ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 7, Problem 64P

(a)

Interpretation Introduction

Interpretation: Out of the two indicated brominated system the one molecule that would undergo E2 reaction on treatment with sodium ethoxide in ethanol should be identified and explained.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7, Problem 64P , 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 64P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:Whether anti or syn elimination occurs in the indicated reactions should be written.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7, Problem 64P , additional homework tip  3

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 64P , additional homework tip  4

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