Chemistry - ALCOHOL & ETHER Question with Solution | TestHub

The reaction proceeds via an acid-catalyzed hydroperoxide rearrangement (similar to the Hock rearrangement). Protonation of the hydroperoxide ($-$O$-$O$-$H) group, followed by the loss of water, creates an electron-deficient oxygen atom. The aromatic ring with the highest migratory aptitude shifts from the central carbon to this oxygen atom. Due to the electron-donating $+R$ effect, the migratory aptitude order is 4-methoxyphenyl $>$ 4-methylphenyl $>$ phenyl. The 4-methoxyphenyl group selectively migrates, and subsequent hydrolysis yields 4-methoxyphenol and 4-methylbenzophenone.