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 $-\text{O}-\text{CH}_2-$ bond is cleaved to give the product.
In the light of the above statements, choose the correct answer from the options given below :

Question

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

-\text{O}-\text{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 :

Quantrex Academy · Accepted Answer

Correct answer: D. Statement I is false but Statement II is true

The given reactant is phenyl benzyl ether (C_6H_5-O-CH_2-C_6H_5

).<br><br>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.<br><br>The

C_6H_5-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-CH_2

bond is a weaker single bond. Moreover, cleavage of the

O-CH_2

bond can proceed via a highly stable benzyl carbocation (in an

S_N1

mechanism) or undergo facile

S_N2

attack by the iodide ion (I^-

) at the less sterically hindered and activated benzylic carbon.

Therefore, the

I^-

ion attacks the

CH_2

group, cleaving the

O-CH_2

bond. The products formed are phenol (C_6H_5OH

) and benzyl iodide (C_6H_5CH_2I

).

Statement I claims the products are benzyl alcohol and iodobenzene, which is incorrect. Thus, Statement I is false.

Statement II claims that the

-O-CH_2-

bond is cleaved to give the product, which is correct. Thus, Statement II is true.

Answer: Statement I is false but Statement II is true

Consider the following reaction. Statement I : In the above...