Which is the following cannot be prepared by using Williamson synthesis ?

Options

A. Di-tert-butyl ether
B. Methyoxybenzene
C. Benzyl p-nitrophenyl ether
D. Methyl tertiary butyl ether

Answer

A

Explanation

Di-tery-butyl ether can not be prepared made by Williamson's synthesis, since tert-alkyl halides prefer to undergo elimination rather than substitution, i.e.
`CH_(3)-overset(CH_(3))overset("| ")underset(CH_(3))underset("| ")"C "-Br+CH_(3)-overset(CH_(3))overset("| ")underset(CH_(3))underset("| ")"C "-O^(-)Na^(+) overset(Delta)underset(-NaBr)rarrCG_(3)-overset(CH_(3))overset("| ")"C "=CH_(2)+CH_(3)-overset(CH_(3))overset("| ")underset(CH_(3))underset("| ")"C "-OH`