Question

In which of the following reactions, the product obtained is tert-butyl methyl ether?

• A. $C{H}_{3}OH+HO-C{H}_2-C{H}_3\stackrel{Conc.H_{2}S{O}_4}{\to }$
• B. $H_{3}C-\stackrel{C{H}_3}{\stackrel{|}{\underset{C{H}_3}{\underset{|}{C}}}}-Br+C{H}_{3}OH\stackrel{O{H}^{-}N{a}^{+}}{\to }$
• C. $C{H}_{3}Br+N{a}^{+}{O}^{-}-\stackrel{C{H}_3}{\stackrel{|}{\underset{C{H}_3}{\underset{|}{C}}}}-C{H}_3\to$
• D. $C{H}_3-O^{-}N{a}^{+}+C{H}_3-\stackrel{C{H}_3}{\stackrel{|}{\underset{C{H}_3}{\underset{|}{C}}}}-Br\to$

Answer 1

Answer: (C)

$C{H}_{3}Br+N{a}^{+}{O}^{-}-\stackrel{C{H}_3}{\stackrel{|}{\underset{C{H}_3}{\underset{|}{C}}}}-C{H}_3\to$

The product can be obtained by Williamson's synthesis and it involves an $S_{N}2$ pathway.
Thus we can see that Option D is not possible as it will lead to $E2$ products.
Therefore, Option C is the correct option.