Physical properties of aromatic nitro compounds

         (i) Aromatic nitro compounds are insoluble in water but soluble in organic solvents.

         (ii) They are either pale yellow liquids or solids having distinct smells. For example, nitro benzene (oil of Mirabane) is a pale yellow liquid having a smell of bitter almonds.

Chemical properties of aromatic nitro compounds

         (i) Resonance in nitrobenzene imparts a partial double bond character to the bond between carbon of benzene nucleus and nitrogen of the - NO₂ group with the result the - NO₂ group is firmly bonded to the ring and therefore cannot be replaced other groups, i.e., it is very inert.

         (ii) Displacement of the - NO₂ group : Although - NO₂ group of nitrobenzene cannot be replaced by other groups, but if a second - NO₂ group is present on the benzene ring of nitrobenzene in the o- or p- position, it can be replaced by a nucleophile. For example,

         (iii) Reduction : Aromatic nitro compounds can be reduced to a variety of product as shown below in the case of nitrobenzene.

         The nature of the final product depends mainly on the nature (acidic, basic or neutral) of the reduction medium and the nature of the reducing agent.

         (a) Reduction in acidic medium

         Reduction of dinitrobenzene with respect to ammonium sulphide reduces only one - NO₂ group (selective reduction)

         (b) Reduction in neutral medium :

         (c) Reduction in alkaline medium :

         Azoxybenzene on further reduction yields azobenzene and hydrazobenzene.

         (d) Electrolytic reduction :

         · Weakly acidic medium of electrolytic reduction gives aniline.

         · Strongly acidic medium gives phenylhydroxylamine which rearranges to p-aminophenol.

         · Alkaline medium of electrolytic reduction gives all the mono- and di-nuclear reduction products mentioned above in point (c).

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