SINHA I. I.T.

CHEMISTRY
How to identify Geometrical Isomers.

Organic compounds which have same molecular formula but different non-interchangable
geometry due to different orientation of atoms in space are called Geometrical Isomers.

Example.
H3C CH3 H3C H

H H H CH3
cis-but-2-ene trans)-but-2-ene

Geometrical Isomers are

1. different compounds i.e non-superimposable i.e. cannot be interconverted without bond
dissociation
2. A type of configurational isomers i.e. they differs in orientation at least at one carbon
atom. Or ( stereo center)
3. Being isomers they have same molecular formula , empirical formule , % composition
4. They have a defined geometry.
5. As they geometrically differs therefore have different dipole moments , mp, bp, vapour
pressure , solubility.

Geometrical Isomerism is found in compounds which have

a. Planner geometry (real or virtual)
b. Different substituent on either side of imaginary or real planner geometry.
c. No interconvertibility ( Presence of Pi bond , continuous pi bond etc.

Planner geometry (real or virtual) :-It is found in following cases.

H3C H

2
sp carbon

1. Alkene. H CH3

2.Alkene (cumulene with odd no of pi bonds)

H3C
C C CH3
H H
.
Z Z
Y
Y
Y
H3C CH3
C C
H H X

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3 Cycloalkanes
XZ plane
H3C CH3

H H
4. Odd no Spiranes
H3C CH3

H H
5.Odd no combination of spiro & cumulene
H3C
CH3
H H

6.Cycloalkene with carbon greater than 8

H

H
H cis H trans
7 Fused rings also have cis & trans orientation
H3C

H
H
trans
CH3

cis
Notation system:
1. cis & trans.
2. Syn and anti
3. E & Z.
1. cis & trans cis and trans notation is used only if there are two identical groups on either
side of the planer geometry.

cis trans none

Ex.

2. Syn and Anti notation is used only if there are C=N or N=N bond with different
substituents ( Historical approach used by fisher for Oximes).

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Ex.
H3C OH H OH H3C OH

N N N

H anti H3C syn H3C none

H3C CH3
CH3
N N
N N
syn H3C anti

3.E and Z notations are introduced to designate geometrical isomers of any type.
1. H3C 1. H3C
Cl Br 1.

Ex. H E Br 1. H Z Cl 1. represent high priority group

No. of geometrical units and no of geometrical isomers.

Total no of geometrical isomers depends on

1. no of geometrical units
2. symmetry/ unsymmetry
3. other structural limitations.
CH3
CH3

H3C
H3 C

1. C C CH3 C C CH3
2.

Ex. H3C CH3 H CH3

CH3

H3C H 3C CH3

H 3C CH3
3. C C H H
4.
H
H H H H
H3C H3C CH3
CH36.
H3C
H
5. H
H H
H CH3
H3C H

H3C CH3
H3C CH3
8.
7.
H H
H H H3C H

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 SINHA I. I.T. CHEMISTRY
H3C CH3 H H
9.
CH3

H H CH3
H CH 3

H 3C C C CH 3

10 C C

H 3C H H H H

H
H3C
11. H

H CH3

H H
H3C
12. H

H CH3
CH3
H
H H

14. 15.
13.

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