neighboring -CO2H group withdraws electron density inductively and thus

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 4E
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This first pka value for oxalic acid is 1.3, which is more acidic than a typical carboxylic
acid with a pKa value of ~4.5. What is the reason for this observation?
O There is no good answer, as it is what it is.
O Better resonance stabilization of the resultant anion lowers the first pK, value.
O The neighboring -CO2H group withdraws electron density inductively and thus
lowers the first pK, value.
O Keto-enol tautomerization lowers the first pk, value.
O The first -CO2H group has an inherently lower first pK, value.
Transcribed Image Text:This first pka value for oxalic acid is 1.3, which is more acidic than a typical carboxylic acid with a pKa value of ~4.5. What is the reason for this observation? O There is no good answer, as it is what it is. O Better resonance stabilization of the resultant anion lowers the first pK, value. O The neighboring -CO2H group withdraws electron density inductively and thus lowers the first pK, value. O Keto-enol tautomerization lowers the first pk, value. O The first -CO2H group has an inherently lower first pK, value.
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