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 69: 3.32

Answer

The compound on the left is more acidic.

Work Step by Step

1. Draw the conjugate bases. - In both cases, remove the hydrogen, and give the oxygen a negative charge. 2. Compare these bases. The only significant difference is caused by induction: - Alkyl groups act like electron donators, which makes the oxygen with the negative charge less stable. - Since the structure on the left has less alkyl groups, it is more stable. - Therefore, the compound on the left is more acidic.
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