How can diastereomers be chiral?

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How can diastereomers be chiral?

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Answer 1 · 2016-06-19T09:51:50

Diastereomers are geometric isomers that are NOT mirror images.

Explanation:

Given this definition, it is fairly easy to suggest examples. Now take $cis-butene$ $"cis-butene"$ versus $trans-butene$ $"trans-butene"$ . The connectivity is the same for each isomer: $C 1$ $C1$ connects to $C 2$ $C2$ ........to $C 4$ $C4$ , however, these isomers are manifestly geometrically different.

If we go to an organic molecule with 2 stereocentres, which I acknowledge was the subject of your question, there could be $R, R$ $R,R$ versus $S, S$ $S,S$ , which are clearly optical isomers; but there could also be the other pair, $R, S$ $R,S$ , and $S, R$ $S,R$ . Sometimes $S, R$ $S,R$ is the same as $R, S$ $R,S$ , i.e. in a symmetric meso compound. We would say that $R, R$ $R,R$ and $R, S$ $R,S$ share a diastereomeric relationship; i,e. same connectivity but different geometry.

It is worth trying to get your head around this, and also practise building models, and representing those models on the printed page.

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How can diastereomers be chiral?

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