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Question

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Attempt

I thought that the bromine atom farther from the ring would be substituted because of less hindrance, but the book says opposite, why?

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The reaction proceeds by SN2, which is highly accelerated at the benzylic position, due to stabilisation of the transition state by conjugation with the aromatic ring.

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So you'll have to replace the benzylic bromine.

References: Benzyl chloride: chemtube3d

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