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Sian McDonald

Optical isomerism is a form of stereo isomerism. This is when molecules have the same
molecular formula but different spatial arrangements of atoms. There are 2 types of stereo
isomerism, E-Z isomerism and optical isomerism. In E-Z isomerism a carbon-carbon double
bond is necessary but optical isomerism only requires single bonds attached to a central
carbon atom.
A molecule is optically active if it contains a chiral carbon atom with 4 different groups
attached. Due to the tetrahedral shape around the carbon atom, it has no lines of
symmetry. This leads to pairs of optical isomers or enantiomers. These are non-
superimposable mirror images of each other.

Thalidomide is an optically active compound. A racemic mixture, meaning 50% of each
isomer, was used as a drug in the 1950’s and 60’s to treat symptoms such as morning
sickness in pregnant women. It was later found that the drug caused birth defects in babies.

Each isomer has a different effect in the body because they have a different arrangement of
groups around the chiral carbon atom. One isomer R-thalidomide is an antiemetic which
means it prevents vomiting and nausea. The other isomer S-thalidomide was a teratogen,
meaning it caused birth defects. Because the drug administered was a racemic mixture,
both effects were seen. The drug was removed from the market however scientists still
continued research to see if the isomers could be separated. It was eventually found that
even if separated, and only the R-thalidomide was given, it would still convert to S-
thalidomide in the body. However the drug is still used now to treat some forms of cancer.

= Chiral carbon
Sian McDonald

How to Distinguish Between Optical Isomers
Optical isomers have exactly the same physical properties, except for their effect on plane
polarised light.

the enantiomers. Each sample has equal concentration so that they The samples used are
will both rotate the light to the same degree.
Key Terms
Optical Isomerism - Molecules that have a carbon atom with 4 different groups attached,
they are of tetrahedral geometry
Enantiomers - Pairs of optical isomers that are non-superimposable mirror images of one
Chiral - A carbon atom with 4 different groups attached
Non-superimposable - When a molecule can be placed on top of another and they do not fit,
for example when you put your hands on top of each other.
Racemic mixture - A sample that contains equal amounts of each enantiomer. They are
optically inactive as the 2 effects cancel each other out. They also don’t affect a polaroid
plane of light. It leads chemists to think that optical isomers aren’t present.

This is unpolarised
light. It is travelling in
all directions.
The light has now
travelled through a
polaroid filter. This
causes just a single
plane of polarised
light to be left.
The R or D isomer
rotates the polarised
light to the right.
The L or S isomer
rotates the polarised
light to the left.
Sian McDonald