JEE Challenger
More from Alcohols, Phenols and Ethers
ChemMedMain 2026 • 6th Apr - Shift 2

Cleavage of Ether with Hydroiodic Acid Statement Analysis

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−CH2−-\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 Diagram 1

Options

A

Both Statement I and Statement II are true

B

Both Statement I and Statement II are false

C

Statement I is true but Statement II is false

D

Statement I is false but Statement II is true

Correct

Topics & Concepts

Alcohols, Phenols and EthersAlcohols and Ethers

Step-by-Step Solution

To evaluate the given statements, let us analyze the reaction mechanism of the ether cleavage of benzyl phenyl ether (C6H5−O−CH2−C6H5\text{C}_6\text{H}_5-\text{O}-\text{CH}_2-\text{C}_6\text{H}_5) with hydroiodic acid (HI\text{HI}):

  1. Protonation Step:
    The oxygen atom of the ether gets protonated by HI\text{HI} to form an oxonium ion: C6H5−O−CH2−C6H5+H+⇌C6H5−O∣H+−CH2−C6H5\text{C}_6\text{H}_5-\text{O}-\text{CH}_2-\text{C}_6\text{H}_5 + \text{H}^+ \rightleftharpoons \text{C}_6\text{H}_5-\overset{\underset{\text{H}}{\vert}}{\text{O}}{}^+-\text{CH}_2-\text{C}_6\text{H}_5

  2. Bond Cleavage and Product Formation:
    There are two distinct C−O\text{C}-\text{O} bonds present in the molecule:

    • Csp2−O\text{C}_{sp^2}-\text{O} Bond (Phenyl-Oxygen bond): The lone pair of electrons on oxygen is conjugated with the aromatic benzene ring, imparting partial double-bond character to the Csp2−O\text{C}_{sp^2}-\text{O} bond. Consequently, this bond is very strong and cannot be easily cleaved under standard conditions.
    • Csp3−O\text{C}_{sp^3}-\text{O} Bond (−O−CH2−-\text{O}-\text{CH}_2- bond): The bond between oxygen and the benzyl carbon is a single Csp3−O\text{C}_{sp^3}-\text{O} bond. Furthermore, cleavage of this bond via an SN1\text{S}_\text{N}1 pathway produces a resonance-stabilized benzyl carbocation (C6H5CH2+\text{C}_6\text{H}_5\text{CH}_2^+), or proceeds via nucleophilic attack (SN2\text{S}_\text{N}2) by iodide ion (I−\text{I}^-) at the benzyl carbon.

    Therefore, the −O−CH2−-\text{O}-\text{CH}_2- bond is selectively cleaved, leading to the formation of: C6H5−O−CH2−C6H5+HI⟶C6H5OH (Phenol)+C6H5CH2I (Benzyl iodide)\text{C}_6\text{H}_5-\text{O}-\text{CH}_2-\text{C}_6\text{H}_5 + \text{HI} \longrightarrow \text{C}_6\text{H}_5\text{OH} \text{ (Phenol)} + \text{C}_6\text{H}_5\text{CH}_2\text{I} \text{ (Benzyl iodide)}

  3. Analysis of the Statements:

    • Statement I: Claims that the products formed are benzyl alcohol and iodobenzene. This is False, as the actual products are phenol and benzyl iodide.
    • Statement II: Claims that the −O−CH2−-\text{O}-\text{CH}_2- bond is cleaved to give the product. This is True.

Thus, Statement I is false but Statement II is true, which corresponds to option D.

Cleavage of Ether with Hydroiodic Acid Statement Analysis | Chemistry PYQ Solution - JEE Challenger