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Are all the nitro-compounds having at least one alpha-$\ce{H}$ soluble in $\ce{NaOH}$? And what does solubility has to do with alpha-$\ce{H}$?
I was reading about tautomerism today and got stuck on this thing. Is it due to its conversion to the enol form? Does the keto form also show this? What could be the possible reasons?
The compounds containing nitro groups when dissolved in basic medium, the following things can happen.
The base can take the $\ce{$\alpha$-H}$ of the nitro-group, which will create a negative charge on that $\ce{$\alpha$-C}$, 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 $\ce{$\alpha$-C, N }$ and two $\ce O$ atoms. and also there will be a $\delta$- charge on the $\ce{$\alpha$-C }$ atom as well as on the $O$ atoms. , and $\delta$+ charge on the $N$ atoms.Due to such salt like compound formation, it becomes soluble.
This $\delta$- 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 $10-12$ C atoms may not be at all soluble in base because of such large Hydrophobic part and destabilisation of the $\delta$- charge.
