Iodine, dissociation strength

If one looks at the average bond dissociation energies for X2, C-X, H-X, and C-H bonds (Table 2.2), an average heat of reaction for the halogenation of alkanes can be calculated. The results in kcal/mol are as follows F = -101, Cl = -22, Br = -4, and I = 16. The variation in these numbers comes from a continual decrease in H-X and C-X bond strengths in the series F, Cl, Br, and I. These heats of reaction reflect a dramatic change in reactivity. Free radical fluorination is so exothermic that it occurs spontaneously and very explosively. Chlorination and bromination can be controlled and are useful reactions. Free radical iodination rarely occurs. 

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