7.1.1 The Formation of Diazonium Salts
Addition of aqueous solution of NaNO2 to a solution of amine hydrochloride in presence of excess of HCl which is cooled by an ice-bath such that the temperature of the reaction remains below 5°C diazotization of primary aromatic amine occurs.
Mechanism
If electron withdrawing groups are attached to aromatic nucleus then the aromatic amines are difficult to diazotize because the nucleophilicity of the amino-nitrogen is reduced by the partial withdrawal of the unshared electron pair into the nucleus.
