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Chemistry Question 66 – JEE-MAIN 2026

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Consider the following reaction. Benzene ring−O−CH2−Benzene ring+HI⟶Product 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− bond is cleaved to give the product. In the light of the above statements, choose the correct answer from the options given below :

Recall the general mechanism for the cleavage of ethers by hydrogen halides, especially for unsymmetrical ethers.

Step 1: Identify the Ether and Reagent✦ Active

The reactant is Benzyl Phenyl Ether (C6H5−O−CH2−C6H5) and the reagent is HI. This is an ether cleavage reaction.

Step 2: Determine the Cleavage Site and Products○ Expand

In unsymmetrical ethers containing an aryl group and an alkyl group (like benzyl), the Caryl−O bond (phenyl-oxygen bond) is strong due to resonance and does not cleave. The Calkyl−O bond (specifically the O−CH2 bond of the benzyl group) is cleaved. The iodide ion (I−) attacks the benzyl carbon, leading to the formation of Phenol (C6H5OH) and Benzyl Iodide (C6H5CH2I). The reaction proceeds via an SN1 or SN2 mechanism, with the benzyl carbocation being resonance stabilized.

C6H5−O−CH2−C6H5+HI⟶C6H5OH+C6H5CH2I
💡 Teacher's Secret Hint

Remember that aryl-oxygen bonds are resistant to cleavage due to resonance.

Step 3: Evaluate Statements○ Expand

Statement I: "In the above reaction, product formed will be a mixture of benzyl alcohol and iodobenzene." This is incorrect. The products are phenol and benzyl iodide. Thus, Statement I is false.

Statement II: "In the above reaction, the −O−CH2− bond is cleaved to give the product." This is correct. The bond between the oxygen and the CH2 group of the benzyl moiety is cleaved. Thus, Statement II is true.

Therefore, Statement I is false, and Statement II is true, which corresponds to option 4.

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