Question

Illustrate with examples the limitations of Williamson's synthesis for the preparation of certain types of ethers.

Answer 1

In Williamson synthesis for the preparation of ethers, alkoxide ion acts as a nucleophile and attacks (via $S_{N}2$ mechanism) a primary alkyl halide (or methyl halide). However, when secondary or tertiary alkyl halide is used instead of primary alkyl halide, along with substitution, elimination is possible. Elimination will give alkenes as alkoxide ion can also act as a strong base.