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Which one is most reactive towards SN1 reaction?

1. C6H5CH(C6H5)Br
2. C6H5CH(CH3)Br
3. C6H5C(CH3)2(C6H5)Br
4. C6H5CH2Br

Correct answer: C6H5C(CH3)2(C6H5)Br

Solution

The SN1 reaction proceeds via a carbocation intermediate, and the stability of the carbocation determines the reactivity. Option C forms a highly stable benzylic tertiary carbocation due to resonance and hyperconjugation, making it the most reactive.

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