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 - 9.6 Using All Four Factors - Problems - Page 224: 9.34

Answer

This reaction will proceed via an $S_N2$

Work Step by Step

1. Substrate - The carbon connected to the leaving group is connected to 1 other carbon, which makes the reaction only possible by $S_N2$ 2. Nucleophile - $Cl^-$ is a strong* nucleophile, which favors $S_N2$ reactions. *(You can consult the table on page 216) 3. Leaving group - "$Br^-$": Good leaving group, which favors $S_N2$. 4. Solvent - DMSO: Polar aprotic, which makes it only $S_N2$
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