Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 28.5, Problem 15P
Interpretation Introduction

Interpretation:

The differences in the products obtained under photochemical and thermal condition should be accounted for the given reaction.

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 rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Organic Chemistry (8th Edition), Chapter 28.5, Problem 15P

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

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

NumberofpairsofelectronsinthereactingsystemReactionconditionsAllowedmodeofbond formationEvennumberThermalAntarafacialPhotochemicalSuprafacialOddnumberThermalSuprafacialPhotochemicalAntarafacial

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