Why does a primary and a secondary nitro compound behave as an acid in the presence of strong alkali whereas tertiary nitro compounds do not? Can anyone explain it with reactions?

  • $\begingroup$ How many $\alpha$ hydrogens are there on a tertiary nitro compound? $\endgroup$ – bon Jan 29 '16 at 13:04
  • $\begingroup$ there is no alpha hydrogen in tertiary nitro compound $\endgroup$ – Mukilan S C Jan 29 '16 at 13:10
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    $\begingroup$ There is your answer then. $\endgroup$ – bon Jan 29 '16 at 13:10

In order for a compound to act as an acid, it must have a proton which can be abstracted. As you correctly pointed out, tertiary nitro compounds have no $\alpha$ hydrogens and therefore they cannot be deprotonated at the $\alpha$ position.

Of course, they could be deprotonated elsewhere, but if the other groups are just alkyl groups then this isn't really feasible as they have such a high $\mathrm{p}K_\mathrm{a}$.


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