Can phenols be utilized directly in the Williamson ether synthesis, and if so, what is their specifi — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

Phenols cannot act as the substrate (alkyl halide equivalent) in a Williamson synthesis because the $C-O$ bond has partial double bond character and resists nucleophilic attack. However, when treated with a base like $NaOH$, phenol is converted to the highly nucleophilic phenoxide ion, which can easily attack a primary alkyl halide to form an alkyl aryl ether (e.g., phenetole).