question_answer

The products obtained when benzyl phenyl ether is heated with HI in the mole ratio\[1:1\]are

1. phenol

2. benzyl alcohol

3. benzyl iodide

4. iodobenzene

A) 1 and 3 only       

B) 3 and 4 only

C) 1 and 4 only       

D) 2 and 4 only

E)  2 and 3 only

Correct Answer: A

Solution :

Benzyl phenyl ether is an unsymmetrical ether, so halide ion of HI is attached to the simple alkyl group and the reaction takes place by following mechanism: (i) Protonation of ether \[\underset{benzyl\text{ }phenyl\text{ }ether}{\mathop{{{C}_{6}}{{H}_{5}}C{{H}_{2}}O{{C}_{6}}{{H}_{5}}}}\,+HI\to {{C}_{6}}{{H}_{5}}C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  H \end{smallmatrix}}{\overset{\begin{smallmatrix}  \oplus  \\  \bullet \,\bullet  \end{smallmatrix}}{\mathop{O}}}\,-{{C}_{6}}{{H}_{5}}+{{I}^{-}}\] (ii) Nucleophilic attack         \[\underset{benzyl\text{ }iodide}{\mathop{{{C}_{6}}{{H}_{5}}C{{H}_{2}}I}}\,+\underset{phenol}{\mathop{{{C}_{6}}{{H}_{5}}OH}}\,\]