Which of the following compounds is formed as a major product when the unsymmetrical ether shown below is treated with an excess of HI ?

Step-by-step solution

The reaction of an alkyl aryl ether with HI proceeds via the protonation of the ether oxygen followed by nucleophilic attack by the iodide ion. Due to the partial double bond character of the C - O bond between the phenyl ring and the oxygen atom (arising from resonance), this bond is stronger and difficult to break. Furthermore, nucleophilic substitution ( S_N2 ) does not occur at an sp^2 hybridized aromatic carbon. Therefore, the iodide ion ( I^- ) attacks the sp^3 hybridized carbon of the alkyl group, breaking t