Interpretation:
Ring opening reaction of the trans-cyclobutene isomer shown takes place readily at a lower temperature than a similar ring opening of the cis-cyclobutene isomer. This temperature effect is to be explained and the stereochemistry of each reaction, conrotatory or disrotatory, is to be identified.
Concept introduction:
An electrocyclic reaction involves the cyclization of a conjugated acyclic system. These reactions are reversible and are highly stereospecific.
In elecrocyclic reactions involving even number of electron pairs, a thermal reaction occurs in conrotatory manner and a photochemical reaction occurs in disrotatory manner.
In elecrocyclic reactions involving odd number of electron pairs, a thermal reaction occurs in disrotatory manner and a photochemical reaction occurs in conrotatory manner.
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Organic Chemistry
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning