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According to markovnikof addition the product becomes (c) but if hydride shift is taken into account then the carbocation formed will be more stable by resonance . Now if resonance occurs then the positive charge will move through the ring and will be delocalised how then will the chlorine (nucleophile) attack at the aryl attached carbon ? Can you also provide actual yield data ?

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  • $\begingroup$ I think you are overthinking the effect of resonance. It is a useful model for explaining the stablisation of the benzylic cation, but you need to remember that the cation remains located at the benzylic site. $\endgroup$
    – Waylander
    Oct 10 at 9:11