Final answer:
When a phenyl ether is cleaved under acidic conditions, it generally forms phenol and an alkyl halide or alcohol, through a mechanism that involves the protonation of the ether oxygen and subsequent nucleophilic attack resulting in cleavage of the C-O bond.
Step-by-step explanation:
When a phenyl ether is cleaved under acidic conditions, the typical reaction that occurs is an acid-catalyzed cleavage of the ether bond, leading to the formation of phenol and an alkyl halide. The mechanism involves the protonation of the ether oxygen to form a more reactive oogonium ion, which is then attacked by a nucleophile (in some cases, a halide ion). The nucleophilic attack results in the cleavage of the C-O bond and the subsequent formation of two products—the phenol and an alkyl halide or, under certain conditions, an alcohol.
For example, the cleavage of anisole (methoxybenzene) under acidic conditions might yield phenol and methyl chloride or methyl alcohol, depending on the specific conditions and nucleophiles present in the reaction mixture. This transformation is a representation of ether cleavage under acidic conditions, which might also involve catalysts such as hydrohalic acids (HBr or HCl).