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JEE Main · 2023 · 24 Jan 2023 · Shift 1 · Alcohols Phenols and Ethers

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'A' and 'B' formed in the following set of reactions are :
  1. (A)(see structures)
    Structure A
    A
    Structure B
    B
  2. (B)(see structures)
    Structure A
    A
    Structure B
    B
  3. (C)(see structures)
    Structure A
    A
    Structure B
    B
  4. (D)(see structures)
    Structure A
    A
    Structure B
    B
    ✓ Correct

Answer: (D)

Solution

In the first reaction the ring-bound hydroxyl is phenolic and is not replaced by hydrogen bromide, whereas the benzylic is converted to , so A is 3-(bromomethyl)phenol. In the second reaction the phenolic hydroxyl again survives, while hot hydrogen bromide cleaves the aromatic methyl ether at its alkyl–oxygen bond, expelling methyl bromide and leaving a second hydroxyl on the ring, so B is benzene-1,3-diol. The products are 3-(bromomethyl)phenol and benzene-1,3-diol.

JEE Main · 2023 · 24 Jan 2023 · Shift 1 · Single correct option

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