Anisole (methoxybenzene) is heated with a single equivalent of concentrated hydroiodic acid (). What — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

In alkyl aryl ethers like anisole, the oxygen atom is directly attached to an $sp^2$ hybridized aromatic carbon. Resonance imparts partial double bond character to the $O-Aryl$ bond, making it stronger and much harder to cleave than the $O-Alkyl$ bond. Therefore, the $I^-$ nucleophile exclusively attacks the less hindered methyl group, cleaving the $O-CH_3$ bond to yield phenol and methyl iodide.