Chapter 17: Q34P (page 890)
Propose a mechanism for the bromination of ethyl benzene shown above.
Short Answer
Initiation:

Propagation:

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Chapter 17: Q34P (page 890)
Propose a mechanism for the bromination of ethyl benzene shown above.
Initiation:

Propagation:

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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 reaction of benzyl bromide with ethanol to give benzyl ethyl ether (shown above).
What products would you expect from the following reactions?

Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.
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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