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Preparation of Amines by Reduction
Concepts tested here
- Products of nitrobenzene reduction
All Questions
2005 AIPMT 1 question
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Electrolytic reduction of nitrobenzene in weakly acidic medium gives :-The reduction of nitrobenzene takes place in steps: $C_6H_5NO_2 \rightarrow C_6H_5NO$ (nitrosobenzene) $\rightarrow C_6H_5NHOH$ (N-phenylhydroxylamine) $\rightarrow C_6H_5NH_2$ (aniline).
The final product depends on the medium.
In a weakly acidic medium the reduction goes to completion, and the product of electrolytic reduction is aniline: $C_6H_5NO_2 + 6H^+ + 6e^- \rightarrow C_6H_5NH_2 + 2H_2O$
In a strongly acidic medium (conc. $H_2SO_4$), the intermediate N-phenylhydroxylamine rearranges to p-aminophenol (p-hydroxyaniline).
In a neutral medium (for example with Zn and $NH_4Cl$), N-phenylhydroxylamine is the main product.
So electrolytic reduction in weakly acidic medium gives aniline.