Equilibrium Constant of Hydration Question

[deleted92121]

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I was asked to compare F3CCOOH (trifluoroacetic acid) to Acetone and determine if it has a larger or smaller equilibrium constant for hydration than Acetone.

My thought is that it has a smaller quilibrium constant for hydration due to trifluoracetic acid being more willing to lose its proton as it is a stronger acid.

Makes sense or am I off base?

Thanks

 

[chiddler]

acetone is not very acidic. it has a relatively acidic proton (pKa ~19) because of resonance stabilization with the enol being formed. I say relatively when comparing to simple hydrocarbons.

TFA is a borderline strong acid (pka 0.23). Acetone doesn't even come close lol. So you're right.

Are you sure you weren't supposed to compare TFA with plain acetic acid?

 

[deleted92121]

acetone is not very acidic. it has a relatively acidic proton (pKa ~19) because of resonance stabilization with the enol being formed. I say relatively when comparing to simple hydrocarbons.

TFA is a borderline strong acid (pka 0.23). Acetone doesn't even come close lol. So you're right.

Are you sure you weren't supposed to compare TFA with plain acetic acid?

nope, it is acetone. I double checked. thanks for the confirmation on my thought process.