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 - 3.1 Factor 1 - What Atom Is The Charge On? - Problems - Page 56: 3.3

Answer

The proton on the right is more acidic.

Work Step by Step

If we remove the left proton, the conjugate base will have these changes: - The Hydrogen on the left will be removed. - The Carbon that was connected to the Hydrogen will get a negative charge, because the electrons that were making the bond will turn into a lone pair. If we remove the proton on the right, the conjugate base will have these changes: - The Hydrogen on the right will be removed. - The Nitrogen that was connected to the hydrogen will get a negative charge, because the electrons that were making the bond will turn into a lone pair. Since Nitrogen is more electronegative than Carbon, the proton on the right will be more acidic.
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