ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 7, Problem 63P
Interpretation Introduction

Interpretation:Out of the three chlorinated compounds, one that does not give the indicated alkene product should be identified and explained.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7, Problem 63P , additional homework tip  1

Concept introduction: Experimental evidence for E2 mechanism pathway suggests that it readily occurs if the leaving group with respect to the proton is in anti- orientation in stable chair conformation. For instance, when cis-1-bromo-4-(1,1-dimethylethyl)cyclohexane is treated with a strong base it leads to faster bimolecular elimination to afford the corresponding alkene relative to trans-1-bromo-4-(1,1-dimethylethyl)cyclohexane . This is because in the transition state for E2 elimination as illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7, Problem 63P , additional homework tip  2

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