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Electrophilic Aromatic Substitution in Aromatic Amines

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Estimated time: 2 minutes
Maharashtra State Board: Class 12

Key Points: Electrophilic Aromatic Substitution in Aromatic Amines

  • Bromination: Aniline reacts with Br₂/H₂O to give 2,4,6-tribromoaniline + 3HBr (all three ortho/para positions substituted).
  • Nitration: Aniline with conc. HNO₃ + conc. H₂SO₄ at 288 K gives p-nitroaniline (51%), m-nitroaniline (47%) and o-nitroaniline (2%).
  • Getting p-nitroaniline as a major product: —NH₂ is first protected by acetylation, then nitration is carried out, and finally the amide is hydrolysed.
  • Sulphonation: Aniline + H₂SO₄ first forms anilinium hydrogen sulphate, which on heating at 453–473 K gives sulphanilic acid (47%).
  • Zwitter ion: Sulphanilic acid exists in equilibrium with its dipolar (zwitter ion) form (2%) carrying —NH₃⁺ and —SO₃⁻ groups.
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