Question

The following is not an appropriate reaction for the preparation of tert.-butyl ethyl ether
$C_2{H}_{5}ONa+(C{H}_3{)}_{3}C-Cl\to (C{H}_3{)}_{3}C-O-C_2{H}_5$.
Write a suitable reaction for the preparation of tert., butyl ethyl ether. Justify your answer in both cases.

Answer 1

The given reaction is depicted in Option A. Here, $C_2{H}_5{O}^{-}$ ion would have to undergo an $S_{N}2$ reaction with the bulky tert-butyl chloride. This reaction is highly unlikely and $E2$ reaction would occur instead.
But Option B provides a sound solution if the reagents are taken in the following manner
$(C{H}_3{)}_{3}C-ONa+C_2{H}_{5}Cl\to (C{H}_3{)}_{3}C-O-C_2{H}_5$
Here, $(C{H}_3{)}_{3}C-O^{-}$ will act as a nucleophile and undergo $S_{N}2$ reaction with the far less bulky $C_2{H}_5-Cl$. Hence, the reaction will be possible.