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.
![99_chemical properties of nitro.png](https://www.expertsmind.com/../CMSImages/99_chemical properties of nitro.png)
(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,
![815_chemical properties of nitro1.png](https://www.expertsmind.com/../CMSImages/815_chemical properties of nitro1.png)
(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
![614_chemical properties of nitro3.png](https://www.expertsmind.com/../CMSImages/614_chemical properties of nitro3.png)
Reduction of dinitrobenzene with respect to ammonium sulphide reduces only one - NO2 group (selective reduction)
(b) Reduction in neutral medium :
![873_chemical properties of nitro5.png](https://www.expertsmind.com/../CMSImages/873_chemical properties of nitro5.png)
(c) Reduction in alkaline medium :
![998_chemical properties of nitro6.png](https://www.expertsmind.com/../CMSImages/998_chemical properties of nitro6.png)
Azoxybenzene on further reduction yields azobenzene and hydrazobenzene.
![228_chemical properties of nitro7.png](https://www.expertsmind.com/../CMSImages/228_chemical properties of nitro7.png)
(d) Electrolytic reduction :
· Weakly acidic medium of electrolytic reduction gives aniline.
· Strongly acidic medium gives phenylhydroxylamine which rearranges to p-aminophenol.
![1744_chemical properties of nitro8.png](https://www.expertsmind.com/CMSImages/1744_chemical%20properties%20of%20nitro8.png)
· Alkaline medium of electrolytic reduction gives all the mono- and di-nuclear reduction products mentioned above in point (c).
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