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20.9: Radical Formation: Elimination

JoVE Core
Organic Chemistry

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Radical Formation: Elimination

20.9: Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to the radical, leading to the formation of an unsaturated molecule as the byproduct.


Figure 1. The elimination reaction of dibenzoyl peroxide for the formation of radicals.


Radical Formation Elimination Process Addition Route Instability Of Radical Dibenzoyl Peroxide Unstable Radicals Homolysis Elimination Via C-C Bond Cleavage More Stable Phenyl Radical Mechanism Unsaturated Molecule Formation Of Radicals

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