# Acidic strength of diethyl malonate vs ethyl acetoacetate [duplicate]

Which would be more acidic, diethyl malonate $$\left(\ce{CH2(CO2Et)2}\right)$$ or ethyl acetoacetate $$(\ce{CH3COCH2OOC2H5})$$

In the above compounds, I have marked the hydrogen which I think will be the most acidic. Now removing that hydrogen would yield a carbocation. Both the carbocations would be equally stabilized due to resonance effect. In fact diethyl malonate acid would be more stabilized due to the extra inductive effect of the extra oxygen. Yet Wikipedia shows that ethyl acetoacetate has a p$$K_\text{a}$$ less than that of diethylmalonate acid.

What is making it more acidic?

• That's diethyl malonate, not malonic acid... If you're looking at malonic acid on Wikipedia, that's going to be a completely different pKa value. – orthocresol May 15 at 4:19
• good catch.. edited it – gauri agrawal May 15 at 8:25
• chemistry.stackexchange.com/q/18987/16683 – orthocresol May 15 at 9:22
• Also carbanions not cations... – Mithoron May 15 at 14:32