Chemical properties of Nitroalkanes

         (a) Reduction : Nitro alkanes  are reduced to corresponding primary amines with Sn and HCl or Fe and HCl or catalytic hydrogenation using nickel as catalyst.

         However, when compact with a neutral reducing agent (Zinc dust + NH₄Cl), nitro alkanes form substituted hydroxylamines.

         (b) Hydrolysis : Primary nitro alkanes on hydrolysis form hydroxylamine and carboxylic acid.

         secondary nitro alkanes on hydrolysis creates ketones.

         (c) Action of nitrous acid : Nitrous acid reacts with primary, secondary and tertiary nitro alkanes differently.

         Tertiary nitro alkanes do not act with nitrous acid.

         (d) Thermal decomposition : .

         On rapid heating nitro alkanes decompose with great violence.

         (e) Halogenation : Primary and secondary nitro alkanes are readily halogenated in the a-position  by treatment with chlorine or bromine.

         (f) Condensation with aldehyde :

         (g) Reaction with grignard reagent : The aci-form of nitroalkane reacts with Grignard reagent forming alkane.

•           The nitrogen of -NO₂ carrying a positive charge exerts a powerful - I effect and thus activates the hydrogen atom of the a-carbon. Thus the important reactions of nitroalkanes are those which involve a-hydrogen atom of primary and secondary nitroalkanes (tertiary nitroalkanes have no a-hydrogen atom and hence do not undergo such type of reactions).

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