Question

Account for the following:

1. Aniline does not undergo Friedel-Crafts reaction.

2. Diazonium salts of aromatic amines are more stable than those of aliphatic amines.

Answer 1

1. Aniline is a base due to electron donating nature of lone pair on N atom of -NH₂ goup. Aniline therefore, forms salt with AICI₂ which is Lweis acid and a catalyst used in Friedel Craft’s reaction.

So the catalyst will not be available to produce electrophile.

2. Arenediazonium ion is resonance stabilised whereas no resonance stabilisation occurs in alkyl diazonium ion.