Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism? A) I B) II C) III D) IV

IV

Explanation:

The complete question is shown in the image attached.

Let us call to mind the fact  that the SN1 mechanism involves the formation of carbocation in the rate determining step. The order of stability of cabocations is; tertiary > secondary > primary > methyl.

Hence, a tertiary alkyl halide is more likely to undergo nucleophilic substitution reaction by SN1 mechanism since it forms a more stable cabocation in the rate determining step.

Structure IV is a tertiary alkyl halide, hence it is more likely to undergo nucleophilic  substitution reaction by SN1 mechanism.

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