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JEE Main 2026 Apr 6 Shift 2, Chemistry Q16: Properties of Ether

JEE Main2026Apr 6, Shift 2Chemistry
Q.

Consider the following reaction:

Statement I: In the above reaction, the product formed will be a mixture of benzyl alcohol and iodobenzene.

Statement II: In the above reaction, the –O–CH– bond is cleaved to give the product.

In the light of the above statements, choose the correct answer from the options given below:

  1. A

    Both Statement I and Statement II are true

  2. B

    Both Statement I and Statement II are false

  3. C

    Statement I is true but Statement II is false

  4. D

    Statement I is false but Statement II is true

Solution

For mixed alkyl-aryl ethers, HI cleaves the alkyl–O bond (S2-type attack on the sp carbon). The aryl–O bond is not broken because S2 at sp carbon is unfavourable.

Therefore phenyl benzyl ether (PhO–CHPh) + HI gives phenol (PhOH) and benzyl iodide (PhCHI), not benzyl alcohol and iodobenzene.

Statement I is false. Statement II correctly identifies that the –O–CH– bond (the benzyl C–O bond) is cleaved — true.

Concept behind this question

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