Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 28, Problem 28.31AP
Interpretation Introduction

(a)

Interpretation:

The stereochemistry of compounds B and C in Fig. P28.31 is to be predicted.

Organic Chemistry, Chapter 28, Problem 28.31AP

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation
4n Thermal
Photochemical
Con
Dis
4n + 2 Thermal
Photochemical
Dis
Con

Interpretation Introduction

(b)

Interpretation:

The stereoisomer of A also gives compound C on heating is to be stated.

Concept introduction:

When the diene is having the oxygen at C3 or C4 position the sigmatropic reaction is called as oxy cope reaction. Notably, when the alkoxide fragment is involved it is referred as anionic oxy cope reaction.

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