Electrolytic reduction:

Electrolytic reduction: Electrolytic reduction C H NH + H O An weakly acidic strongly acidic iline NH NO NH p-aminophenol Phenylhydroxyl amine Rearrangment Reduction of catalytic and metal hydrides Nitrobenzene reduction with Ni (or) Pt, (or) LiAlH to give aniline C H - NO + [H] Ni (or) Pt / H (or) LiAlH C H - NH + H O Selective reduction of polynitro compounds NO NO + (NH ) S NO NH + 6NH + 2H O + 3S m-dintrobenzene m-nitroaniline Electrophilic substitution reaction The electrophilic substitution reactions of nitrobenzene are usually very slow and vigorous reaction condition have to be employed (- NO group is stongly deactivating and m – directing). Nitrobenzene NO Chlorination Cl / AlCl (Lewis acid) NO Cl - chloronitrobenzene Nitration 373K Con HNO / Con H SO NO NO NO NO , - dinitrobenzene , , - trinitrobenzene (TNB) Nitration 473K Con HNO / con.H SO NO SO H - Nitrobenzene sulphonic acid O N Sulphonation Con H SO / XII U13-Organic Nitrogen XII U13-Organic Nitrogen - - - - Nitrobenzene does not undergo Friedel – Crafts reactions due to the strong deactivating nature of -NO group. Evaluate yourself Predict the major product that would be obtained on nitration of the following compounds i) COOH Con.HNO Con H SO ? O N NO NO iii) ii) NO ? i) Na Cr O ii) Sodalime ? Con.HNO Con H SO + acid