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Dear student,
The examples of organic optical isomers required at A' level all contain a carbon atom joined to four different groups. These two models each have the same groups joined to the central carbon atom, but still manage to be different: Obviously as they are drawn, the orange and blue groups aren't aligned the same way. Could you get them to align by rotating one of the molecules? The next diagram shows what happens if you rotate molecule B. They still aren't the same - and there is no way that you can rotate them so that they look exactly the same. These are isomers of each other. They are described as being non-superimposable in the sense that (if you imagine molecule B being turned into a ghostly version of itself) you couldn't slide one molecule exactly over the other one. Something would always be pointing in the wrong direction. The essential difference between the two examples we've looked at lies in the symmetry of the molecules. If there are two groups the same attached to the central carbon atom, the molecule has a plane of symmetry. If you imagine slicing through the molecule, the left-hand side is an exact reflection of the right-hand side. Where there are four groups attached, there is no symmetry anywhere in the molecule. A molecule which has no plane of symmetry is described as chiral. The carbon atom with the four different groups attached which causes this lack of symmetry is described as a chiral centre or as an asymmetric carbon atom. The molecule on the left above (with a plane of symmetry) is described as achiral. Only chiral molecules have optical isomers.
The examples of organic optical isomers required at A' level all contain a carbon atom joined to four different groups. These two models each have the same groups joined to the central carbon atom, but still manage to be different:
Obviously as they are drawn, the orange and blue groups aren't aligned the same way. Could you get them to align by rotating one of the molecules? The next diagram shows what happens if you rotate molecule B.
They still aren't the same - and there is no way that you can rotate them so that they look exactly the same. These are isomers of each other.
They are described as being non-superimposable in the sense that (if you imagine molecule B being turned into a ghostly version of itself) you couldn't slide one molecule exactly over the other one. Something would always be pointing in the wrong direction.
The essential difference between the two examples we've looked at lies in the symmetry of the molecules.
If there are two groups the same attached to the central carbon atom, the molecule has a plane of symmetry. If you imagine slicing through the molecule, the left-hand side is an exact reflection of the right-hand side.
Where there are four groups attached, there is no symmetry anywhere in the molecule.
A molecule which has no plane of symmetry is described as chiral. The carbon atom with the four different groups attached which causes this lack of symmetry is described as a chiral centre or as an asymmetric carbon atom.
The molecule on the left above (with a plane of symmetry) is described as achiral.
Only chiral molecules have optical isomers.
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