Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

In the reaction:

the product is:

Options:

Correct Answer:

Explanation:

The correct answer is option 3.

 

The reaction of benzyl methyl ether (C₆H₅–CH₂–O–CH₃) with HI gives: C₆H₅–CH₂I + CH₃OH

Ethers react with HI by cleavage of the C–O bond after protonation of the oxygen.

  1. First step: Protonation of ether oxygen

    The oxygen atom gets protonated by HI, forming an oxonium ion.

  2. Second step: Nucleophilic attack by I⁻

    The bond breaks preferentially at the benzyl carbon because a benzyl carbocation is resonance stabilized.

  3. Products formed

    • Benzyl iodide (C₆H₅–CH₂I)

    • Methanol (CH₃OH)

Thus the reaction is:

C₆H₅–CH₂–O–CH₃ + HI → C₆H₅–CH₂I + CH₃OH

The reaction will be as follows:

Mechanism: