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Several methods are known for the reduction of a nitro compound to an amine, including catalyctic hydrogenation. I am wondering if this can be done by electrolysis.

If we take the simplest nitroalkane, $\ce{CH3NO2}$, would it be reduced to the primary amine $\ce{CH3NH2}$ at the cathode of an electrolytic cell?

Furthermore, could the same method be applied to an unsaturated aromatic nitroalkane as in this question? I noticed that the only methods mentioned are catalytic processes or reduction to a ketone followed by reductive amination, so I am assuming not. In either case I'd like to know why.

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    $\begingroup$ Nitromethane is not ionic; why would it undergo electrolysis in the first place? $\endgroup$ – Ivan Neretin Oct 23 '17 at 10:28
  • $\begingroup$ @IvanNeretin I know that a current-carrying electrolyte would be required, but I don't believe that only ionic compounds can be electrolysed. Water can be oxidised to oxygen and reduced to water via electrolysis, and is certainly not ionic. $\endgroup$ – Mack Oct 23 '17 at 10:44
  • $\begingroup$ Water is ionic, albeit to a tiny extent, and that's precisely why it can be electrolysed. $\endgroup$ – Ivan Neretin Oct 23 '17 at 11:04
  • $\begingroup$ Does that refer to water's self-ionisation or the character of the bonds? What about p-Benzoquinone? I have read that it is reduced to hydroquinone by electrolysis. $\endgroup$ – Mack Oct 23 '17 at 11:44
  • $\begingroup$ You can put it into cathode space and add some acid. Releasing hydrogen could help reduction $\endgroup$ – wolphram Oct 23 '17 at 11:54

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