Do we have a good idea of what the pKa would be of an aldehydic hydrogen? I don't mean the hydrogens alpha to the carbonyl, but the hydrogen directly
attached to the carbonyl, the one in CHO. For example, how strong of a base would we need to turn formaldehyde into CHO-? I was thinking by analogy
with a vinylic hydrogen: we know ethylene to have a pKa of ~44 and formaldehyde is just ethylene with one side replaced by the more electronegative
oxygen. So, presumably the more negative oxygen would stabilize the negative charge more and give us a pKa lower than 44. clearly_not_atara - 2-3-2024 at 08:36
Look up "acyl anion"DraconicAcid - 2-3-2024 at 10:42
I think most bases are more likely to do a nucleophilic attack on the carbonyl.gemar14 - 2-3-2024 at 12:55
