Question

In Williamson synthesis if tertiary alkyl halide is used than

• A. ether is obtained in good yield
• B. ether is obtained in poor yield
• C. alkene is the only reaction pro
• D. a mixture of alkene as a major product and ether as a minor product forms.

Answer 1

Answer: (C)

alkene is the only reaction pro

Answer 2

If a tertiary alkyl halide is used, an alkene is the only reaction product and no ether is formed. For example, the reaction of $CH_3ONa$ with $(CH_3)3_C-Br$ gives exclusively 2-methylpropene.
It is because alkoxides are not only nucleophiles but strong bases as well. They react with alkyl halides leading to elimination reactions.