Which of the following halides would undergo nucleophilic substitution most readily (SN₁ )?

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1 - Chloro - 1 - butene

3 - Chloro - 1 - butene

2 - Chloro - 1 - butene

4 - Chloro - 1 - butene

answer is C.

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Detailed Solution

As in this nucleophilic substitution reaction, compounds follow SN¹
mechanism and allylic carbocation is most stable among all so 3-chloro-1-butene is most reactive.

For SN¹ reactions, formed allylic carbocation is most stable among all so correct order of reactivity is allyl chloride > alkyl chloride >vinyl chloride.

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