Give reason The phenyl methyl ether reacts with HIHI to form phenol and iodomethane and not iodobenzene and methanol.
Because HI is a powerful acid; hydrogen ions are easily produced. As oxygen contains lone pairs, this produced hydrogen ion attacks the oxygen atom of phenyl methyl ether. When oxygen makes three bonds and has a positive charge, it becomes unstable. As a result, nucleophilic addition occurs. Because the charge on the methyl group is unstable, and there is a resonance between oxygen and the benzene ring, it undergoes the SN2SN2 process. There will be a transition state when the methyl group's carbon atom has 5 bonds when it is attacked by a nucleophile. As iodine ions are big, and the benzene ring is even bigger than the methyl group. There will be a lot of steric repulsions if the iodine and benzene groups approach each other. Phenol and methyl iodide are produced as a result.
