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

Answer

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.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.