Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 28.5, Problem 12P

(a)

Interpretation Introduction

Interpretation: The kind of sigmatropic rearrangement that occurs in each of the given reactions has to be given.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”.  There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

  1. 1) Electrocyclic reactions
  2. 2) Cycloaddition reactions
  3. 3) Sigmatropic reactions

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Organic Chemistry (8th Edition), Chapter 28.5, Problem 12P , additional homework tip  1

Sigmatropic rearrangement reactions are named with digits.  For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

(b)

Interpretation Introduction

Interpretation: Using arrows the electron rearrangement takes place in the given reactions has to be shown.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”.  There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

  1. 1) Electrocyclic reactions
  2. 2) Cycloaddition reactions
  3. 3) Sigmatropic reactions

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Organic Chemistry (8th Edition), Chapter 28.5, Problem 12P , additional homework tip  2

Sigmatropic rearrangement reactions are named with digits.  For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

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