Optical Isomerism Test (JEE ADVANCED Pattern)

SECTION-I : (Maximum Marks: 36)

• This section contains TWELVE questions.
• In this section, question has FOUR options (A), (B), (C) and (D). ONLY ONE of these four options
are correct.
• For each question, darken the bubble corresponding to the correct option in the ORS.
• For each question, marks will be awarded in one of the following categories :
Full Marks : +3 If only the bubble corresponding to the correct option is darkened.
Zero Marks : 0 If none of the bubbles is darkened.
Negative Marks : –1 In all other cases

1. The number of stereoisomers of D–glucose (a six carbon sugar) is :-

(A) 8
(B) 12
(C) 16
(D) 24

CH3

2. In the structure H OH , the configurations at the chiral centres are-

H Br
CH3
(A) 2R, 3R
(B) 2S, 3R
(C) 2R, 3S
(D) 2S, 3S

3. Which of the following combinations amongst the four Fischer projections represents the same
absolute configurations ?
CH3 OH CH=CH2 H

H OH H CH3 CH3 OH HO CH=CH2

CH=CH CH=CH H CH
(I) (II) (III) (IV)
(A) (II) and (III)
(B) (I) and (IV)
(C) (II) and (IV)
(D) (III) and (IV)

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Optical Isomerism JEE Advanced Paper

4. Which of the following will not show optical isomerism as well as geometrical isomerism :
CH3 CH3
(A) C
H
CH3
(B) C
CH3
CH3 CH3
C
(C) H
CH3
CH3 CH3
C
(D) CH3
CH3

5. The IUPAC name of the given compound is :-

CHO
Br Cl
(A) (2R, 4Z)-4-bromo-2-chloro-2-methyl-4-hexenal
(B) (2R, 4E)-4-bromo-2-chloro-2-methyl-4-hexenal
(C) (2Z, 5R)-3-bromo-5-chloro-5-formyl-2-hexene
(D) (2S, 4E)-4-bromo-2-chloro-2-methyl-4-hexenal

CH3 C2H5
H SH HS H
6. OH
H OH H
C2H5 CH3
(A) Diastereomers
(B) Enantiomers
(C) Identical
(D) Constitutional isomers

7. Which of the following will not show optical isomerism :

Me Me
(A) (B) Me
H
CH3
(C) Me (D)
Cl H

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Optical Isomerism JEE Advanced Paper

8. The total number of optically active isomer for 𝐂𝐇𝟐 𝐎𝐇(𝐂𝐇𝐎𝐇)𝟑 CHO is -
(A) 2
(B) 4
(C) 8
(D) 12

9. Which of the following have same configuration

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

10. Which of the following pairs of compounds are enantiomers :

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

11. Total number of stereoisomer of following compounds are respectively :-

OH
OH

OH
(A) 4, 6
(B) 8, 6
(C) 6, 6
(D) 8, 8

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Optical Isomerism JEE Advanced Paper

12. False statement about the following compound is

CN
CH2–CH2–OH

(A) It is having two chiral center

(B) Its configuration at double bond is E
(C) It shows optical isomerism
(D) It shows geometrical isomerism

SECTION–II : (Maximum Marks : 16)

• This section contains FOUR questions.
• In this section question has FOUR options for correct answer(s). ONE OR MORE THAN ONE
of these four option(s) is (are) correct option(s).
• For each question, choose the correct option(s) to answer the question.
• Answer to each question will be evaluated according to the following marking scheme:
Full Marks : +4 If only (all) the correct option(s) is (are) chosen.
Partial Marks : +3 If all the four options are correct but ONLY three options are chosen.
Partial Marks : +2 If three or more options are correct but ONLY two options are chosen,
both of which are correct options.
Partial Marks : +1 If two or more options are correct but ONLY one option is chosen
and it is a correct option.
Zero Marks : 0 If none of the options is chosen (i.e. the question is unanswered).
Negative Marks : –2 In all other cases.

13. Which of the following compounds has one of the stereoisomer as a meso compound ?
Cl

Cl
(A)

Br

(B)
Br

(C)

(D) 2, 3 - Dimethyl butane

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Optical Isomerism JEE Advanced Paper

14. Structure of naturally occurring steroid cholesterol is given :

18 Me 22 26

20
23 Me
12 Me 17 25
24
27
11 16
Me
13 Me
1
2 9 14 15
10 8
3
5 7
HO 4 6

Which of the following statements is/are correct ?

(A) There are nine chiral centres in the cholesterol.
(B) It is a pentacyclic compound.
(C) There are two 4° C atoms in the compound.
(D) There are seven 𝟑° C atoms in the compound.

15. The correct statement about the compoud (A), (B) and (C) is :–

(1) (2) (3)

(A) (1) and (2) are identical
(B) (1) and (2) are diastereomers
(C) (1) and (3) are diastereomers
(D) (1) and (2) are enantiomers

16. Which of the following compounds is chiral ?

Me

Me Me
NH
H
(A) (B)

Me
CH3

Br
(C) (D) Br
Br

Br

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Optical Isomerism JEE Advanced Paper

SECTION–III : (MAXIMUM MARKS : 6)

• This section contains TWO questions.
• Each question has matching lists. The codes for the lists have choices (A), (B), (C) and (D) out
of which ONLY ONE is correct
• For each question, marks will be awarded in one of the following categories :
Full Marks : +3 If only the bubble corresponding to the correct option is darkened.
Zero Marks : 0 If none of the bubbles is darkened.
Negative Marks : –1 In all other cases

17.
Column I Column II
Compounds Number of Isomers
(a) Number of diastereomers of 𝐂𝟐 𝐅𝐂𝐈𝐁𝐫𝐈 (p) 4
(b) Number of isomeric alcohols of (q) 3
𝐂𝟒 𝐇𝟏𝟎 𝐎 (excluding stereoisomer)
(c) Number of isomeric esters of 𝐂𝟒 𝐇𝟖 𝐎𝟐 (r) 6
(excluding stereoisomer)
(d) Number of stereoisomers of (s) 2

Me

Me
(e) Number of stereoisomers of
Me

Me
(A) (a → r), (b → p), (c → p), (d → s), (e → q)
(B) (a → p), (b → r), (c → p), (d → q), (e → s)
(C) (a → r), (b → p), (c → s), (d → p), (e → q)
(D) (a → p), (b → s), (c → p), (d → s), (e → s)

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Optical Isomerism JEE Advanced Paper

18.
Column I Column II
Compounds Characteristics
(a) COOH COOH (p) Diastereomers
H Br and H Br
H Br Br H
COOH COOH
(b) Me Me (q) Conformation
H OH and HO H
HO H H OH
Me Me
(c) Me Me (r) Position isomers
Me and H
H H
H Me
(d) Me Me (s) Enantiomers
H Me H H
and

H H H H
H Me
(A) a → p, b → r, c → q, d → p
(B) a → s, b → r, c → p, d → q
(C) a → p, b → q, c → r, d → s
(D) a → p, b → s, c → p, d → q

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Optical Isomerism JEE Advanced Paper

Answer Key
Question 1 2 3 4 5 6 7 8 9 10
Answer C B C B A D D C A A
Question 11 12 13 14 15 16 17 18
Answer A A AB ACD CD AB A D

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Optical Isomerism JEE Advanced Paper

Solutions
SECTION - I
1. Ans. (C)
D-glucose :-
CHO
H * OH
HO * H
H * OH
H * OH
CH2OH
 n=4
 unsymmetrical
 Total stereoisomers = 24 = 24 =16

2. Ans. (B)
3 CH3
1
CH3 CH3
4 1
S H OH
H 2
OH  H 2
OH
4H
2 1
Br
3 H Br R
H Br
4
5
3 CH 2–CH3
C2H5 C2H5
(2S, 3R)

3. Ans. (C)
3 CH3 1 OH 2 CH=CH2 4H
S 1 3 3 1 2
4
H OH H CH3 CH3 OH HO CH=CH2
4 R S 1 R
2 2 CH=CH 4 3
CH=CH2 2 H CH3
(I) (II) (III) (IV)

4. Ans. (B)
CH3 * CH3 CH3
(A) * C (B) C
H CH3
⇒ show both OI & GI ⇒ Don't show O.I. & G.I.
CH3 * CH 3
CH3 * CH 3

(C) C (D) C POS

* H * CH3
CH3 CH3
⇒ No POS & COS in trans form Show OI and G.I.
⇒ Show OI

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Optical Isomerism JEE Advanced Paper

5. Ans. (A)
3 4
R 1 2
even number
R
CHO of interchange
Br Cl 2
3
1 4

(1) Z
CHO
Br Cl
1
Br CHO
Z R 6 5 Z 3 2
⇒ ⇒ CH3–CH=C–CH2–C–CH3
R
CHO
Br Cl Cl
(2R, 4Z) –4-Bromo-2-chloro-2-methyl-4-hexenal

6. Ans. (D)
1 5
CH3 CH2CH3 4
2
H SH HS H
3 3
H OH H
2
OH
5
4
CH2–CH3 1 CH3
2–SH & 3-OH 2–OH & 3–SH
⇒ Position of –SH & OH are different. They are constitutional isomers.

7. Ans. (D)
Me
Me
Me * Me
(A) (B)
H H * Me
Me

⇒ No POS ⇒ No POS
⇒ Show OI ⇒ Show OI
Me CH3
(C) (D) CH3
* Cl H

CH3
⇒ only 1 chiral centre ⇒ No chiral centre
⇒ Show OI ⇒ Not show OI

8. Ans. (C)
OH OH OH
HO–H2C–CH–CH–CH–CHO
* * *
23 = 8

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Optical Isomerism JEE Advanced Paper

9. Ans. (A)
Br 1 H4
3 4 S
F R H R 2 Br 1
(I) (II) C Cl (III) C
Cl Br H F3 F
2 1 4 3 Cl 2
3 4 1 4
R S
2 1 2 3

10. Ans. (A)

CH3 CH3
H OH HO H
HO H H OH
CH3 CH3

Non-super imposable minor image

11. Ans. (A)

OH OH
*
trans cis
Optically active
OH
OH
,

cis cis trans trans

Optically inactive

4 isomers
OH OH
Optically Active Optically Inactive

2 1
OH OH
OH OH OH OH

Optically Inactive Optically active

1 2
6 isomers

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Optical Isomerism JEE Advanced Paper

12. Ans. (A)

CN 1
C
1 CH2–CH2–OH

*
* configuration at double bond E.
* only one chiral centre
* Compound will show optical isomerism
* It will show geometrical isomerism

SECTION–II
13. Ans. (A, B)
Cl Cl
Cl Cl
(1) * * * *
&

meso POS No POS

Br CH3 CH3

(2) * POS (3)

*
Br
Meso
⇒ No chiral centre
⇒ Not meso
CH3
H CH3
(4) POS
H CH3
CH3
no chiral centre
(3) & (4) so no meso compound

14. Ans. (A,C,D)

Me * Me
3°
Me * 3°
3°

Me
* 4°
Me
4° 3° 3°
* * *
* 3°

* 3°
HO *

(1) 9- chiral centres

(2) It is tetra-cyclic compound
(3) 2- 𝟒° C present
(4) 7- 𝟑°C present

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Optical Isomerism JEE Advanced Paper

15. Ans. (C, D)

COOCH3 COOCH3 COOCH3 COOCH3
H OH HO H H OH H OH
H OH HO H H OH HO H
COOH COOH COOH COOH
A B A C

Enantiomers diastereomers

16. Ans. (A, B)

Me Me

Me Me
No plane of Non super imposable
Symmetry No centre mirror Image
off symmetry chiral
Molecule
O
Me
O I chiral centre optically active
H * NH
O
CH3

POS is present optically inactive compound.

Br
Br
Br POS is present optically inactive

Br

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Optical Isomerism JEE Advanced Paper

SECTION–III

17. Ans. (A)

F I F Br
(a) C=C C=C
Br Cl I Cl

F I F Cl
C=C C=C
Cl Br I Br

F Br F Cl
C=C C=C
Cl I Br I

(b) C4 H10 O :- CH3 CH2 – CH2 – CH2 – OH CH3–CH2–CH–CH3

OH
OH
CH3–CH–CH2–OH CH3—C—CH3
CH3 CH3

O O
(c) C4 H8 O2 : CH3–CH2–C–O–H3 CH3–C–O–CH2–CH3
O O
H–C–O–CH2–CH2–CH3 H–C–O–CH–CH3
CH3

Me
Me
Me
(d) ⇒ &
Me Me Me

*
Me
Me Me
(e) ⇒ *
Me
Me Me No POS
(1) (2)
⇒ (a→ r) , (b → p) (c → p), (d → s), (e → q)

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18. Ans. (D)

COOH COOH
H Br H Br
(a) H Br Br H → (p)

COOH COOH
Diastereomers
Me Me
H OH HO H
(b) H H OH → (s)
HO
Me Me
Non-super imposable mirror image enantiomers

Me Me
(c) Me H → (q)
H H
H Me
Diastereomers
Me Me
H Me H H
(d)

H H H H
H Me
Gauch form Anti form
conformations

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 Optical Isomerism JEE Advance PYQs

CH3
Cl2/hv Fractional distillation
1. CH3–CH–CH2–CH3 N (no. of isomers) (F), (N) and (F) are :
(A) 6, 4
(B) 4, 4
(C) 6, 6
(D) 3, 3
[IIT-2006]

2. The number of stereoisomers obtained by bromination of trans–2–butene is :

(A) 1
(B) 2
(C) 3
(D) 4
[IIT-2007]

3. Statement-I : Molecules that are not superimposable on their mirror images are chiral
Because
Statement-II : All chiral molecules have chiral centres.
(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.
(D) Statement-1 is False, Statement-2 is True.
[IIT-2007]

4. The correct statement(s) about the compound given below is (are) :-

Cl H

H3C CH3

Cl H
(A) The compound is optically active
(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
[IIT-2008]

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Optical Isomerism JEE Advance PYQs

5. The correct statement(s) about the compound H3 C(HO)HC – CH = CH – CH(OH)CH3 (X) is (are) :

(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

[IIT-2009]

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

HO Cl
HO H H
H OH
Cl CH3
HO H OH HO
H H

CH3 Cl CH3
M N O

CH3 CH3

H OH HO H

H HO H
HO
Cl Cl
P Q

(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

[IIT-2012]

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Optical Isomerism JEE Advance PYQs

7. P & Q are isomers of dicarboxylic acid C4 H4 O4 . Both decolorize Br2 /H2 O, On heating P forms the
cyclic anhydride.
Upon treatment with dilute alkaline KMnO4 , P as well as Q could produce one or more than one
from S, T and U.
COOH COOH COOH
H OH H OH HO H
H OH HO H H OH
COOH COOH COOH
(S) (T (U)
)
Compounds formed from P and Q are respectively
(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
[JEE (Advance) 2013]
8. The total number of stereoisomers that can exist for M is :
H3C CH3

H3C O
M
[JEE (Advance) 2015]
9. In the following monobromination reaction, the number of possible chiral products is :
CH2–CH2–CH3
Br2 (1.0 mole)
H Br 300°C
CH3
(1.0 CH
mole)
(enatiomerically
pure) [JEE (Advance) 2016]
10. For the given compound X, the total number of optically active stereoisomers is____.
HO HO
This type of bond indicates that the configuration at the
specific carbon and the geometry of the double bond is
fixed.
HO HO This type of bond indicates that the configuration at the
X specific carbon and the geometry of the double bond is
NOT fixed.
[JEE (Advance) 2018]
11. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the
molecular formula C4 H8 O is ___
[JEE (Advance) 2019]

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Answer Key
Question 1 2 3 4 5 6 7 8 9 10
Answer A A C AD AD ABC B 2 5 7
Question 11
Answer 10

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Optical Isomerism JEE Advance PYQs

Solutions
1. Ans. (A)

* × 2 chiral molecules
Cl
Cl

*
× 2 chiral molecules
Cl

Cl
(a) Total isomers = 6
(b) Total no. of fractions obtained
After fractional distillation = 4

2. Ans. (A)
Br Br

and are Identical.

Br Br

3. Ans. (C)
Chiral molecule has non-superimposable mirror image. However, the presence of chiral centres
is not a necessary condition for chirality.

4. Ans. (A,D)
C2 – axis of symmetry is present.

5. Ans. (A,D)
OH

(Symmetric structure)
OH
R cis R

S cis S
R cis S Meso

R trans R

S trans S
R trans S Meso

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Optical Isomerism JEE Advance PYQs

6. Ans. (A,B,C)
M and N are non-mirror images and are non-super imposable → A
M and O are identical → B
M and P are Enantiomers
M and Q are diastereomers

7. Ans. (B)
O
COOH

O
COOH
O
Maleic acid Maleic anhydride

COOH

No cyclic
HOOC anhydride
fumaric acid is formed
Br COOH Br COOH
COOH
Br2/H2O
(anti-addition)
+
COOH COOH COOH
HO HO
Racemic mix ()
COOH
COOH
1% dil H OH
(Meso/1-product)
KMnO4 H OH
COOH
(syn-addition) COOH

COOH Br COOH
Br2/H2O
(anti-addition)
HOOC
HOOC Br
(Meso/1-product only)

COOH
COOH
1% dil H OH
+ Mirror image
KMnO4 H OH
HOOC
COOH
(syn-addition)
Racemic mixture /(±)

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Optical Isomerism JEE Advance PYQs

8. Ans. (2)

O O

Enantiomers

9. Ans. (5)
CH2–Br CH3 CH3
CH2 H Br Br H
CH2 CH2 CH2
H Br H Br H Br
CH3 CH3 CH3
(I) (II) (III)

CH3 CH3 CH3 CH3

CH2 CH2 CH2 CH2
H Br Br H CH2 CH2
H Br H Br Br Br H Br
CH3 CH3 CH3 CH2–Br
(IV) (V) (VI) (VII)
All are chiral molecules except II and VI.

10. Ans. (7)

Number of stereoisomers = 2n , (where n is number of variable stereocentres)
= 23 = 8 stereoisomers
But one of them is meso and all others are optically active or chiral molecules.

11. Ans. (10)

O O
O
*
(2-isomers)
O O

* O * *
(2-isomers) (3-isomers)
So, total number of cyclic ethers possible for C4 H8 O is ten.

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