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NEET levelSingle correct optionDifficulty 1 of 3o3060

The best Williamson synthesis of tert-butyl methyl ether $(CH X_{3}) X_{3} C - O - CH X_{3}$ uses

A $CH X_{3} - ONa$ and $(CH X_{3}) X_{3} C - Br$
B $CH X_{3} - ONa$ and $(CH X_{3}) X_{3} C - ONa$
C $(CH X_{3}) X_{3} C - ONa$ and $CH X_{3} Br$
D $(CH X_{3}) X_{3} C - OH$ and $CH X_{3} - Br$ with no base

Answer: C

Williamson ether synthesis is an SN2 reaction of an alkoxide with an alkyl halide, so the halide must be methyl or primary.

(CH X_{3}) X_{3} C - Br

with the basic methoxide would mainly eliminate to isobutene. Therefore the tertiary group must come from the alkoxide and the methyl group from

CH X_{3} Br

.

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