Organic Chemistry As a Second Language, 3e: First Semester Topics

Published by John Wiley & Sons
ISBN 10: 111801040X
ISBN 13: 978-1-11801-040-2

Chapter 3 - Acid-Base Reactions - 3.7 Predicting The Position Of Equilibrium - Problems - Page 71: 3.36


The equilibrium lies to the left.

Work Step by Step

- Compare the stability of the conjugate bases. 1. Atom - Both bases have their charges on an oxygen, so that isn't a factor. 2. Resonance: - The conjugate base on the left can spread its charge between 2 oxygens. - The conjugate base on the right has its charge spread over only one oxygen. - Therefore, the base on the left should be more stable. 3. Induction: - Induction will not be significant in this case. 4. Orbitals: - The orbitals will be insignificant in this case. - Based on factor 2, we know that the base on the left is more stable. - Therefore, the equilibrium will lie to the left.
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