The replacement reactions that can be achieved by using diazonium salts are illustrated inparts (h) through (n). In all cases molecular nitrogen is lost from the ring carbon to which itwas attached and is replaced by another substituent.(o)The nitrogens of an aryl diazonium salt are retained on reaction with the electron-rich ring ofa phenol. Azo coupling occurs.(p)Azo coupling occurs when aryl diazonium salts react with N,N-dialkylarylamines.22.33(a)Amides are reduced to amines by lithium aluminum hydride.N-EthylanilineC6H5NHCH2CH31. LiAlH4, diethyl ether2. H2OAcetanilideC6H5NHCCH3OBenzenediazoniumhydrogen sulfate
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