Consider the following reaction [figure] Identify products A and B :-
- [figure]
- [figure]
- [figure]
- [figure]
Answer
(2) [figure]
Solution
With HI, the ether oxygen is protonated and I- attacks the benzylic carbon (the benzylic C–O bond breaks easily; the stable benzyl cation can also form).
The aryl C–O bond is not cleaved because it has partial double bond character (resonance of the O lone pair with the ring).
[figure]
[figure]
A = benzyl iodide and B = phenol.
Answer: (2)