Having discussed some of the basic concepts of stereochemistry,
it is necessary to understand some of the language used to describe
stereochemistry.
We have already met the term enantiomer.
It is defined as: "A species with a non-superimposable mirror
image." An example of a pair of enantiomers is lactic
acid:
Optical isomerism is used to describe the phenomenon
of molecules that rotate plane-polarized light.
A racemic mixture, or
racemate is a mixture of exactly equal quantities of both
enantiomers, so that it does not rotate plane-polarized light in
either direction (as the effects of both enantiomers cancel out.
| Compounds that exist in two enantiomeric forms are
said to be chiral (from the Greek for
"hand"). Chiral molecules do not have a plane of
symmetry (and equally, molecules without a plane of symmetry are
chiral). The examples above used a carbon with four different
groups (an asymmetric carbon, or stereocentre)
to achieve the condition of not having a mirror-image. However,
that is by no means the only way; consider the following molecule,
an allene: |
 |
It does not have an asymmetric carbon, and yet is
chiral.
A compound with more than one stereocentre is more
complicated to deal with in terms of stereochmistry. For example:
The above two molecules are enantiomers, however,
they are not the only stereoisomers of this molecule, there is another,
distinct species:
This molecule, however, is not an enantiomer of the
above two, as it does have a plane of symmetry. It is known
as a diastereomer (or diastereoisomer).
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