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JEE Main · 2020 · 07 Jan 2020 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

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A solution of m-chloroaniline, m-chlorophenol and m-chlorobenzoic acid in ethyl acetate was extracted initially with a saturated solution of to give fraction A. The left over organic phase was extracted with dilute NaOH solution to give fraction B. The final organic layer was labelled as fraction C. Fraction A, B and C contain respectively
  1. (A)m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline✓ Correct
  2. (B)m-chlorophenol, m-chlorobenzoic acid and m-chloroaniline
  3. (C)m-chlorobenzoic acid, m-chloroaniline and m-chlorophenol
  4. (D)m-chloroaniline, m-chlorobenzoic acid and m-chlorophenol

Answer: (A)

Solution

Separation here follows acid strength. Sodium bicarbonate, a weak base, neutralises only the strongest acid, so it draws the carboxylic acid into fraction A as m-chlorobenzoic acid. The stronger base NaOH then extracts the weaker phenol into fraction B as m-chlorophenol, leaving the neutral m-chloroaniline in the organic layer as fraction C.
Structure m-chloroaniline
m-chloroaniline
Structure m-chlorobenzoic acid
m-chlorobenzoic acid
Structure m-chlorophenol
m-chlorophenol

JEE Main · 2020 · 07 Jan 2020 · Shift 1 · Single correct option

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