Although the addition of HCN to an alkene could be envisioned to occur by a free-radical

Chapter 5, Problem 5.4

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Although the addition of HCN to an alkene could be envisioned to occur by a free-radical chain mechanism, such a reaction is not observed. Justify each of the following reasons with appropriate calculations using bond dissociation energies. (a) The reaction of HCN with initiating (CH3)3CO? radicals is not a good source of ?CN radicals. (b) The second propagation step of the free-radical addition is energetically unfavorable:

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