Malonic acid, HO2CCH2CO2H, is a diprotic acid. The pKa for the loss of the first proton

Chapter 3, Problem 3.37

(choose chapter or problem)

Malonic acid, HO2CCH2CO2H, is a diprotic acid. The pKa for the loss of the first proton is 2.83; the pKa for the loss of the second proton is 5.69. (a) Explain why malonic acid is a stronger acid than acetic acid (pKa = 4.75). (b) Explain why the anion, -O2CCH2CO2H, is so much less acidic than malonic acid itself.

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