JEE Main 2021 · 26 February · morning · Single correct · +4 / −1

An amine on reaction with benzensulphonyl chloride produces a compound insoluble in alkaline solution. This amine can be prepared by ammonolysis of ethyl chloride. The correct structure of amine is :

  1. (a) CH₃CH₂NH₂
  2. (b) CH₃CH₂CH₂NHCH₃
  3. (c) CH₃CH₂CH₂N(H)-CH₂CH₃
  4. (d)
    Option (d)
Answer and solution

Answer (c) CH₃CH₂CH₂N(H)-CH₂CH₃

Solution

Chemistry ma’am · 3 steps

Two checks: Hinsberg says secondary amine, and ethyl chloride says an ethyl group must sit on N.

  1. Read the Hinsberg result. With C₆H₅SO₂Cl, a primary amine gives C₆H₅SO₂NHR. Its N–H is acidic, so it dissolves in alkali. A secondary amine gives C₆H₅SO₂NR₂, which has no H on N and stays insoluble in alkali. So the amine is secondary.
  2. Read the ammonolysis clue. Ammonolysis of C₂H₅Cl means an N–H group attacks the alkyl halide. That attaches a C₂H₅ group to nitrogen. For example, CH₃CH₂CH₂NH₂ + C₂H₅Cl → CH₃CH₂CH₂NHC₂H₅ + HCl. So the amine must carry an ethyl group on N.
    OptionType of amineEthyl group on N?
    (a) CH₃CH₂NH₂primaryyes
    (b) CH₃CH₂CH₂NHCH₃secondaryno, it is methyl
    (c) CH₃CH₂CH₂NHCH₂CH₃secondaryyes
    (d) C₆H₅NHCH₂CH₂CH₃secondaryno, phenyl and propyl
  3. So. Only (c), N-ethylpropan-1-amine, passes both checks. It is secondary, and its ethyl group can come from ethyl chloride.

The idea to keep. A Hinsberg product that is insoluble in alkali means a secondary amine, because no acidic N–H is left. Then match the alkyl groups on N to the alkyl halide you are told was used.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Amines & Diazonium Salts

Asked about 170 times in JEE Main since 2020. This question is from 2021.