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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1146

4-Hydroxybenzaldehyde is treated with exactly one equivalent of in dry ether and then worked up with dilute . The organic product (apart from evolved) is

  1. A1-(4-hydroxyphenyl)ethanol
  2. Bunchanged 4-hydroxybenzaldehyde
  3. C4-hydroxyacetophenone
  4. D4-methoxybenzaldehyde

Answer: B

The phenolic O-H is far more acidic than any C-H, so the first (and only) equivalent of is consumed by deprotonation, giving and the magnesium phenoxide. No Grignard is left to attack the aldehyde, and acid work-up regenerates the starting phenol-aldehyde. Addition to C=O would need a second equivalent.
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