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

Chapter 9, Problem 9.55

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In the Williamson ether synthesis, an alkoxide reacts with an alkyl halide to give an ether.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)3COCH3. You have decided to delegate this task to two of your staff chemists. One chemist, Ima Smart, allows (CH3)3CO K+ to react with H3CI and indeed obtains a good yield of the desired ether. The other chemist, Dimma Light, allows CH3O Na+ to react with (CH3)3CBr. To his surprise, no ether was obtained, although the alkyl halide could not be recovered from the reaction. Explain why Dimma Lights reaction failed.

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