Monday, 13 July 2015

organic chemistry - Why does formaldehyde exist primarily as the gem-diol in aqueous solution?


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.



enter image description here



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

readings - Appending 内 to a company name is read ない or うち?

For example, if I say マイクロソフト内のパートナーシップは強いです, is the 内 here read as うち or ない? Answer 「内」 in the form: 「Proper Noun + 内」 is always read 「ない...