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Chapter 18: Q 76. (page 728)

Question: Draw a stepwise, detailed mechanism for the dienone鈥損henol rearrangement, a reaction that forms alkyl-substituted phenols from cyclohexadienones.

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01

Dienone-phenol rearrangement

The dienone-phenol rearrangement changes dienone to phenol. The dienone has diene in conjugation with the ketone group. Therefore, in the acidic medium, it changes to phenol.

02

Explanation

The mechanism involves the abstraction of a proton by the carbonyl oxygen in the first step.

The second step involves the delocalization of electrons in conjugation. The third step involves the abstraction of a proton from the base.

Mechanism of dienone-phenol rearrangement

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