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JEE Main · 2020 · 07 Jan 2020 · Shift 2 · Alcohols Phenols and Ethers

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In the following reaction sequence, structures of A and B respectively will be
  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

first reduces the ester to a primary alcohol, giving the intermediate A — a ring bearing the hydroxy-propyl chain alongside the benzylic bromide and the phenol. Base then deprotonates that alcohol, and the alkoxide displaces the benzylic bromide in an intramolecular Williamson ether synthesis, closing a six-membered oxygen-containing ring while the phenolic survives. The pair of structures A and B matching this reduction-then-cyclisation sequence is the correct one.

JEE Main · 2020 · 07 Jan 2020 · Shift 2 · Single correct option

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