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To prepare $tert$-butyl methyl ether by Williamson synthesis, the better partner pair is
A$tert$-butyl bromide + methanol
B$tert$-butanol + methanol
C$tert$-butyl bromide + sodium methoxide
D$tert$-butoxide + methyl bromide
Answer & Solution
Correct answer: D. $tert$-butoxide + methyl bromide
The $S_N2$-style coupling fails on $tert$-butyl halide because elimination (E2) dominates on a 3° substrate. Pair the unhindered electrophile (methyl bromide, perfect for $S_N2$) with the hindered alkoxide ($tert$-butoxide).
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