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 - 3.5 Ranking The Four Factors - Problems - Page 68: 3.19

Answer

The proton on the right is more acidic.

Work Step by Step

Follow the ARIO order. 1. Atom: Both hydrogens are connected to a oxygen, so there is no difference. 2. Ressonance: The proton on the left doesn't make a conjugate base with resonance structures, so the charge is only spread to one oxygen. In the other side, the proton on the right creates a conjugate base that has resonance structures (There will be a lone pair next to a pi bond), so, the charge will be more delocalized. Therefore, the proton on the right is the more acidic.
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