Chapter 17: Q42P (page 845)
1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with
(a) buta-1,3-diene
(b) cyclopenta-1,3-diene
Short Answer

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Chapter 17: Q42P (page 845)
1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with
(a) buta-1,3-diene
(b) cyclopenta-1,3-diene

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To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel–Crafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

m-ethylbenzenesulfonic acid
A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Ephedrine Methamphetamine
Propose a mechanism for the bromination of ethyl benzene shown above.
Propose mechanisms for the Birch reductions of benzoic acid and anisole just shown. Show why the observed orientation of reduction is favored in each case.
Propose a mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine.
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