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 - 3.3 Factor 3 - Induction - Problems - Page 63: 3.14

Answer

The proton on the right is more acidic.

Work Step by Step

Both conjugate bases will have the negative charge localizated in a single nitrogen, so ressonance is not the difference. But, the little alkyl group on the left of thenitrogen, normally gives electrons, so, it will affect the stability of the negative atom. Since the right nitrogen doesn't have this group next to it, it will be more stable, and the proton that is connected to it will be more acidic.
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