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Structure

While studying about Cannizzaro reaction, it came to my mind as a wild thought what if this HCH(ONa)(ONa) molecule could pop out in some step of this reaction (not giving much details about how I thought it as it would be irrelevant). Then I thought this molecule might have some problem with stability. The $\mathrm{sp^3}$ hybridized carbon might have some have problem with spacing two -ONa groups close together.

So, is this molecule stable or not? If not why?

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  • $\begingroup$ I guess it's sort of follow-up of chemistry.stackexchange.com/questions/55692/… and answer is similar I guess - it's highly basic intermediate. $\endgroup$ – Mithoron Aug 7 '16 at 19:34
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    $\begingroup$ Oxygen and sodium will hardly form a covalent bond. $\endgroup$ – aventurin Aug 7 '16 at 20:07
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The species you are proposing would be a methanediol dianion (CH2O22–) with two sodium cations “attached” to it in some way, depending on the nature of the solvent.

While methanediol can indeed readily form an anion, with a pKa of 13.3, I find no mention of the dianion or any measure (or prediction) of the second pKa of methanediol.

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