EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
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Chapter 16, Problem 56PP

(a)

Interpretation Introduction

Interpretation:

For each of the given reactions, the product should be determined.

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.

(b)

Interpretation Introduction

Interpretation:

For each of the given reactions, the product should be determined.

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.

(c)

Interpretation Introduction

Interpretation:

For each of the given reactions, the product should be determined.

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.

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