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 - 10.3 The Stereochemical Outcome Of An E2 Reaction - Problems - Page 231: 10.5

Answer

We expect the formation of Zaitsev product because the reaction does not employ a sterically hindered base.

Work Step by Step

The double bond is formed between α and β positions. Because β position has only one proton we expect this reaction to be stereospecific, rather than stereoselective. After drawing the Newman projection we need to draw the conformation in which H (on position β) and leaving the group (Cl; on position α) are antiperiplanar because E2 reactions proceed in this conformation. Newman projection shows us the stereochemical outcome.
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