Anisole, C6H5-O-CH3, is heated with one equivalent of HI. The products are

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Anisole, $C X_{6} H X_{5} - O - CH X_{3}$ , is heated with one equivalent of $HI$ . The products are

The ether oxygen is protonated and iodide attacks the methyl carbon by SN2. The

C X_{6} H X_{5} - O

bond is not broken because the sp2 carbon is resistant to nucleophilic attack, so phenol and

CH X_{3} I

form.