Which pair of reactants is best for preparing the ether shown by the Williamson synthesis?

A $(CH X_{3}) X_{3} CONa$ and $CH X_{3} I$
B $CH X_{3} ONa$ and $(CH X_{3}) X_{3} CBr$
C $(CH X_{3}) X_{3} CONa$ and $CH X_{3} ONa$
D $(CH X_{3}) X_{3} CBr$ and $CH X_{3} Br$

Answer: A

The ether is methyl tert-butyl ether. The Williamson synthesis is an

S_{N} 2

reaction, which works with a methyl or primary halide. Sodium tert-butoxide with methyl iodide gives the ether, whereas sodium methoxide with tert-butyl bromide gives mainly 2-methylpropene by elimination.

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