Question

Why do we get phenol and methyl iodide and not phenyl iodide methyl alcohol by the reaction of anisole with hi at 373k?

Answer 1

Answer:

This is due to the steric hindrance and the strength of the CARBON-Oxygen bond between phenyl group and oxygen.

This is due to resonance.

Explanation:

First, The hydrogen from HI is abstracted by the lone pair of carbon.

Then The I- anion makes a SN2 Nucleophilic attack. From the methyl side.

Another reason is that the oxygen cannot be cleaved from the phenyl group as it is attached to sp2 hybridised carbon.