Reaction between anisole and concentrated HI in excess Question:



My Attempt:  In most of the ethers reaction of HI in excess yields alkane iodide products. But in case of anisole two scenarios are possible, I believe:


The HI breaks bond between methyl and oxygen leading to formation of phenol and methyliodide.
The phenol formed further reacts to form phenyliodide.


But would HI be strong enough to break partial double bond in phenol?
The correct answer here should be C. $\ce{I-}$ is an excellent nucleophile, it would attack the $\ce{C-O}$ bond in the methly group because phenoxide is a good leaving group as it is resonance stabilized and quite polarizable. So, the products are phenol and methyliodide. As for the excess of conc. $\ce{HI}$, it is just there so that some other nucleophile like $\ce{OH-}$ doesn't grab the limelight. I don't think it is energetically favourable to remove hydroxide from phenol to make it iodobenzene.