ORGANIC CHEMISTRY

ISOMERISM SHEET

EXERCISE - I
JEE MAIN LEVEL
Single correct questions :
1. Examine the relation between the following pairs of compounds.

IR
Cl OH

IS
Cl Cl OH OH
(I) and (II) and
Cl OH

R
COOH
AT
COOH
(III)
and
HOOC COOH
H

(A) All I, II, III are identical (B) All I, II, III are isomers
(C) I, II are identical, III is isomer (D) I is identical and II, III are isomer
K

OH OH
| |
2. CH3  CH2  CH2  CH2 and CH3  C  CH3 are
T

|
CH3
EE

(A) chain isomers (B) positional isomers (C) both (D) none

3. Which of the following cannot be written in an isomeric form?

(A) CH3–CH(OH)–CH2–CH3 (B) CH3 – CHO
N

(C) CH2 = CH – Cl (D) Cl – CH2CH2 – Cl

VI

4.

The above compounds differ in

(A) configuration (B) conformation (C) structure (D) chirality

5. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are

(A) enantiomers (B) geometrical isomers
(C) metamers (D) conformational isomers
6. The molecular formula of diphenyl methane, CH2 , is C13H12.

How many structural isomers are possible when one of the hydrogen is replaced by chlorine atom
(A) 4 (B) 8 (C) 7 (D) 6

7. Given compound shows which type of isomerism

O O
S—O and S—O
O O
(A) Chain isomerism (B) Positional isomerism
(C) Metamerism (D) Functional group isomerism

IR
8. In the complete rotation of butane from 0º to 360º the gauche (straggered) conformation appears
(A) once (B) Twice (C) Thrice (D) Four times

IS
9. Following eclipsed form of propane is repeated after rotation of
OH

H
H
H
H
R O = – CH3
AT
(A) 45° (B) 90° (C) 120° (D) 180°

10. Which of the following is associated with Torsional strain ?

H

(A) Repulsion between bond pair of electrons (B) Inductive effect

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

11. Relationship in between

CH3 CH3
T

CH3 Cl H Cl
&
EE

H Cl Cl H
H CH3
(A) diastereomer (B) Identical (C) Enantiomer (D) None of these
N

12. Stereoisomers differ from each other in what respect ?

VI

(A) Composition (B) constitution (C) configuration (D) seric hindrance

13. Which of the following compound can not show geometrical isomerism ?
Br CH3
H3C CH3 CH3
Br CH3
(A) Cl (B) (C) (D)
H3C CH3 H3C CH3
Cl

14. The number of geometrical isomers of

CH3CH=CH–CH=CH–CH=CHCl is
(A) 2 (B) 4 (C) 6 (D) 8
15. The total number of geometrical isomers possible in following compound is :

CH=CH–CH=CH

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

16. The number of isomers of C5H10 is

(A) 10 (B) 11 (C) 12 (D) 13

17. Which of the following, compounds displays geometrical isomerism?

(A) CH2 = CHBr (B) CH2 = CBr2 (C) ClCH=CHBr (D) Br2C=CCl2

18. Minimum C atoms required for a compound to show geometrical isomerims:

(A) 2 (B) 3 (C) 4 (D) None of these

IR
19. Total number of geometric diastereomers exist for 1, 3-dichloro-2, 4-dimethyl cydobutane?
(A) 3 (B) 4 (C) 5 (D) 6

IS
20. The molecule(s) that exist as meso structure(s)

(K)
R
(L) (M)
AT
(A) only M (B) both K and L (C) only L (D) only K

21. Which two of the following compounds represents a pair of enantiomers ?

H

HO OH HO OH
K

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

22. Which of the following compounds is (S)–4–chloro–1–methylcyclohexene ?

CH3 CH3
CH3 CH3
N

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

Cl Cl Cl Cl
VI

23. Compound having meso stereoisomer?

(A) 2,3-dimethyl butane (B) 1,3-dichloropentane
(C) 2,4-pentane-diol (D) 2,3-dichloro heptane

24. How many stereoisomers of (CH3)2 CHCH=CHCH2CH(OH)CH2Br are possible ?

(A) 2 (B) 3 (C) 4 (D) 5
25. Which of the following structures represents a chiral compound ?
CH3 CH3 CH3 CH3 CH3
CH3
H H CH3 CH3 CH3
H H
(A) CH3 CH3 (B) CH3 CH3 (C) CH3 CH3 (D) CH
3 CH3
H OH H CH3 HO OH
H CH3

26. Examine the compound on the right. How many stereoisomers having this constitution are possible ?
CH3
H3C
O
H3C
CH3
Br
CH3
CH3
(A) 2 (B) 4 (C) 6 (D) 8

IR
27. How many stereoisomers are possible for the following molecule.

Cl
Br CH = CH

IS
CH3

(A) 4 (B) 8 (C) 16 (D) 32

28.
R
Which of the following heptanols are chiral 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol.
AT
(A) All are chiral (B) 2-heptanol and 3-heptanol
(C) 2-heptanol, 3-heptanol & 4-heptanol (D) 3-heptanol and 4-heptanol
H

29. The necessary and sufficient condition for a molecule to be optically active :
(A) It must contain asymmetric carbon atoms (B) It must be chiral atom
K

(C) It must be identical with its mirror image (D) It must be non-superimpossable with its mirror image

CH3 CH3
T

H Cl H Cl is
30. Optical rotation produced by Cl H is 36° then that product by H Cl
EE

CH3 CH3

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

N

31. Which of the following sugars has the configuration (2S, 3R, 4R) ?

CHO CHO CHO CHO

VI

H OH H OH HO H HO H
H OH HO H H OH HO H
(A) (B) (C) (D)
H OH H OH H OH H OH
CH2OH CH2OH CH2OH CH2OH

32. Which of the following statements is true for a pair of diastereomers ?

(A) they will have identical physical properties.
(B) they will have specific rotations of opposite sign
(C) they will have identical chemical properties (e.g. reactivity)
(D) they will have different physical properties.
33. Meso tartaric acid and d-tartaric acid are
(A) Position isomers (B) Enantiomers (C) Diastereomers (D) Racemic mixture

34. The number of optically active compounds in the isomers of C4H9Br is

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

35. Number of possible 3D-isomers (Stereoisomer) of glucose are

(A) 10 (B) 14 (C) 16 (D) 20

36. The two compounds given below are

IR
(A) enantiomers (B) identical (C) optically inactive (D) diastereomers

IS
37. Sum of stereoisomer in the given compound (a) and (b) are
Cl
Cl Cl = a (stereoisomer) ; = b (stereoisomer)

a+b=?
R Cl
AT
(A) 3 (B) 4 (C) 5 (D) 6

38. The correct statement about the compounds A, B and C is

H

COOCH3 COOH COOH

H OH H OH H OH
K

H OH H OH HO H

COOH COOCH3 COOCH3

T

(A) (B) (C)

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

(C) A and C are enantiomers (D) A and B are enantiomers

39. Which of the following are chiral :

CH3 Cl CH3
N
VI

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

CH3 CH3 Cl CH3
CH3 CH3
(A) 1, 2, 3 (B) 1, 2, 4 (C) 2, 3, 4 (D) 1, 3, 4

40. Which conformer of n-butane is chiral

(A) anti (B) gauche (C) fully-ecllipsed (D) none of these
 F Br
I H Cl CH3
41. What is the relationship between (I) & (II) Br CH3 I H
Cl F
(I) (II)
(A) Enantiomer (B) Diastereomers (C) Constitutional isomer (D) Identical molecules

Subjective questions :
42. Among the following How many compounds are chiral ?
H3C H3C

H3C CH3 CH3 H3C CH3 CH3

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

IR
H3C Cl H3C Cl Cl CH3 H3C Cl

IS
CH3 Cl CH3 H3C Cl Cl CH3
(e) (f) (g) (h)

43.
(a) (i) 2,3-dimethylbutane (ii) 2-bromo-3-methylpentane
(b) (i) 3,4-dimethylhexane (ii) 3,4-diethylhexane
R
Among the following compounds how many has a stereoisomer that is a meso compound ?
(iii) 1-bromo-2-methylcyclohexane
AT
(c) (i) 1,3-dimethylcyclohexane (ii) 1,4-dimethylcyclohexane (iii) 1,2-dimethylcyclohexane

44. Total number of enantiomeric pairs = X, so the value of X is.

CH3 CH3
H

CH3 CH3
(i) H Br & Br C
H (ii) HO H & HO H
C Cl H
H Cl
K

F F CH3
CH3
T

H Br & Br H
(iii) Cl & H Cl (iv) H
Br
EE

H H Br
H Cl Cl H

CH2H CH2CH3
N

(v) & (vi) CH CH C CH3 & CH3 C CH2Cl

3 2
VI

H H
CH3 H CH3 Et
H CH3 Et
(vii) CH3 & (viii) H & Me H
Me
Me H
H Me
CH3 CH3
Et
Et
Br Br
H
H H H H H H H
H Br Br
(ix) & (x) &
H Et H H Et Br OH
H OH H OH
OH
 EXERCISE - II
PREVIOUS YEAR AIEEE/JEE-MAIN QUESTIONS
Single Choice Questions :
1. A similarity between optical and geometrical isomerism is that [AIEEE-2002]
(A) each forms equal number of isomers for a given compound
(B) If in a compound one is present then so is the other
(C) both are included in stereoisomerism
(D) they have no similarity

2. Which of the following does not show geometrical isomerism ? [AIEEE-2002]

IR
(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1,4-dichloro-2-pentene

IS
3. The functional group, which is found in amino acid is [AIEEE-2002]
(A) – COOH group (B) – NH2 group (C) – CH3 group (D) both (a) and (b)

4. R
Which of the following compounds has wrong IUPAC name ?
(A) CH3 – CH2 – CH2 – COO – CH2CH3  ethyl butanoate
[AIEEE-2002]
AT
(B) CH 3 – CH – CH 2 – CHO  3- ethyl-butanal

CH2–CH3
H

(C) CH 3 – CH – CH – CH 3  3-methyl-2-butanol

K

OH CH3
O

(D) CH3 – CH – C – CH2 – CH3  2-methyl-3-pentanone

T

CH3
EE

5. Racemic mixture is formed by mixing two [AIEEE-2002]

(A) isomeric compounds (B) chiral compounds
(C) meso compounds (D) optical isomers
N

6. The IUPAC name of CH3COCH(CH3)2 is [AIEEE-2003]

VI

(A) isopropylmethyl ketone (B) 2-methyl-3-butanone

(C) 4-methylisopropyl ketone (D) 3-methyl-2-butanone

7. The general formula CnH2nO2 could be for open chain [AIEEE-2003]

(A) diketones (B) carboxylic acids (C) diols (D) dialdehydes
8. Among the following four structures I to IV [AIEEE-2003]

CH3 O CH3 H CH3

| || | | |
C2H5 — CH — C3H7 CH3 — C — CH — C2H5 H—C C2H5 — CH — C2H5
|
H
(I) (II) (III) (IV)
it is true that :
(A) all four are chiral compounds (B) only I and II are chiral compounds
(C) only III is a chiral compound (D) only II and IV are chiral compounds

9. Which of the following will have meso-isomer also ? [AIEEE-2004]

(A) 2- chlorobutane (B) 2- hydroxy propanoic acid
(C) 2,3 – dichloropentane (D) 2-3- dichlorobutane

IR
10. Amongst the following compound, the optically active alkane having lowest molecular mass is
[AIEEE-2004]

IS
(A) H3C CH3 (B) H3C
CH
CH3 CH3
CH3
H3C
(C)
C 2H 5
R (D)
H3C CH3
AT
11. Which of the following compound is not chiral ? [AIEEE-2004]
(A) 1- chloropentane (B) 3-chloro-2- methyl pentane
(C) 1-chloro -2- methyl pentane (D) 2- chloropentane
H

12. Which types of isomerism is shown by 2,3-dichlorobutane? [AIEEE-2005]

(A) Tautomerism (B) Optical (C) Geometric (D) Structural
K

13. Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of 2-fluoroethanol
is [AIEEE-2006]
T

(A) Eclipse, Gauche, Anti (B) Gauche, Eclipse, Anti

(C) Eclipse, Anti, Gauche (D) Anti, Gauche, Eclipse
EE

14. Which of the following molecules is expected to rotate the plane of plane polarized light ? [AIEEE-2007]

CHO COOH
H2N NH2
N

HO H H2N H
(A) (B) (C) H H (D)
VI

SH Ph Ph
CH2OH H

15. Which one of the following conformation of cyclohexane is chiral? [AIEEE-2007]

(A) Twist boat (B) Rigid (C) Chair (D) Boat

HO2C CO2H
16. The absolute configuration of is [AIEEE-2008]
HO H OH
H
(A) S, S (B) R, R (C) R, S (D) S, R
17. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]
(A) 2-butene (B) 2-methyl-2-butene (C) propene (D) 2-methyl propene

18. The number of stereoisomers possible for a compound of the molecular formula [AIEEE-2009]
CH3 – CH = CH – CH(OH) – Me is :
(A) 4 (B) 6 (C) 3 (D) 2

19. The IUPAC name of neopentane is : [AIEEE-2009]

(A) 2-methylpropane (B) 2, 2-dimethylbutane
(C) 2-methylbutane (D) 2, 2-dimethylpropane

20. Out of the following, the alkene that exhibits optical isomerism is [AIEEE-2010]
(A) 3-methyl-1-pentene (B) 2-methyl-2-pentene
(C) 3-methyl-2-pentene (D) 4-methyl-1-pentene

IR
21. Identify the compound that exhibits tautomerism. [AIEEE-2011]
(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol

IS
22. The absolute configuration of [JEE Mains-2016]
CO2H
H OH
H
CH3
Cl R
AT
is :
(A) (2R, 3S) (B) (2S, 3R) (C) (2S, 3S) (D) (2R, 3R)
H
K
T
EE
N
VI
 EXERCISE - III
JEE ADVANCED LEVEL
Single Choice Questions :
1. Which of the following is correct set of physical properties of the geometrical isomers

CH3 H CH3 Cl
C=C & C=C
H Cl H H
(I) (II)

Dipole moment Boiling point Melting point Stability

(A) I > II I > II II > I I > II

IR
(B) II > I II > I II > I II > I
(C) I > II I > II I > II I > II
(D) II > I II > I I > II I > II

IS
2. No. of geometrical isomers for following compound is :

CH3

CH2–CH=CH–CH=N–OH
R
AT
(A) 8 (B) 16 (C) 32 (D) 10
H

O OH O
|| | ||
3. S – CH = CH – CH – C – CH3
..
K

Number of chiral centers are.

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

4. Which of the folllowing is properly classified as a meso compound ?

C2H5 C2H5
CH3 H CH3
H OH H OH
OH HO H H
OH H
(A) HO (B) (C) H OH (D) H
N

H OH
CH3 H CH3 C2H5 CH3
VI

5. Which of the following compounds has two stereogenic centers (asymmetric carbons) ?
Cl
Cl Cl O
|| O H
||

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

Cl H3C H
Cl
6. How many stereoisomers are possible for the following compound?

NO2 CHBrMe

CH=CHMe I
(A) 2 (B) 4 (C) 6 (D) 8

7. Which of the following statements must be true for two pure chiral isomers ?
(A) they must be enantiomers (B) they must be diastereomers
(C) they must be stereoisomers (D) they must be optically active

8. How many stereoisomer may have this natural occuring compound.

O

IR
HO CH2 – OH

IS
HO CH=CH–CH=CH–CH2–CH2–CH3
(A) 8 (B) 16 (C) 64 (D) 128

9. R
How many stereoisomers of the following molecule are possible?
HOOC.CH = C = CH.COOH
AT
(A) two optical isomers (B) two geometrical isomers
(C) two optical and two geometrical isomers (D) None
H

10. Which species exhibits a plane of symmetry?

K

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

T
EE

11. Match List I with List II and select the correct answer from the codes given below the lists:
List I

O O
N

|| ||
(A) CH 3  C  O  CH 2  CH 2  CH 3 and CH 3  CH 2  C  O  CH 2  CH 3
VI

(B) and

(C) and
 (D) and

List II
(1) Enantiomer (2) Position isomers (3) Metamers (4) Tautomers
Codes :
(A) (B) (C) (D) (A) (B) (C) (D)
(A) 3 2 4 1 (B) 3 2 1 4
(C) 1 2 3 4 (D) 2 3 4 1

12. Which of the following will not show optical isomerism.

(A) Cl – CH = C = C = CH – Cl (B) Cl – CH = C = C = C = CH – Cl

IR
H
Cl H

(C) (D)

IS
Me Cl
Me
13. Which of following pair is Diastereomers:
CO2H
H OH CO2H CH3 H CH3

(A)
H
H
OH
OH (B)
CH3
C=C
R C
Br
H

Br
C
C=C
H
AT
HO H
CO2H CO2H H H H CH3
CH3 Et Cl Cl
H OH HO H Cl Cl
H

(C) H SH HS H (D)
Et CH3 Cl Cl
K

Me
Me
T

14. H
H
EE

Incorrect statement about this compound is:

(A) It shows geometrical isomerism (B) It posses centre of symmetry
(C) It posses plane of symmetry (D) It shows optical isomerism
N
VI

15. Total number of optically active alkyne possible from molecular formula C3FCl BrI
(A) 2 (B) 4 (C) 6 (D) 8

16. Which Fischer projection represents the given wedge dash structure :
Br

H5C2 CH3
H
Br CH3 CH3 Br
Br Br H
(A) H5C2 CH3 (B) H5C2 (C) (D) H3C C2H5
H H C2H5 H
17. Which of the following compound posses centre of symmetry ?

Br H O CH3

H N–C CH3 H OH H Cl
H
(A) Cl (B) H C (C) OH H (D)
3 C–N H
H Cl H
Br O CH3

18. Compound that has both center of symmetry and plane of symmetry is/are :
Cl Cl Cl CH3 Cl CH3

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

H3C Cl H3C Cl CH3 Cl

19. Number of fractions on fractional distillation of mixture of :

IR
F F Br F
D Cl H I H F H Br
H I D Cl D I Cl D

IS
Br Br Cl I
(I) (II) (III) (IV)
(A) 2 (B) 3 (C) 4 (D) 1

20.
Br Cl Br Cl
R
Which of the following compound has centre of symmetry but not plane of symmetry.
Br Cl Br Cl
AT
(A) (B) (C) (D)

Cl Br Cl Br Cl Br Cl Br
H

One or more than one correct Questions :

K

21. Which of the following compound/s can show optical isomerism ?

COOH Cl
T

H OH
(A) (B) (C) Me–CH=C=CH–Me (D)
H OH
EE

Cl
COOH

22. Which of the following is/are enantiomers of the given compound.

Cl Cl
N

OH OH OH O
VI

Me Me
O OH Cl Cl OH OH OH OH Cl Cl OH O

(A) (B)
Me Me Me Me
O OH Cl Cl OH OH OH Cl Cl OH

(C) (D) HO
Me Me Me Me
23. Statement-1 : This compound will show geometrical isomerism

Statement-2 : Terminal carbon groups are perpendicular to each other

(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

24. C4H6O2 does represent:

(A) A diketone (B) A compound with two aldehyde
(C) An alkenoic acid (D) An alkanoic acid

25. Which of the following compounds is optically active?

(A) 1-Bromobutane (B) 2-Bromobutane

IR
(C) 1-Bromo-2-methylpropane (D) 2-Bromo-2-methylpropane
CH3

IS
26. Which of the following operations on the Fischer formula H OH does not change its absolute
C2H5
configuration?
(A) Exchanging groups across the horizontal bond
(B) Exchanging groups across the vertical bond R
(C) Exchanging groups across the horizontal bond and also across the vertical bond
AT
(D) Exchanging a vertical and horizontal group

27. Which of the following combinations amongst the four Fischer projections represents the same absolute
configurations?
H
K
T
EE

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

28. Which of the following will show optical isomerism as well as geometrical isomerism.
N
VI

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

29. Which of the following compounds can show Optical isomerism as well as geometrical isomerism ?

(A) CH—Me (B) CH—Me (C) CH—Me (D) CH2

30. Which of the following are D sugars:
CHO
H OH
HO H
(A) (B) (C) (D)
H OH
HO–CH2 H
OH

31. The Fischer projection of the molecule as represented in the wedge dash.

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

IR
32. Given compound shows which type of isomersim

IS
and

(A) Chain isomerism

(C) Constitutional isomerism
R
(B) Positional isomerism
(D) None
AT
33. Which of following compound having plane of symmetry.

CO 2H CH2–Br
H H Cl H
H OH
H

(A) (B) H (C) C=C (D)

OH H
HO OH Cl
CO2H
K

34. The number of stereoisomers possible for the below compound (do not change cis/trans configurations of the
olefins) are
T

O CO2H
EE

OH
OH
N

(A) 8 (B) 16 (C) 32 (D) 12

VI

35. Which of the following is/are D-carbohydrate

CHO OH CHO
CH2OH
H OH HO H
(A) (B) H OH (C) H CHO (D)
HO H HO H H OH
CH2OH CH2OH CH2OH
CHO
 EXERCISE - IV
JEE ADVANCED LEVEL
1. Determine if the following pairs are identical, isomers, enanatiomers, or diastereomers.
OH OH HO OH
(i) _________________

OH
OH
(ii) _________________

CHO CH2OH

IR
H OH HO H
(iii) H OH HO H _________________
CH2OH CHO

IS
2. Determine if the following pairs are identical, isomers, enanatiomers, or diastereomers.

HO
H NH2
H2N
R H
OH
AT
(i) HO COOH _________________
HOOC OH
L-DOPA

CH2OH CH2OH
H

H OH H OH
H CH3 H3C H
K

(ii) _________________
T
EE

(iii) _________________
N

3. Classify each of the following pairs of structures as :

I. Identical E. Enantiomers D. Diastereomers
VI

CH = O CH = O
CH = O CH = O
H OH HO H
(a) H OH & HO H (b) &
H OH H OH
CH3 CH3
CH3 CH3

Br Br
Br Br Br Br
(c) Br & Br
4. Classify each of the following pairs of structures (a)–(e) as
I. Identical E. Enantiomers D. Diastereomers

CH3 CH3 CH3 CH2CH3

(a) H Br & Br H (b) H Cl & H CH3
CH2CH3 CH2CH3 CH2CH3 Cl

CH3 CH3 CH3 CH3

H Br H Br H Br Br H
(c) & (d) &
H Br Br H H Br Br H
CH3 CH3 CH3 CH3

Br Br
Br Br

IR
(e) &
Br Br

IS
5. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, different compounds that are not isomeric).

OH
H
CH3
OH
R H
CH3
AT
(a) _________________
H

OH OH CH3
H H
CH3
K

(b) _________________
T

OH OH
H H
EE

CH3 CH3
(c) _________________
N

OH OH
H H
VI

CH3 CH3
(d) _________________

OH OH
H H
CH3 CH3
(e) _________________
6. State the relationship between each of the following five (5) pairs of structures (identical, enantiomers,
diastereomers, structural isomers, conformational isomers, different compounds that are not isomeric).
O O
CH3 CH3
(a) _________________
H3C H3C

O O
CH3 CH3
(b) _________________
H3C H3C

O O
CH3 CH3

IR
(c) _________________
H3C H3C

IS
O O
CH3 CH3
H3C
(d) _________________
H3C R
AT
O O
CH3 H3C
(e) _________________
H

H3C CH3

7. Discuss the optical activity of the following two compounds and also label them as polar and non polar.
K
T

(I) (II)
EE

8. How many isomers are possible for nitrophenol?

9. A compound with molecular formula C4H10O, can show metamerism, functional isomerism and positional
isomerism. Justify the statement.
N

10. With reasons, state whether each of the following compounds I to VII is chiral.
VI

(I) (II) (III)

(IV) (V) (VI)

11. Considering rotation about the C-3 – C-4 bond of 2-methylhexane:
(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.

Assersion & Reasion :

O
Me NH H

12. Statement-1 is opticallyactive.

H NH Me
O
Statement-2 Optically active compound do not have plane of symmetry.
(A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1
(B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1
(C) Statement-1 is true, Statement-2 is false

IR
(D) Statement-1 is false, Statement-2 is true

13. Statement-1 Configuration does not change with change in conformation.

Statement-2 Two different configuration are restricted towards rotation across  bond.

IS
(A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1
(B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1
(C) Statement-1 is true, Statement-2 is false
(D) Statement-1 is false, Statement-2 is true R
Paragraph for Question Nos. 14 to 16
AT
If a molecule contains one carbon atom carrying four different groups it will not have a plane of symmetry
and must therefore be chiral. A carbon atom carrying four different groups is a stereogenic or chiral
centre.
A structure with a plane of symmetry is achiral and superimposable on its mirror image and cannot exist as
H

two enantiomer. A structure without a plane of symmetry is chiral and not superimposable on its mirror
image and can exist as two enantiomer.
K

CH3
H Br
H Cl
T

14.
H F
CH3
EE

Number of enantiomeric pairs are

(A) 2 (B) 4 (C) 8 (D) 10

Cl Cl
N
VI

15.
Cl Cl Cl Cl
(a) (b)
Relation between (a) & (b) is
(A) Enantiomer (B) Diastereomer (C) Identical (D) Structural isomer
16. Compound has both center of symmetry and P.O.S

Cl Cl
Cl
Cl
(A) (B) (C) (D)
Cl Cl
 Paragraph for Question Nos. 17 to 18
If plane-polarized light is passed through one enantiomer of a chiral substance (either the pure enantiomer
or a solution of it), the plane of polarization of the emergent light is rotated. A substance that rotates the
plane of polarized light is said to be optically active. Individual enantiomers of chiral substances are
optically active.

17. HO

Total stereoisomer of given compound will be

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

18. Which of the following compound show optical isomerism (Assuming cyclobutane ring is planar)
F F
F
(A) F (B) (C) (D)

IR
F F

19. Molecular formula C3H6Br2 can have (including stereoisomers) :

(A) Two gem dibromide (B) One vic dibromide

IS
(C) Two tertiary dibromo alkane (D) Two secondary dibromo alkane
20. The number of isomers of C3H5Br3 is (including stereoisomers)
(A) 4 (B) 5 (C) 6 (D) 7

21.
R
How many total isomers are possible by replacing one hydrogens atoms of propane with chlorine
AT
(A) 2 (B) 3 (C) 4 (D) 5

Matrix Match
H

22. Column-I Column-II

K

COOH COOH
(A) A pair of metamer (P) H OH H OH
;
HO H H OH
T

COOH COOH
EE

(B) tautomerism (Q) CH3OC3H7 ; C2H5OC2H5

CH3 CH3

;
N

(C) A pair of geometrical isomer (R) H OH HO H

COOH COOH
VI

H3C CH3 H3C H

(D) A pair of diastereomers (S) C=C ; C=C
H H H CH3

O
||
(E) A pair of optical isomer (T) CH3CH2CH2CH ; CH3CH2CH=CH—OH
23. Match the column :
Column I Column II

(A) (P) Total number of stereoisomers is odd

for the structure

(B) (Q) Total number of stereoisomers is even

for the structure

IR
(C) (R) Odd number of chiral centre

IS
(D) (S) Even number of chiral centre
centres.

24. Match the column :

Column I
R Column II
AT
Cl Cl
Cl Cl
H

(A) (P) Position isomers

K

Cl Cl

Cl
T

Cl
Cl
EE

(B) (Q) Enantiomers

Cl Cl Cl
N

Cl Cl
VI

(C) (R) Diastereomers

Cl Cl Cl Cl
Cl Cl
Cl
(D) (S) Identical
Cl
Cl Cl
25. Column I Column II

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

CH3 Cl
H H
Cl CH3
(B) and (Q) Identical
Et Et

CH3 H
H H3C
OH Et
(C) and (R) Enantiomers

IR
Et OH

IS
H5C2 H5C2
(D) and (S) Diastereomers
OH H H OH

Subjective questions :
26.
R
Mark each chiral center in the following molecules with an asterisk. How many stereoisomers are possible
for each molecule ?
AT
OH
CH2 – COOH
H

(a) CH 3CHCHCOOH (b) CH – COOH (c) (d)

HO OH HO–CH–COOH
K

O OH
T

(e) O COOH (f) (g)

OH
EE

27. Following are four Newman projection formulas for tartaric acid.
N

COOH COOH COOH COOH

H OH HO H HOOC OH H COOH
VI

H OH H OH HO H HO H
COOH COOH H OH
(1) (2) (3) (4)

(a) Which represent the same compound? (b) Which represent enantiomers?
(c) Which represent a meso compound? (d) Which are diastereomers?
28. Total number of stereo isomer in 2, 5-dimethyl piperidine

H
|
N

29. (i) Number of all possible enols of formula C4H8O. (x)

(ii) Number of chiral carbons in Diosgenin. (y)

IR
HO
(iii) Number of geometrical isomer of given compound. (z)

IS
N – NH2

H—C—C—C—H

N N

NH2
R NH2
AT
H
K
T
EE
N
VI
 EXERCISE - V
PREVIOUS YEAR'S JEE QUESTIONS

1. Write structural formulae for all the isomeric alcohols having the molecular formula C4H10O. [JEE 1984]

2. Isomers which can be interconverted through rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers

3. The shows: [JEE 1995(Scr.)]

IR
(A) geometrical isomerism (B) optical isomerism
(C) geometrical & optical isomerism (D) tautomerism

IS
4. How many optically active stereoisomers are possible for butane-2,3-diol? [JEE 1997]
(A) 1 (B) 2 (C) 3 (D) 4

5.
R
When cyclohexane is poured on water, it floats, because:
(A) cyclohexane is in 'boat' form
[JEE 1997]
AT
(B) cyclohexane is in 'chair' form
(C) cyclohexane is in 'crown' form
(D) cyclohexane is less dense than water
H

6. Which of the following compounds will show geometrical isomerism? [JEE 1998]
K

(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene

7. Which of the following compounds will exhibit geometrical isomerism? [JEE 2000 (Scr.)]
(A) 1-Phenyl-2-butene (B) 3-Phenyl-1-butene
T

(C) 2-Phenyl-1-butene (D) 1,1-Diphenyl-1-propene

EE

8. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III. [JEE 2000]
N
VI

9. The number of isomers for the compound with molecular formula C2BrClFI is
(A) 3 (B) 4 (C) 5 (D) 6 [JEE 2001 (Scr.)]
10. Which of the following compounds exhibits stereoisomerism? [JEE 2002 (Scr.)]
(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid
11. In the given conformation, if C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then the
conformation obtained is [JEE 2004 (Scr.)]
4
CH3
H H
3
2
H H
1CH3
(A) fully eclisped conformation (B) partially eclipsed conformation
(C) gauche conformation (D) staggered conformation

12. (i) obs =  i x i

i
where i is the dipole moment of a stable conformer of the molecule, Z–CH2–CH2–Z and xi is the mole
fraction of the stable conformer.
Given : obs = 1.0 D and x (Anti) = 0.82

IR
Draw all the stable conformers of Z–CH2–CH2–Z and calculate the value of (Gauche).
(ii) Draw the stable conformer of Y–CHD–CHD–Y(meso form), when Y= CH3 (rotation about C2–C3)
and Y = OH (rotation about C1 – C2 ) in Newmann projection. [JEE 2005]

IS
13. The number of structural isomers for C6H14 is [JEE 2007]
(A) 3 (B) 4 (C) 5 (D) 6
14. Statement-1 : Molecules that are not superimposable on their mirror images are chiral.
because
R
AT
Statement-2 : 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.
H

(D) Statement-1 is False, Statement-2 is True. [JEE 2007]

K

15. The correct statement(s) about the compound given below is (are) [JEE 2008]
Cl H
T

CH3
H3C
EE

Cl H
(A) The compound is optically active
(B) The compound possesses centre of symmetry
N

(C) The compound possesses plane of symmetry

(D) The compound possesses axis of symmetry
VI

16. The correct statement(s) concerning the structures E, F and G is (are) [JEE 2008]

H3C O H3C OH H3C CH3

H3 C CH3 H3 C CH3 H3C OH

(E) (F) (G)
(A) E, F and G are resonance structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers
17. The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3(X) is (are)
(A) The total number of stereoisomers possible for X is 6 [JEE 2009]
(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

18. The total number of cyclic structural as well as stereo isomers possible for compound with the molecular
formula C5H10 is [JEE 2009]

19. In the Newman projection for 2,2-dimethylbutane [JEE 2010]

X
H3C CH3
X and Y can respectively be
(A) H and H (B) H and C2H5
H H
(C) C2H5 and H (D) CH3 and CH3 Y

20. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is

IR
[JEE 2010]

21. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible

IS
conformations (if any), is (are) [JEE 2011]

H H H
C—C
(A) (B) H — C C—C
H2C CH2 R CH2
AT
(C) H2C = C = O (D) H2C = C = CH2

22. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [JEE 2012]
(A) sp and sp 3 (B) sp and sp 2 (C) only sp2 2
(D) sp and sp3
H

23. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ? [JEE 2012]
K

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

HO H H OH HO H
HO H HO H
EE

CH3 Cl CH3 Cl Cl
M N O P Q

(A) M and N are non-mirror image stereoisomers (B) M and O are identical
N

(C) M and P are enantiomers (D) M and Q are identical

VI

24. The total number of stereoisomers that can exist for M is [JEE Advance 2015]

H3C CH3

H3C
M
O
 ANSWER KEY
EXERCISE-I
1. C 2. A 3. C 4. C 5. C 6. A 7. C
8. B 9. C 10. A 11. B 12. C 13. A 14. D
15. C 16. D 17. C 18. D 19. C 20. B 21. C
22. A 23. C 24. C 25. D 26. D 27. C 28. B
29. D 30. B 31. C 32. D 33. C 34. B 35. C
36. A 37. C 38. D 39. A 40. B 41. B
42. 2 (c, e) 43. (a) 0, (b) 1, (c) 2 44. 4 (i, iii, iv, viii)

EXERCISE-II
1. C 2. C 3. D 4. B 5. D 6. D 7. B

IR
8. B 9. D 10. D 11. A 12. B 13. C 14. A
15. A 16. B 17. A 18. A 19. D 20. A 21. C
22. B

IS
EXERCISE - III
1. C 2. B 3. B 4. A 5. D 6. D 7. D
8.

15.
C

D
9.

16.
A

A
10.

17.
D

B
11.

18.
R
A

A
12.

19.
A

C
13.

20.
B

A
14. B
AT
21. A, B, C, D 22. B, C 23. D 24. A, B, C 25. B 26. C
27. C 28. A, C, D 29. A, B, C, D 30. A, C, D 31. A, C
32. B, C 33. A, B, C, D 34. B 35. D
H

EXERCISE - IV
1. (i) Diastereomers (ii) Enantiomers (iii) Identical
K

2. (i) Identical (ii) Diastereomers (iii) Diastereomers

3. (a) E (b) D (c) I
T

4. (a) E (b) I (c) D (d) I (e) E

5. (a) Diastereomer (b) Diastereomer (c) Not isomer (d) Structural (e) Enantiomer
EE

6. (a) Diastereomer (b) Not isomer (c) Enantiomers (d) Structural isomers (e) Identical
7. Compound I is optically inactive since it contain a plane of symmetry. Compound II is enantiomeric since it
does not contain plane of symmetry, hence chiral. Also compound I is polar while II is non polar ]
N

8. 3
VI

9. (i) Et – O – Et, (ii) CH3 – O – CH2 – CH2 – CH3, (iii) CH3 – CH2 – CH2 – CH2 – OH, (iv) CH3 – CH2 – CH – CH3
|
I & II metamers, I & III functional isomers, III & IV position isomers OH
10. achiral : I, III ; chiral : II, IV, V, VI

Et
Et
H H
11. (a) (b)
H H
H
H H
H
12. D 13. C 14. B 15. B 16. D 17. B 18. B
19. A 20. C 21. A
22. (A) Q; (B) T; (C) S; (D) P, S; (E) P, R 23. (A) Q, S ; (B) Q, S ; (C) P, S ; (D) Q, R
24. (A) R, (B) P, (C) S, (D) S 25. (A) P ; (B) R ; (C) Q ; (D) R
26. (a) 4 (b) 4 (c) 2 (d) 8 (e) 4 (f) 4 (g) 4
27. (a) 3 & 4 (b) 1 & 3, 1 & 4 (c) 2 (d) 1 & 2, 2 & 3, 2 & 4
28. 4 (ae, aa, ee, ea) 29. 12 + 11 + 4 = 27

EXERCISE - V
1. 4 2. A 3. B 4. B 5. D 6. A 7. A
8. enantiomers–I & III; diastereomers – I & II and II & III 9. D 10. D 11. C
1
12. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = – OH
0.18
13. C 14. C 15. A, D 16. B,C,D 17. A, D 18. 7 19. B, D

IR
20. 5 21. B, C 22. B 23. A,B,C 24. 2

IS
R
AT
H
K
T
EE
N
VI