Pulegone, C10H16O, a compound from oil of pennyroyal, has a pleasant odor midwaybetween
Chapter 19, Problem 19.27(choose chapter or problem)
Pulegone, C10H16O, a compound from oil of pennyroyal, has a pleasant odor midwaybetween peppermint and camphor. Treatment of pulegone with steam produces acetoneand 3-methylcyclohexanone. (a) Natural pulegone has the configuration shown. Assign an R or S configuration to itschiral center.(b) Propose a mechanism for the steam hydrolysis of pulegone to the compoundsshown.(c) In what way does this steam hydrolysis affect the configuration of the chiral centerin pulegone? Assign an R or S configuration to the 3-methylcyclohexanone formedin this reaction.
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