ISOMERISM

Preface

As you have gone through the theory part that consists of given fundamental principles,
definitions, concepts involved and solved problems. After going through theory part it
becomes necessary to solve the unsolved problems based on the concepts given. To
solve this purpose we are providing exercise part that comprises of various exercises
based on the theory. By solving various kinds of problems you can check your grasp on
the topic and can determine whether you have been able to find optimum depth in relevant
topic or not.

Students are advised to solve the questions of exercises (Levels # 1, 2, 3, 4) in the same
sequence or as directed by the faculty members, religiously and very carefully.
Level # 3 is not for foundation course students, it will be discussed in fresher or target
courses.

Total No.of questions in Isomerism are -

Level # 1 ....................................................................................... 64
Level # 2 ........................................ ........................................... 50
Level # 3 ........................................ ........................................... 43
Level # 4 ........................................ ........................................... 34

Total No. of questions .............................................................. 191

22
 LEVEL # 1
Questions Q.9 Possible number of disubstituted benzene
based on Structural Isomerism isomers is –
(A) 1 (B) 2
Q.1 The name of which carbon chain starts from (C) 3 (D) 4
'iso' in the following chains –
CC Q.10 Which of the following are isomers -
CCC |
(A) | (B) C  C  C  C (A) Ethanol and ethoxy ethane
CCC (B) Methanol and methoxy methane
CC (C) Propanoic acid and ethyl acetate
| | C CC
(C) C  C  C  C (D) (D) Propionaldehyde and acetone
| |
CCC
Q.11 Functional isomer of CH3COOCH3 is –
Q.2 The total possible number of chain isomers for
(A) CH3CH2COOH
the molecular formula C5H12 would be –
(B) HOCH2—CH2CHO
(A) 3 (B) 2 (C) 4 (D) 5
(C) Both of the above
Q.3 Out of following carbon chains which one is (D) None of the above
different from other three chains –
Q.12 How many aliphatic carbonyl compounds are
(A) (B) possible having the molecular formula
C5H10O –
(C) (D) (A) 4 (B) 5 (C) 6 (D) 7

Q.13 & are –

Q.4 2-chlorobutane & 3-chlorobutane are-
(A) Tautomers (B) Functional
(A) Positional isomers (B) Chain isomers (C) Position (D) All the above
(C) Geometrical (D) None
Q.14 O - Cresol & benzyl alcohol are –
Q.5 The total number of isomeric tolyl groups are – (A) Functional (B) Position
(A) 1 (B) 2 (C) 3 (D) 4 (C) Chain (D) All the above

Q.6 Which one of the following pairs are called Q.15 CH3CONH2 & HCONHCH3 are called –
position isomers – (A) Position (B) Chain
(A) CH2 (OH) CH2COOH & (C) Tautomers (D) Functional
CH3 - CH (OH) COOH
(B) C2H5OH & CH3OH
Q.16 The formula C4H8O2 represents –
(C) (C2H5)2CO & CH3COCH2CH2CH3
(D) All the above (A) Only an acid
(B) Only an ether
Q.7 & are called as – (C) Only an alcohol
(D) Both ether and alcohol
(A) Position isomers (B) Chain isomers
(C) Function isomers (D) Ring chain isomers Q.17 Propene and cyclopropane are –
(A) Chain isomers
Q.8 Methyl propyl thioether and isopropyl methyl (B) Position isomers
thioether are – (C) Geometrical isomers
(A) Metamers (D) None of the above
(B) Position isomers
(C) Chain isomers Q.18 The number of ether metamers represented
(D) Chain and position both by the formula C4H10O is -
(A) 4 (B) 3 (C) 2 (D) 1

23
Q.19 Metamerism is shown by - Q.25 Ethyl acetoacetate shows -
(A) Diethyl ether and n-propyl methyl ether (A) Enantiomorphism
(B) Ethyl alcohol and diethyl ether (B) Geometrical isomerism
(C) Acetone and propionaldehyde (C) Diastereoisomerism
(D) Propionic acid and acetic acid (D) Keto-enol tautomerism

Q.20 Which of the following pairs of compounds are Q.26 W hich of the following does not show
not metamers ? tautomerism ?
(A) CH3OCH2CH2CH3 and CH3CH2OCH2CH3 (A) C6H5COCH3
(B) CH3CH2OCH2CH3 and CH3OCH(CH3)2 (B) CH3CHO
(C) CH3NHCH2CH2CH3 and (C) CH3COCH3
CH3CH2NHCH2CH3 (D) C6H5COC(CH3)3
(D) CH3NHCH2CH2CH3 and
CH3NHCH(CH3)2 Q.27 Which of the following shows tautomerism ?
(A) Benzophenone
Questions
Tautomerism (B) Benzaldehyde
based on
(C) Di-tert butyl ketone
(D) None of the above
Q.21 The phenomenon involving the migration of a
proton to give two structural isomers in Q.28 In keto-enol tautomerism of dicarbonyl
equilibrium with each other is known is – compounds, the enol form is preferred in
(A) Matamerism (B) Tautomerism contrast to the keto-form, this is due to
(C) Cis trans isomerism(D) Stereo isomerism (A) Presence of carbonyl group on each side
of –CH2–
Q.22 In which pair of following tautomers called as (B) Resonance stabilization of enol form
Diad system – (C) Presence of methylene group
(A) H - O - C  N O = C = N - H (D) Rapid chemical exchange.
(B) H - C  N C N-H
(C) CH3 - CH2 - CH = O  CH3 - CH = CH - OH Q.29 Urea and thiourea exhibits -
(D) CH3 - COCH2COOC2H5 (A) Metamerism
 CH3 - C = CH - COOC2H5 (B) Tautomerism
(C) Functional isomerism
Q.23 Which of the following compounds can exhibit (D) Geometrical isomerism
tautomerism

CHO COCH 3 Q.30 Keto – enol tautomerism is an example of –

(A) (B) (A) Anionotropism (B) Cationotropism
(C) Prototropism (D) Resonance
NO 2
(C) (D) CH 3 -CH -CH 3 Questions
Geometrical Isomerism
based on
|
NO 2
Q.31 Which of the following compounds will show
Q.24 Tautomerism is exhibited by - geometrical isomerism -
(A) 2-Butene (B) Propene
(A) CH = CH - OH (C) 1-Phenylpropene (D) Both A & C

Q.32 Geometrical isomerism is due to -

(B) O
(A) The resticted rotation about a double bond
O (B) The presence of keto group
(C) The presence of CH(OH) group
(C) O (D) The presence of an asymmetric carbon
O

(D) All the above

24
Q.33 Which is a pair of geometrical isomers ? Q.39 Which of the following will show geometrical
Cl Br isomerism ?
I. C=C
H Br (A) 1-Butene (B) 1,2-Dibromoethene
Cl (C) Propene (D) Isobutylene
Br
II. C=C
H CH3 Q.40 Maleic acid and fumaric acid are -
(A) position isomers
Cl CH3
III. C=C (B) Functional isomers
Br H (C) Geometrical isomers
H Br (D) optical isomers
IV. C=C
Cl CH3
Q.41 The correct structure of trans-2-hexanal is -
(A) I and II (B) I and III
(A)
(C) II and IV (D) III and IV
(B)
Q.34 But-2-ene exhibits cis-trans-isomerism due to- (C)
(A) rotation around C3–C4 sigma bond
(D)
(B) restricted rotation around C = C bond
(C) rotation around C1–C2 bond Q.42 The ‘E-isomer is -
(D) rotation around C2–C3 double bond
F H
(A) C=C
Q.35 A Fischer projection of (2R, 3S)-2,3- Cl Br
butanediol is : -
H 3C CH3
CH3 CH3
(B) C=C
HO H HO H
(A) (B) H H
HO H H OH
CH3 CH3 CH 3 C2H5
(C) C=C
CH3 H CH(CH3)2
CH3
H OH (D) none of the above
H OH
(C) HO H (D) H
H
CH3
CH3 Questions
Optical Isomerism
based on
Q.36 The number of geometrical isomers of
CH3CH = CH–CH = CH–CH = CHCl is -
Q.43 How many asymmetric carbon atoms are
(A) 2 (B) 4 present in -
(C) 6 (D) 8 (i) 1,2-dimethyl cyclohexane
(ii) 3-methyl cyclopentene
(iii) 3-methyl cyclohexene
Q.37 Compounds containing which of the following (A) Two, one, one (B) One, one one
functional groups can exhibit geometrical (C) Two, none, two (D) Two, none, one
isomerism ? Q.44 Optically active isomers but not mirror images
(A) > C = C < (B) > C = N – are called -
(A) Enantiomers (B) Mesomers
(C) –N = N – (D) All the three above
(C) Tautomers (D) Diastereomers

Q.38 CH3–C–Cl is - Q.45 The priority of groups OH, COOH, CHO, OCH3
attached to a chiral carbon is in order -
Cl–C–Br
(A) OH > COOH > CHO > OCH3
(A) Trans (B) Z (B) OCH3 > OH > CHO > COOH
(C) Both correct (D) None is correct (C) OCH3 > OH > COOH > CHO
(D) OCH3 > COOH > CHO > OH

25
 Q.51 A compound can be divided into two equal halves
Et & contains even 'n' asymmetric carbon atoms.
The number of optical isomer is –
Q.46 Me * OH It has chiral centre (*). It is- (A) 2n (B) 2 (n-1)
(C) 2 (n / 2-1) (D) 2n-1 + 2(n/2-1)
H
(A) R (B) S Q.52 Number of optically active isomers of tartaric
(C) Both (D) None acid is –

CH (OH)COOH
Q.47 The number of optically active isomers possible
for -
|
CH3 - CH - CH - CH - CH2OH is - CH (OH) COOH
| | | (A) 2 (B) 3
OH OH OH (C) 4 (D) 5
(A) 2 (B) 4 (C) 6 (D) 8]

Q.48 Which of the following compounds can not exist Q.53 Meso form of tartaric acid is –
as enantiomers – (A) Dextorotatory
(A) CH3 - CH(OH) COOH (B) Laevorotatory
(B) CH3 - CH2 - CH - CH2OH
| (C) Neither Laevo nor dextro rotatory due to
CH3 internal compensation
(C) C6H5CH2 - CH3 (D) A mixture of equal quantities of dextro and
(D) C6H5CHClCH3 leavo rotatory forms

Q.49 Which of the following contain asymmetric

Q.54 Following two isomers are –
carbon atom –
(A) CH3 - CH2 - CH2 - Br
(B) CH3 - CH - CH - CH3
| |
Br CH3
(C) CH3 - CH2 - CH - CH3
|
Br
(D) Both B & C

(A) Enantiomers (B) Mesomers

Q.50 If optical rotation produced by
(C) Diastereomers (D) Position isomers
CH3
H Cl Q.55 Optical activiity is expected for –
is + 36º then that produced (A) 2–Methyl propanoic acid
Cl H (B) Methyl 2–methyl propanoate
CH3
(C) Methyl 2–chloro propanoate
(D) Propanoic acid
CH3
H Cl
by is- Q.56 The process of separation of racemic
H Cl modifications into d and l enantiomer ; is
CH3 called–
(A) -36º (B) 0º (A) Resolution
(C) + 36º (D) Unpredictable (B) Dehydration
(C) Revolution
(D) Dehydrohalogenation

26
Q.57 Molecular formulae of an optically active organic Q.63 What are the type of isomers in following pairs-
compound is C4H10O . Its structure is
(A) C2H5OC2H5
(B) CH3OC3H7
(C) CH3CH2CH2CH2OH
(D) CH3CHOHCH2CH3 and

Q.58 Which of the following compounds contains

two similar asymmetric carbon atoms -
(A) Conformers (B) Position
(A) CH3CHBrCHOHCH3
(C) Optical (D) Geometrical
(B) CH3CH2CHOHCHOHCH3
(C) C6H5CHBrCHBrCH3
Q.64 At room temperature the eclipsed and the
(D) CH3CHBrCH2CHBrCH3 staggered forms of ethane cannot be isolated
because -
Questions (A) both the conformers are equally stable
based on Conformational Isomerism
(B) They interconvert rapidly
(C) there is a large energy barrier of rotation
Q.59 Isomers which can be interconverted through about the -bond
rotation around a single bond are – (D) the energy difference between the
(A) Conformers conformers is large
(B) Diastereomers
(C) Enantiomers
(D) Positional isomers

Q.60 CH3 - CH2 - CH2 - CH3. There is free rotation about

 C3) bond.The same most stable form is
(C2 ___
repeated after rotation of -
(A) 60º (B) 120º
(C) 240º (D) 360º

Q.61 How many conformations does ethane have –

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

Q.62 The eclipsed and staggered conformation of

ethane is due to -
(A) Free rotation about C-C single bond
(B) Restricted rotation about C - C single bond
(C) Absence of rotation about C - C bond
(D) None of the above

27
 LEVEL # 2
Q.9 Which of the following compounds can exist
Q.1 & show isomerism – as geometrical isomers –
(A) Chain (B) Position (A) CH2Cl2 (B) CH2Cl — CH2Cl
(C) Functional (D) None of these (C) CHBr = CHCl (D) CH2Cl — CH2Br

Q.2 Which of the following does not show functional Q.10 What is true for 1,2– pentadiene –
group isomerism – (A) It is functional isomer of pentyne
(A) C2H6O (B) C3H8O (B) It is position isomer of pentyne
(C) C4H10 (D) C4H10O (C) It is chain isomer of 3–methyl –1–butyne
(D) It is metamer of cyclopentene
Q.3 Ethylethanoate and  – methyl propionic acid
are – Q.11 The total number of structural isomers possible
for hydrocarbon C4H8 is –
(A) Chain isomers
(A) 3 (B) 4
(B) Functional isomers
(C) 5 (D) 6
(C) Geometrical isomers
(D) Optical isomers Q.12 The number of isomers of nitro phenol is –
(A) No isomerim (only one compound is
Q.4 CH3 - CH2 - CHO & CH2 = CH - CH2OH are –
possible.)
(A) Functional (B) Tautomers
(B) Two isomers
(C) Position (D) Metameres
(C) Three isomers
Q.5 Which of the following compounds will exhibit (D) Four isomers
geometrical isomerism – Q.13 In trans 1,2– dichloroethene –
(A) 1–Phenyl–2–butene (A) There are 6 sigma bonds
(B) 3–Phenyl–1–butene (B) The two H atoms are adjacent to each
(C) 2–Phenyl–1–butene other
(C) There is free rotation about the C – C bond
(D)1,1–Diphenyl–1–propene (D) All the atoms lie in the same plane

Q.6 The number of isomers possible for the Q.14 Which of the following pairs of compounds are
compound with the structure – chain isomers -
CH3CH = CH — CH = CH — CH2CHOHCH3 (A) n-Propyl alcohol and isopropyl alcohol
is – (B) isobutyl alcohol and t-butyl alcohol
(C) s-Butyl alcohol and t-butyl alcohol
(A) 2 (B) 4 (C) 6 (D) 8
(D) n-Butyl alcohol and s-butyl alcohol
Q.7 Which of the following will show geometrical
Q.15 Which of the following pairs of compounds are
isomerism – position isomers -
(A) CH3CH = CH2 (A) isobutyl alcohol and s-butyl alcohol
(B) isobutyl alcohol and t-butyl alcohol
Br Br
| | (C) isopentyl alcohol and neopentyl alcohol
(B) CH3 — C  C — CH2 CH3 (D) ethyl alcohol and ethylene glycol

(C) CH3CH2CH2CH = CHCH3 Q.16 Which of the following paris of compounds are
(D) CH2 = CH — CH2 — CH3 not isomers -
(A) Propyne and cyclopropene
Q.8 How many optically active forms are (B) Propyne and propadiene
possiblefor a compound of rational formula - (C) Propene and cyclopropene
CH2OH. CHOH. CHOH. CHOH. CH2OH (D) 1-Propanol and methoxyethane
(A) 2 (B) 3
(C) 4 (D) 8

28
Q.17 Which of the following is not an isomer of allyl Q.24 The number of geometrical isomers in the
alcohol - following compound,
(A) Acetone (B) 1-Propanol CH3 – CH = CH – CH = CH – C2H5 is -
(C) 2-Methyloxirane (D) Cyclopropanol (A) 4 (B) 3
(C) 2 (D) 5
Q.18 The total number of cyclic compounds
(neglecting stereoisomers) with the molecular Q.25 The following compound can exhibit -
formula C5H10 is -
(A) 4 (B) 5 CH3 H
(C) 6 (D) 7 C=C H
CH3 C
Q.19 Which of the following pairs of compounds CH3 COOH
may be regarded both as functional isomers
and position isomers - (A) Geometrical isomerism
(A) Benzyl alcohol and methoxybenzene (B) Geometrical and optical isomerisms
(B) o-Cresol and p-cresol (C) Optical isomerism
(C) Benzyl alcohol and o-cresol (D) Tautomerism
(D) Benzyl alcohol and benzyl methyl ether
Q.26 Structural isomers possible for C4H8Br2 are -
Q.20 Which of the following pairs of compounds are (A) 9 (B) 8 (C) 7 (D) 6
functional isomers -
Q.27 False statement is –
(A) Angle of rotation increases with increase in
(A) and O number of asymmetric carbon atoms
(B) Cis - isomer of a compound is more stable
(B) and than trans form
(C) Fumaric acid on heating produces fumaric
(C) and anhydride
(D) All of them
(D) and
Q.28 Which compound would exhibit optical isomers–
Q.21 Which of the following compounds does not
have geometrical isomers -
(A) 2-Pentenoic acid
(B) 2-Butenoic acid (A) (B)
(C) 3-Pentenoic acid
(D) 3-Butenoic acid

Q.22 Among the following compounds, the one which

does not show geometrical isomerism is -
(A) C6H5N = NC6H5 (C) (D)
(B) C6H5CH = CHC6H5
(C) C6H5 – C = N – OH

CH3 Q.29 The correct stereochemical name of –

(D) C6H5 – C = N – CH3

C6H5 CH 3 H
C=C H
H CH 2 - C
Q.23 Which of the following compounds has no C - CH3
geometrical isomer - |
(A) 1-Phenylpropene COOCH 3
(B) 1, 2-Diphenylethene
(A) Methyl 2–methylhepta (2E, 5E) dienoate
(C) 1, 2-Diphenylpropene
(D) 1,1-Diphenylpropene (B) Methyl 2–methylhepta (2Z, 5Z) dienoate
(C) Methyl 2–methylhepta (2E, 5Z) dienoate
(D) Methyl 2–methylhepta (2Z, 5E) dienoate

29
Q.30 Which of the following structures has the Q.35 Which of the following show geometrical
S-configuration at the chiral centre ? isomerism ?
(A) 1- pentene
CHO COOH (B) 1,2-Dimethylcyclo butane
C C (C) 1,1 Dichloroethene
(A) OH (B) HO
(D) 1,4-Butanedioic acid
HOCH2 H H CH3
Q.36 Which of the following pairs can be resolved?
Br Cl H3C H R2
(C) (D) N R3
(A) R1 R3 R1 N
OH
R2
Q.31 Which of the following statements is not
correct ? OH OH
(A) Molecules that are superimposable on
their mirror images are chiral C C
(B) HOOC HH COOH
(B) Molecules that are not superimposable
on their mirror images are chiral CH3 CH3
(C) A compound whose molecules are chiral

.. 
..
can exist as enantiomers C C
(D) A compound whose molecules are achiral (C) CH3 C2H5 C2H5 CH3
can not exist as enantiomers H H

Q.32 An organic compound will show optical a a

b b
isomerism if –
(D) C=C=C C=C=C
(A) Four groups attahced to C atom are different a a
b b
(B) Three groups attached to C atom are
different
(C) Two groups attached to C atom are different Q.37 In plane clockwise rotation of the projection
(D) All the groups attached to C atom are formula (A) of a compound by 90º and 180º
same yields the projection formulae (B) and (C)
respectively -

Q.33 The compound having asymmetric carbon atom CHO

H
is –
(A) CH3CHOHCH3 H OH HOCH2 CHO
(B) (CH3)2C(C2H5)2
(C) C2H5CHClCH3 CH2OH OH
(D) C2H5CH (CH3)CH2CH3 (A) (B)

CH2OH
Q.34 Which of the following starred C – atom is
asymmetric – OH H

(A) CH3CH2 C HCH3CH2OH CHO
 (C)
(B) CH3CH2CH C H3CH2OH
Which of the following statements is not correct
 about (A), (B) and (C) -
(C) CH3 C H2CHCH3CH2OH
 (A) A and B are enantiomers
(D) CH3CH2CHCH3 C H2OH (B) A and C are identical
(C) B and C are enantiomers
(D) A and C are enantiomers

30
Q.38 Which of the following compounds can exist Q.43 Which of the following compounds possesses
both as a cis pair of enantiomers and a trans a chiral centre -
pair of eantiomers -
(A) CH3CHClCH = CH2 H OH
CH3
(B) CH3CHClCH = CHCH3
(A) (B)
(C) CH2 = CH – CHOHCH = CH2
(D) CH2 = CH – CHClCH = C(CH3)2 O

Q.39 Which of the following statements is not

correct -
(A) Enantiomers are essentially chiral and (C) (D)
optically active
(B) Diastereomers are not neccesarily chiral
and optically active Q.44 Which of the following compounds is a meso
(C) All geometrical isomers aer diastereomers compound -
(D) All diastereomers are chiral and optically
active
(A) (B)
Q.40 The two isomers given below are -

COOH HOOC
H C OH HO C H
(C) (D)
(i) HO C H (ii) H C OH
COOH HOOC

(A) enantiomers (B) diastereomers Q.45 The observed rotation of 2.0 g of a compound
(C) mesomers (D) position isomers in 10 ml solution in 25 cm long polarimeter
tube is +13.4°. The specific rotation of the
Q.41 Correct configuraton of the following is - compound is -
(A) +30.2 ° (B) –26.8°
CH3
H OH (C) +26.8° (D) +40.2°

CH3 OH
Q.46 Which of the following structures represents a
H
threo-stereoisomer -
(A) 1S, 2S (B) 1S, 2R
(C) 1R, 2S (D) 1R, 2R
(A) (B)
Q.42 The terms stereoisomers, enantiomers and
diastereomers will refer
(A) only to configurational isomers including
geometric isomers
CH3
(B) only to conformational isomers
Br OH
(C) to both configurational as well as (C) H (D)
Br
conformational isomers
(D) to neither configurational as well as CH3
conformational isomers

31
Q.47 2-Butene exhibits geometrical isomerism due Q.50 Which of the following pairs of structures
to - represent enantiomers -
(A) rotation about the double bond
(B) rotation about C3–C4 bond
(A) and
(C) restricted rotation about the double bond
(D) rotation about C1–C2 bond

Q.48 The most stable conformation of 2, 3-

dimethylbutane is -
(B) and

(A) (B)

(C) and

(C) (D)
(D) and

Q.49 How may meso steroisomers are possible for

2, 3, 4-pentanetriol -
(A) 1 (B) 2
(C) 3 (D) None

32