Chemie pKS wert?

wieso hat eigentlich 2-oxopropansäure einen niedrigen pKS wert als 2-Hydroxypropansäure? ich vermute weil bei 2-oxopropansäure schon ein proton abgespalten worden ist und somit eine negative ladung hat?

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MeisterRuelps, UserMod Light

I guess because in 2-oxopropanoic acid a proton has already been split off and thus has a negative charge?

Nope.

On the one hand, the charge can be stabilized better by mesomerie because the pKs value is good and on the other hand the carbonyl group has an electron-withdrawing effect, which likewise sets the pKs value downwards.

MeisterRuelps, UserMod Light
Reply to  UniverseBeMine

2-oxopropanoic acid still has a keto group which is electron-withdrawing. I think you’ve ignored so far

MeisterRuelps, UserMod Light

No, mesomerie means that, for example, the charge can be distributed by another arrangement/shift of the bond.

A hydroxy group is definitely not as strongly electron-withdrawing as an aldehyde or ketone, therefore you have stronger positive partial charges along the C-skeleton which facilitate the splitting off of the proton, i.e. reduce the binding strength