Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a rnonoanion and one for the second dissociation into a dianion . For oxalic acid, HO2C-CO.H, the first ionization constant has pKaj = 1.2 and the second ionization constant has pKaz = 4.2. Why is the second carboxyl group so much less acidic than the first?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.4: Substituent Effects On Acidity
Problem 7P: Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a...
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Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a rnonoanion and one
for the second dissociation into a dianion . For oxalic acid, HO,C-CO,H, the first ionization constant has
pKaj = 1.2 and the second ionization constant has pKaz = 4.2. Why is the second carboxyl group so much less
acidic than the first?
Transcribed Image Text:Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a rnonoanion and one for the second dissociation into a dianion . For oxalic acid, HO,C-CO,H, the first ionization constant has pKaj = 1.2 and the second ionization constant has pKaz = 4.2. Why is the second carboxyl group so much less acidic than the first?
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