From Wikipedia,
Methanediol is the product of the hydration of formaldehyde $\ce{H2C=O}$, and predominates in water solution: the equilibrium constant being about $10^3$ and in a 5% by weight solution of formaldehyde in water, 80% is in the methanediol form.
As far as I know, carbonyl compounds usually don't exist in their gem-diol form, unless there's a stabilizing effect (like H-bonding, release of angle strain, inductive effect etc.), which we observe in ninhydrin, chloral, hexafluoroacetone, etc. (relevant image) But such effects don't seem to be the case for formaldehyde.
My question: What is the stabilizing factor in the case of hydration of formaldehyde?
No comments:
Post a Comment