Organic Chemistry Lecture - 03

ISOMERISM

OM PANDEY, IIT Delhi

Topics
1 Geometrical isomerism

2 Optical isomerism
JEE Mains - 2021

Which of the following compound can not show geometrical isomerism?

A Azomethane

B 1-Bromo-2-chloroethene

C 1-Phenylpropene

D 2-Methyl-2-butene
Question

Which of the following compounds will not show geometrical isomerism :

Br
CH3
Br CH3
A B
Cl
Cl
CH3
H3C CH3
C D
H3C CH3 H3C CH3
Question Which of the following can show geometrical isomerism.

H C2H5 CH3 H OH
(i) C=C (ii) (iii) D (iv) C=N
H CH3 CH3
CH3 D
Cl Cl
Br H H
(v) (vi) C (vii) C
CH3 CH3
Cl Cl

(viii) CH2 = CH – CH = CH – Ph
Question
Which of the following is a pair of structural isomers?

CH3 CH3 Cl Cl

A and B and
Cl Cl

CH3 CH3 CH3

CH3
C D
and and
O
O
H2C
CH2
Question
Metamers of ethyl propionate are :

A C4H9COOH and HCOOC4H9

B C4H9COOH and CH3COOC3H7

C CH3COOCH3 and CH3COOC3H7

D CH3COOC3H7 and C3H7COOCH3

Question
n-propyl alcohol and isopropyl alcohol are:

A Position isomers

B Chain isomers

C Tautomers

D Geometrical isomers
Question
Which of the following is/are correct statements (s) ?
O
A are functional isomers to each other
and
OCH3
OH
B and are position isomers to each other
OH

OEt
OMe are chain isomers to each other
C and

D and O are metamers of each other

O
E/Z Nomenclature a b a d
C C C C
c d c b
CIP Rule [ Sequence Rule ]
1) Group having first atom with higher atomic no. is senior . Cl Br
C C
F I

2) The higher mass isotope is senior. Cl D

C C
F H

3) If first atom of group is identical then second atom is observed for seniority.

Cl CH2 — CH3 CH3 CH2 — OH

C C C C
F CH2 — H I CH2 — NH2
4) Group having D.B. / T.B. are treated as following.

F
C C
Cl
O

NH O
NH
O
O

C=C

O
JEE(Main) 2017 Online
In the following structure, the double bonds are marked as I, II, III and IV
II

III

I IV

Geometrical isomerism is not possible at site (s) :

A I

B III

C I and III

D I and IV
JEE(Main) 2015

Which of the following compound 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
Physical Properties of G.I.

Dipole moment Stability

Boiling point Melting point

Solubility in water

Br H Br Br
C C C C
H Br H H
AIEEE 2002 ( H.W. )

Which of the following does not show geometrical isomerism?

A 1, 2-Dichloro-1-pentene

B 1, 3-Dichloro-2-pentene

C 1, 1-Dichloro-1-pentene

D 1, 4-Dichloro-2-pentene
Polarimeter Experiment
+15°0 –15°
+30° –30°
+45° –45°

 → 0o
Optically Inactive

Polarizer Plane Sample cell Analyzer

Polarised Light
 → (+) , Clockwise
Dextro-rotatory
compound
Optical Rotation :

 → (-) , Anti-clockwise
Leavo-rotatory
compound
Specific Rotation [  ]

l → dm
C → gm/ml
 → degree

Specific Rotation is the degree of rotation observed if a 1 dm tube is used and compound
has concn 1gm / ml.
Chiral Centre / Chiral Atom / Asymmetric Atom
1. sp3 Hybridisation
2. 4 different groups/atoms

How many chiral atoms are present in following compounds ?

H
H
Cl
+ N
(a) (b) N CH3
(c)
C2H5 O N
Br
O H
H5C2 D
(d) Si (e) CH3 S C2H5
H3C H
JEE Mains 2022 /29 June/Shift-I

Observe structure of the following compounds

Cl NH2
OH OH
H2N
O O

OH

The total number of structures compounds which possess asymmetric atoms

is ______________.
Chiral Compounds A compound which is non-superimposable on its mirror image
Asymmetric compounds F
H

HO Br

OH

F Br

A compound having only one chiral carbon is Chiral / Optically Active.

AIEEE 2004

Amongst the following compounds, the optically active alkane having lowest molecular
mass is

A CH3 – CH2 – CH2 – CH3 B CH3 – CH2 – CH2 – CH3

C CH3 – C D CH3 – CH2 – C  CH

C2H5
AIEEE 2004
Among the following four structures I to IV.
CH3 O CH3 H CH3

C2H5 – CH – C3H7 CH3 – C – CH – C2H5 H – C C2H5 – CH – C2H5

(I) (II) (IV)
H
(III)
It is true that :

A All four are chiral compounds

B Only I and II are chiral compounds

C Only III is a chiral compound

D Only II and IV are chiral compounds

Rule for Correct Fischer Projection
On the vertical line , main chain is taken with first carbon at top.

CH2OH CH CHO
OH

CH3 CH COOH
NH2
Nomenclature

Absolute Configuration
Relative Configuration
R – S Nomenclature
D – L Nomenclature

Standard : Glyceraldehyde

CHO CHO
H OH HO H
CH3 CH3

Note : Applied only in Correct Fischer Projection

R - S Nomenclature - Fischer Projection
Apply CIP Rule and find priority order . a
c b

Cl CHO
I Br HO CH3
F H
If lowest priority group is at horizontal line then
O
a
CHO C H
c d H Cl HO H
b H3C
H OH

CH2OH

Odd & Even Exchange

CHO
H Cl
H3C