Draw the structures of the two major products formed in the following reaction.

Question

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why. Answer: Reactivity of allylic hydrogens due resonance stability of the radical intermediate to would result in the formation of two major substitution products: (1-bromomethyl-cyclohexene) would be predicted to predominate in this reaction because it would form the more substituted alkene. However, radical characterizes on the secondary carbon may lead to a significant formation of product #1

Explanation / Answer

Endo cyclic double bond in product is more stable than exocyclic double bond in product 1, even though radical stability follows the order tertiary >secondary >primary.

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