How many different b-hydroxyaldehydes and b-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and benzaldehyde with base?

Question

Quizplus · Accepted Answer

The reaction between acetone and benzaldehyde with base forms a mixed aldol product, which can undergo dehydration and further reaction to form b-hydroxyketones and b-hydroxyaldehydes.

There are two possible products from dehydration of the aldol product:

1. Diastereomeric b-hydroxyaldehydes (2 stereoisomers)
2. Diastereomeric b-hydroxyketones (2 stereoisomers)

In addition to these, there are constitutional isomers of the b-hydroxyaldehydes and b-hydroxyketones formed.

Therefore, the total number of different b-hydroxyaldehydes and b-hydroxyketones, including constitutional isomers and stereoisomers, is 3.

How Many Different B-Hydroxyaldehydes and B-Hydroxyketones, Including Constitutional Isomers and Stereoisomers