Do meso compounds have enantiomers? Why or why not?

1 Answer
Mar 9, 2016

No, a #"meso"# compound is an #RS# species, that is equivalent to the #SR# species.

Explanation:

A #"meso"# compound is a symmetric #RS# species, where the 2 (potentially) chiral centres map onto each other upon inversion. Given that #R,S# #=# #S,R#, these are the same structure, and symmetrically equivalent. Of course, the structure could give rise to #S,S# and #R,R# enantiomers, as well as an equivalent pair of #R,S# and #S, R#. In this case, the former pair, #S,S# and #R,R#, ARE enantiomeric.

I urge you to get a set of simple models to demonstrate the isomerism, and also practise representing the isomerism on the printed page.

Start with #H_3C-CH(OH)CH(OH)CH_3#. This is a simple structure, but will generate a pair of non-superposable enantiomers, and a meso-isomer. I forget its trivial name, but the structure is a favorite for examiners.