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 10 - Elimination Reactions - 10.10 Prediction The Products - Problems - Page 243: 10.29

Answer

The solution is shown below.

Work Step by Step

In order to determine the reaction mechanism, we must first determine the function of the reagent (1). The second step is to analyze the substrate (2), and lastly but not least we must consider any relevant regiochemical and stereochemical requirements (3). (1) Reagent in this reaction is EtOH which is both a weak nucleophile and weak base. (2) For tertiary substrates, unimolecular reactions ($S_{N}1$ and $E1$) are favoured but high temperature favors E1 (3) In $S_{N}1$ mechanism nucleophile attacks the carbocation and replaces the leaving group with racemization. And in $E1$ Zaitsev product is always favoured over the Hofmann product.
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