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JEE Main levelSingle correct optionDifficulty 2 of 3hx026

In the Williamson synthesis the best route to tert-butyl methyl ether, $(CH X_{3}) X_{3} C - O - CH X_{3}$ , is

A $CH X_{3} - ONa$ with $(CH X_{3}) X_{3} C - Br$
B $(CH X_{3}) X_{3} C - ONa$ with $CH X_{3} Br$
C $(CH X_{3}) X_{3} C - ONa$ with $CH X_{3} - OH$
D $CH X_{3} - ONa$ with $(CH X_{3}) X_{3} C - Cl$ in ethanol at high temperature

Answer: B

Williamson synthesis is an

S_{N} 2

reaction, so the halide should be methyl or primary. A tertiary halide with an alkoxide gives mainly elimination (2-methylpropene). Hence the bulky alkoxide

(CH X_{3}) X_{3} CO X^{-}

must attack

CH X_{3} Br

.

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