Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

Question

Quizplus · Accepted Answer

The Williamson ether synthesis involves the reaction between an alkoxide ion (from alcohol) and an alkyl halide. In order to get the best yield of ether, one should choose a strong nucleophile and a good leaving group. Among the options given, choice B, using sodium tert-butoxide as a strong nucleophile and iodomethane as a good leaving group, provides the best yield of ether. Choice A uses tert-butyl bromide as a good leaving group, but sodium methoxide is a weaker nucleophile compared to sodium tert-butoxide. Choice C and D include the use of KOH, which is a weaker base compared to sodium tert-butoxide, and may result in lower yields of ether.

Which of the Following Reactions Will Provide the Best Yield