Question

When optically active (R)-2-methylcyclohexanone is treated with either aqueous base or acid, racemization occurs. Explain.

Answer 1

Answer:

See explanation

Explanation:

Racemization is said to occur when a 1:1 ratio of (+) and (-) enantiomers of a compound are produced in a reaction.

The reaction of optically active (R)-2-methylcyclohexanone with either aqueous base or acid leads to the formation of a planar enol species for reaction with acid and a planar enolate species for reaction with base.

Both reactions involves the formation of achiral species which reverts back to the chiral product with equal chances of the formation of both enantiomers of the product during the process. This leads to racemization of the product in both cases.