Concept explainers
(a)
Interpretation:
The following pericyclic reaction is to be classified. (More than one classification is possible.)
Concept introduction:
Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.
(b)
Interpretation:
Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.
Concept introduction:
Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.
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Chapter 28 Solutions
EBK ORGANIC CHEMISTRY
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