ISOMERS

THE SAME BUT DIFFERENT

Other common ring structures, cyclobutane, cyclopentane and
cyclohexane, are all severely constrained in their molecular
movements. Because of their cyclic nature and these rotational
constraints, cycloalkanes have two ‘sides’, a top and a bottom. This
leads to the possibility of isomerism n substituted cycloalkanes.

1, 2-dichlorocyclopropane exists as
two isomers.
These are termed cis (from the Latin
meaning ‘on the same side’) and trans
(from the Latin meaning ‘across’)
isomers, depending on whether the
two chlorine atoms are both on top of
the ring, or on opposite sides of the
ring.
This lack of rotation also occurs at the C = C bond in alkenes, giving rise to
the possibility of cis–trans isomerism in substituted alkenes.
 Geometric isomers
differ in their physical
and chemical
properties
The isomers of but-2-ene-1, 4-dioic acid also differ considerably in their response to
heating. On heating to 150°C the cis isomer loses water readily to produce an acid
anhydride. In the trans form the two carboxyl groups are too far apart to form this cyclic
anhydride. The trans isomer will only produce the anhydride at the much higher
temperature of 250°C.
 ENANTIOMERS ARE SAID TO BE CHIRAL
A chiral molecule and its mirror image cannot be placed so they match exactly.

The most commonly encountered cause of chirality

is the molecule containing a carbon atom bonded to 4 different substituents
CWXYZ
Such a carbon is called asymmetric centre,
and can also be referred to as chiral carbon
How do the physical properties of enantiomers compare?

The physical properties such as melting point, density, and

spectroscopic properties are identical

Only one physical property differs between enantiomers

The direction of rotation of plane – polarized light

Why is this important?

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