The heating of phenylmethyl ether with HI produces:
- Iodobenzene
- Phenol
- Benzene
- Ethyl chloride
Explanation:
Hint: Ether reacts with HI and forms phenol and methyl iodide
Explanation:
When phenylmethyl ether reacts with HI then phenol and methyl iodide are formed as a product.
Step-1:
In presence of acid ether can be dissociated. Start with protonating the oxygen of the ether (by the acid of course).
The lone pair of electrons on the oxygen atom of the ether reacts with a proton (H⁺) from HI.
Step-2:
I− can only ever attack the carbon of the methyl group. The other carbon which is part of the benzene ring is not
at all approachable because the delocalized π electron cloud blocks and prevents nucleophiles from attacking the
sp2 carbon.
The reaction is as follows:
Mechanism:
#89018
Exam: NEET – 2017