Consider the ketones piperitone, menthone, and isomenthone.
Suggest reasonable explanations for each of the following observations:
(a) Optically active piperitone (αD = —32°) is converted to racemic piperitone on standing in a solution of sodium ethoxide in ethanol.
(b) Menthone is converted to a mixture of menthone and isomenthone on treatment with 90% sulfuric acid.
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