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: 3.31


The compound on the left is more acidic.

Work Step by Step

- The only difference between the structures is the triple bond. - One of the carbons in the triple bond is $sp$ hybridized. - A negative charge on an $sp$ atom is more stable than one in an $sp^2$ atom (from the double bond in the structure on the right). - Therefore, the compound on the left is more acidic.
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