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Unit 2 PART 1

Geometrical isomerism, also known as cis-trans isomerism, occurs in alkenes due to restricted rotation around carbon-carbon double bonds, leading to different spatial arrangements of groups. Cis isomers have similar groups on the same side, while trans isomers have them on opposite sides, with trans isomers generally being more stable due to reduced steric strain. The E/Z nomenclature is used for more complex alkenes where cis/trans designations are ambiguous, based on the priority of substituents at each end of the double bond.

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Unit 2 PART 1

Geometrical isomerism, also known as cis-trans isomerism, occurs in alkenes due to restricted rotation around carbon-carbon double bonds, leading to different spatial arrangements of groups. Cis isomers have similar groups on the same side, while trans isomers have them on opposite sides, with trans isomers generally being more stable due to reduced steric strain. The E/Z nomenclature is used for more complex alkenes where cis/trans designations are ambiguous, based on the priority of substituents at each end of the double bond.

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Unit -2: Geometrical Isomerism

Geometrical Isomerism/ Cis-trans isomerism:


There is free rotation about carbon-carbon double bonds. However, free rotation cannot occur
around the carbon-carbon double bond of an alkene because of its electronic structure. Thus
the groups bonded to the carbon atoms of the double bond can exist in different spatial or
geometric arrangements. These isomers have the same connectivity of atoms but differ from
each other in the geometry about the double bond. Hence these compounds are called geometric
isomers or cis-trans isomers.
Example: Consider an alkene whose formula is YXC=CXY

I II
(Cis) ( Trans)
Two structures are possible (I & II). The two structures represent different molecules. In
structure (I), two Y groups are on the same side of the molecule. This is the Cis-isomer. On the
other hand, in Structure II, both the Y groups are on opposite sides. This is called trans isomer.
Cis and trans isomers are possible only if the alkene has two different atoms or groups of atoms
attached to each double-bonded carbon atom. Due to this reason, Cis-trans
isomerism/geometrical isomerism is not possible for all alkenes.
Example 1: CH3CH═CH2 (Propene)

Here, no geometrical isomers are possible. This is because one of the double-bonded carbon
has two identical groups attached to it.
Example 2: CH3CH2CH═ CHCH2CH3 ( 3- Hexene)

Cis 3- Hexene Trans 3- Hexene


Geometrical isomers are possible for 3-Hexene. This is because each double-bonded carbon
atom is attached to two different groups.
Stability:
Trans isomers are more stable than the corresponding cis isomers. Thus is because in Cis-
isomer, the bulky groups are on the same side of the double bond. The steric strain of the groups
makes the cis isomer less stable than the trans isomer in which the bulky groups are far apart
(opposite sides).

Cis-2- Butene Trans-2- Butene


(Steric strain) ( No steric strain)

Geometrical isomerism in Cyclic compounds


Geometrical isomerism is also possible in cyclic Compounds. There can be no rotation about
carbon-carbon single bonds forming a ring because the rotation would break the bonds and
break the ring.
Example: 1,2- dimethyl cyclopropane

(Cis) (Trans)
E,Z System of nomenclature:
The cis and trans designation fails to describe the isomeric trisubstituted and tetrasubstituted
alkenes.
For example: Even the relatively simple compounds cannot be designated as cis or trans
isomers.

When the alkene is trisubstituted, the term cis and trans either become ambiguous or cannot be
applied at all. The alkenes with less than two hydrogen atoms may also exits in isomeric forms
but the prefixes cis and trans have no meaning. Instead, the spatial relationship among the
groups are denoted by the letter E or Z which are based on the priorities of the substituents at
each end of the double bond.
E→ German word “ Entgegen” which means across
Z→ German word “ Zusammen” which means together
When the higher priorities substituents at each end are on the same side of the double bond, the
compound is a Z-isomer. If the higher priorities substituents at each end are on the opposite
sides of the double bond, the compound is E-isomer.
The priorities of the substituents are determined by CIP rules.

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