ISOMERISM

•
 ISOMERISM

• Two or more compounds having same molecular formula but different structural
formulas and properties are called isomers and this phenomenon is called isomerism.
• For example,
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• Classification of Isomerism
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• Structural isomerism (constitutional isomerism)
Two or more compounds having same molecular formula but
different with respect to arrangement of atoms within the molecule are
called structural isomers and this phenomenon is called structural
isomerism
For example,

• This type of isomerism is classified into 5 different types:-

1. Chain Isomerism
2. Position Isomerism
3. Functional Group Isomerism
4. Metamerism
5. Tautomerism
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1. Chain Isomerism

Two or more compounds having same molecular formula but different with respect to nature of
carbon chain are called chain isomers and this phenomenon is called chain isomerism.
For example:-
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2. Position isomerism

Two or more compounds having same molecular formula but different with respect to position
of functional group are called position isomers and this phenomenon is called position isomerism.
For example:-
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3. Functional Group Isomerism

Two or more compounds having same molecular formula but different with respect to
functional group are called functional group isomers and this phenomenon is called functional group
isomerism.
For example:-
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4. Metamerism

Two or more compounds having same molecular formula but different with respect to
distribution of carbon atom on either side of functional group are called metamers and this
phenomenon is called metamerism.
For example:-
 Alkl Amine Alcohol Phenol Aldehyd Ketone Carboxyl ester
halide e ic acid
Chain 1 1 1 1 1 1 1 1
isomeri s
Position 1 1 1 1 0 0 0 0
Function Alc and Ald and ket Carbox and ester
al gp ether

Metameri ket and 1

sm ether
Tautomer 1 1
ism
• Functional groups
• 1. As a branch position isomerism
• 2. In between metamerism
• 3. At terminals no position isomerism and metamerism
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5. Tautomerism

Two or more compounds having same molecular formula but different with respect to position
of proton from one atom to other in the same molecule are called tautomers and this phenomenon is
called tautomerism.
For example:-
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• Stereoisomerism (configurational/spatial)
Two or more compounds having same molecular formula, same structural formula but different
with respect to position of identical groups in space are called stereoisomers and this phenomenon is
called stereoisomerism.

There are two types of stereoisomerism:-

1. Geometrical Isomerism or Cis-Trans Isomerism
2. Optical Isomerism
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• Geometrical Isomerism or Cis-Trans Isomerism

This type of isomerism arises due to restricted rotation
about double bonds, or about single bonds in cyclic compounds.
For example:-

• Necessary conditions for a compound to exhibit Geometrical

Isomerism or Cis-Trans Isomerism
1. Two groups attached to same carbon atom must be different.
2. There must be a double bond between two carbon atoms .
All alkenes do not show geometrical isomerism
• The cis isomer is the one in which two similar groups are on the same side of
the double bond
• The trans isomer is the one in which two similar groups are on the opposite
sides of the double bond
• Trans isomers are more stable than cis isomers due to less stearic hindrance
• In cyclic compounds
• There can be no rotation about carbon carbon
single bonds forming a ring
• Because rotaion would break the bonds and
break the ring
1,2 dimethyl propane
• Requirements
• There must be at least two other groups beside
hydrogen on the ring
• And these must be attached on the different carbon atoms in the ring
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OPTICAL ISOMERISM
Two or more compounds having same molecular formula,
same structural formula but different with respect to rotation of
plane polarized light in opposite direction are called optical isomers
and this phenomenon is called optical isomerism.

Chirality is a necessary and sufficient condition for optical activity.

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• chiral object has a mirror image that is different from the original object
• Req for optical isomerism(chirality)
• The isomers must be non superimposable mirror images of each other
• The molecule should be asymmetric(lack plane of symmetry)

• Enantiomers
• Any compound that is chiral must have an enantiomer. Any compound that is
achiral cannot have an enantiomer.
• Diastereomers
• Diastereomers are defined as stereoisomers that are not mirror images.
• Determine chiral centres in the following molecules
Structures F and G are achiral. The former has a plane of symmetry passing through the chlorine atom
and bisecting the opposite carbon-carbon bond. The similar structure of compound E does not have such
a symmetry plane, and the carbon bonded to the chlorine is a chiral center (the two ring segments
connecting this carbon are not identical). Structure G is essentially flat. All the carbons except that of the
methyl group are sp2 hybridized, and therefore trigonal-planar in configuration. Compounds C,
D & H have more than one chiral center, and are also chiral. Remember, all chiral structures may exist
as a pair of enantiomers. Other configurational stereoisomers are possible if more than one stereogenic
center is present in a structure.
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• MCQs
1. Ether show the phenomenon of:
(A) Positional Isomerism (B) Functional Group
Isomerism
(C) Metamerism (D) Cis-trans isomerism
2. Which of the following compound may exist as cis-trans isomerism?
(A) 1-Butene (B) 2-Butene
(C) 3-Butene (D) 4-Butene
3. Pentane show how many chain isomerism?
(A) 2
(B) 3
(C) 4
(D) 5

Why there is no free rotation around a double bond and a free rotation around a single bond?