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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

Draw the products formed when phenol ( C6H5OH) is treated with each set of reagents.

a. [1] HNO3, H2SO4; [2] Sn, HCl

b. [1] CH3CH22COCl,AlCl3; [2] Zn(Hg), HCl

c. [1] CH3CH2Cl,AlCl3; [2]Br2,hν

d. [1] CH32CHCl,AlCl3; [2] KMnO4

Question: Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.

Classify each substituent as electron donating or electron withdrawing.

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

You have learned two ways to make an alkyl benzene: Friedel–Crafts alkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.
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