Answer to Question #76627 in Organic Chemistry for Mayank

Question #76627
why do nitro compounds dissolve in sodium hydroxide?
Expert's answer
The compounds containing nitro groups when dissolved in basic
medium, the following things can happen.
The base can take the α-Hα-H of the nitro-group, which will create
a negative charge on that α-Cα-C, which can further delocalise
with the Nitro-group (similar to Nitro-Acinitro tautomerism). 
So, the whole compound will be in the state of a Resonance
Hybrid where there will be partial double bond character
between α-C,Nα-C,N and two OO atoms. and also there will be
a δδ- charge on the α-Cα-Catom as well as on the OO atoms. ,
and δδ+ charge on the NN atoms.Due to such salt like compound
formation, it becomes soluble.
This δδ- charge created on the Carbon atom is stable if the side
chain is short, but starts to get destabilised as the side chain
grows longer. So, I think the solubilities of the Nitro-compounds
decrease as the side chain grows longer, and the compound
with 10−1210−12 C atoms may not be at all soluble in base
because of such large Hydrophobic part and destabilisation of
the δδ- charge.

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