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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc035

A mixture of benzoic acid, aniline and nitrobenzene dissolved in ether is shaken first with aqueous and then, after separation, with dilute . The substance remaining in the ether layer at the end is:

  1. Abenzoic acid
  2. Banilinium chloride
  3. Cnitrobenzene
  4. Daniline

Answer: C

Benzoic acid reacts with bicarbonate to give water-soluble sodium benzoate and leaves the ether layer. Aniline is basic and reacts with dilute to give water-soluble anilinium chloride, which also leaves the ether. Nitrobenzene is neutral and not basic enough to be protonated, so it stays in the ether.
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