Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa values of 4–5). One of the reasons for its acidity is resonance stabilization of its conjugate base, which is shown below. Add curved arrows to the structure on the left to show how it is converted to the other resonance contributor shown to the right.

Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa values of 4–5). One of the reasons for its acidity is resonance stabilization of its conjugate base, which is shown below. Add curved arrows to the structure on the left to show how it is converted to the other resonance contributor shown to the right.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 26VC: Which of the following structures are identical? (Green = Cl.)

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