Chapter 17: Q37P (page 891)
Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether (shown above).
Short Answer
The mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

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Chapter 17: Q37P (page 891)
Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether (shown above).
The mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

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Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.
Reagents Desired Product
(a) benzene + n-butyl bromide n-butylbenzene
(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene
(c) bromobenzene + ethyl chloride p-bromoethylbenzene
(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide
(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.
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.
What substituted alkene would you use in the Heck reaction to make the following products?

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
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