Which order correctly gives the enol content of the following compounds?

Both 1,3-dicarbonyl compounds have enols stabilised by conjugation and a chelating hydrogen bond, so both far exceed propanone, whose enol content is about $10^{-6}$ percent. In the diketone the second group is a ketone, a better partner for conjugation than the ester group, whose carbonyl is partly stabilised by $\mathrm{OR}$ resonance. Hence pentane-2,4-dione has the most enol (about 80 percent neat), ethyl acetoacetate about 8 percent, propanone least.