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This is the second part of a multi-part module on Free Radical Halogenation.
View the first part here: Part 1: The Mechanism
Radical bromination will always replace the C-H bond on the MOST subsituted carbon center because the stability of the radical intermediate is higher with increasing substituents on the carbon center.
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This selectivity is the same, but a weaker consideration, for radical chlorination which obeys Hammond’s Postulate in that stability of the radical center is outweighed by the extreme exothermicity of radical chlorination (compared to bromination), thus a mixture of chlorinated products is observed.
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Check out Part 3: Stereoslectivity – Determining stereochemistry of carbon centers
