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: 9.35


This reaction will proceed via an $S_N1$.

Work Step by Step

1. Substrate - The carbon connected to the leaving group is connected to 3 other carbons, which makes the reaction only possible via $S_N1$. 2. Nucleophile - $ROH$ is a weak* nucleophile, which favors $S_N1$ reactions. *(You can consult the table on page 216) 3. Leaving group - "$Tosylate$": Good leaving group, which favors $S_N2$. 4. Solvent - Not mentioned: not a factor.
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