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ISOMERISM
Keane A. Campbell MSc; BSc; ASc. September 25, 2013

DEFINE, WITH EXAMPLES, STRUCTURAL ISOMERISM

Structural isomerism is the existence of different compounds sharing the same molecular formula but have different structural formulae. Example: there are three structures for the hydrocarbon C5H12, corresponding to the molecules: pentane, 2methylbutane, and 2,2-dimethylpropane.

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CHAIN ISOMERS

These are isomers that have different arrangements of their carbon skeletons. They possess the same functional group, and belong to the same homologous series, e.g. pentane, 2-methylbutane and 2,2dimethylpropane. Chain isomers may have different physical properties because the different shapes will alter the strength of the dispersion forces. Pentane boils at 360C, 2-methylbutane at 280C, and 2,2-dimethylpropane at 100C. Their chemical properties, however, are virtually the same because they are all alkanes.

FUNCTIONAL GROUP ISOMERS

These are isomers that have different functional groups and belong to different homologous series. They have different physical properties as well as different chemical properties because the functional group is different. Some examples are as follows: An alcohol and an ether with the same molecular formula

a)

b)

An aldehyde and a ketone: C3H6O

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FUNCTIONAL GROUP ISOMERS

c)

A carboxylic acid and one or more esters: C4H8O2

POSITIONAL ISOMERS

These are isomers that have a functional or substituent group in different positions in the same carbon skeleton. The isomers are chemically similar because they possess the same functional group, e.g. Propan-1-ol and Propan-2-ol

a)

b)

Pent-1-ene and Pent-2-ene

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POSITIONAL ISOMERS
c)

This type of derivatives.

isomerism

is

found

in

benzene

EXPLAIN STEREOISOMERISM

Stereoisomers have the same molecular formula and also the same structural formula i.e. they have the same bonding sequence, but they differ in their orientation of their atoms in space. There are two types of steroisomerism:

1.

Geometrical (cis/trans) isomerism and

Optical isomerism (Enantiomers)

2.

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GEOMETRICAL ISOMERISM (DIASTEREOMERS)

These are compounds that have restriction of rotation about a C=C double bond thereby giving rise to cis-trans isomerism. These stereomisomers are not mirror images of each other. They do not have the same physical and chemical properties. The alkene isomers cis- and trans-1,2-dichloroethene, shown here, are stereoisomers that are diastereomers:

OPTICAL ISOMERS

These are isomers of a compound containing one chiral centre existing in two forms that are non-superimposable mirror images of each other. A chiral centre is an asymmetric carbon atom that is attached (bonded) to four different atoms or groups. Thus, optical isomerism is due to asymmetry in molecules. Also, students, a carbon atom is said to be an asymmetric carbon atom if it is bonded to four different atoms or groups. The two enantiomers of the amino acid alanine:

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OPTICAL ISOMERS
In Layman terms

What is the difference between your left hand and your right hand? They look similar, yet a left-handed glove does not fit the right hand. The same principle applies to your feet. They look almost identical, yet the left shoe fits painfully on the right foot.

The relationship between your two hands or your two feet is that they are non-superimposable (non-identical) mirror images of each other. Students they simply cannot fit.