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The increasing order of boiling point of the following amines is

  • A.\(\mathrm{C_2H_5N(CH_3)_2 \lt (C_2H_5)_2NH \lt C_4H_9NH_2}\)
  • B.\(\mathrm{C_4H_9NH_2 \lt C_2H_5N(CH_3)_2 \lt (C_2H_5)_2NH}\)
  • C.\(\mathrm{C_2H_5NH(CH_3)_2 \lt C_4H_9NH_2 \lt (C_2H_5)_2NH}\)
  • D.\(\mathrm{(C_2H_5)_2NH \lt C_4H_9NH_2 \lt C_2H_5N(CH_3)_2}\)
  • E.\(\mathrm{(C_2H_5)_2NH \lt C_2H_5N(CH_3)_2 \lt C_4H_9NH_2}\)

Answer: A

The increasing order is \(\mathrm{C_2H_5N(CH_3)_2 \lt (C_2H_5)_2NH \lt C_4H_9NH_2}\).

The three amines are isomers (C4H11N), so their boiling points depend on intermolecular hydrogen bonding. A primary amine has two N-H hydrogens and bonds most strongly; a secondary amine has one; a tertiary amine has none.

So the tertiary amine boils lowest, then the secondary, then the primary. The other orders place the tertiary amine above an amine that can hydrogen-bond, or put the secondary above the primary.

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