Stability of Allyl Radicals

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Radical Halogenation of Alkanes • Since the observed ratio between CH 3CH 2CH 2Cl and (CH 3) 2CHCl is 1:1, the 2° C–H bonds must be more reactive than the 1° C–H bonds. • Thus, when alkanes react with Cl 2, a mixture of products results, with more product formed by cleavage of the weaker C–H bond than you would expect on statistical grounds. 16
Chlorination vs Bromination • Although alkanes undergo radical substitutions with both Cl 2 and Br 2, chlorination and bromination exhibit two important differences. 1. Chlorination is faster than bromination. 2. Chlorination is unselective, yielding a mixture of products, but bromination is more selective, often yielding one major product. 17
Page 1 and 2: Stability of Allyl Radicals • The
Page 3 and 4: Structure of Radicals • Carbon ra
Page 5 and 6: General Features of Radical Reactio
Page 7 and 8: Reaction of a Radical X• with a C
Page 9 and 10: Radical Halogenation of Alkanes •
Page 11 and 12: Halogenation of Alkanes—Mechanism
Page 14 and 15: Figure 15.4 Energy Diagram for Radi
Page 18 and 19: Energy of Halogenation • The diff
Page 20: Energy of Radical Formation • Cal

Stability of Allyl Radicals

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