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Question

Which would undergo SN1 reaction faster in the following pair and why?
CH3CH2Br and CH3CH3|C|BrCH3

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Solution

Reactivity in SN1 reaction depends upon the stability of carbocation intermediate formed after ionization of alkyl halide. Since H3CCH3|C|BrCH3 will give more stable 3 carbocation ⎜ ⎜CH3CH3|C+CH3⎟ ⎟, therefore, it is more reactive than CH3CH2Br which upon ionization gives 1 carbocation (CH3+CH2) of lesser stability.

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