Identify the compounds formed when anisole is heated with concentrated HI.

Step-by-step solution

Anisole is methoxybenzene ( C₆H₅OCH₃ ). When anisole is heated with concentrated HI, the ether oxygen is protonated to form an oxonium ion. The iodide ion ( I^- ) acts as a nucleophile and attacks the less sterically hindered methyl carbon via an S_N2 mechanism. The C-O bond between the benzene ring and oxygen has partial double bond character due to resonance, making it difficult to break. Furthermore, nucleophilic substitution does not occur on the sp^2 hybridized carbon of the benzene ring. Thus, the cleavage oc