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JEE Main · 2025 · 07 Apr 2025 · Shift 2 · General Organic Chemistry

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Mixture of 1 g each of chlorobenzene, aniline and benzoic acid is dissolved in 50 mL ethyl acetate and placed in a separating funnel, 5 M NaOH ( 30 mL ) was added in the same funnel. The funnel was shaken vigorously and then kept aside. The ethyl acetate layer in the funnel contains :
  1. (A)benzoic acid
  2. (B)benzoic acid and aniline
  3. (C)benzoic acid and chlorobenzene
  4. (D)chlorobenzene and aniline✓ Correct

Answer: (D)

Solution

Of the three compounds only benzoic acid is acidic enough to react with sodium hydroxide; it is turned into water-soluble sodium benzoate and passes into the aqueous layer. Aniline is only feebly basic and is untouched by sodium hydroxide, while chlorobenzene is neutral and unreactive, so both remain dissolved in the ethyl acetate. The organic layer therefore holds chlorobenzene and aniline.

JEE Main · 2025 · 07 Apr 2025 · Shift 2 · Single correct option

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