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: 3.29


$CH_3SH$ is more acidic.

Work Step by Step

- In the first compound $(CH_3SH)$, the conjugate base will have a Sulfide with the negative charge. - In the second compound $(CH_3OH)$, the conjugate base will have a Oxygen with the negative charge. Since they are in the same column, we need to compare their sizes: - $S$ is bigger than $O$, so the charge is better stabilized on the $S^-$. - Therefore, $CH_3SH$ is more acidic.
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