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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap162

A mixture of phenol, benzoic acid and methoxybenzene in ether is shaken first with aqueous , the ether layer is separated and shaken with aqueous , and the ether layer is separated again. Which of the following correctly describes what ends up where?

  1. Abenzoic acid and phenol both in the layer, methoxybenzene in the layer
  2. Bbenzoic acid in the layer, phenol in the layer, methoxybenzene remains in the ether
  3. Cphenol in the layer, benzoic acid in the layer, methoxybenzene remains in the ether
  4. Dbenzoic acid in the layer, methoxybenzene in the layer, phenol remains in the ether

Answer: B

Benzoic acid ( 4.2) is strong enough to react with bicarbonate and goes into water as sodium benzoate, with evolved. Phenol ( 10) is not acidic enough for bicarbonate but dissolves in as sodium phenoxide. Methoxybenzene has no acidic hydrogen and stays in the ether.
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