Pulegone, C,H160, a compound from oil of pennyroyal, has a pleasant odor mid- way between peppermint and camphor. Treatment of pulegone with steam produces acetone and 3-methylcyclohexanone. steam + H,O Pulegone 3-Methylcyclohexanone Acetone

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In what way does this steam hydrolysis affect the configuration of the chiral center in pulegone? Assign an R or S configuration to the 3-methylcyclohexanone formed in this reaction.

Pulegone, C,H160, a compound from oil of pennyroyal, has a pleasant odor mid-
way between peppermint and camphor. Treatment of pulegone with steam produces
acetone and 3-methylcyclohexanone.
steam
+ H,O
Pulegone
3-Methylcyclohexanone
Acetone
Transcribed Image Text:Pulegone, C,H160, a compound from oil of pennyroyal, has a pleasant odor mid- way between peppermint and camphor. Treatment of pulegone with steam produces acetone and 3-methylcyclohexanone. steam + H,O Pulegone 3-Methylcyclohexanone Acetone
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