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Chapter 18: Q 76. (page 728)

Question: Draw a stepwise, detailed mechanism for the dienone–phenol 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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Most popular questions from this chapter

D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used for type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.

What acid chloride would be needed to prepare each of the following ketones from benzene using a Friedel–Crafts acylation?

Which substituents have an electron-withdrawing and which have an electron-donating inductive effect

aCH3CH2CH2CH2-

bBr-

cCH3CH2O-

Write out the two-step sequence that converts benzene to each compound.

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.
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