MolSynapsequestion bank
MolSynapse / Question bank / Amines and Aromatic Nitrogen Compounds / Diazonium salts: preparation and synthetic uses
JEE Main levelSingle correct optionDifficulty 2 of 3nc136

Aromatic diazonium salts are stable in solution at 273-278 K, but aliphatic diazonium salts decompose at once, mainly because

  1. Athe bond in the aryl case is longer than in the alkyl case
  2. Bthe positive charge on the aryl diazonium ion is delocalised over the benzene ring by resonance
  3. Caryl groups have a stronger +I effect than alkyl groups
  4. Daryl diazonium ions are bound to chloride by a covalent bond

Answer: B

Resonance delocalises the positive charge of into the ring and the aryl C-N bond has partial double-bond character, giving stability at low temperature. An alkyl diazonium ion has no such stabilisation and loses at once to form a carbocation.
Practice Amines and Aromatic Nitrogen Compounds More on Diazonium salts: preparation and synthetic uses

More questions on Diazonium salts: preparation and synthetic uses