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Radical halogenation - Alkyl Free Radicals They are...

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1 Radical Halogenation of Alkanes Alkyl Free Radicals They are 7-electron neutral reactive intermediates. Alkyl free radicals are thought to be mostly planar although there is some disagreement about this. The more highly substituted the more stable the radical (3°>2 °>1 °>methyl). It is easy to see stability in terms of bond dissociation energies (BDEs). Why? BDEs represent homolytic cleavage of the C-H bond, as the stability of the neutral radical increases, the BDE gets smaller. Fig. 4.17 Two possible structures for the carbon radical Fig. 4.18 Delocalization of electron density: Methyl vs. Ethyl
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2 Chlorination of Methane • Initiation • Propagation • Termination See the board What about different types of carbon? What about different halogens? What can we say about the structure of the intermediate and the transition state? Hammond’s Postulate Hammond’s Postulate “If two states, as for example, a transition state and an unstable intermediate occur consecutively during a
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