–CH2–CH2–Z draw the Newman projection formula of all the stable conformational isomers,
if obs = 1D, and xanti = 0.82, and find gauche. Now draw the Newman projection formula of the most stable
conformation of meso Y–CHD–CHD–Y.
RA

(a) If Y is CH3 (rotation about C2 – C3 bond)

(b) If Y is OH (rotation about C1 – C2 bond)

5. Statement-1 : Molecules that are not superimposable on their mirror images are chiral. because
Statement-2 : All chiral molecules have chiral centres. [IIT-JEE-2007, 3/162]
IN

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

(D) Statement-1 is False, Statement-2 is True.

6.* The correct statement(s) about the compound given below is (are). [IIT-JEE-2008, 4/163]

(A) The compound is optically active

SA

(B) The compound possesses centre of symmetry

(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry

7.* The correct statement(s) about the compound H3C(HO)HC–CH=CH–CH(OH)CH3 (X) is(are) :
[IIT-JEE-2009, 4/160]
(A) The total number of stereoisomers possible for X is 6.
(B) The total number of diastereomers possible for X is 3.
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4.
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2.

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8. The total number of cyclic structural as well as stereo isomers possible for a compound with the molecular
formula C5H10 is [IIT-JEE-2009, 4/160]
9.* In the Newman projection for 2,2-Dimethylbutane

X and Y can respectively be : [IIT-JEE-2010, 3/163]

(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3

B]
10.* Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is (are) [JEE-2011, 4/180]

T
(A) (B) H–C

[II
(C) H2C=C=O (D) H2C=C=CH2 [IIT-JEE-2011, 4/180]

11. The number of optically active products obtained from the complete ozonolysis of the given compound is:
NA
[IIT-JEE- 2012, 3/136]
RA

(A) 0 (B) 1 (C) 2 (D) 4

IN

12.* Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ?
CH
SA

(A) M and N are non-mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical
13. The total number(s) of stable conformers with non-zero dipole moment for the following compound is
(are) : [JEE(Advanced)-2014, 3/120]

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14. The total number of stereoisomers that can exist for M is [JEE(Advanced)-2015, 4/168]

15. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are)

[JEE(Advanced)-2015, 4/168]

B]
H Br H Br
(A) (B) H2C CH3
H3C CH3

T
H

[II
Br
H2C Br H
(C) CH3 (D) H 2C CH3
CH3
NA
16. In the following monobromination reaction, the number of possible chiral products is : [JEE-2016]

CH2CH2CH3
RA

Br2(1.0 mole)
H Br
300ºC
CH3
(1.0 mole)
(enatiomerically pure)
IN

17. For the given compound X, the total number of optically active stereoisomers is____.
CH

[IIT-JEE 2018]

HO HO
This type of bond indicates that the configuration at the
SA

specific carbon and the geometry of the double bond is fixed

This type of bond indicates that the configuration at the
specific carbon and the geometry of the double bond is NOT fixed
HO HO
X

18. Total number of isomers considering both structural and stereoisomers, of cyclic ethers with the molecular
formular C4H8O is- [IIT-JEE 2019]

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PART - II : JEE (MAIN) / AIEEE PROBLEMS (PREVIOUS YEARS)

1. Which type of isomerism is shown by 2,3-dichlorobutane ? [AIEEE 2005]
(1) diastereomerism (2) optical-isomerism
(3) geometric-isomerism (4) structural-isomerism
2. Increasing order of stability among the three main conformations (i.e. eclipse, anti, gauche) of 2-fluoroethanol
is [AIEEE- 2006]
(1) eclipse, gauche, anti (2) gauche, eclipse, anti
(3) eclipse, anti, gauche (4) anti, gauche, esclipse
3. Which of the following molecules is expected to rotate the plane of polarized light? [AIEEE 2007, 3/120]

B]
(1) (2)

T
[II
(3) (4)
NA
4. Which one of the following conformations of cyclohexane is chiral? [AIEEE-2007, 3/120]
(1) Chair (2) Boat (3) Twist boat (4) Rigid
RA

CO2H
HO2C

5. The absolute configuration of H is [AIEEE 2008, 3/105]

H HO
OH
IN

(1) R, R (2) R, S (3) S, R (4) S, S

6. The alkene that exhibits geometrical isomerism is : [AIEEE 2009, 4/144]
(1) 2-methyl propene (2) 2-butene (3) 2-methyl-2-butene (4) propene
CH

7. The number of stereoisomers possible for a compound of the molecular formula CH3–CH=CH–CH(OH)–Me is:
[AIEEE 2009, 4/144]
(1) 2 (2) 4 (3) 6 (4) 3
SA

8. Out of the following, the alkene that exhibits optical isomerism is. [AIEEE 2010, 4/144]
(1) 3-methyl-2pentene (2) 4-methyl-1-pentene (3) 3-methyl-1-pentene (4) 2-methyl-2-pentene

9. The IUPAC name of the following compounds is : [JEE-MAIN-2012]

CH3 H
C=C
H C C–CH2CH3
(1) (Z)–5 hepten–3–yne (2) (Z)–2-hepten–4–yne
(3) (E)–5-hepten–3–yne (4) (E)–2-hepten–4–yne

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10. Arrange in the correct order of stability (decreasing order) for the following molecules:
[JEE-MAIN 2013]
H
Me
H Me H
H
H
H H Me
Me
Me Me
Me (III) (IV)
Me (I) H
(II)
(1) (I) > (II) > (III) > (IV) (2) (IV) > (III) > (II) (I)
(3) (III) > (I) (II) > (IV) (4) (I) > (ll) (III) > (IV)

B]
11. Which of the following compound will exhibit geometrical isomerism ? [JEE(Main) 2015, 4/144]
(1) 1-Phenyl-2-butene (2) 3-Phenyl-1-butene
(3) 2-Phenyl-1-butene (4) 1,1-Diphenyl-1-propane

T
12. The absolute configuration of : [JEE-MAIN-2016]

[II
CO2H
H OH
H
NA
Cl
CH3

(1) (2R, 3R) (2) (2R, 3S) (3) (2S, 3R) (4) (2S, 3S)
RA

13. In the follwoing structure, the double bonds are marked as I, II, III and IV. [JEE-MAIN-2017]

I
IN

I IV
CH

Geometrical isomerism is not possible at site (s) :

(1) I (2) III (3) I & III (4) I & IV
SA

14. In the following skew confromation of ethane. H'–C–C–H" dihedral angle is : [JEE-MAIN-2019]

H H’
H
29°
H

H’’ H

(1) 58° (2) 149° (3) 120° (4) 151°

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ANSWER KEY
EXERCISE # 1
PART - I
A-1. Essential conditions for geometrical isomerism are
(1) Restricted rotation must present.
(2) Two different groups must be present on both restricted atoms.
(3) Groups responsible to show geometrical isomerism must be nearly in the same plane.
A-2. The bond across which atoms cannot rotate without breaking the bonds is called restricted rotation. e.g.

B]
C=C, C=N, ring etc. (a b, d e)

A-3. (iii) , (iv) , (vi) , (vii) and (viii) A-4. 5 (i, ii, iv, v ,vi )

T
B-1. ZEEZ

[II
B-2. (a) Z-5-Methylhex-2-en-1-al NA (b) Z-6-Methyl-7-phenyloct-6-en-1-yne

B-3. (a)

dipole moment : II > I

(b) Because of good packing of trans isomers.
RA

(c)
bZ bZ
Cis has higher boiling point due to more polarity.
IN

C-1. (11)
CH3
O
CH

*
* *
H3C
* O
H3C * *
* *
SA

* *
Sol. *
HO
C-2. 2

C-3. (i) =9 (ii) =8

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JEE (Adv.)-Chemistry Stereoisomerism
D-1. (I) R (II) S (III) R (IV) (R, R)
D-2. (I) D (II) (2D, 3D)

(III) Equivalent fischer projection is and configuration L.

D-3. RRRR
E-1. (i) Plane of symmetry and Centre of symmetry. (ii) Plane of symmetry.
(iii) Plane of symmetry. (iv) Plane of symmetry.
(v) Plane of symmetry and Centre of symmetry.

B]
E-2. (i) POS present and COS, AOS absent. (ii) POS present and COS, AOS absent.
(iii) POS, AOS present and COS absent. (iv) POS, COS present and AOS present.
(v) POS present and COS,AOS absent. (vi) POS, COS and AOS absent.

T
[II
Compound has a single chiral centre which has no plane of symmetry..
NA
F-1. (I) Enantiomers (II) Position isomers (III) Identical (IV) Diastereomers
F-2. (i) Mixture of I, II and III give two fraction on fractional distillation.
(ii) I, II and III all are optically active
(iii) I and II are pair of enantiomers
RA

(iv) I and III are optical diastereomer.

F-3. (i) Enantiomers (ii) Diastereomers (iii) Enantiomers
G-1. D/L represent nomenclature (relative configuration) while d/ represents direction of optical rotation.
IN

G-2. Specific rotation is the number of degrees of rotation observed if a 1-dm (10-cm) tube is used and the
compound has concentration 1 gm/mL. Thus specific rotation [ ] is

[ ]t =
CH

C
[ ] = Specific rotation ; = observed angle of rotation (degree)
= Pathlength (dm) ; C = concentration (gm/ml)
= wavelength (nm) ; t = temperature (25°C)
SA

observed optical rotation

G-3. % Optical purity = optical rotation of pure enantiomer × 100

|d | excess of one enantiomer over other

% Enantiomeric excess = × 100 = entire mixture
× 100
d

G-4. 4

CH3 CH3 CH3 CH3

R–COOH + H OH + H OH H OCOR + H OCOR

(±)
D C2H5 D C2H5
2-Diastereomer 2-Diastereomer
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JEE (Adv.)-Chemistry Stereoisomerism
H-1. i, ii, iii, iv H-2. ii, iii, v, vi
I-1. 3 (oct-2-ene, oct-3-ene, oct-4-ene)

* *
I-2. (I) CH3 – C H – CH CH – CH3
|
OH
Number of stereocentres = 2 so total number of stereoisomers = 22 = 4
(II) All 4 isomers are optically active.
(III) Total enantiomeric pairs are 2, hence number of fraction will be 2.

Me H
I-3. total=7 H Me

T B]
I-4. (R = COOEt)

[II
NA
I-5. 6 J-1.

CH3
RA

H H
J-2. antiform, it is most polar & stable.
H H
NO2
IN
CH

J-3. (I) (II) (III)

SA

J-4. (i) (II) (iii)

(iv) (v) (vi)

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JEE (Adv.)-Chemistry Stereoisomerism

K-1. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans

K-2. (i) trans (ii) cis (iii) trans (iv) cis

(v) trans (vi) cis (vii) cis
K-3. First is more stable because of less steric repulsion between groups at equitorial position.
PART-II
A-1. (C) A-2. (4) A-3. (D) A-4. (A) A-5. (D) B-1. (A) B-2. (D)
C-1. (B) C-2. (A) C-3. (B) D-1. (C) D-2. (D) D-3. (C) D-4.. (4)
D-5. (C) D-6. (A) D-7. (A) D-8. (A) E-1. (B) E-2. (C) E-3. (A)
F-1. (A) F-2. (D) F-3. (4) F-4. (D) F-5. (A) F-6. (B) G-1. (B)

B]
G-2. (B) -G3. (B) G-4. (C) G-5. (A) G-6. (A) G-7. (D) H-1*. (C)
H-2. (D) H-3. (A) H-4.* (CD) I-1. (A) I-2. (B) I-3. (B) I-4. (A)
I-5. (C) I-6. (A) I-7. (D) I-8. (C) I-9. (C) J-1. (C) J-2. (C)

T
J-3. (A) J-4. (D) J-5. (C) J-6. (A) J-7. (B) J-8. (C) K-1. (D)

[II
K-2. (D) K-3. (A) K-4. (A) K-5. (C) K-6. (D)

PART - III
1. (A) P ; (B) R ; (C) Q ; (D) R
NA
2. (1-S, 2–R, 3–Q, 4–Q)
3. (A)
4. (A - P,S) ; (B - P,S) ; (C - P,S) ; (D - Q,R)

EXERCISE # 2
RA

PART - I

1. (D) 2. (C) 3. (B) 4. (A) 5. (D) 6. (C) 7. (C)

IN

8. (B) 9. (C) 10. (A) 11. (D) 12. (B) 13. (A) 14. (B)
15. (B)
PART - II
CH

1. 8 2. 7 3. 2 4. 4 (i, ii, iii, iv) 5. 7. (i, ii, iii, iv, v, viii, ix)

6. 5 (All geometrical) 7. 1 (ii) 8. 3+1=4 9. 5 (iii, v, vi, vii, viii)

SA

10. 4 (q,r,s,t) 11. 25 12. 30 13. 4 14. 6 15. 4

16. 4 17. 8 18. 12

PART - III
1. (A) 2. (AD) 3. (ABC) 4. (CD) 5. (ABD) 6. (ABCD)
7. (BCD) 8. (BD) 9. (ABC) 10. (ACD) 11. (BC) 12. (ABC)
13. (ABCD) 14. (ABCD) 15. (AC)
PART - IV
1. (B) 2. (C) 3 (A) 4 (A)

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JEE (Adv.)-Chemistry Stereoisomerism

EXERCISE # 3
PART - I
1. (A)

2. + +

]
TB
3. Least stable staggered form of n–butane is

[II
This is due to Vander Waal’s strain developed between the methyl groups at C2 & C3. There is no torsional
NA
strain in the staggered form at torsional angle 60º .

4.
RA

obs
= 1D xgauche = 0.18
1
= x 1= × 0.18 + 0.82 × 0 = = 5.55 D
obs i i gauche gauche 0 .18
IN
CH

meso
SA

(a) If Y is CH3 , the Newman projection is

(b) If Y is OH, the Newman projection is

5. (C) 6.* (AD) 7.* (AD) 8. 7 9.* (BD) 10.* (BC) 11. (A)
12.* (ABC) 13. 3 14. 2 15. (D) 16. 5 17. 7 18. 10.00
PART - II
1. (2) 2. (3) 3. (3) 4. (3) 5. (1) 6. (2) 7. (2)
8. (3) 9. (4) 10. (3) 11. (1) 12. (3) 13. (1) 14. (2)
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