Problem

(a) Based on what you know about the relative stabilities of alkyl cations and benzy...

(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.

(b) Propose a mechanism for this reaction.

(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.

(d) Propose a mechanism for this reaction.

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