Which is more acidic

[failedmagician]

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By this information:

This looks like a diketone is MORE ACIDIC than a diester...

BUT, the charge can be stabilized over 2 oxygens in the diester (4 total). Why is the diketone more acidic?

Why are ketones more acidic than esters in general? Again, esters have that additional oxygen to stabilize the charge right? This seems counterintuitive.

 

[TooQuickSlick]

the lower the pka the more acidic and plus you have donating groups which makes the molecules less acidic

 

[UCB05]

The negative charge isn't distributed over the ester O's. If anything the esters are stronger e- donating groups than methyls, which lowers the overall acidity of the molecule. Same concept as the fact that ether functional groups are stronger electron donating groups than alkyls in electrophilic aromatic substitutions. except in this case, it's a bad thing.