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Question 780009
JEE Chemistry · Hard

Alcohols, Phenols and Ethers: Ether cleavage MCQ

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Ether cleavageHardQuestion 780009

Question

Cleavage of ethers with HI proceeds by:
  1. A
    SN2 on the smaller alkyl group (with primary ethers)
    Correct
  2. B
    Elimination
  3. C
    Addition
  4. D
    Radical mechanism

Correct answer

SN2 on the smaller alkyl group (with primary ethers)

Explanation

Ether cleavage: R−O−R' + HI → ROH + R'I (or RI + R'OH). With I⁻ as nucleophile and H⁺ protonating O first, SN2 occurs on the less sterically hindered (smaller) alkyl group. With 3° groups, SN1 occurs.

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