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

Answer

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.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.