DIAZONIUM SALT:

 

When primary aromatic amine is treated with nitrous acid in a cool solution, product is unstable compound, known as diazonium salt.

 

      872_DIAZONIUM SALT.JPG

 

This reaction is known as diazotisation. Diazonium salts have the structure

 

      1409_diazotisation.JPG

 

Mechanism of diazotisation:      

 

      197_Mechanism of diazotisation.JPG

 

Illustration . Why ice cold condition have to be maintained in the diazotisation reaction of aniline?

 

Solution.      Because benzene diazonium chloride is unstable and decomposes to give phenol above 278 K.                                                

 

Exercise .     

 

      Explain:

 

      (i) mineral acid is added in excess in diazotization of arylamines.

 

      (ii) Aryl diazonium ions are more stable than alkyl diazonium ions. Explain

 
 

Reactions of diazonium salts:

 

These salts give substitution reactions and coupling reactions as follows:

 

Substitution reactions:

 

 

 2134_Substitution reactions.JPG

 
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