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Consider the following reactions of ethylbenzene (PhCH2CH3) with chlorine or iodine: (Ph-CH +.CI PhCH2-CH2 H-Cl PhCH-CH2H PhCH-CH2-H +-cl+PhCH-CH3 + 1 2ã Using the bond dissociation energies given below, calculate the ì¨1° for each of the four pathways. PhCH-CH DHkmol 356 PhCH,CHH 410 431 297 H-CI H-I Which reaction (chlorination or iodination) is more thermodynamically favorable? Why? Which intermediate free radical (1° PhCH2CH2 or 2°/benzylic PhCHCH3) is more stable? Show why. Which reaction (chlorination or iodination) will be more selective for substitution at the secondary (2 /benzylic, Ph-CH2) carbon than at the primary carbon (-CH>)? Using reaction vs potential energy profiles, explain in terns of the Hammond-Lefler postulate. (Use the backside of this page for your answer). What would be the structure(s) of the final product(s) of the chlorination and iodination reactions?
