In the Williamson ether synthesis, an alkoxide reacts with an alkyl halide to give an ether. You

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In the Williamson ether synthesis, an alkoxide reacts with an alkyl halide to give an ether.R-: + R'-X: R-O-R' +:X-

You are in charge of a research group for a large company, Ethers Unlimited, and you have been assigned the task of synthesizing tert-butyl methyl ether, (CH3)3C—O—CH3. You have decided to delegate this task to two of your staff chemists. One chemist, Ima Smart, allows (CH3)3C—O¯K+ to react with H3C—I and indeed obtains a good yield of the desired ether. The other chemist, Dimma Light, allows CH3O¯ Na+ to react with (CH3)3C—Br. To his surprise, no ether was obtained, although the alkyl halide could not be recovered from the reaction. Explain why Dimma Light’s reaction failed.

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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