Account for the following :

(a) Gabriel phthalimide synthesis is not preferred for preparing aromatic primary amines.

(b) On reaction with benzene sulphonyl chloride, primary amine yields product soluble in alkali whereas secondary amine yields product insoluble in alkali.

 

 

 

 
 
 
 
 

Answers (1)
S Sumit

(a) Aromatic 1^{\circ} amines such as aniline, fluidences etc. cannot be prepared by Gabriel Phthalimide because aryl halides do not undergo nucleophilic substitution reaction.

(b)

The product formed in case of 1^{\circ} amine contains acidic hydrogen on the N-atom which makes it soluble whereas, in case of 2^{\circ} amine, no acidic hydrogen is present on N-atom 

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