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$\degree$C C) t-butyl bromide + bromomethane in presence of NaOH D) sodium t-butoxide + bromomethane

Question

Quizplus · Accepted Answer

The formation of t-butyl methyl ether involves an S_N2 reaction, so a good nucleophile is required. In this case, the best nucleophile is the t-butoxide ion, which is formed by deprotonating t-butanol with sodium metal. Bromomethane is a good electrophile, which can undergo an S_N2 reaction with t-butoxide. Therefore, the best choice is option D. Options A and C are not good choices because the methoxide and hydroxide ions are not strong enough nucleophiles to undergo an S_N2 reaction with t-butyl chloride and t-butyl bromide respectively. Option B suggests an acid catalyzed esterification reaction, which would not produce t-butyl methyl ether.

Which One of the Following Reactions Would Produce T-Butyl Methyl °\degree°

Which One of the Following Reactions Would Produce T-Butyl Methyl $\degree$