Chemistry: Isomerism Theory & Questions

SESSION 2021-22
CHEMISTRY
ISOMERISM THEORY & QUESTIONS
Contents
S.NO. TOPIC NAME PAGE NO.
1. Theory (Isomerism) ................................................................................ 01 – 37
2. Theory (Isomerism) ................................................................................ 38 – 70
3. Class Rivision Problems (CRP) ............................................................ 71 – 79
4. Exercise – 1 (Level – 1) .......................................................................... 80 – 84
5. Exercise – 2 (Level – 2) .......................................................................... 85 – 93
6. Exercise – 3 (Level – 3) .......................................................................... 94 – 106
7. Exercise – 4 (More than One) ................................................................ 107 – 110
8. Exercise – 5 (Comprehension) ............................................................... 111 – 113
9. Exercise – 6 (Matrix Match) ................................................................... 114
10 Exercise – 7 (Interger) ............................................................................ 115 – 116
11. Exercise – 8 (Flash Back) ....................................................................... 117 – 120
12. Answer Key ............................................................................................. 121 – 123
Author
Er. Arvind Tripathi
B.Tech. (Chemical Engg.) IIT-BHU
ISOMERISM (THEORY)
ISO MERP
Same Unit
Definition
Different compound having same M. F. but different properties are isomers and the
phenomena is known as isomerism.
Isomers have –
1. Same General formula
2. Same Empirical formula
3. Same Molecular formula
4. Same Empirical formula weight
5. Same Molecule weight
6. Same V. D. ( VD = )
7. At least one different physical or chemical property for their separation.
Classification of Isomerism
Structural Isomerism Stereoisomerism

Constitutional isomerism or Space isomerism
Regio isomerism or Stereo isomerism
Same MF Same MF
Different Structure Sane Structure
Different IUPAC Name Same IUPAC Name
Different arrangement
Chain Isomerism in 3D-Space
Position Isomerism
Functional Isomerism
Ring - chain Isomerism
Metamerism
Tautomerism
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Classification of Stereoisomerism
Congormational Isomerism Configurational Isomerism
Rotamers Amine flipping Geometrical Optical

() conformers Isomerism Isomerism
(across  bond)
Note : No two stereoisomers can ever be structural isomers and vice – versa.
Explanation of Structural Isomerism
They have Same MF but
 Different Structure
 Different IUPAC Name
Case-I: Chain Isomerism –
 Different Root Word
 Same F. G.
Example-1: Example-2:
Case-II: Position Isomerism –
 Different position of  bond, prefix, Suffix, bridgehead etc.
 Same Root word and Same F. G.
Note : Acid, Ester, Cynide, Aldehyde, acid halide, amide, anhydride will not show position
isomerism for mono functional group.
Case-III: Functional Isomerism –
 Different functional Groups (Not Tautomers)
Note : (1) 1o, 2o, 3o alcohol are same F. G.
(2) 1o, 2o, 3o amine and amides are different F. G.
(3) Alcohol and phenol are different F. G.
Case-IV: Ring Chain Isomerism –
 Different family of compounds ie closed chain and open chain.
 Also known as functional isomers but priority is given to RCI.
Questions: Identify the relation in following pair of compounds.
(1) (2) (3)
Cl
CN
(4) (5) (6)
CN
Cl
Cl Cl OH
Cl
(7) (8) (9)
Cl Cl OH
Cl
OH Cl Cl
OH
Br Br
(10) (11) (12)
Br
OH OH
Br
NH2
(13) (14) (15)
NH2 NH2 OH
NH O
OH OH
(16) (17) (18) NH2
OH
O
NH2
OH
(19) (20) (21)
OH
(22) (23) (24)
D D D
D D D
(25) (26)
D D
Case-V: Metamerism
 Different Groups (Size or nature) Attached on different sides of a polyvalent
functional group.
 Same F. G.
Example: Can C4H10O show metamerism.
Note: Metamers may be C. I. or P. I. simultaneously but priority is given to metamerism.
Questions: Identify the relation in following pairs.

O
(1) NH (2) O (3)
O
O
NH H O
O
O O
|| ||
(4) (5) – C –O – (6) –C –O –
O O O O
|| ||
– C –O – –C –O –
(7) MeO
EtO
PRIORITY ORDER
R T F M C P d
STEREOISOMERISM d
Definition
 Same M. G.
 Same Structure
 Same IUPAC Name
 Different arrangement of atoms in 3D – space
CONFORMERS | ROTAMERS
 Compounds having same MF but different arrangement of atoms or groups in space,

which are inter convertible are known as conformations.
 Free rotation of  bond

 Inter Convertible
 Remain in dynamic equilibrium
 Known as Rotamers (For open chain compounds)
 Not true isomers
 Infinite conformers for a given  bond.
 Energy required for rotation is available at R. T.
(R. T. energy is approx 84 kJ/mole)
TYPES OF STRAIN
Case-I: Static Strain
Strain developed by the restricted movement of objects like due to  bond.

a a
b b
Case-II: Angle Strain
It is due to difference in angle required and actual angle.
Case-III: Vander Waal Strain | Steric strain
Strain developed in a molecule due to steric repulsion between bulkier groups.
Case-IV: Torsional Strain
The strain developed in a molecule due to the repulsion between bonding electron
pairs is known as T. S. and energy required to overcome this strain is torsional
energy.
It is the property of Eclipsed form.

a
a
a
c
a
b
b c
c c b
b
Terminology used in conformational analysis
TYPES OF CONFORMERS
(1) Eclipsed form
Form in which valencies are hiding each other or in front of each other. It is of two
types –
(a) Fully Eclipsed or total Eclipsed :
Corrosponding valencies are in front of each other. Dihedral angle is zero.
Newman Projection formula Sawhorse / Andiron projection formula
(b) Partially Eclipsed : Different valencies are in front of each other. Dihedral angle is
zero.
(2) Staggered form or Anti form: Corresponding valencies are at maximum distance ie at
180o.
(3) Gauche form: When corresponding valencies are at 60o.
(4) Skew form: Other than the major conformers ie. Eclipsed, staggered and gauche, rest
all are skew forms.
Note: Staggered and Gauche are considered as only stable conformations.
DIHEDRAL ANGLE:
Angle between two inter secting planes of front atom valency to back atom valency is
known as dihedral angle.
EXAMPLES OF CONFORMERS
(1) Draw conformation of CH2 – CH2 along C – C  bond and draw it’s potential
| |
X X
energy diagram
Z
z
H
H H
H
Torsional Strain TE PE G St
Steric Strain
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Stability Order :
Energy Order :
Potential energy diagram :
P. E.
60 120 180 240 300 360
No. of Stable conformers ≤ No. of PE minima
Total Conformers =
(2) Draw conformers of CH3 – CH3. (C – C  bond)
H
H
H
H H
H
Stability 
T. S. 
Energy 
Mole fraction at RT. 
3.0 k Cal/mol
P. E.
60 120 180 240 270 360
Eclipsed  3 in No. in 360o.

Staggered  3 in No. in 360o.
Each form is repeated after 60o.

(3) Conformers of CH3 – CH2 – CH3.
(4) Conformers of CH3 – CH2 – CH2 – CH3. (C1 – C2 bond)
(5) CH3 – CH2 – CH2 – CH3. (C2 – C3)
QUESTIONS FOR JEE ADVANCED
Question-1: Explain why anti conformation is unusually stabilized than eclipsed conformation?
Solution:
Question-2: Conformation obtained on rotating C2 carbon by 120o anticlockwise.

CH3
H CH3
H H
H
Gauche

CH3
H H
Question-3: If conformation is of
H Y
X
(a) n – pentane (b) Iso – pentane
Find X & Y
X
H H
Question-4: If is an isomer of isobutane then (X, Y)
H H
Y
Y
Cl H
Cl
Question-5: If is conformation of then (X, Y) is
H H
X
(a) Me, Et (b) H, Et (c) Et, H (d) Me, Me
Question-6: What is the relation in following pair of compounds.
Me Me
Me Me Me
Me H Me Me
H
(1) (2)
Cl
H
H Cl H H Cl H
H Cl Cl Cl
Cl Cl
H
H
Me H Me H D
Me H Me H
H Me Me
Me D
(4)
(3) D
D
Et Cl Pr H
Cl Cl
D
H Me
Me H
H Me H
Me D
(5)
D
D

Question-7: Calculate total no. of stable conformers in following
(i) CH3 – CH3 (ii) CH3 – CH2Cl (iii) CH3 – CHCl2
(iv) CH3 – CCl3 (v) CD3 – CT3 (vi) CH3 – CH2 – CH3
 Whenever there is electrostatic attraction or hydrogen bonding Gauche becomes more stable
that anti.
Question: Draw most stable conformer in following :
(i) CH2 – CH2 (ii) CH2 – CH2 (iii) CH2 – CH2

| | | | | |
OH OH OH F OH NH2
(iv) CH2 ––– CH2 (v) CH2 ––– CH2 (vi) CH2 ––– CH2
| | | | | |
+
NH3 COO– +
NR3 COO– COOH COOH
(vii) CH2 ––––– CH2 (viii) CH2 ––– CH2

| | | |
– + – +
COO Na COO Na F NH2
GAUCHE EFFECT
For stable conformation of a compound along C hetro atom bond, bulkier group must be
placed to maximum Gauche position of lone pair of hetro atom.
CH3 ––– CH2 ––– NH2

QUESTION-1: Draw most stable conformation & also calculate total no. of stable conformers.
CH3
|
(a) CH3 –– CH2 –– OH (b) CH3 –– CH –– OH
CH3
|
(c) CH3 –– CH –– NH2 (d) CH3 –– C –– NH2
| |
CH3 CH3
Dipole Moment
Compounds which exist in various conformation its dipole moment can be calculated.
Question-1: Calculate dipole moment of Gauche conformation of CH2 –– CH2 if its net dipole
| |
Z Z
moment is 1D and mole fraction of anti is 0.82. Dipole moment can be calculated
by the formula = ∑ .

Question-2: Compounds having non-zero dipole moment.
Cl OH
(i) (ii) (iii)
Cl OH
NO2
COONa NO2
(iv) (v) (vi)
NaOOC NO2 O2N
SH CN CH3
(vii) (viii) (ix)
SH CN OH
Case-I: Cyclopropane
H
BA = 60
o H H
H
o ''
H AS = 49 28
o ''
Total AS = 49 28 × 3
H
H
H
Result:

Case-II: Cyclobutane
H
o
H BA = 87
H
H AS = 22o28'
H H
o
H Total AS = 22 28' × 4
H
Case-III: Cyclopentane
H
H
H H BA = 108
o
o
H H H H AS = 1 28'
o
Total AS = 1 28' × 5
H H
Case-IV: Cyclohexane
What ever the small angle strain is present in cyclohexane, it is distributed among its
conformers.
o
BA = 109
AS = 28'
Total AS = 28' × 6
Stability Order:
6>5>7>4>3
Conformation in Cyclohexane
1. Chair Conformation
(a) How to draw chair
P Q
PQ || RS
U T PT || UR
US || QT
S R

Axial Position Equatorial Position
H H H
H H
H
H
H H
H H H
Complete chair conformation
Newmann Projection formula of chair
2. Boat Conformation
Newmann Projection

3. Twist Boat Conformation
H H
H H
H
H H H
H H H
H
4. Half Chair Conformation
H
H H H
H
H H H
H H
H H
Stability Order : Chair > Twist boat > Boat > Half Chair
PE Order : Half Chair > Boat > T Boat > Chair
PE Daigram
Half Chair
Boat
T. Boat
Chair
 Total No. of stable conformations = 3
 Total No. of conformations = ∞

FLIPPING IN CONFORMERS
Note: 1. During flipping each axial converts into equatorial and vice – versa.
H H H H
H H H H
H H H
H
H H H H
H H H H
H H H H
2. During flipping configuration does not changes.
CONFORMATION IN SUBSTITUTED CYCLOHEXANE
H
G
G
H G
[ ]
= [ ]
Hence, equatorial position is more preferred by bulky group for higher stability.
Question-1: Most stable conformer of methyl cyclohexane is
(a) (b)
(c) (d) None of these
Question-2: Predict keq.
(1) (2)

Me Me
Me
Me
(3) (4) Me
Me
Me Me Me
Me
(5) (6) Et
Et
Cl Br
Cl Br
(7) (8)
Cl Me Me
Cl
Me Me
(9) Br (10)
Br
Cl Br
Cl
Br Cl Cl
(11) (12)
Br
Br
Et
Et
(13) OH (14)
Me
HO OH OH Me
Question-1: Draw stable conformer of following –
(1) (2) (3)

Note: Geometrical isomerism in chair form of cyclohexane
Question-2: Draw most stable conformer.
Me Me Me Me
(1) (2) (3)
Me Me Me Me
OH
(4) (5)
HO
CONFIGURATIONAL ISOMERISM
 Same MF
 Same Structure
 Different arrangement of atoms in 3 - D space
 Non – interconvertible
STEREOCENTER OR STEREOGENIC ATOM
Any atom to which if two groups attached are interchanged, we get a new stereoisomer.
PLANER STEROCENTER

NON PLANAR STEREOCENTER
Question: Calculate number of Stereocenters in following :
1. 2.
Cl
3. 4.
5. 6.
GEOMETRICAL ISOMERISM
Conditions are
(a) Restricted rotation (C = C, C = O, C = N, N = O)
(b) Different Terminal Groups
Case-I: GI in Alkene
A D
C=C
B E
AB
DE
Case-II: GI in Imines
A H
C=N
B

Case-III: GI in Diazo Compounds
H H
N=N
Case-IV: GI in Oximes
H+
O + NH2 – OH N – OH
Aldoxime / Ketoxime
Ald or Ketone
Case-V: GI in Cyclo Alkane
a b
Questions: Which of the following will show G. I.
(1) (2) (3) (4)
Cl Cl
(5) (6) (7) NH (8) N – OH
Cl
(9) N – OH (10) H2N2O2 (11) (12)
Br Cl Br F
(13) (14) (15) (16)
Cl Br I Cl

(31) (32) (33) (34)
O O
O
(35) (36) O
O
O
(37) Calculate total number of structural isomers of C2FClBrI which can show G.I.
Case-VI: GI in Cyclo Alkene
Result: No. of C atoms G. I.

3 ×
4 ×
5 ×
6 ×
7 ×
8 
9 
10 
 

Case-VII: GI in Cumulated Polyene
Case-VIII: GI in Cycloalkylidenes
Case-IX: GI in Spiro alkanes
Case-X: GI in Bycyclo and Bridged bycyclo compounds

 For bicycle smallest size 410.
 For bridged bicycle smallest size is 431.
Case-X: GI in Triphenyls
(A) Biphenyls
A D
B C
(B) Triphenyls
A D
B C
Questions: Which of the following will show GI.
(1) (2) (3)
Br F
(4) (5) -2
O = C = C = O SO4 (6) C=C=C=C=C
I Cl

(7) (8) (9)
(10) (11) (12)
(13) (14) (15)
O
(16) (17) (18) NH
Br I Cl Br NO2
(19) (20) (21)
NO2
(22) (23) CH3 – CH = S = CH – CH3
SOME MORE QUESTIONS
(1) (2) (3)

F Cl
O O
(4) (5) (6)
(7) (8) (9)
(10) (11) (12)
(13) (14) (15)

O
NH O
NH NH
(16) (17) (18)
NH
O
O
NH NH
(19) (20) NH (21)
NH
O
H CH3
(22) (23) C–N (24) NH2 NH2
O H
REPRESENTATION OF GI
Case-I: Cis and Trans Representation
Case-II: Syn – Anti Representation
Questions: Identify Cis/Trans and Syn/Anti in following :
Cl
(1) (2) (3) (4)
Cl
F Cl F Me
(5) (6) (7) (8) C=N
H
Cl OH

Me
Me Me H
(9) (10) (11) (12)
Cl
H Me
Me
N – OH
HO OH HO OH
(13) (14) (15) C=N (16)
(17) (18) (19) (20)
Case-III: E – Z Representation
E : Entgegen
Z : Zussaman
 First of all assign priority to the two groups attached to stereocenter as per CIP Rules
(Cahn – Ingold – Prelog)
 If same priority groups are present on same side then Z otherwise E.
(1) (1) (1) (2)

C=C C=C
(2) (2) (2) (1)
CIP SEQUENCE RULES TO DECIDE PRIORITY

Questions: Compare priority as per CIP Rules
(1) F Cl Br I
(2) F OH NH2
(3) – CH3 –H
(4) – CH3 – CH2D – CHD2 – CD3
(5) – CH3 – CD3 – CT3
(6) – CH3 – CH2 – CH3 – CH2 – CH2 – CH3
12 14
(7) – CH3 – CH3

(8) – CH2 – CH2 – CH2 – CH3 – CH – CH3
|
CH3
CH3
|
(9) – CH2 – CH3 – CH – CH3 –– C –– CH3
|
CH3
(11) – OH – CH2Cl
14 12
(12) – CH3 – CD3
(13) – CH = CH2 – CH = O
(14) – CH = CH2 – C  CH
(15) – CH = O – COOH
(16) – CH = CH2 –– CH –– CH3

| |
CH3 CH3
(17) – C  CH –– CH –– CH2
| |
CH3 CH3
O O –C– C–
(18)
C – C– O–
C– O – C–
O O–C–C–
Note: Cis > Trans
Z > E
R > S
 Lone Pair is always first priority.

Question: Assign E and Z in following :
F Br
(1) (2) (3) (4)
Cl I Cl
Cl H Me
(5) (6) (7) (8)
H Cl
Me Cl
OHC OH Me OH
(9) (10) C=N (11) N
HOOC CH2Cl H OH
Ph HO O
(12) C=N (13) (14) C=C
N=N O
Me OH OH
O
H CH3
(15) C=C (16) (17)
D CD3
(18) (19) (20)
CN
(21) N
N
OH

PROPERTIES OF GI
Dipole Moment
  When attached atoms or groups have same nature
     
  When groups are different
   
Properties Related to 
 Cis > Trans
BP Cis > Trans
Solubility in Water Cis > Trans
Question: Compare , BP and SH2 O
Cl Cl Cl
(1) (2)
Cl
HO OH HO HO NO2 HO
(3) (4)
OH NO2
COOH COOH HOOC F OH F

(5) (6)
COOH OH

STABILITY
Usually trans isomer is more stable than Cis because of steric crowding in Cis but in few
cases Cis may be more stable than trans.
Examples:
(1)
HO OH HO
(2)
OH
PROPERTIES RELATED TO STABILITY
Stability Cis < Trans
M.P. Cis < Trans (Due to higher packing fraction in trans)

HOH Cis > Trans
HOC Cis > Trans
Note:
Question: Compare stability

HO OH HO
(1) (2)
OH
(3) (4)
F F F Br Br Br
(5) (6)
F Br
I I I
(7)
I

Note: GI are also known as diasteromers. They can be easily separated due to difference in
physical and chemical properties.
CALCULATION OF GEOMETRICAL ISOMERS
n : No. of sites which can show GI
Case-I: It compound is unsymmetrical
GI = 2n
Case-II: It compound is symmetrical
n even n odd
n –1
GI = 2n–1 + 2 n+1 –1
GI = 2n–1 + 2 2
QUESTIONS FOR JEE MAIN | NEET
Calculate total number of GI in following
(1) (2)
(3) (4)
(5) (6)
(7) (8)
(9) CH3 (CH = CH )4 Cl (10)

NH

CH3 – CH = CH
(1) C = CH2
CH3 – CH = CH
CH3 – CH = CH CH = CH – CH3
(2) C = CH
CH3 – CH = CH
(3) C=C
(4) (5) (6)
Cl
(7) (8) (9)

(10) (11) (12)
Cl
Cl
(13) (14) (15)
Br Cl Br Cl
(16) (17) (18)
Br Cl Cl Br
Cl Cl Cl Cl
(19) (20) (21)
Cl Cl Cl Br
(22)

OPTICAL ISOMERISM
BASIC INFORAMATION
 As Discussed in definition of stereocenter –
 Planer Compounds may be inverted as well as rotated
 Fischer projection can be rotated by 1800 only but it can never be inverted.
DEFINITION OF OPTICAL ISOMERISM
Compounds having same molecular formula and same IUPAC name but different optical
activity with PPL.
SYMMETRIES
There are four types of symmetries.
Case-I: Plane of Symmetry (POS) (n)
It is defined as an imaginary plane, along which a molecule is devided into halves which
are exact mirror image of each other.
QUESTION: Find number of POS in following
Cl Cl
Cl
Cl
(1) (2) (3) (4) Cl

Cl
Cl
Cl
(5) Cl (6) Cl Cl (7) Br (8)
(9) (10) CH4 (11) CH3Cl (12) CH2Cl2
(13) CHCl3 (14) CH3Cl (15) CF2ClBr (16) CFClBrI
(17) Chair form of cyclohexane (18) Boat form of cyclohexane
(19) Twisted boat form of cyclohexane (20) Nail (21) Screw
(22) Hockey Stick (23) (24) (35)
(26) (27)
Case-II: Center of Symmetry (COS)
It is defined as an imaginary point along which a straight line is drawn and same atom
appear at both terminal in whole compound.
QUESTION: Which of the following possess COS.

Me
Me
(1) (2) (3) Me (4) Me
Me
Me Me
(5) Me (6) Cl (7) (8) Me

Me
Me Me
Cl H
Me Me
(9) Me (10) (11) (12) H Cl
Me H Cl
(13) (14) Cl H Me
Case-III: Axis of Symmetry (AOS) (Cn)
360 o
Defined as an imaginary line along which when a molecule is rotated by and same
n
appearance is obtained, line is named Cn axis of symmetry.
360
n= ,  is angle of reappearance
θ
Example : BF3
F
B
F F
Note :   Cn
30o C12
60o C6
45o C8
90o C4
120o C3
180o C2

Case-IV: Alternating AOS (Improper) (Sn)
360 o
It is defined as imaginary line along which If a molecule is first rotated by and
n
then reflected along a mirror plane which is perpendicular direction of initial line. It final
image is same as initial then it is Sn AAOS.
Question-1: Identify the type of symmetry in following compounds.

Assymetric Compounds :
Dissymetric Compounds :
FACT :
 All asymmetric and dissymmetric compounds have non – super imposable mirror image.
These compounds are optically active.
 Presence or absence of AOS has no effect on optical activity.
CONDITIONS FOR OPTICAL ISOMERISM
1. Presence of chiral atom or

2. Absence of symmetry with or without chiral atom.
CHIRAL ATOM
sp3 hybridised tetrahedral atom with four different groups.
Question : Calculate the No. of chiral atoms in following –

Cl
(1) (2) (3)

Cl Cl
Cl Br Cl Cl
(4) (5) (6)

Cl Cl

(7) (8) (9)
Cl
(10) (11) (12)
Cl
Cl
O O
(13) (14) S (15) P

N Cl OH
H
(16) (17) (18)
(19) (20)
O
OH
REPRESENTATION OF CHIRAL ATOM
Case-I: Fischer Projection
 Vertical line  Away from viewer

 Horizontal line  Coming towards viewer
Note : A chiral atom may be represented in 24 ways on fischer projection but actual number of
isomers is only 2.

Absolute Carliguration of Chiral atom (R, S Configuration)
 A Single chiral atom has only 2 optical isomers named R and S.
 R≠d S≠d
≠ ≠
Golden Rule to find R. S
Follow sequence Rules –
1. First of all assign priority to all the four groups attached to chiral atom according to CIP
rules.
2. Now move from 1  2  3  keeping 4 on vertical position
3. If it is clockwise then R and if anti clockwise then S.
F OH
I Cl Cl CH2OH
Br H
* LPG must be above or below on vertical line.
* If LPG is on horizontal line then invert the configuration.
R in place of S Clockwise S
Means
S in place of R AnticlockwiseR
Result : Even number of interchanges on chiral atom gives same molecule and odd number of
interchanges gives it’s stereoisomer.
QUESTION FOR JEE-MAIN | NEET
Question: Assign R and S in following :
H F CH2Cl
(a) Me OH (b) Br I (c) H OH
Et Cl D

Me Me
H Cl H Cl
(d) (c) (f)
H Cl Cl H
Me Me
Me COOH Me
H Cl H OH H Cl
(g) (h) (i) H Cl
Cl Me OH H
H Br
H COOH
Me
QUESTION FOR JEE ADVANCED
Question: Assign R and S in following
O O
O
(a) (b) H (c)
O N
Me Me
COOH
H OH H OH
H Cl
(d) (e) H Cl (f) H Cl
H OH OH
H HO H
COOEt Me Me
Concept of Pseudo Chiral Atoms:
 Fate of pseudo chiral atom depends on other chiral atom’s configuration attached to it.

Note : As per CIP Rules –
E<Z
R>S
C>T
Question: In which of the following C – 3 is chiral.
Me Me Me
H OH H OH H OH
(a) H Cl (b) H Cl (c) H Cl
H OH HO H H Br
Me Me Me
Case-II: Dash – Wedge Representation of Chiral atom

On Plane
Toward viewer
Away from veigwer
In this case LPG should be on dash.

Rest of the rules are same
Example :
CH3 COOH
OH Me
(a) (b)
H OH
H
COOH
INTER CONVERSION OF DASH WEDGE AND FISCHER

COOH CH3
Me H COOH
COOH
(a) (b) (c)
H OH CH3
OH
OH H

OH H H OH CH3 Cl
(d)
(e) (f)
CH3 Cl Cl CH3 H OH
Cl
Cl
(g) (h) (i)
Cl
QUESTION FOR JEE-MAIN | NEET
Question: Assign R and S

OH Me Br CH3
(1) (2) (3)
COOH Cl
CH3 CH3 Cl
CH3 CH3
CH3
(4) (5) (6)
Cl Br
Cl Cl
(7) (8) (9)
Cl
Question: Assign R and S to each chiral atom

Me
Me H Me
Cl
(1) H (2) (3)
Cl Me
Cl Cl
Cl Cl
Cl Cl
Cl Cl
(4) (5)
OH
OH

Case-III: Newman and Sawhorse Projection :
CHIRAL AND ACHIRAL MOLECULES
Chiral Molecules (obs ≠ 0)
Means  Assymetric Compound
 Dissymetric Compound
 Resolvable Compound
 Mirror image non super imposable
 Optically active except in few cases.
Achiral Molecules (obs = 0)

Means  Symmetric Compound
 Non – Resolvable Compound
 Mirror image Super imposable
 Optically inactive Compound
Exceptions of Chiral Compounds
Example-1: Ammine flipping / Umbrella flipping
Example-2: 1, 3 trans dimethyl Cyclohexane

OPTICAL ISOMERS
First observe
Chiral centre
Present Absent
observe symmetry
Always shows
Optical isomerism All absent If any one is
presnest
CH3 CH3
H Cl Always shows Never shows
H Br Cl Optical Isomerism
H Optical Isomerism
Cl CH3 H
Optically Active
C
H3C CH3 H
H
C=C=C H
H
H
Question : Identify chiral and achiral compound. Also comment if there is any meso
compound.
Cl F Me
H Cl
(1) (2) Cl I (3)
H Cl
Br Me
Me Me
Me
H Cl
H Cl H Cl
(4) (5) (6) H OH
Cl H Cl Me
H Cl
Me H Me
H Cl Cl Cl Cl Cl
(7) (8) (9)

Me
H
Me H
Cl
Cl Cl Cl
Cl Br
(10) (11) (12)
OH

Cl Me
Me
Cl Cl
Cl
(13) (14) (15)
Me Me Me
(16) (17) (18)

Me Cl
Me
Me Me Me
(19) (20) (21)
Cl
Me Me
Me
Me Me
Me
(22) (23) (24)
Cl Cl
Me Me Me
Me Cl Cl
(25) (26) (27)
Me Me Me
(28) (29) (30)
Me Me Cl
Me
Me Me
(31) (32) (33)
Me Me
Cl
Me Me Me
(34) (35) (36)
Cl Cl Me

Me Me Me
(37) (38) (39)
Me Cl Cl
Me
(40) (41) (42)
Me Me Me Cl
Me
(43) (44) (45)
Me Cl
CHIRAL AND ACHIRAL COMPOUNDS WITHOUT CHIRAL ATOM
Case-I : Cumulated dienes

H H
H H
(1) C=C=C (2) C=C=C
H H H CH3
H Me
Me Me
(3) C=C=C (4) C = C = C= C
H Me H H
H
Me Cl H
(5) C = C = C = C= C C=C=C
Me
(6)
H H CH3
Case-II : Cycloalkylidenes
H H
(1) =C (2) =C
H CH3
H H H
H
(3) =C (4) =C
H3C H H3C CH3
H H H
(5) =C=C=C (6) =
H3C CH3
CH3
CH3
H
(7) CH3 = C (8)
CH3
CH 3

Case-III: Spiro Compounds
(1) (2) (3)
(4) (5) (6)
Case-IV: Biphenyls
Me Me CH3 NO2
(1) (2) (3)
NO2 NO2 NO2 NO2 COOH
(4) (5) (6)
NO2 COOH COOH NO2
OH OH NO 2 NO2
(7) (8)
(A) Cl C (P) Chiral center present

I
Br
H3C Cl
(B) C=C=C (Q) Chiral Compound
H Br
H3C CH3
(C) (R) Optically acitive
H H
Cl
H
(D) Cl (S) It's all stereoisomers are

CH3 Optically active
H
CH3

SOME IMPORTANT TERMS USED IN OPTICAL ISOMERISM
Case-I : Diastereomers
 Stereoisomers which are not mirror image of each other.
 Diastereomers have different physical and chemical properties so they can be easily
separated like fractional distillation or fractional recrystallisation. Chemical
properties are similar but not identical.
 Diastereomers are of three types
(a) Only GI
(b) Only OI
(c) Both GI and OI
HOW TO IDENTIFY DIASTEREOMERIC PAIR

 They are not image.
 Partial difference in R and S configuration at chiral atom.
 Partial difference in dash – wedge at chiral atom.
Examples:
Me Me
H OH H OH
H OH HO H
Me Me
CH3 CH3
S=O S=O
H OH HO H
Me CH3

EPIMERS
 All diastereomers having difference only at a single chiral atom are epimers.
 All epimers are diastereomers but converse in not true.
Example-1:
Me Me
H OH H OH
H Cl H Cl
H Br Br H
Me Me
Example-2:
Me Me
H Cl H Cl
H Br Br H
H I I H
Me Me
MIRROR IMAGE
 Change in R, S at each chiral atom.
 Change in dash – wedge at each chiral atom.
Example:
Cl
Br
ENANTIOMERS
 Stereoisomers which are non – super imposable mirror image of each other.
 Mirror image with out symmetry
 Opposite R, S at each chiral atom without symmetry.
 Opposite in dash – wedge at each chiral atom without symmetry.

Example:
F F
Cl
(1) Br I (2)
Cl Cl
I Br Cl
Br
Me Me Br
H Cl Cl H (4)
(3)
Cl H H Cl Cl
Cl
Me Me
Me CH3 CH3
Me
C=O C=O
H Cl Cl H
(5) (6) H OH HO H
Cl H Cl Me
CH3 CH3
Me H
PROPERTIES OF ENANTIOMERS
(1) Have same physical properties like MP, BP, refractive index, solubility in water etc.
(2) Can not be separated by distillation methods.
(3) Similar chemical properties with achiral reagents but different with chiral reagents.
(4) Have different biological properties.
(5) Same magnitude but opposite angle of rotation.
SEPERATION OF ENANTIOMERS
Can be separated by any one of the following methods.
(1) Biochemical Separation:
This is the method of destroying one at the cost of other with the help of bacteria or fungi.
Example: Penicillium Glaucum eats only d – tartaric acid out of mixture of d and  tartaric acid.
(2) Circular Dichroism:

It is based on spectroscopy method of absorption of left and right circularly polarized light.
(3) Reaction with optically active reagents :
It is the method of converting enantiomeric pairs into diastereomeric pair then again
extracting them from solution.
Example:

(4) Fractional Recrystallization method :
QUESTIONS FOR JEE - ADVANCED
Question-1: Calculate the number of products
(a) () – 2 – methyl butanoic acid + (+) – 2 – butanol 
(b) () – 2 – butanol + (+) – 2 – methyl butanoic acid 
(c) () – 2 – butanol + (+) – 2 – methyl butanoic acid 
Question-2: Compounds which can convert enantiomeric mixture of – 2 – methyl butanoic

acid to diastereomeric mixture is / are
OH
(a) (b) (c) (d)
OH
OH Me OH
NH2 Me
NH2
(e) OH (f) (g) (h)
Me NH2
NH2
(i) (j) H2N – CH2 CH3
C=C=C
H H

TYPES OF ENANTIOMERS
THREO AND ERYTHRO ENANTIOMERS

Threo  Common groups at chiral atoms are on opposite side.
Threo  Common groups at chiral atoms are on same side.
Question : Identify threo and Erythro in following :
Me Me Me
H Cl H Cl Cl
H
(a) (b) (c)
H OH Cl H Me H
Me Me Cl
Me Me Cl
(d) (e) (f)
Cl Et
Cl
QUESTIONS FOR JEE MAIN / NEET
Question : Identify the relation in following pairs

Me
Me
Me Me
Me Me
H OH H OH
(1) (2)
H OH OH H
Me Me
(3) (4)
Me Me
Cl Cl Cl Cl
(5) (6)
Cl Cl Cl Cl
Me Me Me Me
(7) (8)
Me
Me Me Me

Cl Me Me
Cl
H H
(9) (10) (11)

Cl Cl
Me Me
Me Me Cl Cl
Question : Identify the relation in following pair of compounds.
Cl Cl
Me Me
H Cl Cl H
(1) H Br H Br (2)
H I I H
Me Me
Me Me
Me Me Me Me
(3) (4)
Me Me
Me Me
Me Me Me Me
(5) C=C=C C=C=C
H H H H
Me Me Me Me
(6) (7)
Cl Cl Cl Cl Br Br
Cl Cl
Me Me
Me Me
Cl H Cl H Cl
H H Cl
(9) H OH HO H
(8) H OH HO H
Cl H Cl H
H Cl H Cl
Me Me Me
Me
Cl Br Br Cl
(10)
MESO COMPOUNDS
 Optically inactive due to symmetry and internal compensation.

 Inseperable mirror image.
 All meso are inactive but all inactive are not meso.

 Mirror image superimposable.
 Opposite R, S at all chiral atoms along with symmetry.
 Opposite dash – wedge at all chiral atom along with symmetry.
Question : Identify the meso compound in following –
Me Me
Me Me
H OH H OH
(1) (2) (3)
H OH Me H
H H
Me OH
Me
Me
Me
H OH
(4) H OH (5) (6)
H OH
Me
Me Me
Cl Me
Me HOOC H Me
H Br
(7) H Cl (8) (9)
H Cl
H Br
H Me Me
Me Cl
HO O
Cl
Me Me C
(10) (11) H OH (12)

Me H OH
Me
C Cl
O OH
Cl Me
Me
Cl Cl
(13) (14) (15)
Cl Cl Me
Me Me
Cl
Cl Cl
(16)
Cl Cl

ANGLE OF ROTATION
MEASUREMENT OF ANGLE OF ROTATION
(POLARIMETER EXPERIMENT)
It depends on
 Nature of Chiral atom (Groups Attached)
 A particular chiral atom has two optical isomers having equal and opposite rotation.
 Wavelength of light source
In experiment usually Na lamp is used. Wavelength remains constant.
 Temperature
Room temperature conditions are maintained.
 Light of sample tube
On increasing length of sample tube obs .
obs      …… (1)
 is taken in dm.
 Concentration of sample
On increasing concentration obs increase
obs  C    …… (2)
C is taken in g/ml.
If sample is pure Substance  C = density
Solution  C = Strength
Gas  C = Partial Pressure
 Nature of Solvent
Solvent must be chemically and optically inert.
From (1) & (2)
obs  C .
obs  [ ] .C
[ ] =


Question : 1.5 M solution of 2 – Butanol is taken in a sample tube of length 10 cm. It’s observed
angle of rotation observed is +2o. Calculate
(a) [ ]
(b) [ ] and obs if length is halved
(c) [ ] and obs if dilution is doubled
(d) [ ] and obs if length is halved & dilution is double.
D, L Configuration of Chiral Atom
(Absolute Configuration)
Carbohydrate :
(1) These are polyhydroxy aldehyde or ketone or those compounds which on hydrolysis give
such compounds.
(2) Smallest carbohydrate : Glyceraldehyde and dihydroxy acetone.
Formula: CnH2nOn
How to find D and L

(1) Carbon chain must be vertical
(2) F. G. – CHO or > C = O at topmost position.
(3) If OH group attached to last chiral atom is on right then D and if on left then L.
Example:
CHO CHO
H OH HO H
CH2OH CH2OH
D-Glyceraldehyde L-Glyceraldehyde
Note: (1) D and L are enantiomers of each other.
(2) Except dihydroxy acetone all other carbohydrates show O. I.

Question: Define D and L in following
CHO
CHO CHO
=O
H OH H OH HO H
(1) (2) (3)
H OH HO H H OH
CH2OH CH2OH CH2OH

CH2OH OH
(4) H OH (5) H CHO
CHO CH2OH
Recall
Epimers : Diastereomers having different configuration at only one chiral atom.
Structure of D – Glucose
CHO
H OH
HO H
H OH
H OH
CH2OH
D-Glucose
Question : Draw C – 2 and C – 4 epimer of glucose and name them.
TERMS RELATED TO ENANTIOMERS
Recemic Mixture or Recemate
 Equimolar mixture of enantiomers is known as recemic mixture.
 Net rotation is zero due to external compensation.
 It is known as 100 % optically impure.
OPTICALLY IMPURE MIXTURE
d Mixture
R + S
 Mixture
50% 50%

Resolution
1. Seperation of d –  mixture in pure d and  form is known as resolution.
2. All optically active compounds are resolvable.
ENANTIOMERIC EXCESS OR OPTICAL PURITY

(% of Enantiomer in mixture)
If enantiomers are present in unequal amount then partial recemisation will take place and
mixture will be optically active.
Question: Fill in the blanks

__d__ ____ % Recemisation E. E. Mode of rotation
2 mole 1 mole ______________ _____ ________________
_40 %_ _60 %_ ______________ _____ ________________
______ ______ ______________ _30 % _____Leavo______
CALCULATION OF OPTICAL ISOMERS

Case-I: Compounds with Single chiral atom or single unit showing O. I.
Cl
* ' ' '
Me Me
Cl H H Cl
Et Et
Enantiomeric Pair = 1
Optically Active = 2
Optically Inactive = 0
Meso = 0
Case-II: Compounds with two chiral atoms.

(a) Two identical chiral atoms.

Result :
R R Enantiomeric Pair
S S
R S Meso, Identical
S R
Total O. I. = 3 Active = 2
Inactive (Meso ) = 1 Enantiomeric pair = 1
Dia. Pair = 3C2 – 1 = 2
(b) Two different chiral atoms.
Example:
Result :
R R Enantiomeric Pair
S S
R S e. pair
S R
Total O. I. = 4 Active = 4
Inactive (Meso ) = 0 Enantiomeric pair = 2
Dia. Pair = 4C2 – 1 = 4
If n : number of units which can show G.I. /O. I.

SHORTCUT
Case-I: Compound is unsymmetrical
Optically active = 2n
Optically inactive = 0
Enantiomeric pair = = 2n – 1
Case-II:
Compound is Symmetrical
A = 2n – 1 A = 2n – 1 – 2
M=2 M=2
Total = 2n – 1 + 2 Total = 2n – 1
Enantiomeric Pair = = 2n – 2 Enantiomeric Pair =
Questions: Complete following Table
Compound n Total OI active Meso e-pair dia-pair

Cl
(1)
Cl Cl
(2)
Cl Cl
Cl Br
(3)
Cl
Cl Cl
(4)
Cl

(5)
Cl
(6)
(7)
Cl Br
Question : Calculate total stereoisomers (GI and OI) in following

Cl Cl Br
(1) (2) (3)

Br
Cl Cl
* **
(4) (5) (6)
Cl
G. I AND O. I IN CYCLIC COMPOUNDS

Cl
(1) (2) (3)

(4) (5) O
PARCTICS QUESTIONS (JEE ADVANCED)
Question: Calculate total stereoisomers in following :
(1) (2) (3) (4)

Cl
Cl
Cl
Cl Cl Cl
(5) (6) (7) (8)

Cl Cl Cl
Cl
(9)
RANKER’S QUESTIONS
Question: Calculate total stereoisomers in following :
OH OH OH OH
HO OH
(1) (2) (3)
HO HO OH
OH OH

HOOC Ph HOOC Ph
(4) (5) (6)
HOOC Ph Ph COOH
O
O
(7) (8) Me Me (9)
O
O HO
O Cl
(10) (11) (12)
Br
Br I
(13)
Cl
Cl
14. Draw all isomers of C5H10 and C4H8.

15. Calculate total isomers of C6H12 containing a 4 member ring.
SOME OTHER QUESTIONS
Question-1: Which of the following is a meso compound?
H Cl Cl
CH3 H CH2CH3
(a) Cl H (b) H3C Cl (c) H H
H3C H H3C
Cl CH2CH3 Cl
H3C H
Cl Cl
(d) H H (e) H3C CH2CH3
Cl Cl
CH3 H
Question-2: Which of the following molecules is/are chiral?

OH
Br H Br H
OH H COOH
(I) Cl (II) (III)
OH HO H
COOH
(a) I (b) II (c) III (d) I, II
Question-3: A compound was synthesized by student, but its structure was not identified.
However, his wonderfully helpful instructor told him that it was a meso compound
with 5 carbons and 2 stereogenic centers. Which of the following structure should
the student consider as possibilities for his compound?
OH CH2H Br
(I) (II) HO2C OH (III)

Br
Br Br
OH OH
Br Br
(IV) (V)
(a) I, II, III (b) II, IV (c) I, III, V (d) II, IV, V

Question-4: Which of the structure given below are chiral?
H
CH3 CH2OH CH2OH
O
Cl HO H
O O H
(I) (II) (III) HO H
HO H
Cl H
O
CH3 CHO
H CH2OH
CH2OH
HO H
(VI) HO H (V)
HO H
H3C CH3
CH2OH O
(a) I, II, III (b) I, II, V (c) II, III (d) I, II
Question-5: Which of the following molecules are chiral?
OH OH CH3
HO H
(I) (II) (III)
OH OH
HO H
CH3
(IV) (V)
(a) I and II (b) I and V (c) II and III (d) I, II, IV

MOMENTUM
EXERCISE
(CLASS REVISION PROBLEMS)
Class Revision Problems - 01

1. How many alkene isomers are possible for compound with molecular formula C5H10?
(a) 3 (b) 4 (c) 5 (d) 6
2. The no. of isomers of the compound C2H4Cl2 is-
(a) 2 (b) 4 (c) 3 (d) None
3. The total no. of isomers of the compound C5H12O is -
(a) 12 (b) 8 (c) 14 (d) 16
H
|
4. The compounds CH3 – CH2 – COOH and CH 3  C|  H are-
CHO
(a) Chain isomers (b) Position isomers

(c) Functional isomers (d) None
5. Compound C4H10O can show –
(a) Metamerism (b) Functional isomers
(c) Positional isomers (d) All above
6. Which of the following is an example of isomerism –
C| C| C| C|
(a) C  C  C  C & C  C  C (b) C  C  C  C & C  C  C
| |
C C
C C|
C |
(c) C – C – C & CC C (d) C  C  C & C  C  C  C
C | | |
C C C
7. Which of the following are isomers -
(a) Ethanol and ethoxy ethane (b) Methanol and methoxy methane
(c) Propanoic acid and ethyl acetate (d) Propionaldehyde and acetone
8. Rearrangement reaction converts any compounds into -
(a) Higher homologue (b) Lower homologue
(c) Isomers (d) Uncertain
9. Alkynes are isomers of-
(a) Cycloalkane (b) Alkadiene
(c) Alkene (d) All of the above
10. Number of isomeric forms of C7H9N having benzene ring will be -
(a) 7 (b) 6 (c) 5 (d) 4
11. Which of the following is an isomer of diethyl ether-
(a) (CH3)3COH (b) (CH3)2CHOH (c) C3H7OH (d) (C2H5)2CHOH
MOMENTUM Education Pvt. Ltd. : Betiahata Chowk, Gorakhpur. PH. 6389138701 # 71

MOMENTUM
12. CH3CHCl2 and CH2Cl. CH2Cl show which type of isomerism -
(a) Functional (b) Chain (c) Position (d) Metamerism
13. & are

(a) Tautomers (b) functional (c) position (d) all
14. O – Cresol & benzyl alcohol are

(a) Functional (b) position (c) chain (d) all are
15. How many isomers are possible for alkyl group C4H9 –
(a) 2 (b) 3 (c) 4 (d) 5
16. C7H7Cl shows how many isomers:

(a) 4 (b) 5 (c) 3 (d) 2
17. C7H8O shows how many isomers:

(a) 2 (b) 3 (c) 4 (d) 5
18. Which of the following pairs of compounds are not isomers ?
(a) (b)
(c) (d)
19. CH3  CH2  CH2  CN & CH3  CH |

 CH3 are which type of isomers.
CN
(a) positional (b) optical (c) functional (d) chain
20. Alkane, C5H12, in which all H-atoms are equivalent is :

(a) n-pentane (b) 2-methylbutane
(c) 2, 2-dimethylpropane (d) cyclopentane
21. How many isomers of C5H11OH will be alcohols:-

(a) 2 (b) 3 (c) 4 (d) 6

1.

MOMENTUM
2.
3.
4.
5.
6.
7.
8.
9. An alkene exists as geometrical isomers. The minimum number of carbon atoms in the molecules is -
(a) 1 (b) 2 (c) 3 (d) 4
10. Which of the following cannot show geometrical isomerism ?
(a) CH3CH = CHC2H5 (b) (CH3)2 C = CHC2H5
(c) CH3CH = CHCH3 (d) All the three
11. Which of the following will not show cis-trans isomerism ?
(a) Butanedioic acid (b) 1,2-dimethyl cyclopropane
(c) 1,2-dichloroethene (d) Butene dioic acid
MOMENTUM
12. Which one of the following will not show geomemtrical isomerism -
(a) (b)
(c) (d) CH3CH2CH = CHCH2CH3
13. Which of following will exhibit geometrical isomerism ?

(a) 1-phenyl-2-butene (b) 3-phenyl-1-butene
(c) 2-phenyl-1-butene (d) 1,1-diphenyl-1-propene
14.
15.
16. Which one of the alkenes shown below has the Z-configuration of its double bond ?

1.

MOMENTUM
2.
3.
4.
5.
6.
7.
8.
9. The maximum number of stereoisomers possible for 2-hydroxy -2-methyl butanoic acid is -
(a) 1 (b) 2 (c) 3 (d) 4

MOMENTUM
COOH
H OH
10. Meso-tartaric acid is optically inactive due to the presence of:-
H OH
COOH
(a) Molecular symmetry (b) Molecular asymmetry

(c) External compensation (d) Two asymmetric carbon atoms
11. The molecules 3 -penten-2-ol can exhibit -

(a) Optical isomerism (b) Geometrical isomerism
(c) Metamerism (d) Tautomerism
The correct answer is
(a) a and b (b) a and c (c) b and c (d) a and d
12. it has chiral centre (*). It is -
(a) R (b) S (c) Boths (d) None
13. The number of optically active isomers possible for -

CH3 – CH – CH – CH – CH2OH is -
| | |
OH OH OH
(a) 2 (b) 4 (c) 6 (d) 8
14. The number of chiral centers present in 3,4-dibromo-2-pentanol is -

(a) 1 (b) 2 (c) 3 (d) 4
15. The number of enantiomers of the compound CH3CHBrCHBrCOOH is :

(a) 2 (b) 3 (c) 4 (d) 6
16. The following two compounds are

Cl Br
H F and F Cl
Br H
(a) Enantomers (b) Diastereomers (c) Identical (d) Epimers
MORE THAN
17.

MOMENTUM
18. .

1.
2.
3.
4.
5.
6. Which of the following cyano cyclohexane conformations will have high Keq value?
(a) (b)
(c) Both have same Keq (d) Can’t predict

MOMENTUM
7.
8.
MORE THAN
9.
COMPREHENSION TYPE
10.
11.

MOMENTUM
12.
13.
14.
15.

MOMENTUM
EXERCISE # 1
LEVEL-1
A – STRUCTURAL ISOMERISM
A-1. The possible number of alkynes with the formula C5H8 is-
(a) 2 (b) 3 (c) 4 (d) 5
A-2. How many isomers of C5 H11OH will be primary alcohols -
(a) 2 (b) 3 (c) 4 (d) 5
A-3. How many isomers can be obtained from the alkane C6H14-
(a) 4 (b) 5 (c) 3 (d) 7
A-4. How many structural formulae are possible for C5H11Cl -
(a) 6 (b) 8 (c) 10 (d) 12
A-5. Which one fo the following pairs are called position isomers
(a) CH2(OH) CH2COOH & CH2 – CH (OH) COOH
(b) C2H5OH & CH3OH
(c) (C2H5)2CO & CH3COCH2CH2CH3
(d) Both A and C
A-6. CH3CONH2 & HCONHCH3 are called
(a) Position (b) Chain (c) Tautomers (d) Functional
A-7. & show isomerism

(a) chain (b) position (c) functional (d) ring chain
A-8. An isomer of ethanol is :
(a) methanol (b) acetone (c) diethyl ether (d) dimethyl ether
A-9. Isomerism exhibited by acetic acid and methyl formate is :
(a) functional group (b) chain (c) position (d) geometrical
A-10. Butene-1 and cyclobutane exhibit:
(a) ring-chain isomerism (b) position isomerism
(c) tautomerism (d) functional isomerism
A-11. Consider the following formulae:
Cl Cl
| |
(i) CH 3  CH 2  C H  CH 2  CH 3 (ii) CH 3  CH 2  C  CH 3
|
CH 3
These show:
(a) position and functional isomerism (b) chain isomerism
(c) chain and functional isomerism (d) an extraordinary type of isomerism
A-12. Aldehydes and ketones are:
(a) homologues (b) isomers (c) allotropes (d) polymers

MOMENTUM
A-13. Chain isomer of cyclobutane is :
(a) CH3CH2CH = CH2 (b) CH 3CH  CHCH 3 (c) CH3 (d) CH 3C  CH 2
|
CH3
A-14. Consider the following structures :
CH3CH2CH2CH2Cl CH3 C CHCH2CH3
|
Cl
(I) (II)
Type of isomerism shown by I and II is :
(a) chain (b) position (c) both (d) none
A-15. The minimum number of carbon atoms present in an organic compound to show chain isomerism is
(a) 2 (b) 3 (c) 5 (d) 4
A-16. The minimum number of carbon atoms present in an organic compound to be able to show position
isomerism is:-
(a) 3 (b) 4 (c) 2 (d) 5
A-17. The simplest pair of compounds exhibiting functional group isomerism have a minimum of
(a) Four carbons (b) Three carbons (c) Five carbons (d) Two carbons
A-18. Which of the following compund is isomeric with propanoic acid:-
(a) CH3  C  OC 2H5 (b) CH 2  CH 2  C  H
|| | ||
O OH O
(c) CH3– CH(OH)– CH3 (d) CH3O – CH2 – CH2OH
A-19. CH3– NH – C2H5 and (CH3)3N show which type of isomerism:-
(a) Position (b) Functional (c) Chain (d) None
A-20.
A-21.
(a) (b)
(c) (d)
A-22.
(a) (b)
(c) (d)

MOMENTUM
A-23.
A-24.
A-25.
A-26.
A-27.
B – GEOMETRIC ISOMERISM
B-1. Which type of isomerism is shown by benzaldoxime ?
CH = N – OH
(a) Optical isomerism (b) Functional group isomerism

(c) Geometrical isomerism (d) Constitutional isomerism
B-2. Which of the following would exhibit cis-trans isomerism?

(a) CH3CH2CH = CH2 (b) ClCH = CHCl (c) ClCH = CCl2 (d) CH2 = CH – COOH
B-3. The number of geometrical isomers in case of a compound with the

structure CH3 – CH = CH – CH = CH – C2H5
(a) 4 (b) 3 (c) 2 (d) 5
B-4. Maximum number of isomers for an alkene with molecular formula, C4H8 is:
(a) 5 (b) 4 (c) 3 (d) 2
B-5. Number of isomers of molecular formula C2H2Br2 is:

(a) 1 (b) 2 (c) 3 (d) 4
B-6. Select the pair of compounds which exhibit cis-trans (geometrical) isomerism:
(a) fumaric acid and maleic acid (b) malonic acid and succinic acid
(c) lactic acid and tartaric acid (d) acetic acid and crotonic acid
B-7. Two geometrical isomers are given by which of the following compounds:
(a) ethylene dibromide (b) ethenylidene dibromide
(c) acetylene dibromide (d) none
B-8.

MOMENTUM
C – OPTICAL ISOMERISM
C-1. Which of the following compounds can not exist as enantiomers :
(a) CH3 - CH(OH) COOH (b) CH3  CH2  CH  CH2OH
|
CH3
(c) C6H5CH2 – CH3 (d) C6H5CHClCH3
C-2. Optical isomerism is exhibited by the compound which contains:
(a) at least one double bond (b) at least one triple bond
(c) at least one asymmetric carbon atom (d) at least one polar group
C-3. The simplest alkanol exhibiting optical activity is
(a) n-butyl alcohol (b) Isobultyl alcohol (c) s-butyl alcohol (d) t-butyl alcohol
H3C H
C-4. C=C H Exhibits -
H3C C
H3C COOH
(a) Tautomerism (b) Optical isomerism
(c) Geometrical isomerism (d) Geometrical and optical isomerism
C-5. Which is optically active molecule:-
(a) C6H5  C  OH (b) CH3  CH C2H5 (c) C6H5  CH OH (d) C6H5 CH  CH3
|| | | |
O OH H CH3
C-6. The number of stereo isomers of glucose (a six carbon sugar) is:-
(a) 8 (b) 12 (c) 16 (d) 24
C-7. The pair of structures given below represents:
CH3 CH2–CH3
H
C HO C
HO CH2–CH3 H CH3
(a) Enantiomers (b) Diastereomers (c) Homomers (d) Position isomers
C-8. Number of chiral carbon atoms in the compound X, Y and Z respectively would be :
Me
X
Me
Me
Me
(a) 2,1,1 (b) 1,1,1 (c) 2,0,2 (d) 2,0,1

C-9. Which of the following compounds can exhibit enantiomerism?
(a) 3 – hydroxy propanoic acid (b) 3 – hydroxy butanoic acid
(c) 4 – hydroxy butanoic acid (d) None of these
MOMENTUM
C-10. Which of the following is a chiral molecule?
(a) 1 – chloro propane (b) 2 – chloro propane
(c) 1 – chloro butane (d) 2 – chloro butane
C-11.
D – CONFORMATIONAL ISOMERISM
D-1. When temperature is increased -
(a) % of eclipsed form increases (b) % of skew form increases
(c) % of staggered form increases (d) No effect on any form
D-2. The correct energy gradation of different conformers is -
(a) Staggard > skew > eclipsed (b) Skew > staggard > eclipsed
(c) Eclipsed > skew > staggard (d) Skew > staggard > eclipsed
D-3. Most stable form of cyclohexane is -
(a) Boat (b) Chair (c) Skew (d) eclipsed
D-4.
D-5.
D-6.
D-7. The pair of structures represents:-

Me Me
H Me H H
H H H H
Cl CH 2Cl
(a) Enantiomers (b) Position isomers (c) Conformers (d) None

MOMENTUM
EXERCISE # 2
LEVEL-2
A-1. Which of the following is an example of position isomerism
(a) Isopentane and neopentane (b) Glucose and fructose
(c) Ethanol and dimethyl ether (d) a-naphthol and b - naphthol
A-2 are called as

&
(a) position isomers (b) chain isomers (c) function isomers (d) ring chain isomers
A-3. CH3  C H  CH2  C  O and CH3  CH2 CH2  C  Cl are constitute a pair of :-
| | ||
Cl H O
(a) Position isomers (b) Metamers

(c) Optical isomers (d) Functional group isomers
A-4. The total number of benzene derivatives with molecular formula C6H3Cl3 is -
(a) 2 (b) 3 (c) 4 (d) 5
A-5. An organic compound of formula CnH2nO has an acyclic skeleton with no carbon-carbon multiple bonds.
if the molecular weight of the compound is 58, which of the following may be the structure of the com-
pound ?
(a) CH 2  CH  O  CH 3 (b)
(c) CH3  CO  CH 3 (d) CH 2  CH  CH 2 OH
A-6. are
(a) Metamers (b) Geometrical isomers (c) Enantiomers (d) Diasterioisomers
A-7. are
(a) positional isomers (b) chain isomers

(c) metamers (d) tautomers
A-8. The minimum number of carbon atoms in to show metamerism :-
(a) 3 (b) 4 (c) 5 (d) 6
A-9. Which are metamers :-
CH3
(a) CH3– O -– CH2CH2CH3, CH3 – O– CH
CH3
(b) C2H5– O – C2H5, CH3CH2CH2CH2OH

MOMENTUM
(c) CH3– O – C2H5, CH3– CH2– O – CH3
(d) CH 3  C  CH3 , CH 3  CH 2  C H
|| ||
O O
A-10. Number of structural isomers of C6H14 is -
(a) 3 (b) 4 (c) 5 (d) 6
A-11.
A-12.
A-13.
B-1. Which show Geometrical isomerism ?
(a) (b) (c) (d) both (a) & (c)
B-2. Type of isomerism shown by the product of the reaction between benzaldehyde and hydroxyl amine is :
(a) syn and anti geometrical (b) cis and trans geometrical
(c) E and Z geometrical (d) none is correct
B-3. configuration at C1 and C2 atoms are :
(a) d and d (b) l and l (c) R and R (d) R and S
B-4. Which of the following has Z-configuration

C H5 Br CH(CH )
(a) H 3C C = C 2 (b) HOCH C = C CH –CH3 2
H H 2 2 3
H
(c) Cl C=C (d) All of above
Br D
MOMENTUM
B-5. Which will not show geometrical isomerism ?
(a) CH3CH = NOH (b) (c) (d) HO - N = N - OH
B-6. Which of the following compounds does not have any geometrical isomers?
(a) (b) (c) (d)
B-7. Which of the following has E-configuration :-

H3C CHO HN OH
(a) H
C=C
CH2OH
(b) H2 C C = C CH OH
3 2
HOH2C CH3 H COOH

(c) C=C (d) H C C = C CHO
H2N CH(CH3)2 3
B-8. Which of the following represents the structure having cis arrangement around each double bond :-
H
(a) (b) (c) (d)
H H H
B-9. Which is a pair of geometrical isomers :-

Cl Br Cl Br Cl H H Br
C=C C=C Br C = C H Cl
C=C
H Br H CH3 CH3
(I) (II) (III) (IV)
(a) I and II (b) I and III (c) II and IV (d) III and IV
B-10. The IUPAC name of compound
H Me
Me
O
is -
C2H5
Me
(a) (Z)-4,6,7-Trimethyl hept-4-en-3-one (b) (E)-4,6-Dimethyl oct-4-en-3-one
(c) (Z)-4,6-Dimethyl oct-4-en-3-one (d) (E)-4,6-Dimethyl oct-4-en-6-one
B-11. Which can show ‘Geometrical isomerism’ :-
CH H H CH3
(a) CH 3 C = C H
(b) C=C
H
3 H
CH3 CH CH3
(c) CH3 C = C H
(d) H3 C = C CH3
H
B-12. Geometrical isomerism is shown by :
I CH3 CH CH3
(a) H
H
C=C
CH3
(b) CH C = C H (c) CH 3 C = C H (d) Br
Br
C=C
CH3
H 3 3 H
B-13. Which is a pair of geometrical isomers :-
Cl Me Br H Ph OH Me
(a) Br C = C H
and C=C
Me
(b) Me C = N and
Ph
C=N
Cl OH
Me Ph H Ph
(c) Br Br and Br Br (d) C=C and C=C
H Me Me Me

MOMENTUM
C-1. Among the following compounds, the one which can exhibit chirality is -
(a) (b) (c) (d)
C-2. If optical rotation produced by the compound (i) is -650, then rotation produced by compound (ii) is -
(i) (ii) 0
(a) + 650 (b) – 650 (c) Zero (d) Unpredictable

C-3. Which of the following compoundis optically inactive:
OH H CH3
|
(a) CH3  CH2  C H  CH3 (b)
H3C CH 3
CH 3
H
(c) C=C=C (d)
H3C H
Cl H
C-4. The correct stereochemical name of
(a) Methyl 2-methylhepta (2E, 5E) dienoate (b) Methyl 2-methylhepta (2E, 5Z) dienoate
(c) Methyl 2-methylhepta (2E, 5Z) dienoate (d) Methyl 2-methylhepta (2Z, 5E) dienoate
C-5. A molecule is said to be chiral, only if -
(a) it is superimposable on its mirror image
(b) it is non superimposable on its mirror image
(c) it possesses stereogenic centers
(d) it can have different configuration
C-6. Which of the following compounds possesses chiral carbon ?
(a) (b)
(c) (d)

MOMENTUM
C-7. are -
(a) Enantiomers (b) Diastereomers (c) Geometrical isomers (d) Same structure
C-8. What will be the effect on observed rotation of an optically active substance containing 0.5 gm/ml in 10 cm
tube, if its concn. or length of the tube is doubled
(a) Remain same (b) Doubled (c) Halved (d) Becomes one fourth
C-9. molecules are -
(a) Identical (b) Enantiomers (c) Epimers (d) Diastereomers

C-10. By Fischerprojections glyceryl aldehyde is represented as:
(a) (b) (c) both ture (d) none is true
C-11. The minimum number of carbon atoms in ketone to show position isomerism :-
(a) 3 (b) 4 (c) 5 (d) 6
C-12. I and II are :
(a) achiral-identical mirror images (b) chiral-enantiomers

(c) geometrical isomers (each separately) (d) racemic mixture
C-13. Identify R configuration
COOH CN CHO COOH
(a) H (b) CH3 C CH (c) H OH (d) H2N H
CH3 CH2OH CH2OH CH3
C-14. The no. of possible enantiomeric pair that can be produced during monochlorination of 2-methyl-butane is
(a) 2 (b) 3 (c) 4 (d) 1
C-15. How many stereoisomers are possible for the following molecule ?
(a) 1 (b) 2 (c) 3 (d) none

MOMENTUM
C-16. Which of the following pairs of compounds are enantiomers ?
C-17. The correct statement about the compound (A),(B) and (C) is :-
COOCH3 COOH COOH
H OH H OH H OH
(A) H OH (B) H OH 0(C) HO H
COOH COOCH3 COOCH3
(a) (A) and (B) are identical (b) (A) and (B) are diastereomers
(c) (A) and (C) are enantiomers (d) (A) and (B) are enantiomers
COOH
C-18. Compound H C NH2 is -

CH 3
(a) D-form (b) L-form (c) R-form (d) Z-form
C-19. Among the following structure I to III
C2H5  CH  C3H7 ,CH3  C CH  C2H5 , C2H5 CH  C2H5
| || | |
CH3 O CH3 CH3
It is true that :-
(a) All three are chiral compounds (b) Only I and II are chiral compounds
(c) Only II is chiral compound (d) Only I and III are chiral compounds
C-20. The absolute configuration of the compound is :

CH3
Cl H
Cl H
C2H5
(a) 2S, 3R (b) 2S, 3S (c) 2R, 3S (d) 2R, 3R
C-21. Which one of the following is a meso-compound.
COOH CH3 COOH CH2OH
H OH H OH HO H H Cl
(a) (b) HO (c) HO H
(d) H
H OH H Cl
CH2OH CH3 CH3 CH2OH

MOMENTUM
C-22. The complete IUPAC name of the compound :-
CH3 H
C Br
(a) (R)-1-Bromo-1-phenyl ethane (b) (S)-1-Bromo-!-phenyl ethane

(c) (E)-1-Bromo-1-phenyl ethane (d) (Z)-1-Bromo-1-phenyl ethane
C-23. Which of the following is optically active :-
COOH OH CH3
| HO H
H OH H H  C  CH2 CH3
(a) (b) (c) (d) H
H OH | CH3
Cl
COOH
C-24. Which is incorrect statement :-

H H
Me Me H H
(a) and are conformations
H H H Me
H Me
Cl Cl
(b) is a meso-compound
H H
(c) and are Geometrical isoers
H H H H
(d) Me
C=C=C Me and Me C=C=C
Me
are Enantiomers
C-25. The IUPAC name of the given compound is :-
CHO
Br Cl
(a) (2R, 4Z)-4-bromo-2-chloro-2-methyl-4-hexenal
(b) (2R, 4E)-4-bromo-2-chloro-2-methyl-4-hexenal
(c) (2Z, 5R)-3-bromo-5-chloro-5-formyl-2-hexene
(d) (2S, 4E)-4-bromo-2-chloro-2-methyl-4-hexenal
COOH COOH
H OH OH are -
C-26. and H3C
HO CH3 HO H
COOH COOH
(a) Enantiomers (b) Position isomers (c) Geometrical isomers (d) Homomers

MOMENTUM
C-27. The correct configuration assigned for compounds (I) and (II) respectively are -
COOH
HO CH3
H OH C
Br CH2CH3
CH3 (II)
(I)
(a) R, R (b) S, S (c) R, S (d) S, R
C-28.
C-29.
C-30.
C-31.
C-32.

MOMENTUM
C-33.
C-34. Amongst the following, which one could be the structure of an optically inactive monosaccharide having
the molecular weight 150 :-
CH2OH
CHO CH2OH
CH2OH
H OH C=O H
HO H HO
(a) HO H (b) H OH (c) C=O (d) C=O
H OH H OH H OH H OH
CH2OH CH2OH CH2OH
CH2OH
C-35. The total number of configurational isomers of the given compound are :-
CH3– CH = CHCHOHCHOHCH3
(a) 2 (b) 4 (c) 6 (d) 8
D-1. CH3 - CH2 - CH2 - CH3. there is free rotation about (C2 s C3) bond, The same most stable form is
repected after rotation of -
(a) 600 (b) 1200 (c) 2400 (d) 3600
D-2. The puckered form of cylopentane is called the
(a) chair conformation (b) boat conformation
(c) twist–boat conformation (d) envelop conformation
D-3. Which one of the following is the most stable conformation of 2, 3-butanediol :-
OH OH OH OH
H OH H CH3 HO CH3 HO CH3
(a) (b) (c) (d)
H CH3 H CH3 CH3 H H CH3
CH3 OH H H

MOMENTUM
EXERCISE # 3
LEVEL-3
A-1. Which of the following pairs of structures do not represent isomers ?
(a) and (b) and

O O O
OH
O
O O
(c) and (d) and
O
A-2. The molecular formula of diphenylmethane,
How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom?
(a) 6 (b) 4 (c) 8 (d) 7
B-1. What is the relationship between the pair of compounds shown ?
(a) identical, super imposable without bond rotation

(b) conformation
(c) stereoisomers
(d) constitutional isomers.
B-2. Which of following compound can show geometrical isomerism ?
(a) (b)
(c) (d)

MOMENTUM
B-3.
C-1. The correct IUPAC name of the compound H Br
(a) (2R, 3R)–3–bromo–2–butanol Ch3
(b) (2R, 3S)–3–bromo–2–hydroxybutane
(c) (2R, 3S)–3–bromo–2–butanol H3C
(d) (2S, 3R)–3–bromo–3–butanol H
OH
C-2. In which of the following structures is the the central carbon (C-3) not a chiral centre ?
CH3 CH3 CH3 CH3
H OH H Br Br H Br H
(a) H Br (b) H OH (c) H OH (d) OH H
H Br H Br Br H H Br
CH3 CH3 CH3 CH3
C-3. Consider the following structures (A), (B), (C) and (D)
CH3 C2H5 Cl Cl
(A) Cl Br (B) Cl Br (C) CH3 Br (D) C2H5 CH3
C2H5 CH3 C2H5 Br
Which of the following is not correct -
(a) B & C are identical (b) A & B are enantiomers
(c) A & C are enantiomers (d) B & D are enantiomers
C-4. Which of the following pairs of structures conformational isomers ?
(a) (b) and

and
(c) and (d) C and C
C-5. The number of asymmetric carbon atoms and the number of optical isomers in, CH3(CHOH)2COOH, are
respectively
(a) 3 and 4 (b) 1 and 4 (c) 2 and 4 (d) 2 and 3

MOMENTUM
C-6. A Natural occuring element has the constitutional shown.
How many stereoisomer may have this constitution ? O
(a) 8 (b) 16 HO CH2–OH
(c) 64 (d) 128
HO CH=CH–CH=CH–CH2–CH2–CH3
C-7. Which of the following are not the enantiomers of the compound shown below ?
H
Me Br
Br H
Me OH
Et
Me H H H
H Br Me Br Me Br Me Br
(a) H Br (b) H Br (c) H Br (d) H Br
HO Me Me OH Me OH Me OH
Et Et Et Et
C-8. What is the relationship between the two structures ?
(a) constitutional isomers

(b) stereoisomers
(c) different drawings of the same conformation of the same compound
(d) different conformations of the same compound.
C-9. Which of the following statement is wrong ?

(a) Maleic and fumaric acids are geometrical isomers
(b) cis-2-Butene and trans-2-butene are diastereomers
(c) trans-2-Butene has zero dipole moment
(d) Maleic acid is less soluble in water than fumaric acid.
C-10. The conversion of enantiomer into racemic mixture is known as
(a) resolution (b) racemisation (c) revolution (d) inversion
C-11. How many stereo centre are present in this compound?
(a) 1 (b) 2 (c) 3 (d) 4

MOMENTUM
C-12. Molecular structure shown are related to each other as,
(a) (I) and (II) are enantiomeric (b) (I) and (II) are identical
(c) (I) and (II) are diastereomers (d) (I) and (II) are anomeric
C-13. Which of the following compounds is not chiral?

(a) 1-chloropentane (b) 2-chloropentane
(c) 1-chloro-2-methyl pentane (d) 3-chloro-2-methyl pentane
C-14. How many chiral centers are in the following compound ?
(a) 4 (b) 5 (c) 6 (d) 7

C-15. The structure of (S)-2-fluorobutane is best represented by -
(a) (b) (c) (d)
C-16. The maximum number of stereoisomers that could

exist for the compound below ?
(a) 6 (b) 8
(c) 10 (d) 16
C-17. The following pair of compounds is best described as -
(a) identical (b) diastereomers (c) enantiomers (d) none of the above
C-18. Which of the following compounds are meso forms ?
(a) 1only (b) 3 only (c) 1 and 2 (d) 2 and 3

MOMENTUM
C-19. The separation of a racemic mixture into pure enantiomers is termed as -
(a) Racemization (b) Isomerization (c) Resolution (d) Equilibration
C-20. On Pluto, where everything is frozen, astronauts discovered two forms of butane gauche and anti.
Assuming that there are no rotations around single bonds, which statement about the two forms is
correct ?
(a) They are enantiomers
(b) They are diastereoisomers
(c) The are meso compounds
(d) The gauche form has two stereogenic centers, and the anti has only one
C-21. How many isomers are possible for the following molecule ?
(a) 1 (b) 2 (c) 3 (d) 4
C-22. What is the relationship between the molecules in the following pairs ?
(a) enantiomers (b) diastereomers (c) identical (d) structural isomers
B-23. Assingn double bond configurations to the following -
(a) E (b) Z (c) E, E (d) Z, Z
C-24. Which one of the following is a diastereomer of (R)-4-bomo-cis-2-hexene?

(a) (S)-4-bromo-cis-2-hexene (b) (S)-5-bromo-trans-2-hexene
(c) (R)-4-bromo-trans-2-hexene (d) (R)-5-bromo-trans-2-hexene
C-25. Which of the following statements best describes the stereochemical relationships of compound I, II and
III shown below ?

MOMENTUM
(a) All compounds are chiral

(b) None of the compounds is chiral
(c) I and II are meso compounds
(d) I and II are diastereomers, and III is meso compound
(e) I and II are chiral
C-26. The structural formula of sativene is shown below. How many stereogenic centres are there in this molecule?
(a) 2 (b) 3 (c) 4 (d) 5
C-27. Which of the following depict the same stereoisomer ?
(a) 1 and 2 (b) 1 and 3 (c) 2 and 3 (d) 1, 2 and 3
C-28. The absolute configurations of two chiral centers in the following molecule are -
(a) 2(R), 3(S) (b) 2(R), 3(R) (c) 2(S), 3(S) (d) 2(S), 3(R)
C-29. The total number of stereoisomers possible for 2, 3-dichloro butance -

(a) 2 (b) 3 (c) 4 (d) 5

MOMENTUM
C-30 . Which of the following structures is (are) not meso-2-,3-butanediol ?
CH3 OH
H OH H CH3
(a) (b)
H CH3 H CH3
OH OH
CH3 CH 3
HO H HO CH3
(c) (d) H OH
H CH3
OH CH3
C-31.
The molecules represented by the above two structures are -

(a) identical (b) enantiomers (c) diastereomers (d) epimers
C-32. Which of the following is a meso compound -
(a) (b) (c) (d) All
C-32. Which dimethylcyclobutane is optically active ?

(a) trans-1,2 (b) cis-1,2 (c) trans-1,3 (d) cis-1,3
C-33. How many different stereoisomers are possible for the following compound ?
(a) 1 (b) 2 (c) 3 (d) 1
C-34. The following compounds are best described as -

(R)-PhCH(OH)CH3 and (S)-PhCH(OH)CH3
(a) enantiomers
(b) diastereomers
(c) not stereoisomers
(d) conformational isomers (differing by single bond rotation)
MOMENTUM
C-35. Total number of stereoisomers of the compound 1-bromo-3-chlorocyclobutane -
(a) 0 (b) 1 (c) 2 (d) 3
C-36. Total number of stereoisomers of the 1,3-dichlrocyclohexane -

(a) 0 (b) 1 (c) 3 (d) 4
C-37. Total number of stereoisomers of the compound 1,4-dichlorocyclohexane is -

(a) 0 (b) 1 (c) 2 (d) 4
C-38. Total number of stereoisomers of the compound 2-4-dichloroheptane -

(a) 0 (b) 2 (c) 3 (d) 4
C394. Calculate enantiomeric excees of mixture containing 6g of (+) 2–butanol and 4g (–)–2–butanol.
(a) 10% (b) 20% (c) 40% (d) 33%
C-40. Which is the correct structure of D-glyceraldehyde ?
(a) (b) (c) (d) All
C-41. Match the Column-I with Column-II according to the configuration of molecules :
Column-I Column-II
(A) (P) R-(rectus)
(B) (Q) S-(sinister)
(C) (R) D
(D) (S) L
MOMENTUM
C-42. Which one of the following statements regarding the projection shown below is correct ?
(a) Both the projections represent the same configuration

(b) Both (I) and (II) are optically active
(c) Only (I) is optically active
(d) Only (II) is optically active
C-43. Which of the following erythro form and optically inactive ?
(a) (b) (c) (d)
C-44. The compound has -
(a) plane of symmetry (b) axis of symmetry

(c) center of symmetry (d) no symmetry
C-45. Which of the following compounds is chiral ?
(a) (b) (c) (d)
C-46. Which of the following dienes is chiral ?

(a) CH3–CH=C=CH2 (b) CH3–CH=CH–CH=CH2
(c) CH3–CH=C=CH–CH3 (d) CH2=CH–CH2–CH=CH2
C-47.
MOMENTUM
C-48.
C-49.
C-50.
C-51.
C-52.
MOMENTUM
C-53.
C-54.
C-55.
C-56.
C-57.
MOMENTUM
C-58.
C-59.
C-60.
C-61.
C-62.
MOMENTUM
D-1. The most stable conformation of ethylene glycol is -
(a) Anti (b) Gauche (c) Partially eclipsed (d) Fully eclipsed
D-2.
D-3.
D-4.
D-5.
D-6.
MOMENTUM
EXERCISE # 4
(MORE THAN ONE CORRECT OPTION)
1.
2.
3.
4.
MOMENTUM
5.
6.
7.
8.
9.
10.
11.
MOMENTUM
12.
13.
14.
15.
16.
17.
MOMENTUM
18.
19.
20.
21.
22.
23.
MOMENTUM
EXERCISE # 5
(Comprehension Type Questions)
Passage-1
1.
2.
3..
MOMENTUM
Passage-2
5.
6.
Passage-3
MOMENTUM
7.
8.
9.
MOMENTUM
EXERCISE # 6
(MATRIX MATCH)
1.
2.
3.
MOMENTUM
EXERCISE # 7
(INTEGER TYPE QUESTIONS)
1.
2.
3.
4.
MOMENTUM
5.
6.
7.
MOMENTUM
EXERCISE # 8
(Flash Back)
1. The compound which is not isomeric with diethyl ether is [IIT-JEE 1981]
(a) n-propyl methyl ether (b) Butan-1-ol
(c) 2-methylpropan-2-ol (d) butanone
2. An isomer of ethanol is [IIT-JEE 1986]
(a) methanol (b) diethyl ether (c) acetone (d) dimethyl ether
3. Only two isomeric monochloro derivatives are possible for [IIT JEE 1986]
(a) n-butane (b) 2,4-dimethylpentane
(c) benzene (d) 2-methylpropane
4. The number of isomers of C6H14 is [IIT-JEE 1987,2007]
(a) 4 (b) 5 (c) 6 (d) 7
5. The compound which has one isopropyl group is [IIT-JEE 1989]
(a) 2,2,3,3-tetramethylpentane (b) 2,2-dimethylpentane
(c) 2,2,3-trimethylpentane (d) 2-methylpentane
6. Isomers which can be interconverted through rotation around a single bond are [IIT-JEE 1992]
(a) Conformers (b) Diastereomers (c) Enantiomers (d) Positional isomers
7. The structure shows [IIT-JEE 1995]
H3C H
C C H
H3C C
COOH
CH3
(a) geometrical isomerism (b) optical isomerism
(c) geometrical and optical isomerism (d) tautomerism
8. How many optically active stereoisomers are possible for butane-2, 3-diol? [IIT JEE 1997]
(a) 1 (b) 2 (c) 3 (d) 4
9. Which of the following compounds will show geometrical isomerism? [IIT JEE 1998]
(a) 2-butene (b) propene (c) 1-phenylpropene (d) 2-methyl-2-butene
10. Which of the following compounds will exhibit geometrical isomerism? [IIT JEE 2000]
(a) 1-Phenyl-2-butene (b) 3-Phenyl-1-butene
(c) 2-Phenyl-1-butene (d) 1,1-Diphenyl-1-propene
11. A similarity between optical and geometrical isomerism is that [IIT JEE 2002]
(a) each forms equal number of isomers for a give compound
(b) if in a compound one is present then so is the other
(c) both are included in stereoisomerism
(d) they have no similarity
12. Which of the following does not show geometrical isomerism ? [IIT JEE 2002]
(a) 1,2-dichloro-1-pentene (b) 1,3-dichloro-2-pentene
(c) 1,1-dichloro-1-pentene (d) 1,4-dichloro-pentene
13. Racemic mixture is formed by mixing two [IIT JEE 2002]
(a) isomeric compounds (b) chiral compounds
(c) meso compounds (d) enantiomers with chiral carbon
MOMENTUM
14. Following type of compounds (as I, II)
CH 3CH  CH CH 2 C HO H
|
[IIT JEE 2002]
CH 2CH 3
are studied in terms of isomerism in
(a) chain isomerism (b) position isomerism (c) conformers (d) stereoisomerism
15. Which of the following will have a mesoisomer also ? [IIT JEE 2004]
(a) 2,3-Dichloropentane (b) 2,3-Dichlorobutane
(c) 2-Chlorobutane (d) 2-Hydroxypropanoic acid
16. The number of stereoisomers obtained by bromination fo trans-2-butene is [IIT JEE 2007]
(a) 1 (b) 2 (c) 3 (d) 4
17. The alkene that exhibits geometrical isomerism is - [IIT JEE 2009]
(a) 2-methyl propene (b) 2-butene (c) 2-methyl-2-butene (d) propene
18. The number of stereoisomers possible for a compound of the molecular formula [IIT JEE 2009]
(a) 2 (b) 4 (c) 6 (d) 3
19. The correct statement(s) about the compound [IIT JEE 2009]
H3C (HO) HC – CH = CH – CH (OH) CH3 (X) is are
(a) Th total number of stereoisomes possible for X is 6
(b) The total number of diastereomers possible for X is 3
(c) If the stereochemistry about the double 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
20. Write the total number of cyclic structural as well as stereoisomers possible for compound with the mo-
lecular formula C5H10 is [IIT JEE 2009]
21. Write the total number of cyclic isomers possible for a hydrocarbon with the molecular formula, C4H6.
[IIT JEE 2010]
22. Find out the maximum number of isomers (including stereoisomers) that are possible on monochlorination
of the given compound. [IIT JEE 2011]
CH3
|
CH 3  CH 2  C  CH 2  CH 3
|
H
23. Amongst the given options, the compounds in which all the atoms are one plane in all the possible confor-
mations (if any) is (are) - [IIT JEE 2011]
(a) (b) (c) H2C = C = O (d) H2C = C = CH2
24. Which of the given statements about N, O, P and Q with respect to M is are correct? [IIT JEE 2012]
MOMENTUM
(a) M and N are non-mirror image stereoisomers
(b) M and O are identical
(c) M and P are enantiomers
(d) M and Q are identical
Passage
P and Q are isomers of dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. On heating, P forms the
cyclic anhydride.
Upon treatment with dilute alkaline KMnO4, P as well as Q could produce one or more than one from S,
T and U. [JEE ADV. 2013]
25. Compound formed from P and Q are, respectively

(A) OPticaly active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
26. The total number (s) of stable conformers with non-zero dipole moment for the following comound is
(are) [JEE ADV. 2014]
27. Which of the following compounds will exhibit geometrical isomerism? [IIT MAIN 2015]
(A) 1–Phenyl–2–butene (B) 3–Phenyl–1–butene
(C) 2–Pheny–1–butene (D) 1, 1–Diphenyl–1–propene
28. The total number of stereoisomers that can exist for M is - [JEE ADV. 2015]
29. The structure of D–(+) –glucose is [JEE ADV. 2015]
MOMENTUM
The strcuture of L-(–) glucose is
(A) (B) (C) (D)
30. The absolute configuration of [IIT MAIN 2016]
is:
(A) (2S, 3S) (B) (2R, 3R) (C) (2R, 3S) (D) (2S, 3R)
31. For the given compound X, the total number of optically active stereoisomers is ____.
[IIT ADVANCED 2018]
32. Which of these factors does not govern the stability of a conformation in acyclic compounds?
(A) Torsional strain (B) Angle strain [JEE MAIN 2019]
(C) Steric interaction (D) Electrostatic forces of interaction
33. In the following skew conformation of ethane, H' – C – C – H'' dihedral angle is : [JEE MAIN 2019]
(A) 120o (B) 58o (C) 149o (D) 151o
34. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______ . [JEE ADVANCED 2019]
MOMENTUM
ANSWER KEY
1.D 2.A 3.C 4.D 5.D 6.A 7.D 8.C 9.B 10.C 11.A 12.C 13.B 14.A
15.C 16.A 17.D 18.D 19.D 20.C 21.C

1.C 2.C 3.C 4.B 5.C 6.D 7.C 8.C 9.D 10.B 11.A 12.A 13.A 14.C
15.D 16.C

1.B 2.C 3.D 4.A 5.B 6.B 7.C 8.D 9.B 10.A 11.A 12.B 13.D 14.C
15.C 16.A MORE THAN : 17.BCD 18.ABC .

1.B 2.D 3.D 4.D 5.C 6.B 7.B 8.B MORE THAN : 9.AC
COMPREHENSION TYPE : 10.D 11.C 12.D 13.C 14.D 15.B
EXERCISE–1 (OBJECTIVE LEVEL–1)

A-1.B A-2.C A-3.B A-4.B A-5.D A-6.D A-7.D A-8.D A-9.A
A-10.A A-11.B A-12.B A-13.C A-14.D A-15.D A-16.C A-17.D A-18.B
A-19.B A-20.D A-21.C A-22.B A-23.A A-24.C A-25.D A-26.C A-27.C
B-1.C B-2.B B-3.A B-4.A B-5.C B-6.A B-7.D B-8.D C-1.C
C-2.C C-3.C C-4.B C-5.B C-6. C-7. C-8.D C-9.B C-10.D
C-11.D D-1.A D-2.B D-3.B D-4.B D-5.D D-6.D D-7.B

A-1.D A-2A A-3.D A-4.B A-5.C A-6.A A-7.C A-8.C A-10.C
A-11.B A-12.C A-13.B B-1.D B-2.A B-3.C B-4.D B-5.C B-6.D
B-7.D B-8. B-9.C B-10.C B-11. B-12.B B-13.D C-1.D C-2.C
C-3.D C-4.D C-5.B C-6.D C-7.A C-8.B C-9.A C-10.A C-11.C
MOMENTUM
C-12.A C-13.C C-14.A C-15.D C-16.C C-17.D C-18. C-19.B C-20.C
C-21.D C-22.A C-23.C C-24. C-25.A C-26.D C-27.A C-28.A C-29.C
C-30.B C-31.A C-32.D C-33.B C-34.D C-35.D D-1.D D-2.D D-3.C

A-1.D A-2.B B-1.C B-2.D B-3.C C-1.C C-2.D C-3.D C-4.B
C-5.C C-6.C C-7.BCD C-8.A C-9.D C-10.D C-11.B C-12.B C-13.A
C-14.C C-15.C C-16.C C-17.D C-18.B C-19.C C-20.B C-21.D C-22.C
B-23.C C-24.C C-25.E C-26.D C-27.D C-28.A C-29.C C-30 .A C-31.A
C-32.D C-32.A C-33.D C-34.A C-35.C C-36.C C-37.C C-38.D C394.B
C-40.D C-41. A-PR, B-QS, C-QS, D-PR C-42.D C-43.A C-44.C C-45.B C-46.C
C-47.D C-48.B C-49.B C-50.A C-51.B C-52.A C-53.D C-54.A C-55.A
C-56.A C-57.B C-58.D C-59.D C-60.B C-61.C C-62.B D-1.B D-2.D
D-3.A D-4.C D-5.A D-6.C
EXERCISE-4 (MORE THAN ONE CORRECT)

1.AB 2.BD 3.ABC 4.AB 5.ABD 6.CD 7.AD
8.BCD 9.AB 10.ABC 11.AC 12.ABC 13.BCD 14.ABD
15.ABC 16.BCD 17.ABC 18.ACD 19.AC 20.ACD 21.BCD
22.ABD 23.AD
EXERCISE-5 (COMPREHENSION TYPE QUESTIONS)

1.C 2.B 3.A 4.C 5.D 6.A 7.B 8.C 9.D
EXERCISE-6 (MATRIX MATCH)

1. A-PQ, B-PR, C-PS, D-PS 2. A-QR, B-QR, C-S, D-P 3. A-RS, B-PR, C-RS, D-PRS
EXERCISE-7 (INTEGER TYPE QUESTIONS)

1. (8) 2.(7) 3.(4) 4.(8) 5.(3) 6.(4) 7.(5)
MOMENTUM
EXERCISE-8 (FLASH BACK)
1.D 2.D 3.AD 4.B 5.D 6.A 7.B
8.B 9.AC 10.A 11.C 12.C 13.D 14.D
15.B 16.A 17.B 18.A 19.AD 20.(7) 21.(5)
22.(8) 23.BC 24.ABC 25.(B) 26.(3) 27.(A) 28.(2)
29.(A) 30.(D) 31.(7) 32.B 33.C 34. (10)

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SESSION 2021-22

2. Theory (Isomerism) ................................................................................ 38 – 70

3. Class Rivision Problems (CRP) ............................................................ 71 – 79

4. Exercise – 1 (Level – 1) .......................................................................... 80 – 84

5. Exercise – 2 (Level – 2) .......................................................................... 85 – 93

6. Exercise – 3 (Level – 3) .......................................................................... 94 – 106

7. Exercise – 4 (More than One) ................................................................ 107 – 110

8. Exercise – 5 (Comprehension) ............................................................... 111 – 113

9. Exercise – 6 (Matrix Match) ................................................................... 114

10 Exercise – 7 (Interger) ............................................................................ 115 – 116

11. Exercise – 8 (Flash Back) ....................................................................... 117 – 120

12. Answer Key ............................................................................................. 121 – 123

7. At least one different physical or chemical property for their separation.

Structural Isomerism Stereoisomerism

Congormational Isomerism Configurational Isomerism

Rotamers Amine flipping Geometrical Optical

Explanation of Structural Isomerism

They have Same MF but

 Different IUPAC Name

Case-I: Chain Isomerism –

 Different Root Word

Case-III: Functional Isomerism –

 Different functional Groups (Not Tautomers)

(2) 1o, 2o, 3o amine and amides are different F. G.

(3) Alcohol and phenol are different F. G.

Case-IV: Ring Chain Isomerism –

 Different family of compounds ie closed chain and open chain.

 Also known as functional isomers but priority is given to RCI.

Questions: Identify the relation in following pair of compounds.

(1) (2) (3)

(19) (20) (21)

(22) (23) (24)

Example: Can C4H10O show metamerism.

Note: Metamers may be C. I. or P. I. simultaneously but priority is given to metamerism.

Questions: Identify the relation in following pairs.

 Same IUPAC Name

 Different arrangement of atoms in 3D – space

 Compounds having same MF but different arrangement of atoms or groups in space,

 Free rotation of  bond

Case-I: Static Strain

Strain developed by the restricted movement of objects like due to  bond.

Case-II: Angle Strain

It is due to difference in angle required and actual angle.

Case-III: Vander Waal Strain | Steric strain

Strain developed in a molecule due to steric repulsion between bulkier groups.

Case-IV: Torsional Strain

It is the property of Eclipsed form.

Terminology used in conformational analysis

(1) Eclipsed form

Corrosponding valencies are in front of each other. Dihedral angle is zero.

Newman Projection formula Sawhorse / Andiron projection formula

(3) Gauche form: When corresponding valencies are at 60o.

Note: Staggered and Gauche are considered as only stable conformations.

MOMENTUM Education Pvt. Ltd. : Betiahata Chowk, Gorakhpur. PH. 6389138701 C - 10

Potential energy diagram :

60 120 180 240 300 360

No. of Stable conformers ≤ No. of PE minima

(2) Draw conformers of CH3 – CH3. (C – C  bond)

60 120 180 240 270 360