Question

Which of the following is not a good method to prepare tert-butyl methyl ether?

• A. ${\left(C{H}_3\right)}_{3}C{O}^{-}N{a}^{+}+C{H}_{3}Br\to$
• B. ${\left(C{H}_3\right)}_{3}CBr+C{H}_3{O}^{-}Na\to$
• C. $H_{2}C=C{\left(C{H}_3\right)}_2+C{H}_{3}OH\stackrel{H^{+}}{\to }$
• D. All of these

Answer 1

Answer: (B)

${\left(C{H}_3\right)}_{3}CBr+C{H}_3{O}^{-}Na\to$

In the presence of a strong base, such as sodium methoxide ion, tert-butyl bromide will undergo dehydrobromination to form 2-Methylprop-1-ene and not ether. Because the alkyl halide is tertiary which gives elimination reaction rather than substitution.

Hence, this is not a good method for the preparation of tert-butyl methyl ether.

Option B is correct.