Exercise

ISOMERISM Page # 55
Exercise - I (Only one option is correct)

1. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are 6. The number of cis-trans isomer possible for the
(A) chain isomers (B) geometrical isomers following compound
(C) metamers (D) conformational isomers
Sol.
(A) 2 (B) 4 (C) 6 (D) 8

Sol.
2. C7H7Cl shows how many benzenoid aromatic

isomers?
(A) 4 (B) 3 (C) 5 (D) 6
Sol. 7. The number of isomers of dibromoderivative of an
alkene (molear mass 186 g mol–1) is
(A) 2 (B) 3 (C) 4 (D) 6
Sol.
3. How many minimum no. of C-atoms are required

for position & geometrical isomerism in alkene?
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3 8. Increasing order of stability among the three main
Sol. conformation (i.e. eclipse, anti, gauche) of ethylene
glycol is :
(A) Eclipse, gauche, anti
(B) Gauche, eclipse, anti
(C) Eclipse, anti, gauche
4. How many structural formula are possible when (D) Anti, gauche, elipse
one of the hydrogen is replaced by a chlorine atom in Sol.
anthracene?
(A) 3 (B) 7 (C) 4 (D) 6
Sol.
9. How many primary amines are possible for the

formula C4H11N?
(A) 2 (B) 3 (C) 4 (D) 5
Sol.
5. Which of the following connot be written in an
isomeric form?
(A) CH3 – CH(OH) – CH2 – CH3
(B) CH3 – CHO
(C) CH2 = CH – Cl
(D) Cl – CH2CH2 – Cl
Sol. 10. A pure simple of 2-chlorobutane shows rotation
of PPL by 30º in standard conditions. When above
sample is made impure by mixing its opposite form, so
that the composition of the mixture become 87.5% d-
form and 12.5% l-form, then what will be the observed
rotation for the mixture.
(A) –22.5º (B) +22.5º (C) +7.5º (D) –7.5º
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Page # 56 ISOMERISM
Sol. 14.
CH3 Cl
H Cl H Br
11. 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 Br H H CH3
& specific angle of rotation if above solution diluted to COOH COOH
1 Litre.
(A) 16º & 36º (B) 6º & 30º (A) Comformers (B) Diastereomers
(C) 3º & 30º (D) 6º & 36º (C) Enantiomers (D) Position isomers
Sol. Sol.
12. The R/S configuration of these compounds are

respectively.
HO 15. Geometrical isomers can be

H NH2
CF3 (A) Diastereomers or Enantiomers
HS
COOH (B) Structural isomers
(C) Inter convertable at room temprature.
H CH3 (D) none of these
CHO Sol.
(A) R, R, S (B) R, S, R (C) R, S, S (D) S, S, S

Sol.
16. Phenol and benzyl alcohol are

(A) functional isomers
13. How many planes (pos) are presents i n (B) Homologous
Anthracene (C) position isomers
(D) none of these
Sol.
Anthracene
(A) 1 (B) 2 (C) 3 (D) 6
Sol.
ISOMERISM Page # 57
Exercise - II (only one option is correct)
4. Am on g t he fo l l o w i n g , a p a i r of re s ol v a b l e
O OH O
configurational enantiomers is given by
1. S C CH C C CH3
H H (A) cis-1, 2-dimethylcyclohexane
(B) cis-1, 3-dimethylcyclohexane
(C) cis-1, 4-dimethylcyclohexane
Number of chiral centers are:
(D) trans-1, 3-dimethylcyclohexane
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
Sol.
5. Which two of the following compounds are identical ?
2. In the given following compound find out the pair OH

of enantiomers and diastereomers OH OH
OH O
(I) (II)
O O
R R' OH OH
R OH
(A) 2, 2 (B) 2, 4 (C) 4, 4 (D) 4, 2
OH OH
Sol.
HO OH OH
(III) (IV)
O O
OH
(A) I & II (B) II & IV (C) III & IV (D) I & III
Sol.
3. The molecule (s) that exist as meso structure(s)
(K) (L) (M)

6. Which two of the following compounds are
(A) only M (B) both K and L
diasteromers ?
(C) only L (D) only K
Sol. OH
OH OH
(I) (II)
O O
OH OH
OH
Page # 58 ISOMERISM
(A) I & II (B) II & III (C) III & IV (D) II & IV
OH OH Sol.
HO OH OH
(III) (IV)
O O
OH
(A) I & II (B) II & IV (C) III & IV (D) I & III
Sol.
9. Which of the follownig compounds is (S)–4-chloro-

1-methylcyclohexene ?
CH3 CH3
7. Which of the following is properly classified as a (A) (B)

meso compound ?
H Cl Cl
CH3
CH3
H OH HO
(A) (B) HO
H CH3 CH3
HO H CH3
CH3
C2H5 (C) (D)
C2H5
H OH Cl Cl
HO H
Sol.
(C) (D) H H
H OH
H OH
C2H5
CH3
Sol.
10. Which of the following compounds has two

stereogenic centers (asymmetric carbons) ?
Cl
8. Which two of the following compounds represents Cl Cl
a pair of enantiomers ?
(A) (B)
HO OH
Cl Cl
(I) (II)
HO OH O
HO OH O H
(III) (IV) (C) (D)

HO OH
H
H3C
ISOMERISM Page # 59
11. 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
14. What common symmetry of elements if any are
H H found in the stable chair conformer of trans-1, 2-
dichlorocyclohexane ?
(A) the cis and trans isomers rapidly interconvert.
(A) A single mirror plane and a C2 rotational axis.
(B) the compound is actually a meso structure.
(B) A single mirror plane & C3 rotational axis.
(C) the chair conformers rapidly interconvert producing
(C) Two orthogonal mirror planes and a C2 rotational
a recemic mixture.
axis.
(D) method for resolving alkyl chlorides are not available.
(D) A single C2 rotational axis but no mirror plane.
Sol.
Sol.
12. How many stereoisomers of (CH3)2CHCH =

15. Which of the following structures represents a
CHCH2CH(OH)CH2Br are possible ?
chiral compound ?
(A) 2 (B) 3 (C) 4 (D) 5
Sol. CH3 CH3 CH3 CH3
H H
(A) H C CH3
(B) H C CH3
3 3
H OH H CH3
CH3 CH3 CH3 CH3

H H3C
H
(C) (D)
H3C CH3 H3C CH3
HO OH H CH3
Sol.
13. What kind of reagent would be needed to resolve

a recemic amine, such as 2-aminobutane?
(A) the pure optically active amine to serve as a
template forcrystallization.
(B) an achiral carboxylic acid to give a recemic mixture
of amine salts.
(C) an enantiomerically pure chiral carboylic acid to
give a diastereomeric mixture of amine salts.
(D) a recemic chiral carboxylic acid to give a complete
mixture of isomeric amine salts. 16. Examine the compound on the right. How many
Sol.
Page # 60 ISOMERISM
stereoisomers having this constitution are possible ? following compound ?

CH3 NO2 MeBrHC
H3 C
O
H3C
CH3
Br
CH3 CH=CH-Me I
CH3 (A) 2 (B) 4 (C) 6 (D) 8
(A) 2 (B) 4 (C) 6 (D) 8 Sol.
Sol.
20. Which of the following will exhibit geometrical

17. How many stereoisomer are possible for the isomerism ?
following molecule ?
(A) 1-phenyl-2-butene
Cl
Br CH CH (B) 3-phenyl-1-butene
CH3 (C) 2-phenyl-1-butene
(D) 1, 1-diphenyl-1-propene
(A) 4 (B) 8 (C) 16 (D) 32 Sol.
Sol.
CH3
H Cl
21. Optical rotation produced by is 36° then
18. Which of the following heptanols are chiral 1- Cl H
heptanol, 2-heptanol, 3-heptanol, 4-heptanol. CH3
(A) All are chiral
(B) 2-heptanol and 3-heptanol CH3
(C) 2-heptanol, 3-heptanol & 4-heptanol H Cl
(D) 3-heptanol and 4-heptanol that product by is
H Cl
Sol.
CH3
(A) –36° (B) 0°

(C) +36° (D) upredictable
Sol.
19. How many stereoisomers are possible for the
ISOMERISM Page # 61
25. Dextrorotatory α-pinene has a specific rotaiton

CH3 Et [α]D20 = +51.3°. A sample of α-pinene containing both
the enantiomers was found to have a specific rotationa
22. (A) H OH (B) HO H value [α]D20 = +30.8°. The percentages of the (+) and
(–) enantiomers present in the sample are, respectively.
Et CH3
(A) 70% and 30% (B) 80% and 20%
(C) 20% and 80% (D) 60% and 40%
Relation between given pair is
Sol.
(A) Enantiomer (B) Diastereomer
(C) Identical (D) Structural isomer
Sol.
26. (+)-mandelic acid has a specific rotation of 158°.

What would be the observed specific rotation of a
mixture of 25% (–)-mandelic acid and 75% (+)-mandelic
23. Following eclipsed form of propane is repeated acid ?
after rotation of (A) +118.5° (B) –118.5°
(C) –79° (D) +79°
OH Sol.
O=–CH3
H
H HH
(A) 45º (B) 90º (C) 120º (D) 180º

Sol.
27. Number of structural isomers of compound having
molecular formula C4H7Cl.
(A) 4 (B) 8 (C) 12 (D) 16
Sol.
OH
OH
24. CH3 CH2 CH2 CH2 and CH3 C CH3 are
CH3
(A) chain isomers (B) positional isomers

(C) both (D) none
Page # 62 ISOMERISM
28. Stereoisomers differ from each other in what Sol.

respect ?
(A) Composition (B) constitution
(C) configuration (D) steric hindrance
Sol.
31. 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.
29. Which of the following sugars has the configuration reactivity)
(2S 3R, 4R) ? (D) they will have different physical properties.
Sol.
CHO CHO
H OH H OH
(A) H OH (B) HO H
H OH H OH
CH2OH CH2OH
32. How many stereoisomer may have this natural

CHO CHO occuring compound.
HO H HO H
O
(C) H OH (D) HO H
HO CH2 OH
H OH H OH
CH2OH CH2OH
HO CH=CH–CH=CH–CH2–CH2–CH3
Sol.
(A) 8 (B) 16 (C) 64 (D) 128
Sol.
30. Which of the following statements must be true

for two pure chiral isomers ?
(A) they must be enantiomers
33. An optically pure compoud X gave an [α]D25 =
(B) they must be diastereomers
+20.0°. A mixture of X and its enantiomer Y gave
(C) they must be stereoisomers
[α]D25 = +10°. The ratio of X to Y in the mixture is
(D) they must be optically active
(A) 2 : 1 (B) 1 : 3 (C) 3 : 1 (D) 1 : 2
ISOMERISM Page # 63
34. Molecular formular C3H6Br2 can have (including Sol.

stereoisomers):
(A) Two gem dibromide
(B) One vic dibromide
(C) Two tertiary dibromo alkane
(D) Two secondary dibromo alkane
Sol. 38. The number of optically active compounds in the
isomers of C4H9Br is
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
35. The number of isomers of C5H10 is

(A) 10 (B) 11 (C) 12 (D) 13
Sol.
CH3
H Cl
39. The compound with the above
HO H
C2H5
configuration is called.
(A) (2S, 3S)-2-chloro-3-hydroxypentane
(B) (2S, 3R)-2-chloro-3-hydroxypentane
36. Mesotartaric acid and d-tartaric acid are
(C) (2R, 3R)-2-chloro-3-hydroxypentane
(A) positon isomers (B) enantiomers (D) (2R, 3S)-2-chloro-3-hydroxypentane
(C) diastereomers (D) racemic mixture Sol.
Sol.
40. The prefered conformati on of trans-1, 2-

37. The nubmer of isomers of C3H5 Br3 (including dibromocyclohexane is:
stereoisomers)
(A) diaxial (B) diequatorial
(A) 4 (B) 5 (C) 6 (D) 7
(C) axial/equatorial (D) neither A, B nor C
Sol.
Sol.
Page # 64 ISOMERISM
41. How many stereoisomers of the following molecule Sol.

are possible? HOOC.CH=C=CH.COOH
(A) Two optical isomers
(B) Two geometrical isomers
(C) Two optical & two geometrical isomers
(D) None
Sol.
CO2H CO2H CO2H

H OH H OH HO H
44. (I) H OH (II) HO H (III) H OH
H OH H OH H OH
CO2H CO2H CO2H
42. The structures shown here are related as being
H Br CO2H
CO2H
C H OH
HO H
CH3 CH3 (IV) HO H (V) HO H
Br HO H
HO H
C H3C CO2H
C CO2H
Br H H
Which of the above formula represent identical
H3C compounds ?
C H (A) I and II (B) I and IV
Br (C) II and IV (D) III and IV
Sol.
(A) conformers
(B) enantiomorphs
(C) geometrical isomers
(D) diastereosiomers
Sol.
CO2H CO2H CO2H

45. (I) (II) (III)
H OH H OH HO H
H OH HO H H OH
H OH H OH H OH
CO2H CO2H CO2H
43. Which of the following cannot be written in an
isomeric form ? CO2H CO2H
(A) CH3 – CH(OH) – CH2 – CH3 HO H H OH
(B) CH3 – CHO (IV) HO H (V) HO H
(C) CH2 = CH – Cl HO H HO H
(D) Cl – CH2CH2 – Cl CO2H CO2H
ISOMERISM Page # 65
which of the above compounds are in enantiomers Ph Ph

(A) II & III (B) III & IV
(C) III & V (D) I & V H H
(D) H H
Sol.
COOH COOH
Sol.
46. H Cl H Cl
48. Number of possible 3D-isomers (Stereoisomer) of

glucose are
H Cl Cl H
(A) 10 (B) 14 (C) 16 (D) 20
The above compounds differ in Sol.
(A) configuration (B) conformation
(C) structure (D) chirality
Sol.
49. The compound C2H5OC2H5 and CH3OCH2CH2CH3 are

(A) enantiomers
(B) geometrical isomers
47. Which species exhibits a plane of symmetry ?
(C) metamers
COOH (D) conformational isomers
CH3 H
Sol.
H H H
(A)
H CH3
H H
(B)
OH H
H COOH
H H
(C) H H
H 50. Which of the following, compounds displays
HOOC
geometrical isomerism ?
H OH
(A) CH2 = CHBr (B) CH2 = CBr2
(C) ClCH = CHBr (D) Br2C = CCl2
Page # 66 ISOMERISM
Sol. 52. The number of optically active isomers observed

in 2,3-dichlorobutane is
(A) 0 (B) 2 (C) 3 (D) 4
Sol.
51. Match List I with List II and select the correct

answer from the codes given below the lists: List-I 53. How many total isomers are possible by replacing
O one hydrogens atoms of propane with chlorine
(A) 2 (B) 3 (C) 4 (D) 5
(A) CH3 C O CH2 CH2 CH3 and
O Sol.
H3C CH2 C O CH2 CH3
CH3 CH3
CH3
(B) and
54. On chlorination of propane number of products of

CH3
the formula C3H6Cl2 is
O OH (A) 3 (B) 4 (C) 5 (D) 6

Sol.
(C) and
O O HO OH
CHO H
(D) H C OH and H3C C CHO 55. The two compounds given below are
CH3 OH D Cl
H Br
I H
List II
H Cl D H
(1) Enantiomer (2) Position isomers
(3) Metamers (4) Tautomers
I Br
Codes:
(A) (B) (C) (D) (A) (B) (C) (D) (A) enantiomers (B) identical
(A) 3 2 4 1 (B) 3 2 1 4 (C) optically inactive (D) diastereosmers
(C) 1 2 3 4 (D) 2 3 4 1 Sol.
Sol.
ISOMERISM Page # 67
56. Which of the following will not show optical

isomerism.
(A) Cl – CH = C = C = CH – Cl
(B) Cl – CH = C = C = C = CH – Cl
O
H
COOH C O Cl
Cl H
(C) H OH (D) H3C
C C
H OH
Me Cl H
H
COOH
Me
Sol. (A) Functional group isomerism
(B) Geometrical isomerism
(C) Metamerism
(D) Position isomerism
Sol.
57. Given compound show which type of isomerism?
O
S O and
O
59. Which conformer of cyclohexane is chiral
(A) Chair (B) Boat
O
(C) Twisted boat (D) None of these
S O
Sol.
O
(A) Chain isomerism

(B) Positional isomerism
(C) Metamerism
(D) Functional group isomerism
Sol.
60. Which of following pair is Diastereomers:
CO2H CO2H
H OH
H OH
(A)
HO H H OH
58. Shows which type of isomerism
CO2H CO2H
O
Cl C O H
H CH3 CH3
and H
C C H3 C C Br C H
H CH3 (B) C C Br C C
H H CH3
H
Page # 68 ISOMERISM
Me
CH3 Et
Me
H OH HO H
(C) 3. H Incorrec t st at e me nt a bout t hi s
H SH HS H
H
Et CH3 compound is
(A) it shows geometrical isomerism
Cl Cl (B) it posses centre of symmetry
Cl Cl (C) it posses plane of symmetry

(D) (D) it shows optical isomerism
Cl Cl Sol.
Sol.
64. Minimum C atoms required for a compound to show

geometrical isomerism :
61. Sum of stereoisomer in the given compound (a) (A) 2 (B) 3
and (b) are: (C) 4 (D) None of these
Sol.
Cl Cl = a (stereoisomer)
Cl
= b (stereoisomer) a + b = ?
Cl
(A) 3 (B) 4 C2H5 CH3
(C) 5 (D) 6 H3C CH3 H C2H5
Sol. N
65. (I) (II) N
H H3C
CH3 CH3
CH3
Et H3C CH3
Keq.
Et (III)
62.
H H
Me
Me N
equilibrium constant for above reaction is: H C2H5
(A) K = 1 (B) K > 1 (C) K < 1 (D) K = 0
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
ISOMERISM Page # 69
(C) I & II are functional isomers while I & III are Sol.
conformational isomers
(D) None of these
Sol.
70. The number of stereoisomers obtained by

bromination of cis-2-butene is
(A) 1 (B) 2 (C) 3 (D ) 4
66. How many planes are presents in nepthalene Sol.
Nepthalene
(A) 1 (B) 2 (C) 3 (D) 6
71. The number of stereoisomers obtained by reaction
Sol. cis-2-butene with bromine in the presence of water is :
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
67. Total number of optically active alkyne possible

from molecular formula C3FClBrI 72. The number of stereoisomers obtained by
bromination of trans-2-butene is :
(A) 2 (B) 4 (C) 6 (D) 8
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
Sol.
68. Total number of geometrical isomer of given

compound will be
73. The number of stereoisomers obtained by
O O bromination of 1-butene is :
(A) 1 (B) 2 (C) 3 (D) 4
Sol.
(A) 2 (B) 4 (C) 6 (D) 8
Sol.
74. isobutene + Br2 → number of possible products

(A) 1 (B) 2 (C) 3 (D) 4
Sol.
69.
Number of geometrical isomer of given compound will

be :
(A) 2 (B) 3 (C) 4 (D) 5
Page # 70 ISOMERISM
Exercise - III (One or more than one option correct)
1. In which of the following molecule show chirality. (A) Statement-1 is true, statement-2 is true and
statement-2 is correct explanation for statement-1
Me (B) Statement-1 is true, statement-2 is true and
(I)
COOMe statement-2 is NOT correct explanation for statement-1
(C) Statement-1 is true, statement-2 is false
Me (D) Statement-1 is false, statement-2 is true
(II) Cl
Sol.
(A) I is trans & chiral (B) II is trans & chiral
(C) I is cis & chiral (D) II is trans & achiral
Sol. 4. Which of the following compounds is optically
active ?
NO2 HO2C
(A)
NO2 HO2C
2. Total number of stereoisomer is odd number for H3C H
(B)
H CO2H
(A) (B)
NO2 HO2C
CHO (C)
CO2H
H OH CO2H O2N
H OH CO2H
(C) (D)
H OH
H OH H OH
H OH HO H
CO2H (D)
CH2–OH H OH
Sol.
CO2H
Sol.
Cl Cl
3. Statement-1 : C C C This compound 5. C4H6O2 does represent
H H (A) A diketone
will show geometrical isomerism. (B) A compound with two aldehyde
Statemen t-2 : Termi na l ca rb on g roup s are (C) An alkenoic acid
perpendicular to each other. (D) An alkanoic acid
ISOMERISM Page # 71
Sol. (A) The symbol D indicates the dextrorotatory natures

of the compound
(B) The sign (+) indicates the dextrorotatory nature
of the compound
(C) The symbol D indicates that hydrogen atom lies
left to the chiral centre in the Fischer projection
diagram.
6. Which of the following statement is/are not (D) The symbol D indicates that hydrogen atom lies
correct? right to the chiral centre in the Fischer projection
(A) Metamerism belongs to the category of structural diagram.
isomerism Sol.
(B) Tautomeric structures are the resonating structures
of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes.
Sol.
9. Which of the following compounds is optically

active ?
(A) 1-Bromobutane (B) 2-Bromobutane
(C) 1-Bromo-2-methylpropane
(D) 2-Bromo-2-methylpropane
7. Which of the following statements is/are correct ? Sol.
(A) A meso compound has chiral centres but exhibits
no optical activity.
(B) A meso compound has no chiral centres and thus
are optically inactive.
(C) A meso compound has molecules which are
superimposable on their mirror images even through
they contain chiral centres. 10. Which of the following operations on the Fischer
CH3
(D) A meso compound is optically inactive because
the rotation caused by any molecule is cancelled by
an equal and opposite rotation caused by another formula H OH does not change its absolute
molecule that is the mirror image of the first.
Sol.
C2H5
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.
8. Which of the following statements is/are not

correct D-(+) glyceraldehyde ?
Page # 72 ISOMERISM
11. Which of the following combinations amongst the (A) CH3.CHOH.CH2CH3

four Fischer projections represents the same absolute (B) H2C = CH . CH2.CH = CH2
configurations ?
H Cl
CH3 OH C C C
(C)
Cl H
(I) H OH (II) H CH3
CH=CH2 CH=CH2 COOH

O 2N
H (D)
CH=CH2
HO CH=CH2 HOOC
(III) H3C OH (IV) NO2
CH3 Sol.
H
(A) II and III (B) I and IV
(C) II and IV (D) III and IV
Sol.
14. Which of the following will show optical isomerism

as well as geometrical isomerism.
C H3 H3C
CH3 CH3
12. Which of the following statements for a meso (A) C (B) C
compound is/are correct ? CH3
H
(A) The meso compound has either a plane or a point
H3C H3C
of symmetry CH3 CH3
(B) The meso compound has at least one pair of similar C C
(C) (D)
stereocenters
H3C H H3C CH3
(C) The meso compound is achiral
Sol.
(D) The meso comopound is formed when equal
amounts of two enantiomers are mixed
Sol.
15. Which of the following are correct represents of

L-amino acids
NH2
COOH C
(A) H2N H (B) H
13. Which of the following compounds are optically COOH
active ? CH2OH HOH2C
ISOMERISM Page # 73
OH a X
NH2 COOH
C (C) X b (D) b d
C H
(C) (D) C NH2 d a
H2C
COOH H3C
H Sol.
H
Sol.
18. Given compound shows which type of isomerism
16. WHich of the following are D sugars.
CHO CHO and

H OH H OH
HO H HO H
(A) (B) (A) Chain isomerism
H OH H OH
(B) Positional isomerism
H3C H H CH2OH
(C) Constitutional isomerism
OH OH (D) None
OH CH2OH Sol.
OHC H C O
HO H HO H
(C) (D)
H OH H OH
HO CH2OH H OH 19. Which of following compound having plane of

CH2OH symmetry
H
Sol.
CO2H
H H
H OH
(A) (B)
H OH
OH OH
CO2H
CH2 Br
17. The Fi scher projection of the molecule as
Cl H
represented in the wedge edge.
(C) C C (D)
a
H Cl
d
c
is Sol.
b
X
X X
(A) d b (B) a b
a d
Page # 74 ISOMERISM
Exercise - IV (One or more than one option correct)

Sol.
1. Determine if the following pairs are identical,
isomers, enantiomers, or diastereomers.
OH
OH OH HO
(i) ______
HO
OH 3. Classify each of the following pairs of structure as

(ii) _______ I. Identical E. Enantiomers. D. Diastereomers
CH = O CH = O
CHO CH2OH
H OH HO H
H OH HO H (a)
(iii) H OH HO H _____________ CH3 CH3
CH2OH 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
2. Determine if the following pairs are identical,

isomers, enantiomers, or diastereomers. Sol.
HO
H NH2
OH
H 2N H
(i) HO COOH
____
L-DOPA HOOC OH
CH2OH CH2OH
H OH H OH
H CH3 H3C H 4. Classify each of the following pairs of structure
(a)-(e) as:
(ii) _____________
I. Identical E. Enantiomers. D. Diastereomers
CH3 CH3
(a) H Br & Br H
(iii) _________
CH2CH3 CH2CH3
ISOMERISM Page # 75
OH OH
H H
CH3 CH2CH3
(d) CH3 CH3______
H Cl
(b) &H CH3
OH OH
CH2CH3 Cl H H
(e) CH3 CH3_______
CH3 CH3
Sol.
H Br H Br
(c) &
H Br Br H
CH3 CH3
CH3 CH3
H Br Br H
(d) &
H Br Br H
CH3 CH3 6. State the relationship between each of the

following five (5) pairs of structures (identical,
enantiomers, diastereomers, structural isomers,
Br Br
Br Br conformational isomers, different compounds that are
not isomeric)
(e) &
O O
Br Br
CH3 CH3
Sol. (a) _______
H3C H3C
O O
CH3 CH3
(b) ______
H3C
H3C
5. State the relationship between each of the O O
following five (5) pairs of structures (identical, CH3 CH3
enantiomers, diastereomers, structural isomers,
(c) ______
different compounds that are not isomeric)
OH OH H3C H3C
H H
O O
(a) CH3 CH3_______
CH3 H3C CH3
OH
(d) ______
OH CH3
H H
H3C
(b) CH3 _______ O O
CH3 H3 C
OH OH (e) ______
H H
CH3 CH3______ H3C CH3
(c)
Page # 76 ISOMERISM
7. Select chiral molecule out of the following list Sol.

compound
H
CH3
HOOC OH
HO H
(i) (ii)
HO H 9. (18) Now for some questions about stereochemical
O relationships.
COOH
Column A Circle the word (s) in this
column that describe the
molecules in column A.
C C C
(iii)
Br
(A) chiral achiral
meso none of these
H3C H
O
C H3C H
C6H5 (B) chiral achiral
N meso none of these
(iv) H OH
N
HO2C
CO2H
N N CH3
(v)
HO2C
(C) chiral achiral
(Azodiformic acid)
Sol. meso none of these
CH3
OH
HO OH
(D) chiral a chiral
meso none of these
8. Discuss the optical activity of the following two

compounds and also lable them as polar and non polar.
ColumnB Circle one word in
this colum
Cl Cl
that best describes the
H H re l a ti onshi p of the
(I) molecules in columns A and B
CH3
(a) enantiomers diastereomers
Br identical none of these

H
Cl H
H3C H
H Cl
(II)
(b) HO enantiomers diastereomers
identical none of these
ISOMERISM Page # 77
CH3 13. Calculate the total number of stereoisomers in

the following compounds.
CHO H H
(c) enantiomers diastereomers
CH3 identical none of these CHOH
OH
(I) (II) HOOC COOH
CHOH
HO OH
(d) enantiomers diastereomers CH2OH
identical none of these

COOH
Sol.
CHOH
(III) CHOH
CHOH
COOH
Sol.
10. 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.
Sol.
14. In what stereoisomeric forms would you expect

the following compounds to exist ?
(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H
(c) (d)
11. How many isomers are possible for nitrophenol ?
O
Sol.
H H
(e) C C C C (f) Et(Me)C=C=C(Me)Et

H H
I
Ph CO2H
12. A compound with molecular formula C4H10O, can

(g) (h)
show metamerism, functional isomerism and positional
isomerism. Justify the statement. Ph CO2H Br
Sol.
H
(i) (j)
394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564 H
Page # 78 ISOMERISM
16. Considering rotation about the C-3 – C-4 bond of

Cl 2-methylhexane
(a) Draw the Newman projection of the most stable
(k) confomrer
(b) Draw the Newman projection of the least stable
confomrer
O
Sol.
H H
e) C C C C
H H
Sol.
17. Determi ne whether each of the fol l owi ng

compounds is a cis isomer or a trans isomer.
Br
H H
H3C H
(a) Br Cl (b)
15. With reasons, state whether each of the following
compounds I to VII is chiral. H
Cl Cl H
H
Br
H H H CH3
(I) (II) (c) (d)
Cl CH3
H
Br H
H Cl
Cl CO2H O O
H H
(III) C C C (IV)
Cl Me Cl
CH3 CH3 CH3
(e) (f)
Ph
H H
Sol.
Me
(V) (VI) S O
Ph
CO2H
Sol.
18. An object that has no element of symmetry is

called what?
(A) Tetrahedral (B) achiral
(C) symmetric (D) asymmetric
ISOMERISM Page # 79
Sol.
19. Draw all the possible stereoi somers of 3-

pentene-2-ol.
Sol.
20. Draw optically active stereo isomer of the following

compound.
Cl
Cl Cl
Cl Cl
Cl
Page # 80 ISOMERISM
Exercise - V(A) (One or more than one option correct)

5. How many optically active stereoisomers are
1. True and False: [JEE 1985]
possible for butane-2, 3-diol ? [JEE 1997]
m-c hl orobromobenzene i s an i s omer of m -
(A) 1 (B) 2 (C) 3 (D) 4
bromochlorobenzene.
Sol.
Sol.
2. True or false [JEE 1990]

6. When cyclohexane is poured on water, it floats,
2, 3, 4-Trichloropentane has three asymmetric carbon
because [JEE 1997]
atoms.
Sol. (A) cyclohexane is in ‘boat’ form
(B) cyclohexane is in ‘chair’ form
(C) cylclohexane is in ‘crown’ form
(D) cyclohexane is less dense than water
Sol.
3. Isomers which can be interconverted through

rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers
(C) Enantiomers (D) Postitional isomers
Sol.
7. Which of the following compounds will show

geometrical isomerism ? [JEE 1998]
(A) 2-butene (B) propene
H3 C H (C) 1-phenylpropene (D) 2-methyl-2-butene
Sol.
C C H
4. The shows:[JEE 995(Scr.)]
H3 C C
COOH
CH3
(A) geometrical isomerism (B) optical isomerism

(C) geometrical & optical isomerism (D) tautomerism
Sol.
8. Which of the following compounds will exhibit
geometrical isomerism ? [JEE 2000(Scr.)]
(A) 1-Phenyl-2-butene
(B) 3-Phenyl-1-butene
(C) 2-Phenyl-1-butene
(D) 1, 1-Diphenyl-1-propene
ISOMERISM Page # 81
9. The number of isomers for the compound with 12. The number of structural isomers for C6H14 is
molecular formular C2BrClFI is [JEE 2001(Scr.)] [JEE 2007]
(A) 3 (B) 4 (C) 5 (D) 6 (A) 3 (B) 4 (C) 5 (D) 6
Sol. Sol.
10. Which of the following compounds exshibits 13. Statemen t-1: M ol ec ul es t ha t are not
stereoisomerism ? [JEE 2002(Scr.)] superimposable on their mirror images are chiral.
(A) 2-methylbutene-1 (B) 3-methylbutyne-1 because
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid Statement-2: All chiral moleculs have chiral
Sol. 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 is NOT correct expl anation for
statement-1
(C) Statement-1 is true, statement-2 is false
(D) Statement-1 is false, statement-2 is true
11. In the given conformation, if C2 is rotated about Sol.
C2 – C3 bond anticlockwise by an angle of 120° then
the conformational obtained is
[JEE 2004(Scr.)]
4
CH3
H H
3
2
H H
1 14. The correct statement(s) about the compuond
CH3
(A) fully eclisped conformation given below is (are) [JEE
(B) partially eclipsed conformation 2008]
(C) gauche conformation Cl H

(D) staggered conformation
H3 C
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
Page # 82 ISOMERISM
15. The corre ct st atement(s) conce rni ng the X

structures E, F and G is (are) [JEE 2008]
H3C CH3
H3C O H3C OH
(E) (F ) H H
H3 C CH3 H3C CH3 Y
X and Y cn respectively be
H3C CH3
(A) H and H (B) H and C2H5
(G) (C) C2H5 and H (D) CH3 and CH3
H3 C OH Sol.
(A) E, F and G resonance structures

(B) E, F and E, G are tautomers
(C) F and G are geometrical isomers
(D) F and G are diastereomers
Sol.
18. Amongst the given options, the compound(s) in

which all the atoms are in one plane in all the possible
conformations (in any), is (are)
[JEE 2011]
H H
16. The correct statement(s) about the compound C C

(A)
H3C(OH)HC – CH = CH – CH (OH)CH3(X) is (are) H2 C CH2
[JEE 2009]
(A) The total numbre of stereoisomers possible for X H
is 6
H C C C
(B) The total number of diastereomers possible for X (B)
is 3 CH2
(C) If the stereochemistry about the double bond in X
(C) H2C = C = O
is trans, the number of enantiomers possible for X is 4.
(D) H2C = C = CH2
(D) If the stereochemistry about the double bond in X
Sol.
is cis, the number of enantiomers possible for X is 2.
Sol.
19. In Allene (C3H4), the type (s) of hybridisation of

the carbon atoms is (are) [JEE 2012]
(A) sp and sp3 (B) sp and sp2
17. In the Newman projection for 2, 2-dimethylbutane (C) only sp2 (D) sp2 and sp3
[JEE 2010]
ISOMERISM Page # 83
Sol.
CH3 CH3
H OH HO H
HO H HO H
Cl Cl
P Q
20. The number of optically active product obtained (A) M and N are non-mirror image stereoisomers
from the complete ozonolysis of the given compound is (B) M and O are identical
[JEE 2012] (C) M and P are enantiomers
(D) M and Q are identical
CH3 H Sol.
CH3–CH=CH–C–CH=CH–C–CH=CH–CH3
H CH3
(A) 0 (B) 1 (C) 2 (D) 4

Sol.
21. Which of the following molecules in pure from is

(are) unstable at room temperature [JEE 2012]
O O
(A) (B) (C) (D)
Sol.
22. Which of the given statement(s) about N, O, P

and Q with respect to M is (are) correct?
[JEE 2012]
Cl
HO H HO H H
OH
HO Cl H CH3 HO
H OH H
CH3 Cl CH3
M N O
Page # 84 ISOMERISM
Exercise - V(B) (One or more than one option correct)

Sol.
1. Write structural formulae for all the isomeric
alcohols having the molecular formula C4H10O.
[JEE 1984]
Sol.
4. The total number of cyclic structural as well as

stereo isomers possible for compound with the
molecular formular C5H10 is [JEE 2009]
Sol.
2. Id enti fy t he p ai rs of enanti om er s and
diastereomers from the following compounds I, II and
III. [JEE 2000]
CH3 CH3 CH3

H OH HO H HO H
(I) (II) (III)
HO H HO H H OH
CH3 CH3 CH3
5. The total number of cyclic isomers possible for a
Sol. hydrocarbon with the molecular formula C4H6 is
[JEE 2010]
Sol.
3. (i) µobs = ∑µ xi
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
Draw all the stable conformers of Z – CH2 – CH2 – Z
and calculate the value of µ(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]
ISOMERISM Page # 85
Exercise - VI
1. Match the column:
Column-I Column-II
O OH
H
(A) (P) Total number of stereoisomers isodd for structure

H
CH3
O
H
H
CH3
(B) H (Q)Total nubmer of streiosmers is even for the structure
3C C
H2C
CO2H
H OH
(C) (R) Odd number of chiral centrec
H OH
CO2H
OH
H
HO
(D) CH2NH2 (S) Even number of chiral centre
HO
2 . M a t c h t h e c o l u m n :
Column-I Column-II
Me COCH2CH2COOH
N
Me Me
(A) (P) Show optical isomerism
Br
Me
Me COCH2CH2COOH
N
Me Me
(B) (Q) Show geometrical isomerism

Br Br
Me
Cl
(C) Me – CH – CH = C = CHCl (R) resolvable

H
Me
(D) (S) non-resolvable
H
Me
Page # 86 ISOMERISM
3. Match the column: 4. Match the column :

Column-I Column-I
Cl Cl
Cl Cl Cl O
(A) (A)
Me
Cl Cl
Me Cl
Cl Cl Br
Cl
(B)
Br
(B)
Cl Cl
H Cl
Cl C
(C)
C
Cl Cl Cl H
(C) COOH
H OH
Cl Cl Cl Cl (D)
HO H
COOH
Cl Cl Column-II
Cl (P) Total number of stereo isomers are odd.
(D) Cl (Q) Tota l num ber of stereocentres are e ven
Cl or have centre of symmetry
Cl
(R ) Comp ound s ha vi ng s pl ane of s ym me try
Column-II or axis of symmetry
(P) Position isomers (S) Compounds have zero dipole in given form.
(Q) Enantiomers Sol.
(R) Diastereomers
(S) Identical
Sol.
ISOMERISM Page # 87
5. Match the column : CH3

Column-I H Br
CH3 H 6. H Cl
H CH2OH and H3C CH2NH2
(A) H F
NH2 OH CH3
Number of enantiomeric pairs are
CH3 Cl (A) 2 (B) 4 (C) 8 (D) 10
H Cl and H CH3
(B) Sol.
Et Et
CH3 H
H OH and H3C Et
(C)
Et OH
H5C2 H5C2
and
(D)
HO H H OH
Column-II 7. (a) (b) Cl
Cl
(P) Structural isomer
(Q) Identical
(E) Enantiomers
(S) Diastereomers Cl Cl Cl Cl
Sol. Relation between (a) & (b) is
(A) Enantiomer (B) Diastereomer
(C) Identical (D) Structural isomer
Sol.
8. Compound has both center of symmetry and P.O.S
Cl
Cl Cl
Paragraph for Questions Nos. 6 to 8
If a molecule contains one carbon atom carrying Cl
(A) (B)
four different groups it will not have a plane of
symmetry and must therefore be chiral. A carbon atom Cl
Cl
carrying four different groups is a steregoenic or chiral
centre.
A structure with a plane of symmetry is achiral
and superimposable on its mirror image and cannot
exist as two enantiomer. A structure without a plane (C) (D)
of symmetry is chiral and not superimposable on its
mirror image and can exist as two enantiomer.
Page # 88 ISOMERISM
Exercise - VII Subjective

Sol.
1. Calculate the number of aromatic 1º-amine
CH3
NH2
isomers possible of toluidine
2. Calculate the number of aromatic isomeric amides

O 6. H ow m any enat i ome rs a re p os si be on
NH–C–CH3 monochlorination of isopentane.
possible of acetanilide Sol.
3. Calculate the number of isomeric ethers possible
OH
of
7. Find out the total number of cyclic isomers of

Sol.
C5H10 which are optically active?
Sol.
4. How many pair(s) of geometrical isomers are

possible with C5H10(only in open chain structues)
8. Calculate the total number of open chain isomeric
Sol.
compounds of molecular formula C4H8O which can show
geometrical isomerism.
Sol.
5. Total number of compounds with molecular formula

C5H10 which can show geometrical isomerism are (only
cyclic)?
ISOMERISM Page # 89
9. How many steroisomers exist for

(a) 3-methylcyclopentanol?
(b) 1,3-Cyclohexanediol?
(e)
Sol. O COOH
O OH
(f) (g)
OH O
Sol.
10. Total steroisomers of a given compound are ?
Me
H CH=CH=CH-Me
(a) H D
CH=CH-Me
NO2 CH=CH-Me
(b)
COOH Me
Sol.
12.(a) Label the four chiral ceners in amoxicillin, which

belongs to the family of semisynthetic penicillins.
O
HO CH–C–HN S
CH3
NH2 N CH3
O
C
11. Mark each chiral center in the following molecules HO O
with an esterisk. How many stereoisomers are possible Amoxicillin
for each molecule? (b) Mevacor is used clinically to lower serum chloesterol
levels. How many chirality centers does Mevacor have?
CH2–COOH
HO O
CH3CHCHCOOH
CH–COOH
(a) (b) O
OH OH
HO–CH–COOH O
O
OH CH3
CH3
(c) (d)
H3C
Mevacor
Page # 90 ISOMERISM
Sol.
(d) (e) (f)

Sol.
13. Among the following How many compounds are

chiral ?
15. Which of the following compounds are chiral ?
CH3 Which, if any, are meso ?
(a) (b)
CH3 CH3
CH3
CH3
(a) (b) (c) (d)
(c) (d) Sol.

CH3 CH3
CH3
CH3 Cl CH3 Cl
(e) (f)
CH3 Cl CH3
16. Among of the following how many are meso

Cl CH3 CH3 Cl compounds ?
(g) (h) Br Br Br H
CH3 Cl CH3 CH3
Cl C C C C
(i) H H (ii) H
Sol. Br
CH3 CH3 CH3
CH3
HO OH
CH3
(iii) (iv)
OH OH
CH2OH
14. Are the following structures chiral as drawn ? When
placed in a solution at 298 K, which structure will CH3
HO H OH
show an optical rotation? Explain.
(v) (vi) H OH
OH
CH2OH
(a) (b) (c)
ISOMERISM Page # 91
(ii) 1,3-dibromocyclobutane
CHO CH2OH
(iii) 1,3-dichlorocyclopentane
H OH HO H (iv) 1,2-dimethylcyclopentane
(c) (i) 2,4-dibromopentane
(ii) 2,3-dibromopentane
(vii) (viii)
H OH H OH (iii) 1,4-dimethylcyclohexane
CH2OH CH2OH Sol.
CH2OH
H OH
(ix)
H OH
CH2OH
Sol.
19. Are the formulas within each set identical,
enantiomers, or diastereomers ?
Cl H H Cl
(A) and
H OH HO H
H Cl HO H
17. Among the following compounds how many has (b) and
a stereoisomer that is a meso compound ?
H OH H Cl
(a) (i) 2,3-dimethylbutane
(ii) 2-bromo-3-methylpentane H Cl HO H
(iii)1-bromo-2-methylcyclohexane
(C) and
(b) (i) 3,4-dimethylhexane
(ii) 3,4-diethylhexane HO H Cl H
(c) (i) 1,3-dimethylcyclohexane Sol.
(ii) 1,4-dimethylcyclohexane
(iii) 1,2-dimethylcyclohexane
Sol.
20. Following are four Newman projection formulas

for tartaric acid.
18. How many compounds among the following have

a stereoisomer that is achiral ? COOH COOH
(a) (i) 2,3-dichlorobutane H OH HO H

(ii) 2,3-dichloropentane
(iii) 2,3-dichloro-2,3-dimethylbutane
(b) (i) 1,2-dimethylcyclobutane H OH H OH
COOH COOH
394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482,

(1) 93527-21564 (2)
Page # 92 ISOMERISM
H3C CH3
COOH COOH
(b) C C peroxide
+ HBr   → y
HOOC OH H COOH H3C H
(iii) (a) CH3CH2CH2CH = CH2 + HCl → x
H H
HO H HO H
(b) C C H +
H OH + H2O → y
CH3CH2 CH2CH3
(3) (4)
(a) Which represent the same compound ? (c) + HBr → z

(b) Which represent enantiomers ? H3C
(c) Which represent a meso compound ?
Find the value of (x + y + z) ?
(d) Which are diastereomers ?
Sol.
Sol.
21. Following are stereorepresentations for the

three stereoisomers of 2,3-butanediol. The carbons
are numbered beginning from the left, as shown in
(1). 23. Find out the total number of major products (in-
cluding stereoisomers) are obtained in each of the
HO H HO H H OH following reactions.
4 (i) (a) cis-3-heptene+Br2 → x
1 2 3 (b) trans-3-heptene + Br2 → y
H OH HO H HO H (c) trans-3-hexene + Br2 → z
(1) (2) (3)
(a) Assign an R or S configuration to each chiral center.

(b) Which are enantiomers ? (ii) Br2
 → x
CH2Cl2
(c) Which is the meso compound ? CH3 CH3
(d) Which are diastereomers ?
22. Find out the total number of major products
(including stereoisomers) are obtained in each of the (b) H2
→ y
Pt
following reactions. CH3 CH2CH3
(i) (a) 1-butene + HCl → x Sol.
(ii) 1-butene + HBr + peroxide → y
Find the value of (x + y) ?
H3C CH3
(ii) (a) C C + HBr → x
H3C H
ISOMERISM Page # 93
24. 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
CH3 CH3 Pt
H3C CH3
(c) C C Pt
+H2 → z
H3 C CH2CH2CH3
H2
(ii) (a) → x
Pt
CH3 CH3
Br2
(b)  → y
CH2Cl2
CH3 CH2CH3
find the value of (x+y)?
Sol.
Page # 94 ISOMERISM
Page # 94 ISOMERISM
Answers
Exercise-I
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
Ans. C A B A C A B C C B B A C D A D
Exercise-II
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. B B B D B D A C A D C C C D D D C B D A
Qus. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. B C C A B D C C C D D C C A D C C B A B
Qus. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. A D C B C C D C C C A B A C A A C C C B
Qus. 61 62 63 64 65 66 67 68 69 70 71 72 73 74
Ans. C B B D D C D B C B B A B A
Exercise-III
1. AD 2. ABC 3. D 4. BC 5. ABC 6. BCD 7. AC 8. AD 9. B

10. C 11. C 12. ABC 13. ACD 14. ACD 15. ACD 16. ACD 17. AC 18. BC
19. ABCD
Exercise-IV
1. (I) Diasteromers (ii) Enantiomers (iii) Identical

2. (I) Identical (ii) Diastereomers (iii) Diastereomers
3. (a) E (b) D (c) I
4. (a) E (b) I (c) D (d) I (e) E
5. (a) Diastereomers (b) diastereomers (c) not isomer (d) structural
(e) Enantiomer
6. (a) Dia (b) Not isomer (c) Enenatiomers (d) Structural isomers
ISOMERISM Page # 95
(e) Identical
7. (i) achiral, (ii) achiral, (iii) Chiral, (vi) Chiral, (v) achiral
8. 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.
9. (A) Column (a) Chiral (b) chiral (c) meso (d) chiral
(B) Column (a) enantiomers (b) enantiomers (c) diastereomers (d) diastereomers
10. The compound must be 1, 2-cyclobutan-dicarboxylic acid since all other constitutional isomerers are non-
resovable.
COOH COOH
HOOC H Polar but non-resolvable H H Non-polar

due to plane of but resolvable
symmetry COOH
H
(cis-isomer) (trans-isomer)
11. 3
12. (i) Et –O – Et, (ii) CH3 – O – CH2 – CH2 – CH3 (iii) CH3 – CH2 – CH2 – CH2 – OH, (iv) CH3 CH2 CH CH3 I and
OH
II metamers, I & III functional isomers, III & IV position isomers.
13. (I) 4, (II) 3, (III) 4
14. Optical : a, b, c, d, f, g, i, k; Geometrical isomer : c, g, j ; None : e, h,
15. achiral : I, III; chiral : II, IV, V, VI
Et
H H
H
16. (a) H (b)
H
H H
H H
H
17. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans
18. D
Me Me Me Me
H OH HO H H OH HO H
19. Total 4 H H Me Me
Me Me H H
D-Trans L-Trans D-cis L-cis
Page # 96 ISOMERISM
Cl
Cl Cl
20.
Cl Cl
Cl
EXERCISE - V (A)
1. False 2. True 3. A 4. B 5. B 6. D 7. A, C 8. A 9. D
10. D 11. C 12. C 13. C 14. A, D 15. B, C, D 16. A, D 17. B, D 18. B, C
19. B 20. A 21. BC 22. ABC
EXERCISE - V (B)
1. 4 2. enantiomers-I & III; diastereomers-I & II and II & III
1
3. (i) D (ii) Anti form when Y = CH3 & Gauche when Y = -OH
0.18
4. 7 5. 5
EXERCISE - VI MATRIX
1. (A) Q, S; (B) Q, S; (C) P, S; (D) Q, R 2. (A) P, R; (B) S; (C) P, R; (D) P, Q, S

3. (A) R, (B) P, (C) S, (D) S 4. (A) P, Q, R (B) Q, R, S (C) Q, R, S (D) P, Q, R
5. A → P; B → R; C → Q; D → R 6. B 7. B 8. D
EXERCISE - VII SUBJECTIVE

1. 4 2. 9 3. 5 4. 1 5. 1 6. 2 7. 2 8. 2
9. (a) 4 (b) 3 10. (a) 16 (b) 4 11. (a) 4 (b) 4 (c) 2 (d) 8 (e) 4 (f) 4 (g) 4
12. (a) 4 (b) 8 13. 3 14. 2
15. chiral → a, b ; meso → c 16. 5 17. (a) 0 (b) 1 (c) 2
18. (a) 2 (b) 4 (c) 2 19. (a) enantiomer (b) enantiomer (c) diastereomers
20. (a) 3 & 4 (b) 1 & 3 (c) 2 (d) 1 & 2, 2 & 3, 2 & 4
21. (a) 2R 3R, 2R 3S, 2S 3S (b) 1 & 3 (c) 2 (d) 1 & 2 ; 2 & 3
22. (i) 3 (ii) 3 (iii) 5 23. (i) 5 (ii) 4
24. (i) 5 (ii) 3

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ISOMERISM Page # 55

Exercise - I (Only one option is correct)

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

2. C7H7Cl shows how many benzenoid aromatic

3. How many minimum no. of C-atoms are required

9. How many primary amines are possible for the

12. The R/S configuration of these compounds are

HO 15. Geometrical isomers can be

(A) R, R, S (B) R, S, R (C) R, S, S (D) S, S, S

16. Phenol and benzyl alcohol are

Exercise - II (only one option is correct)

5. Which two of the following compounds are identical ?

2. In the given following compound find out the pair OH

(K) (L) (M)

9. Which of the follownig compounds is (S)–4-chloro-

7. Which of the following is properly classified as a (A) (B)

10. Which of the following compounds has two

(III) (IV) (C) (D)

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

12. How many stereoisomers of (CH3)2CHCH =

CH3 CH3 CH3 CH3

13. What kind of reagent would be needed to resolve

stereoisomers having this constitution are possible ? following compound ?

20. Which of the following will exhibit geometrical

(A) –36° (B) 0°

19. How many stereoisomers are possible for the

25. Dextrorotatory α-pinene has a specific rotaiton

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

(A) 45º (B) 90º (C) 120º (D) 180º

(A) chain isomers (B) positional isomers

28. Stereoisomers differ from each other in what Sol.

31. Which of the following statements is true for a

32. How many stereoisomer may have this natural

30. Which of the following statements must be true

34. Molecular formular C3H6Br2 can have (including Sol.

35. The number of isomers of C5H10 is

40. The prefered conformati on of trans-1, 2-

41. How many stereoisomers of the following molecule Sol.

CO2H CO2H CO2H

42. The structures shown here are related as being

CO2H CO2H CO2H

which of the above compounds are in enantiomers Ph Ph

48. Number of possible 3D-isomers (Stereoisomer) of

49. The compound C2H5OC2H5 and CH3OCH2CH2CH3 are

Sol. 52. The number of optically active isomers observed

51. Match List I with List II and select the correct

H3C CH2 C O CH2 CH3

54. On chlorination of propane number of products of

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

56. Which of the following will not show optical

57. Given compound show which type of isomerism?

(A) Chain isomerism

60. Which of following pair is Diastereomers:

Cl Cl (B) it posses centre of symmetry

Cl Cl (C) it posses plane of symmetry

64. Minimum C atoms required for a compound to show

70. The number of stereoisomers obtained by

67. Total number of optically active alkyne possible

68. Total number of geometrical isomer of given

74. isobutene + Br2 → number of possible products

Number of geometrical isomer of given compound will

Exercise - III (One or more than one option correct)