Predict the major product(s) of the following reaction:

Step-by-step solution

The given reactant is a diaryl ether (specifically, 2-bromo-4-methylphenyl phenyl ether). In diaryl ethers, the oxygen atom is directly attached to two sp^2 hybridized carbon atoms of the aromatic rings. The lone pairs of electrons on the oxygen atom are in resonance with the -electron systems of both benzene rings. This resonance imparts a partial double bond character to both C-O bonds, making them significantly stronger and shorter than typical C-O single bonds. For ether cleavage to occur with concentrated HI,