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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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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,h谓

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

Question: Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed

Draw all resonance structures for each compound and use the resonance structures to determine if the substituent has an electron-donating or electron-withdrawing resonance effect.

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

aCH3CH2CH2CH2-

bBr-

cCH3CH2O-

Explain why each of the following reactions will not form the given product. Then, design a synthesis of A from benzene and B from phenol C6H5OH.
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