Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
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Chapter 17, Problem 65IP
Interpretation Introduction

Interpretation:

A mechanism should be proposed for the given transformation.

Concept introduction:

  • Sigmatropic rearrangement reaction is a pericyclic reaction of polyenes (π-system), in which one σ-bond is formed and another σ-bond is broken and remaining π-bonds are shifting their positions. Thereby the transition state is cyclic. The mechanism of rearrangement is represented by using curved arrows.
  • Cope Rearrangement is a [3,3] sigamatropic rearrangement, in which the π-system having 6 carbons and double bonds are situated at both ends.
  • Claisen Rearrangement is a [3,3] sigamatropic rearrangement of allylic vinylic/arylic ethers, in which the ethers will rearranged to carbonyl compound.

To propose: a mechanism for the given transformation.

#assumes the Sigmatropic rearrangements are involved in the given transformation.

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Please answer 1, 2 and 3 on the end
In the box below, specify which of the given compounds are very soluble in polar aprotic solvents. You may select more than one compound. Choose one or more: NaCl NH4Cl CH3CH2CH2CH2CH2CN CH3CH2OH hexan-2-one NaOH CH3SCH3
On the following structure, select all of the atoms that could ACCEPT a hydrogen bond. Ignore possible complications of aromaticity. When selecting be sure to click on the center of the atom.

Chapter 17 Solutions

Organic Chemistry, Binder Ready Version

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