Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 1 - Introduction and Review - Problems - Page 28: Problem 1-16

Answer

The protonation of the other oxygen is shown in the picture. Protonation of the double bonded oxygen is favored because it forms more resonance structures after protonation.

Work Step by Step

The protonation of the other oxygen is shown in the picture. When the double bonded oxygen is protonated there are three resonance forms formed. However, the protonation of the other oxygen does not form a structure stabilized by resonance. Thus, the protonation of the double bonded oxygen is favored because it forms more resonance structures after protonation.
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