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 9 - Substitution Reactions - 9.4 Factor 3 - The Leaving Group - Problems - Page 219: 9.19


The best leaving group, in this case, is the mesylate.

Work Step by Step

1. Identify the possibles leaving groups: - $EtO^-$ ($CH_3CH_2O^-$) - $Mesylate$ ($CH_3O_3S^-$) 2. Determine which one is better. - In this section, we've learned that sulfonate ions, like the mesylate, are good leaving groups (page 219). - And we have also learned that, the $CH_3CH_2O^-$ is a bad leaving group (page 218). Therefore, this mesylate is better.
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