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

Question:

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)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.