JEE Main20266 April 2026Evening ShiftChemistryAlcohols Phenols and EthersActual
Consider the following reaction. Statement I : In the above reaction, product formed will be a mixture of benzyl alcohol and iodobenzene. Statement II : In the above reaction, the - O - CH ₂- bond is cleaved to give the product. In the light of the above statements, choose the correct answer from the options given below :
Options
- ABoth Statement I and Statement II are true
- BBoth Statement I and Statement II are false
- CStatement I is true but Statement II is false
- DStatement I is false but Statement II is true
Correct answer
D. Statement I is false but Statement II is true
Step-by-step solution
The given reactant is phenyl benzyl ether ( C₆H₅-O-CH₂-C₆H₅ ). When it reacts with HI , the ether oxygen is first protonated to form an oxonium ion. The cleavage of the ether linkage then takes place. The C₆H₅-O bond has partial double bond character due to the resonance of the oxygen's lone pair with the benzene ring, making it strong and difficult to break. On the other hand, the O-CH₂ bond is a weaker single bond. Moreover, cleavage of the O-CH₂ bond can proceed via a highly stable benzyl carbocation (in an S_N1