How can meso compounds be recognized?

1 Answer
May 4, 2016

By their symmetry.

Explanation:

A "meso" compound is a symmetric RS compound, with an internal plane of symmetry, such that upon reflection, the R group maps onto S. There are thus 2 chiral centres, with RS or SR configuration. To demonstrate the phenomenon, a favoured molecule is 2,3-"butanediol", which has 3 stereoisomers, one of which is the "meso". (Why does it not 4 stereoisomers: R,R; S,S; S,R; and R,S?)

If you have trouble vizualizing the symmetry or asymmetry, use a model. And do not be ashamed to do so. You have to (i) recognize the symmetry, and (ii) represent that symmetry on the printed page. Neither of these are trivial processes.