Question

When optically active (S)-2-methylcyclopentanone is treated with aqueous base, the compound loses its optical activity. Explain this observation and draw a mechanism that shows how racemization occurs. For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph. Collapse question part 21.55a Get help answering Molecular Drawing questions Get help answering Molecular Drawing questions. Draw (S)-2-methylcyclopentanone.

Answer 1

See explanation and image attached

Step-by-step explanation:

The first step in the reaction is the attack of the hydroxide ion from the base abstracting a proton from (S)-2-methylcyclopentanone.

The abstraction of a proton from water by the substrate yields the enol form in equilibrium with the keto form.

The product formed is racemic hence the optical activity of (S)-2-methylcyclopentanone is lost.