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Will the phenyl group donate electrons more effectively than the methyl group?

The key thing to notice in answering these questions is that the pi electrons of the benzene ring are directly adjacent to the carbocation carbon in the structure on the left.

This is reminiscent of the situation we saw in the addition of HCl to 1,3-butadiene where we encountered resonance stabilization of the carbocation by the pi electrons of the neighboring double bond.

The same situation occurs here, and we can symbolize the resonance stabilization with the following resonance structures.

The effect of this resonance is to make the carbocation more stable when the charge and the electron deficiency are located on a carbon which is directly bonded to the phenyl group. Since there is no such resonance stabilization available when a simple alkyl group is bonded to the carbocationic carbon, the benzylic carbocation is more stable, is formed faster, and the product formed from it is the only one we see.


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