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

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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.27P

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Question

Propose a mechanism for the steam hydrolysis of pulegone to the compounds shown.

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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