My solution manual implied that we can have a racemic mixture of a meso compound.

Is this possible?

I was able to rotate the molecule to make it symmetrical. Sure, the bromination in the nucleophilic solvent gives you an anti product, but from my understanding, if you can rotate the molecule so that it is symmetrical, the molecule can be meso.

I'm thinking no because meso compounds by definition have no enantniomers and a racemic mixture has both enantiomers.

  • $\begingroup$ This question and answer highlight what is sadly too often the case - solutions manuals are not edited very well. $\endgroup$ – Ben Norris Jul 18 '14 at 1:16

You are correct and you enumerated the reasons why. A racemic mixture is a mixture of d and l enantiomers in equal proportion. A meso compound has no d or l isomers, it is achiral.

| improve this answer | |

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.