ISOMERISM Page # 1

EXERCISE – I JEE MAIN

1. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are
Sol.
(A) chain isomers (B) geometrical isomers
(C) metamers (D) conformational isomers
Sol.

7. The number of isomers of dibromoderivative of an

alkene (molear mass 186 g mol–1) is
2. C7H7Cl shows how many benzenoid aromatic (A) 2 (B) 3 (C) 4 (D) 6
isomers? Sol.
(A) 4 (B) 3 (C) 5 (D) 6
Sol.

8. Increasing order of stability among the three main

conformation (i.e. eclipse, anti, gauche) of ethylene
glycol is :
3. How many minimum no. of C-atoms are required (A) Eclipse, gauche, anti
for position & geometrical isomerism in alkene? (B) Gauche, eclipse, anti
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3 (C) Eclipse, anti, gauche
Sol. (D) Anti, gauche, elipse
Sol.

4. How many structural formula are possible when

one of the hydrogen is replaced by a chlorine atom in 9. How many primary amines are possible for the
anthracene? formula C4H11N?
(A) 3 (B) 7 (C) 4 (D) 6 (A) 2 (B) 3 (C) 4 (D) 5
Sol. Sol.

5. Which of the following connot be written in an

isomeric form?
(A) CH3 – CH(OH) – CH2 – CH3 10. The R/S configuration of these compounds are
(B) CH3 – CHO respectively.
(C) CH2 = CH – Cl
HO
(D) Cl – CH2CH2 – Cl H NH2
Sol. CF3
HS
COOH

6. The number of cis-trans isomer possible for the

following compound H CH3
CHO

(A) 2 (B) 4 (C) 6 (D) 8 (A) R, R, S (B) R, S, R (C) R, S, S (D) S, S, S

2
 Page # 3 ISOMERISM

Sol. Sol.

O OH O
11. How many planes (pos) are presents i n
Anthracene 15. S C CH C C CH3
H H

Number of chiral centers are:

(A) 1 (B) 2 (C) 3 (D) 4
Anthracene Sol.
(A) 1 (B) 2 (C) 3 (D) 6
Sol.

12.
16. Which of the follownig compounds is (S)–4-chloro-
CH 3 Cl 1-methylcyclohexene ?
H Cl H Br CH3 CH3

&
Br H H CH3 (A) (B)
COOH COOH
(A) Comformers (B) Diastereomers Cl Cl
(C) Enantiomers (D) Position isomers
Sol. CH3 CH3

(C) (D)

Cl Cl
Sol.
13. Geometrical isomers can be
(A) Diastereomers or Enantiomers
(B) Structural isomers
(C) Inter convertable at room temprature.
(D) none of these
Sol.

17. Which of the following compounds has two

stereogenic centers (asymmetric carbons) ?
Cl
Cl Cl
14. Phenol and benzyl alcohol are
(A) functional isomers (A) (B)
(B) Homologous
(C) position isomers Cl Cl
(D) none of these
3
 ISOMERISM Page # 3

O Sol.

O H

(C) (D)
H
H3C

21. Which of the following will exhibit geometrical

isomerism ?
18. Which of the following structures represents a (A) 1-phenyl-2-butene
chiral compound ? (B) 3-phenyl-1-butene
CH3 CH3 CH3 CH3 (C) 2-phenyl-1-butene
H H (D) 1, 1-diphenyl-1-propene
(A) H C CH3
(B) H C CH3
3 3
H CH3
Sol.
H OH

CH3 CH3 CH3 CH3

H H3C
H
(C) H C (D)
3 CH3 H3C CH3
HO OH H CH3
Sol.

CH3 Et

22. (A) H OH (B) HO H

19. Examine the compound on the right. How many Et CH3

stereoisomers having this constitution are possible ?
CH3 Relation between given pair is
H3C (A) Enantiomer (B) Diastereomer
O
H3C (C) Identical (D) Structural isomer
Sol.
CH3
Br
CH3
CH3
(A) 2 (B) 4 (C) 6 (D) 8
Sol.

23. Following eclipsed form of propane is repeated

after rotation of

OH
20. Which of the following heptanols are chiral 1- O=–CH3
heptanol, 2-heptanol, 3-heptanol, 4-heptanol.
(A) All are chiral H
(B) 2-heptanol and 3-heptanol H HH
(C) 2-heptanol, 3-heptanol & 4-heptanol
(D) 3-heptanol and 4-heptanol (A) 45º (B) 90º (C) 120º (D) 180º

3
 Page # 4 ISOMERISM

Sol. H Cl
27. H Cl

H Cl Cl H
The above compounds differ in
(A) configuration (B) conformation
(C) structure (D) chirality
Sol.
24. Stereoisomers differ from each other in what
respect ?
(A) Composition (B) constitution
(C) configuration (D) steric hindrance
Sol.

28. The compound C2H5OC2H5 and CH3OCH2CH2CH3 are

(A) enantiomers
(B) geometrical isomers
(C) metamers
25. The number of isomers of C5H10 is
(D) conformational isomers
(A) 10 (B) 11 (C) 12 (D) 13
Sol.
Sol.

CH3

H Cl
26. The compound with the above
HO H 29. Which conformer of cyclohexane is chiral
C2H5 (A) Chair (B) Boat
configuration is called. (C) Twisted boat (D) None of these
Sol.
(A) (2S, 3S)-2-chloro-3-hydroxypentane
(B) (2S, 3R)-2-chloro-3-hydroxypentane
(C) (2R, 3R)-2-chloro-3-hydroxypentane
(D) (2R, 3S)-2-chloro-3-hydroxypentane
Sol.

30. Minimum C atoms required for a compound to show

geometrical isomerism :
(A) 2 (B) 3
(C) 4 (D) None of these
Sol.

4
 ISOMERISM Page # 5

EXERCISE – II JEE ADVANCED (OBJECTIVE)

1. A pure simple of 2-chlorobutane shows rotation 5. A m o ng t he f ol l ow i n g , a p ai r o f re s o l v ab l e
of PPL by 30º in standard conditions. When above configurational enantiomers is given by
sample is made impure by mixing its opposite form, so (A) cis-1, 2-dimethylcyclohexane
that the composition of the mixture become 87.5% d-
(B) cis-1, 3-dimethylcyclohexane
form and 12.5% l-form, then what will be the observed
rotation for the mixture. (C) cis-1, 4-dimethylcyclohexane
(A) –22.5º (B) +22.5º (C) +7.5º (D) –7.5º (D) trans-1, 3-dimethylcyclohexane
Sol. Sol.

2. 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 30º. Calculate the angle of rotation 6. Which two of the following compounds are identical ?
& specific angle of rotation if above solution diluted to
1 Litre. OH
(A) 16º & 36º (B) 6º & 30º OH OH
(C) 3º & 30º (D) 6º & 36º (I) (II)
Sol. O O
OH OH
OH
OH OH
HO OH OH
3. In the given following compound find out the pair
(III) (IV)
of enantiomers and diastereomers
O O
OH O OH
(A) I & II (B) II & IV (C) III & IV (D) I & III
R R' Sol.
R
(A) 2, 2 (B) 2, 4 (C) 4, 4 (D) 4, 2
Sol.

7. Which two of the following compounds are

4. The molecule (s) that exist as meso structure(s) diasteromers ?

OH
OH OH
(I) (II)
O O
OH OH
OH
(K) (L) (M) OH
OH
(A) only M (B) both K and L
HO OH OH
(C) only L (D) only K
Sol. (III) (IV)
O O
OH
(A) I & II (B) II & IV (C) III & IV (D) I & III

5
 Page # 6 ISOMERISM

Sol. 10. The drawing on the rigth shows that trans-1, 3-

dichlorocyclohexane is chiral.
Efforts to resolve this compound fail. Why ?
Mirror

H Cl Cl H
Cl Cl
8. Which of the following is properly classified as a H H
meso compound ?
(A) the cis and trans isomers rapidly interconvert.
H CH3
CH3 (B) the compound is actually a meso structure.
H OH HO
(C) the chair conformers rapidly interconvert producing
(A) (B) HO
H a recemic mixture.
HO H CH3
(D) method for resolving alkyl chlorides are not available.
CH3
Sol.
C2H5
C2H5
H OH
HO H
(C) (D) H H
H OH
H OH
C2H5
11. How many stereoisomers of (CH3)2CHCH =
CH 3
CHCH2CH(OH)CH2Br are possible ?
Sol. (A) 2 (B) 3 (C) 4 (D) 5
Sol.

9. Which two of the following compounds represents

a pair of enantiomers ?
12. What common symmetry of elements if any are
HO OH
found in the stable chair conformer of trans-1, 2-
(I) (II) dichlorocyclohexane ?
HO OH (A) A single mirror plane and a C2 rotational axis.
(B) A single mirror plane & C3 rotational axis.
HO OH
(C) Two orthogonal mirror planes and a C2 rotational
(III) (IV) axis.
HO OH (D) A single C2 rotational axis but no mirror plane.
(A) I & II (B) II & III (C) III & IV (D) II & IV Sol.
Sol.

6
 ISOMERISM Page # 7

13. How many stereoisomer are possible for the

OH
following molecule ?
OH
Cl
Br CH CH 16. CH3 CH2 CH2 CH2 and CH3 C CH3 are
CH3
CH3

(A) 4 (B) 8 (C) 16 (D) 32 (A) chain isomers (B) positional isomers
Sol. (C) both (D) none
Sol.

17. Dextrorotatory -pinene has a specific rotaiton

14. How many stereoisomers are possible for the
following compound ? []D20 = +51.3°. A sample of -pinene containing both
NO2 MeBrHC the enantiomers was found to have a specific rotationa
value []D20 = +30.8°. The percentages of the (+) and
(–) enantiomers present in the sample are, respectively.
(A) 70% and 30% (B) 80% and 20%
CH=CH-Me I (C) 20% and 80% (D) 60% and 40%
(A) 2 (B) 4 (C) 6 (D) 8 Sol.
Sol.

CH3 18. (+)-mandelic acid has a specific rotation of 158°.

What would be the observed specific rotation of a
H Cl mixture of 25% (–)-mandelic acid and 75% (+)-mandelic
15. Optical rotation produced by is 36° then
Cl H acid ?
CH3 (A) +118.5° (B) –118.5°
(C) –79° (D) +79°
CH3 Sol.
H Cl
that product by is
H Cl
CH3
(A) –36° (B) 0°
(C) +36° (D) upredictable
Sol.

19. Number of structural isomers of compound having

molecular formula C4H7Cl.
(A) 4 (B) 8 (C) 12 (D) 16

7
 Page # 8 ISOMERISM

Sol. 22. 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.
Sol.

20. Which of the following sugars has the configuration

(2S 3R, 4R) ?

CHO CHO 23. How many stereoisomer may have this natural
H OH occuring compound.
H OH
(A) H OH (B) HO H O
H OH H OH HO CH2 OH
CH2OH CH2OH
HO CH=CH–CH=CH–CH2–CH2–CH3
CHO CHO
(A) 8 (B) 16 (C) 64 (D) 128
HO H HO H
Sol.
(C) H OH (D) HO H
H OH H OH
CH2OH CH2OH
Sol.

24. An optically pure compoud X gave an []D25 =

+20.0°. A mixture of X and its enantiomer Y gave
21. Which of the following statements must be true []D25 = +10°. The ratio of X to Y in the mixture is
for two pure chiral isomers ? (A) 2 : 1 (B) 1 : 3 (C) 3 : 1 (D) 1 : 2
(A) they must be enantiomers Sol.
(B) they must be diastereomers
(C) they must be stereoisomers
(D) they must be optically active
Sol. 25. Molecular formular C3H6Br2 can have (including
stereoisomers):
(A) Two gem dibromide
(B) One vic dibromide
(C) Two tertiary dibromo alkane
(D) Two secondary dibromo alkane

8
 ISOMERISM Page # 9

Sol. 30. How many stereoisomers of the following molecule

are possible? [Link]=C=[Link]
(A) Two optical isomers
(B) Two geometrical isomers
(C) Two optical & two geometrical isomers
(D) None
Sol.

26. Mesotartaric acid and d-tartaric acid are

(A) positon isomers (B) enantiomers
(C) diastereomers (D) racemic mixture
Sol.

31. The structures shown here are related as being

H Br
C

CH3 CH3 Br
27. The nubmer of isomers of C3H5 Br3 (including
stereoisomers) C H 3C
C
(A) 4 (B) 5 (C) 6 (D) 7 Br H H
Sol.
H3C
C H
Br

(A) conformers (B) enantiomorphs

(C) geometrical isomers (D) diastereosiomers
Sol.
28. The number of optically active compounds in the
isomers of C4H9Br is
(A) 1 (B) 2 (C) 3 (D) 4
Sol.

32. Which of the following cannot be written in an

isomeric form ?
(A) CH3 – CH(OH) – CH2 – CH3
29. The prefered conformati on of trans-1, 2- (B) CH3 – CHO
dibromocyclohexane is: (C) CH2 = CH – Cl
(A) diaxial (B) diequatorial (D) Cl – CH2CH2 – Cl
(C) axial/equatorial (D) neither A, B nor C Sol.
Sol.

9
 Page # 10 ISOMERISM

35. Which species exhibits a plane of symmetry ?

CO2H CO2H CO2H
H OH H OH COOH
HO H H
CH3
33. (I) H OH (II) HO H (III) H OH
H OH H OH H H H
H OH (A)
CO2H CO2H CO2H H CH3
H H
CO2H
CO2H
H OH
HO H
(IV) HO H (V) HO H
(B)
HO H
HO H
CO2H
CO2H
OH H
Which of the above formula represent identical
compounds ? H COOH
H H
(A) I and II (B) I and IV H
(C) H
(C) II and IV (D) III and IV H
Sol. HOOC
H OH

Ph Ph

(D) H
H
H H

CO2H CO2H CO2H COOH COOH

34. (I) (II) (III)
H OH H OH HO H
H OH HO H H OH Sol.

H OH H OH H OH
CO2H CO2H CO2H

CO2H CO2H
HO H H OH

(IV) HO H (V) HO H 36. Number of possible 3D-isomers (Stereoisomer) of

HO H HO H glucose are
CO2H (A) 10 (B) 14 (C) 16 (D) 20
CO2H
which of the above compounds are in enantiomers Sol.
(A) II & III (B) III & IV
(C) III & V (D) I & V
Sol.

37. Which of the following, compounds displays

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

10
 ISOMERISM Page # 11

Sol. Sol.

40. How many total isomers are possible by replacing

one hydrogens atoms of propane with chlorine
38. Match List I with List II and select the correct (A) 2 (B) 3 (C) 4 (D) 5
answer from the codes given below the lists: List-I Sol.
O
(A) CH3 C O CH2 CH2 CH3 and
O
H3C CH2 C O CH2 CH3

CH3 CH3
41. On chlorination of propane number of products of
CH3 the formula C3H6Cl2 is
(B) and (A) 3 (B) 4 (C) 5 (D) 6
Sol.

CH3

O OH

(C) and 42. The two compounds given below are

O O HO OH D Cl

CHO H Br
H I H
H Cl D H
(D) H C OH and H3C C CHO
I Br
CH3 OH
(A) enantiomers (B) identical
List II (C) optically inactive (D) diastereosmers
(1) Enantiomer (2) Position isomers Sol.
(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 43. Which of the following will not show optical
Sol. isomerism.
(A) Cl – CH = C = C = CH – Cl
(B) Cl – CH = C = C = C = CH – Cl
H
COOH
Cl H
(C) H OH (D)
39. The number of optically active isomers observed
H OH
in 2,3-dichlorobutane is Me Cl
(A) 0 (B) 2 (C) 3 (D) 4 COOH
Me
11
 Page # 12 ISOMERISM

Sol. Sol.

44. Given compound show which type of isomerism?

46. Which of following pair is Diastereomers:
O
CO2H CO2H
S O and H OH
O H OH
(A)
HO H H OH
O
CO2H CO2H
S O
O H CH3
CH3
(A) Chain isomerism H
H3C C Br C H
(B) Positional isomerism C
(B) C C Br C
(C) Metamerism
H H CH3
(D) Functional group isomerism H
Sol.
CH3 Et
H OH HO H
(C)
H SH HS H
Et CH3

Cl Cl
Cl Cl
(D)
45. Shows which type of isomerism Cl Cl

O Sol.

Cl C O
H
and
C C
H CH3

O
47. Sum of stereoisomer in the given compound (a)
C O Cl and (b) are:
H3C
C C Cl Cl = a (stereoisomer)
H H
Cl
(A) Functional group isomerism = b (stereoisomer) a + b = ?
Cl
(B) Geometrical isomerism
(A) 3 (B) 4
(C) Metamerism
(C) 5 (D) 6
(D) Position isomerism

12
 ISOMERISM Page # 13

Sol. Which of the following statement is correct ?

(A) I & II are conformational isomers while II & III are
functional isomers
(B) I & II are functional isomers while II & III are
conformational isomers
(C) I & II are functional isomers while I & III are
conformational isomers
Et (D) None of these
Keq.
Sol.
Et
48.
Me
Me
equilibrium constant for above reaction is:
(A) K = 1 (B) K > 1 (C) K < 1 (D) K = 0
Sol. 51. How many planes are presents in nepthalene

Nepthalene
Me (A) 1 (B) 2 (C) 3 (D) 6
Sol.
Me
49. H Incorrec t st at e me nt about t hi s
H
compound is
(A) it shows geometrical isomerism
(B) it posses centre of symmetry
(C) it posses plane of symmetry 52. Total number of optically active alkyne possible
(D) it shows optical isomerism from molecular formula C3FClBrI
Sol. (A) 2 (B) 4 (C) 6 (D) 8
Sol.

C2H5 CH3 53. Total number of geometrical isomer of given

H3C CH3 H C2H5 compound will be
N N O O
50. (I) (II)
H H3C
CH3 CH3 (A) 2 (B) 4 (C) 6 (D) 8

CH3 Sol.
H3C CH3

(III)
H H
N
H C2H5

13
 Page # 14 ISOMERISM

Sol.

54.

Number of geometrical isomer of given compound will

be :
(A) 2 (B) 3 (C) 4 (D) 5 60. In which of the following molecule show chirality.
Sol.
Me
(I)
COOMe

Me
(II) Cl

55. The number of stereoisomers obtained by (A) I is trans & chiral (B) II is trans & chiral
bromination of cis-2-butene is (C) I is cis & chiral (D) II is trans & achiral
(A) 1 (B) 2 (C) 3 (D ) 4 Sol.
Sol.

56. The number of stereoisomers obtained by reaction

cis-2-butene with bromine in the presence of water is : 61. Total number of stereoisomer is odd number for
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
(A) (B)

57. The number of stereoisomers obtained by CHO

bromination of trans-2-butene is : CO2H
(A) 1 (B) 2 (C) 3 (D) 4 H OH
H OH
Sol. (C) (D)
H OH
H OH
H OH
Sol. CO2H
CH2–OH

58. The number of stereoisomers obtained by

bromination of 1-butene is :
(A) 1 (B) 2 (C) 3 (D) 4
Sol.

Cl Cl
62. Statement-1 : C C C This compound
H H
will show geometrical isomerism.
59. isobutene + Br2  number of possible products
Statemen t-2 : Termi nal carb on g roup s are
(A) 1 (B) 2 (C) 3 (D) 4 perpendicular to each other.

14
 ISOMERISM Page # 15

(A) Statement-1 is true, statement-2 is true and Sol.

statement-2 is correct explanation for statement-1
(B) Statement-1 is true, statement-2 is true and
statement-2 is NOT correct explanation for statement-1
(C) Statement-1 is true, statement-2 is false
(D) Statement-1 is false, statement-2 is true
Sol.
65. Which of the following statement is/are not
correct?
(A) Metamerism belongs to the category of structural
63. Which of the following compounds is optically isomerism
active ? (B) Tautomeric structures are the resonating structures
of a molecule
NO2 HO2C (C) Keto form is always more stable than the enol
form
(A) (D) Geometrical isomerism is shown only by alkenes.
Sol.
NO2 HO2C

H3C H
(B)
H CO2H

NO2 HO2C
66. Which of the following statements is/are correct ?
(A) A meso compound has chiral centres but exhibits
no optical activity.
(C)
(B) A meso compound has no chiral centres and thus
CO2H O2N are optically inactive.
(C) A meso compound has molecules which are
CO2H superimposable on their mirror images even through
they contain chiral centres.
H OH (D) A meso compound is optically inactive because
HO H the rotation caused by any molecule is cancelled by
(D) an equal and opposite rotation caused by another
H OH molecule that is the mirror image of the first.
CO2H Sol.

Sol.

64. C4H6O2 does represent 67. Which of the following statements is/are not
(A) A diketone correct D-(+) glyceraldehyde ?
(B) A compound with two aldehyde (A) The symbol D indicates the dextrorotatory natures
(C) An alkenoic acid of the compound
(D) An alkanoic acid (B) The sign (+) indicates the dextrorotatory nature

15
 Page # 16 ISOMERISM

of the compound
CH3 OH
(C) The symbol D indicates that hydrogen atom lies
left to the chiral centre in the Fischer projection H OH
diagram. (I) (II) H CH3
(D) The symbol D indicates that hydrogen atom lies
right to the chiral centre in the Fischer projection CH=CH2 CH=CH2
diagram.
Sol. H
CH=CH2
HO CH=CH2
(III) H3C OH (IV)
CH3
H
(A) II and III (B) I and IV
(C) II and IV (D) III and IV
68. Which of the following compounds is optically Sol.
active ?
(A) 1-Bromobutane (B) 2-Bromobutane
(C) 1-Bromo-2-methylpropane
(D) 2-Bromo-2-methylpropane
Sol.

71. Which of the following statements for a meso

compound is/are correct ?
(A) The meso compound has either a plane or a point
of symmetry
69. Which of the following operations on the Fischer
(B) The meso compound has at least one pair of similar
CH3 stereocenters
(C) The meso compound is achiral
(D) The meso comopound is formed when equal
formula H OH does not change its absolute amounts of two enantiomers are mixed
Sol.
C 2 H5
configuration
(A) Exchanging groups across the horizontal bond
(B) Exchanging groups across the vertical bond
(C) Exchanging groups across the horizontal bond and
also across the vertical bond
(D) Exchanging a vertical and horizontal group.
Sol.

72. Which of the following compounds are optically

active ?
(A) [Link].CH2CH3
70. Which of the following combinations amongst the (B) H2C = CH . [Link] = CH2
four Fischer projections represents the same absolute H Cl
configurations ?
C C C
(C)
Cl H

16
 ISOMERISM Page # 17

COOH
O 2N

(D)

75. WHich of the following are D sugars.

HOOC
NO2
Sol. CHO CHO
H OH H OH
HO H HO H
(A) (B)
H OH H OH
H3C H H CH2OH
OH OH
73. Which of the following will show optical isomerism
as well as geometrical isomerism. OH CH2OH
C H3 H3C OHC H C O
CH3 CH3
HO H HO H
C C (C) (D)
(A) (B)
H OH H OH
H CH3
HO CH2OH H OH
H3C H3C H CH2OH
CH3 CH3
C C Sol.
(C) (D)
H3C H H3C CH3

Sol.

76. The Fi scher projection of the molecule as

represented in the wedge edge.
a
d
c
74. Which of the following are correct represents of is
b
L-amino acids X
NH 2 X X
COOH C
(A) d b (B) a b
(A) H2N H (B) H COOH
a d
CH2OH HOH 2 C
a X

OH (C) X b (D) b d
NH2 COOH
C d a
C H Sol.
(C) (D) C NH 2
H2 C
COOH H 3C
H
H
Sol.

18
 Page # 18 ISOMERISM

77. Given compound shows which type of isomerism CO2H

H OH
(C)
H OH

CO2H

and
OH
H
HO
(D) CH2NH2
(A) Chain isomerism
HO
(B) Positional isomerism
(C) Constitutional isomerism Column-II
(D) None (P) Total number of stereoisomers isodd for structure
Sol.
(Q) Total nubmer of streiosmers is even for the
structure
(R) Odd number of chiral centrec
(S) Even number of chiral centre
78. Which of following compound having plane of Sol.
symmetry

CO2H
H H
H OH
(A) (B)
H OH
OH OH
CO2H
80. Match the column:
CH2 Br Column-I
Cl H
C C Me COCH2CH2COOH
(C) (D) N
H Cl
Me Me

Sol. (A)
Br

Me

Me COCH2CH2COOH
N
79. Match the column: Me Me
Column-I
(B)
Br Br
O OH
H
Me
(A)
H Cl
CH3
(C) Me – CH – CH = C = CHCl
O
H
H
H
CH3 Me
(B) H (D)
3C C

H2C H
Me

18
 ISOMERISM Page # 19

Column-II Sol.
(P) Show optical isomerism
(Q) Show geometrical isomerism
(R) resolvable
(S) non-resolvable

Sol.

82. Match the column :

Column-I

81. Match the column:

Cl O
Column-I
Cl Cl (A)
Cl Cl Me

(A) Me Cl
Br

Cl Cl (B)
Cl Cl Br

Cl H Cl
C
(C)
(B) C
Cl Cl Cl H
Cl
COOH

Cl Cl H OH
(D)
HO H
(C)
COOH

Cl Cl Cl Cl Column-II
(P) Total number of stereo isomers are odd.
(Q) Total num ber of stereocentres are e ven
Cl Cl or have centre of symmetry
Cl (R ) Comp ound s havi ng s pl ane of s ym me try
or axis of symmetry
(D) Cl (S) Compounds have zero dipole in given form.
Cl Cl Sol.

Column-II
(P) Position isomers
(Q) Enantiomers
(R) Diastereomers
(S) Identical

19
 Page # 20 ISOMERISM

83. Match the column :

CH3
Column-I
H Br
CH3 H
H CH2OH and H 3C CH2NH2 84. H Cl
(A)
NH 2 OH H F

CH3
CH3 Cl
H Cl and H CH3 Number of enantiomeric pairs are
(B) (A) 2 (B) 4 (C) 8 (D) 10
Et Et Sol.

CH3 H
H OH and H 3C Et
(C)
Et OH

H5C 2 H 5C2
(D) and
85. (a) Cl (b) Cl
HO H H OH
Column-II
(P) Structural isomer
(Q) Identical
Cl Cl Cl Cl
(E) Enantiomers
Relation between (a) & (b) is
(S) Diastereomers
(A) Enantiomer (B) Diastereomer
Sol. (C) Identical (D) Structural isomer
Sol.

86. Compound has both center of symmetry and P.O.S

Cl
Cl Cl

Cl
(A) (B)

Cl Cl
Paragraph for Questions Nos. 84 to 86
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 (C) (D)
carrying four different groups is a steregoenic or chiral
centre.
A structure with a plane of symmetry is achiral Sol.
and superimposable on its mirror image and cannot
exist as two enantiomer. A structure without a plane
of symmetry is chiral and not superimposable on its
mirror image and can exist as two enantiomer.

20
 ISOMERISM Page # 21

EXERCISE – III JEE ADVANCED

1. What kind of reagent would be needed to resolve 3. Determine if the following pairs are identical,
a recemic amine, such as 2-aminobutane? isomers, enantiomers, or diastereomers.
(A) the pure optically active amine to serve as a HO
template forcrystallization. H NH2
OH
H 2N H
(B) an achiral carboxylic acid to give a recemic mixture (i) HO COOH
____
of amine salts. L-DOPA HOOC OH
(C) an enantiomerically pure chiral carboylic acid to
give a diastereomeric mixture of amine salts. CH2OH CH2OH
(D) a recemic chiral carboxylic acid to give a complete H OH H OH
mixture of isomeric amine salts.
Sol. H CH3 H3C H
(ii) _____________

(iii) _________

2. Determine if the following pairs are identical,

isomers, enantiomers, or diastereomers. Sol.
OH
OH OH HO
(i) ______

HO

OH
(ii) _______
4. Classify each of the following pairs of structure as
I. Identical E. Enantiomers. D. Diastereomers
CHO CH2OH CH = O CH = O
H OH HO H
H OH HO H
(iii) H OH HO H _____________ (a)
CH2OH CH3 CH3
CHO
Sol. CH = O CH = O

H OH HO H
(b) H OH H OH
CH3 CH3

Br Br
Br Br Br Br
(c) & Br
Br

21
 Page # 22 ISOMERISM

Sol. OH
OH
H H

(a) CH3 CH3_______

OH OH CH3
H H
CH3
5. Classify each of the following pairs of structure (b) _______
(a)-(e) as:
I. Identical E. Enantiomers. D. Diastereomers

CH3 CH3 OH
OH
H H
(a) H Br & Br H CH3 CH3
(c) ______

CH2CH3 CH2CH3
OH OH
CH3 CH2CH3 H H

(d) CH3 CH3______

H Cl
(b) &H CH3

CH2CH3 Cl
OH OH
H H
CH3 CH3
(e) CH3 CH3
_______
H Br H Br
(c) &
H Br Br H
Sol.
CH3 CH3

CH3 CH3

H Br Br H
(d) &
H Br Br H

CH3 CH3

Br Br
Br Br 7. State the relationship between each of the
following five (5) pairs of structures (identical,
(e) &
enantiomers, diastereomers, structural isomers,
Br Br conformational isomers, different compounds that are
not isomeric)
Sol.
O O
CH3 CH3
(a) _______
H3C H3C

O O
6. State the relationship between each of the
following five (5) pairs of structures (identical, CH3 CH3
enantiomers, diastereomers, structural isomers, (b) ______
different compounds that are not isomeric) H3C
H3C

22
 ISOMERISM Page # 23

Sol.
O O
CH3 CH3
(c) ______
H3C H3C

O O 9. Discuss the optical activity of the following two

CH3 H3C compounds and also lable them as polar and non polar.
CH3
(d) ______ Cl Cl Cl H

H3C H H H Cl
(I) (II)

O O
Sol.
CH3 H3C
(e) ______
H3C CH3

8. Select chiral molecule out of the following list

compound 10. (18) Now for some questions about stereochemical
H relationships.
CH3 Column A Circle the word (s) in this
HOOC OH
column that describe the
HO H molecules in column A.
(i) (ii)
HO H
O
COOH Br
(A) chiral achiral
meso none of these
H3C H

C C C
(iii) H3C H
(B) chiral achiral
meso none of these
OH

O
C C6H5
CH3
N
(iv) H (C) chiral achiral
N
meso none of these
HO2C CH3

CO2H OH

N N HO OH
(v)
(D) chiral a chiral
HO2C
meso none of these
(Azodiformic acid)

23
 Page # 24 ISOMERISM

ColumnB Circle one word in this colum 13. A compound with molecular formula C4H10O, can
that best describes the show metamerism, functional isomerism and positional
re l ati onshi p of the isomerism. Justify the statement.
molecules in columns A and B Sol.
CH3
(a) enantiomers diastereomers

Br identical none of these

H
H3C H

14. Calculate the total number of stereoisomers in

(b) HO enantiomers diastereomers
the following compounds.
identical none of these
CHO H H

CH3 CHOH
(I) (II) HOOC COOH
CHOH
(c) enantiomers diastereomers
CH2OH
CH3 identical none of these
OH
C OO H
HO OH
(d) enantiomers diastereomers C HO H
identical none of these (III) C HO H
Sol.
C HO H
C OO H
Sol.

11. A cyclobutandicarboxylic acid exist in two stereo-

isomeric forms in which one is polar but non-resolvable
whi l e other i s non-pol ar b ut resol vabl e i nto
enanti omers. Ded uce structures of al l these
compounds.
15. In what stereoisomeric forms would you expect
Sol. the following compounds to exist ?
(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H

(c) (d)
O
H H
12. How many isomers are possible for nitrophenol ? (e) C C C C (f) Et(Me)C=C=C(Me)Et
Sol. H H

I
Ph CO2H

(g) (h)

Ph CO2H Br

24
 ISOMERISM Page # 25

H 17. Considering rotation about the C-3 – C-4 bond of

2-methylhexane
(a) Draw the Newman projection of the most stable
(i) (j) confomrer
(b) Draw the Newman projection of the least stable
H confomrer
Cl
Sol.
H H

(k) e) C C C C
H H

O
Sol.

18. Determi ne whether each of the fol l owi ng

compounds is a cis isomer or a trans isomer.

Br
H H
H3C H
16. With reasons, state whether each of the following (a) Br Cl (b)
compounds I to VII is chiral.
H
Cl Cl

H H
H H
(I) (II)
Cl H Br
H CH3
(c) CH3 (d)
H Cl
Br H
Cl CO2H O O
(III) C C C (IV) H H
Cl Me
Cl
CH3 CH3 CH3
(e) (f)
Ph
H H
Sol.
Me
(V) (VI) S O
Ph
CO2H

Sol.

19. An object that has no element of symmetry is

called what?
(A) Tetrahedral (B) achiral
(C) symmetric (D) asymmetric

25
 Page # 26 ISOMERISM

Sol. 23. Calculate the number of aromatic isomeric amides

O
NH–C–CH3
possible of acetanilide

Sol.

20. Draw all the possible stereoi somers of 3-

pentene-2-ol.
Sol.

24. Calculate the number of isomeric ethers possible

OH

of

Sol.

21. Draw optically active stereo isomer of the following

compound.

Cl
Cl Cl

Cl Cl
Cl 25. How many pair(s) of geometrical isomers are
Sol. possible with C5H10(only in open chain structues)
Sol.

22. Calculate the number of aromatic 1º-amine

CH3
NH2
26. Total number of compounds with molecular formula
isomers possible of toluidine C5H10 which can show geometrical isomerism are (only
cyclic)?
Sol.
Sol.

26
 ISOMERISM Page # 27

27. How m any enat i ome rs are p os si be on 31. Total steroisomers of a given compound are ?
monochlorination of isopentane.
Me
Sol.
H CH=CH=CH-Me
(a) H D
CH=CH-Me

CH=CH-Me
NO2

(b)
COOH Me
28. Find out the total number of cyclic isomers of Sol.
C5H10 which are optically active?
Sol.

32. Mark each chiral center in the following molecules

with an esterisk. How many stereoisomers are possible
for each molecule?

29. Calculate the total number of open chain isomeric CH2–COOH

compounds of molecular formula C4H8O which can show CH3CHCHCOOH
geometrical isomerism. CH–COOH
(a) (b)
Sol. OH OH
HO–CH–COOH

OH

(c) (d)

O OH
(e) (f)
O COOH
OH
30. How many steroisomers exist for
(a) 3-methylcyclopentanol?
(b) 1,3-Cyclohexanediol? (g)
Sol. O
Sol.

27
 Page # 28 ISOMERISM

33. (a) Label the four chiral ceners in amoxicillin, which

Cl CH3 CH3 Cl
belongs to the family of semisynthetic penicillins.
O
(g) (h)
HO CH–C–HN S CH3 Cl Cl CH3
CH3
NH 2 N CH3 Sol.
O
C
HO O
Amoxicillin
(b) Mevacor is used clinically to lower serum chloesterol
levels. How many chirality centers does Mevacor have?
HO O 35. Are the following structures chiral as drawn ? When
placed in a solution at 298 K, which structure will
O show an optical rotation? Explain.
O

O
CH 3
CH3 (a) (b) (c)

H 3C
Mevacor
Sol. (d) (e) (f)

Sol.

36. Which of the following compounds are chiral ?

34. Among the following How many compounds are Which, if any, are meso ?
chiral ?

CH3

(a) (b)
CH3 CH3
CH3
(a) (b) (c) (d)

CH3
Sol.
(c) (d)
CH3 CH3
CH3

CH3 Cl CH3 Cl

(e) (f)
CH3 Cl CH3

28
 ISOMERISM Page # 85

37. Among of the following how many are meso (b) (i) 3,4-dimethylhexane
compounds ? (ii) 3,4-diethylhexane

H (c) (i) 1,3-dimethylcyclohexane

Br Br Br
CH 3 (ii) 1,4-dimethylcyclohexane
C C C C
(i) H H (ii) H (iii) 1,2-dimethylcyclohexane
Br
CH 3 CH 3 CH 3 Sol.

CH3
HO OH
CH3
(iii) (iv)
OH OH

CH2OH
CH3
HO H OH
(v) (vi) H OH 39. How many compounds among the following have
OH a stereoisomer that is achiral ?
CH2OH
(a) (i) 2,3-dichlorobutane
(ii) 2,3-dichloropentane
CHO CH2OH (iii) 2,3-dichloro-2,3-dimethylbutane
H OH HO H (b) (i) 1,2-dimethylcyclobutane
(ii) 1,3-dibromocyclobutane
(iii) 1,3-dichlorocyclopentane
(vii) (viii)
(iv) 1,2-dimethylcyclopentane
H OH H OH
CH 2OH CH2OH (c) (i) 2,4-dibromopentane
(ii) 2,3-dibromopentane
(iii) 1,4-dimethylcyclohexane
CH2OH
Sol.
H OH

(ix)
H OH
CH 2OH

Sol. 40. Are the formulas within each set identical,

enantiomers, or diastereomers ?

Cl H H Cl

(A) and
H OH HO H
38. Among the following compounds how many has
a stereoisomer that is a meso compound ? H Cl HO H
(a) (i) 2,3-dimethylbutane
(B) and
(ii) 2-bromo-3-methylpentane
(iii)1-bromo-2-methylcyclohexane H OH H Cl

85
 Page # 86 ISOMERISM

42. Following are stereorepresentations for the

H Cl HO H
three stereoisomers of 2,3-butanediol. The carbons
are numbered beginning from the left, as shown in
(C) and
(1).
HO H Cl H

Sol. HO H HO H H OH
4
1 2 3

H OH HO H HO H

(1) (2) (3)

41. Following are four Newman projection formulas
for tartaric acid. (a) Assign an R or S configuration to each chiral center.
(b) Which are enantiomers ?
COOH COOH (c) Which is the meso compound ?
H OH HO H (d) Which are diastereomers ?
Sol.

H OH H OH
COOH COOH

(1) (2)

COOH COOH

HOOC OH H COOH

HO H HO H
H OH

(3) (4)

43. Find out the total number of major products

(a) Which represent the same compound ? (including stereoisomers) are obtained in each of the
(b) Which represent enantiomers ? following reactions.
(c) Which represent a meso compound ? (i) (a) 1-butene + HCl x
(d) Which are diastereomers ?
(ii) 1-butene + HBr + peroxide y
Sol.
Find the value of (x + y) ?

H3C CH3
(ii) (a) C C + HBr x
H3C H

H3C CH3
(b) C C peroxide
 HBr    y
H3C H

86
 ISOMERISM Page # 87

(iii) (a) CH3CH2CH2CH = CH2 + HCl x Sol.

H H
(b) C C 
H
 H2O  y
CH 3CH2 CH2CH3

(c) + HBr z

H3C

Find the value of (x + y + z) ?

Sol.
45. Find out the total number of major products (in-
cluding stereoisomers) are obtained in each of the
following reactions.

CH3CH2 CH3
(i) (a) C C H2
 x
Pt
CH3 CH2CH3

CH3CH2 CH2CH3
(b) C C H2
 y
CH 3 CH3 Pt

H3C CH3
(c) C C Pt
+H2  z
H3C CH2CH 2CH 3

Find the value of (x + y + z) ?

44. Find out the total number of major products (in-

H2
cluding stereoisomers) are obtained in each of the (ii) (a)  x
Pt
CH 3 CH 3
following reactions.
(i) (a) cis-3-heptene+Br2 x
(b) trans-3-heptene + Br2 y Br2
(b)   y
CH2Cl2
(c) trans-3-hexene + Br2 z CH3 CH2CH3
Find the value of (x + y + z) ?

find the value of (x+y)?

Br2
(ii)   x Sol.
CH2Cl2
CH 3 CH 3

H2
(b)  y
Pt
CH3 CH2CH3

87
 Page # 88 ISOMERISM

EXERCISE – IV PREVIOUS YEARS

LEVEL – I JEE MAIN
Q.4 Geometrical isomerism is not shown by –
Q.1 Stereo - Isomerism includes - [AIEEE-2002]
[AIEEE-2002]
(A) 1, 1– dichloro–1–pentene
(A) Geometrical isomerism only
(B) 1, 2– dichloro–1–pentene
(B) Optical isomerism only
(C) Both geometrical & optical isomerism (C) 1, 3– dichloro–2–pentene
(D) Position & Functional isomerism (D) 1, 4– dichloro–2–pentene
Sol. Sol.

Q.2 Whi ch of the fol l owi ng does not s how

geometrical isomerism -
[AIEEE-2002]
(A) CH3 – CH = CH – CH3 Q.5 Racemic mixture is – [AIEEE-2002]
(B) CH3 – CH2 – HC = CH2 (A) A mixture of chiral carbons
(C) CH3 – C  CH – CH3 (B) A mixture of isomers
| (C) A mixture of aldehydes and ketones
Cl (D) A mixture of alcohols and ethers
(D) ClHC = CH – CH2 – CH3
Sol. Sol.

Q.3 Racemic mixture is formed by mixing two –

[AIEEE-2002] Q.6 Among the following four structures I to IV
(A) Isomeric compounds
(B) Chiral compounds
(C) Meso compounds (i) (ii)
(D) Enanitiomers with chiral carbon
Sol.
(iii) (iv)

It is true that – [AIEEE-2003]

(A) Only (iii) is a chiral compound
(B) Only (ii) and (iv) are chiral compounds
(C) All four are chiral compounds
(D) Only (i) and (ii) are chiral compounds

88
 ISOMERISM Page # 89

Sol. Sol.

Q.10 Increasing order of stability among the three

Q.7 Which of the following compounds is not main conformations (i.e. Eclipse, Anti, Gauche)
chiral ? [AIEEE-2004] of 2-fluoroethanol is [AIEEE 2006]
(A) 1 – chloropentane (A) Gauche, Eclipse, Anti
(B) 2 – chloropentane (B) Eclipse, Anti, Gauche
(C) 1 – chloro –2–methyl pentane (C) Anti, Gauche, Eclipse
(D) 3 – chloro – 2 – methyl pentane (D) Eclipse, Gauche, Anti
Sol. Sol.

Q.8 Which of the following will have a mesoisomer Q.11 Which of the following molecules is expected
also - [AIEEE-2004] to rotate the plane of plane-polarised light?
(A) 2 - Chlorobutane [AIEEE-2007]
(B) 2, 3 - Dichlorobutane
(C) 2,3 - Dichloropentane
(D) 2-Hydroxypropanoic acid (A) (B)
Sol.

COOH

H2N H
(C) (D)
H
Sol.

Q.9 Which types of isomerism is shown by 2,3–

dichlorobutane ? [AIEEE-2005]
(A) Optical (B) Diastereo
(C) Structural (D) Geometric

89
 Page # 90 ISOMERISM

Q.12 Which one of the following conformations of Q.15 The number of stereoisomers possible for a
cyclohexane is chiral ? compound of the molecular formula
[AIEEE-2007] CH3–CH=CH–CH(OH) –Me is :[AIEEE-2009]
(A) Twist boat (B) Rigid (A) 3 (B) 2
(C) Chair (D) Boat (C) 4 (D) 6
Sol. Sol.

Q.13 The absolute configuration of

HO2C CO2H Q.16 Out of the following, the alkene that exhibits
optical isomerism is [AIEEE-2010]
is (A) 3–methyl–2–pentene
OH (B) 4–methyl–1–pentene
HO H H
(C) 3–methyl–1–pentene
[AIEEE-2008] (D) 2–methyl–2–pentene
(A) R, R (B) R, S Sol.
(C) S, R (D) S, S
Sol.

Q.17 How many chiral compounds are possible on

monochlorination of 2–methyl butane?
Q.14 The alkene that exhibits geometrical isomer- (A) 4 (B) 6 [AIEEE-2012]
ism is : [AIEEE-2009] (C) 8 (D) 2
(A) propene Sol.
(B) 2-methyl propene
(C) 2-butene
(D) 2- methyl -2- butene
Sol.

90
 ISOMERISM Page # 91

LEVEL – II JEE ADVANCED

Sol.
1. The number of isomers for the compound with
molecular formular C2BrClFI is [JEE 2001(Scr.)]
(A) 3 (B) 4 (C) 5 (D) 6
Sol.

4. (i) µobs = µ x
i
i i

whre µi is the dipole moment of a stable conformer

of the molcule, Z – CH2 – CH2 – Z and xi is the mole
fraction of the stable conformer.
Given : µobs = 1.0 D and x (Anti) = 0.82
2. Which of the following compounds exshibits
Draw all the stable conformers of Z – CH2 – CH2 – Z
stereoisomerism ? [JEE 2002(Scr.)]
and calculate the value of µ(Gauche).
(A) 2-methylbutene-1 (B) 3-methylbutyne-1 (ii) Draw the stable conformer of Y – CHD – CHD – Y
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid (meso form), when Y = CH3 (rotation about C2 – C3)
Sol. and Y = OH (rotation about C1 – C2) in Newmann
projection. [JEE 2005]
Sol.

3. In the given conformation, if C2 is rotated about

C2 – C3 bond anticlockwise by an angle of 120° then
the conformational obtained is
[JEE 2004(Scr.)]

4
5. The number of structural isomers for C6H14 is
CH3
[JEE 2007]
H H (A) 3 (B) 4 (C) 5 (D) 6
3
2
Sol.
H H
1CH
3

(A) fully eclisped conformation

(B) partially eclipsed conformation
(C) gauche conformation
(D) staggered conformation

91
 Page # 92 ISOMERISM

6. Statemen t-1: M ol ec ul es t hat are not Sol.

superimposable on their mirror images are chiral.
because
Statement-2: All chiral moleculs have chiral centres.
[JEE 2007]
(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 i s NOT correct expl anati on for
statement-1
(C) Statement-1 is true, statement-2 is false
(D) Statement-1 is false, statement-2 is true
Sol.
8. The corre ct st atement(s) conce rni ng the
structures E, F and G is (are) [JEE 2008]

H3C O H3C OH

(E) (F)
H3C CH3 H3C CH3

H3C CH3

(G)
H3C OH
7. The correct statement(s) about the compuond (A) E, F and G resonance structures
given below is (are) [JEE 2008] (B) E, F and E, G are tautomers
Cl (C) F and G are geometrical isomers
H
(D) F and G are diastereomers
H3C Sol.
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

9. The correct statement(s) about the compound

H3C(OH)HC – CH = CH – CH (OH)CH3(X) is (are)
[JEE 2009]
(A) The total numbre 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.

92
 ISOMERISM Page # 93

Sol. 12. In the Newman projection for 2, 2-dimethylbutane

[JEE 2010]

X
H3 C CH3

H H
Y

X and Y cn respectively be
10. The total number of cyclic structural as well as (A) H and H (B) H and C2H5
stereo isomers possible for compound with the (C) C2H5 and H (D) CH3 and CH3
molecular formular C5H10 is [JEE 2009]
Sol.
Sol.

13. Amongst the given options, the compound(s) in

which all the atoms are in one plane in all the possible
11. The total number of cyclic isomers possible for a conformations (in any), is (are)
hydrocarbon with the molecular formula C4H6 is [JEE 2011]
[JEE 2010]
H H
Sol.
C C
(A)
H2C CH2

H C C C
(B)
CH2
(C) H2C = C = O
(D) H2C = C = CH2
Sol.

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 Page # 94 ISOMERISM

14. In Allene (C3H4), the type (s) of hybridisation of 17. Which of the given statement(s) about N, O, P
the carbon atoms is (are) [JEE 2012] and Q with respect to M is (are) correct?
(A) sp and sp3 (B) sp and sp2 [JEE 2012]
(C) only sp2 (D) sp2 and sp3
Sol. Cl
HO H HO H H
OH
HO Cl H CH3 HO
H OH H
CH3 Cl CH3
M N O

CH3 CH3
H OH HO H

HO H HO H
15. The number of optically active product obtained
from the complete ozonolysis of the given compound is Cl Cl
P Q
[JEE 2012]

CH3 H (A) M and N are non-mirror image stereoisomers

(B) M and O are identical
CH3–CH=CH–C–CH=CH–C–CH=CH–CH3
(C) M and P are enantiomers
H CH3 (D) M and Q are identical
Sol.
(A) 0 (B) 1 (C) 2 (D) 4
Sol.

[Link] of the following molecules in pure from is

(are) unstable at room temperature [JEE 2012]

O O

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

Sol.

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 ISOMERISM Page # 95

Answers
Answer Ex–I JEE MAIN
1. C 2. A 3. B 4. A 5. C 6. A 7. B

8. C 9. C 10. A 11. C 12. D 13. A 14. D

15. B 16. A 17. D 18. D 19. D 20. B 21. A

22. C 23. C 24. C 25. D 26. A 27. C 28. C

29. C 30. D

Answer Ex–II JEE ADVANCED (OBJECTIVE)

1. B 2. B 3. B 4. B 5. D 6. B 7. D

8. A 9. C 10. C 11. C 12. D 13. C 14. D

15. B 16. A 17. B 18. D 19. C 20. C 21. D

22. D 23. C 24. C 25. A 26. C 27. C 28. B

29. B 30. A 31. D 32. C 33. B 34. C 35. D

36. C 37. C 38. A 39. B 40. A 41. C 42. A

43. A 44. C 45. C 46. B 47. C 48. B 49. B

50. D 51. C 52. D 53. B 54. C 55. B 56. B

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 Page # 96 ISOMERISM

57. A 58. B 59. A 60. AD 61. ABC 62. D 63. BC

64. ABC 65. BCD 66. AC 67. AD 68. B 69. C 70. C

71. ABC 72. ACD 73. ACD 74. ACD 75. ACD 76. AC 77. BC

78. ABCD 79. (A) Q, S; (B) Q, S; (C) P, S; (D) Q, R 80. (A) P, R; (B) S; (C) P, R; (D) P, Q, S

81. (A) R, (B) P, (C) S, (D) S 82. (A) P, Q, R (B) Q, R, S (C) Q, R, S (D) P, Q, R

83. A P; B R; C Q; D R 84. B 85. B 86. D

Answer Ex–III JEE ADVANCED

1. c

2. (I) Diasteromers (ii) Enantiomers (iii) Identical

3. (I) Identical (ii) Diastereomers (iii) Diastereomers

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

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

6. (a) Diastereomers (b) diastereomers(c) not isomer (d) structural (e) Enantiomer

7. (a) Dia (b) Not isomer(c) Enenatiomers (d) Structural isomers (e) Identical

8. (i) achiral, (ii) achiral, (iii) Chiral, (vi) Chiral, (v) achiral

9. 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 non polar.

10. (A) Column (a) Chiral (b) chiral (c) meso (d) chiral
(B) Column (a) enantiomers (b) enantiomers (c) diastereomers (d) diastereomers

11. The compound must be 1, 2-cyclobutan-dicarboxylic acid since all other constitutional isomerers are
non-resovable.

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 ISOMERISM Page # 97

COOH
COOH

Polar but non-resolvable H H Non-polar

HOOC H

COOH
H
due to plane of but resolvable
symmetry
(cis-isomer) (trans-isomer)
12. 3

13. (i) Et –O – Et, (ii) CH3 – O – CH2 – CH2 – CH3 (iii) CH3 – CH2 – CH2 – CH2 – OH, (iv) CH3 CH2 CH CH3

OH
I and II metamers, I & III functional isomers, III & IV position isomers.

14. (I) 4, (II) 3, (III) 4

15. Optical : a, b, c, d, f, g, i, k; Geometrical isomer : c, g, j ; None : e, h,

16. achiral : I, III; chiral : II, IV, V, VI

Et

H H
H
17. (a) H (b)
H
H H
H H
H

18. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans

19. D

Me Me Me Me

H OH HO H H OH HO H

20. Total 4 H H Me Me

Me Me H H
D-Trans L-Trans D-cis L-cis

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 Page # 98 ISOMERISM

Cl
Cl Cl
21.

Cl Cl

Cl

22. 4 23. 9 24. 5 25. 1 26. 1 27. 2 28. 2 29. 2

30. (a) 4 (b) 3 31. (a) 16 (b) 4 32. (a) 4 (b) 4 (c) 2 (d) 8 (e) 4 (f) 4 (g) 4
33. (a) 4 (b) 8 34. 3 35. 2

36. chiral a, b ; meso c 37. 5 38. (a) 0 (b) 1 (c) 2

39. (a) 2 (b) 4 (c) 2 40. (a) enantiomer (b) enantiomer (c) diastereomers

41. (a) 3 & 4 (b) 1 & 3, 1 & 4 (c) 2 (d) 1 & 2, 2 & 3, 2 & 4

42. (a) 2R 3R, 2R 3S, 2S 3S (b) 1 & 3 (c) 2 (d) 1 & 2 ; 2 & 3

43. (i) 3 (ii) 3 (iii) 5 44. (i) 5 (ii) 4

45. (i) 5 (ii) 3

Answer Ex–IV PREVIOUS YEARS

LEVEL – I JEE MAIN
1. C 2. B 3. D 4. A 5. A 6. D 7. A

8. B 9. A 10. B 11. A 12. A 13. A 14. C

15. C 16. C 17. A

LEVEL – II JEE ADVANCED

1. D 2. D 3. C
1
4. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = -OH
0.18
5. C 6. C 7. AD 8. BCD 9. AD 10. 7 11. 5

12. BD 13. BC 14. B 15. A 16. BC 17. ABC

98