Which one of the following reactions would produce t-butyl methyl ether in high yield? A) t-butyl chloride + sodium methoxide
B) t-butanol + methanol in presence of H2SO4 at 140 C
C) t-butyl bromide + bromomethane in presence of NaOH
D) sodium t-butoxide + bromomethane

D) sodium t-butoxide + bromomethane

Explanation:

The alkoxide ion is a strong nucleophile, that unlike alcohols, will react with primary alkyl halides to form ether. This general reaction is known as the Williamson synthesis, and is a SN₂ displacement. The alkyl halide must be primary so the back side attack is not hindered, and the alkoxide ion must be formed with the most hindered group.

The mechanism can be seen in the attachment.

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