Which of the following would undergo racemization in base?

Question

Quizplus · Accepted Answer

I and V are chiral centers with different groups attached to them. In basic conditions, both the enantiomers will be converted into their respective enolates, and then subsequent protonation will lead to racemization of both the centers. II and III do not have chiral centers and IV has only one chiral center with identical groups attached to it, therefore they will not undergo racemization under basic conditions.

Which of the Following Would Undergo Racemization in Base