Chapter 22.SE, Problem 51AP

Interpretation Introduction

Interpretation:

The observation that when optically active (R)-2-methylcyclohexanone is treated with either aqueous base or acid, racemization occurs is to be explained.

Concept introduction:

During racemization the optically active ketone first yields an achiral, planar enol intermediate. When the intermediate reverts back to the chiral ketone there is equal probability of the formation of both enantiomers which leads to racemization. If the chiral carbon does not take part in enol formation, then the resulting product will be optically active.