Rank the SN1 reaction rates for the following compounds: (A) chloromethane, (B) 3-chloro-3-methylpentane, (C) 1-chloro-3-methylpentane, (D) 2-chloro-3-methylpentane

3-chloro-3-methylpentane,>2-chloro-3-methylpentane>  1-chloro-3-methylpentane, > chloromethane

Explanation:

The rate of SN1 reactions decreases in the order, tertiary > secondary > primary > methyl.

This implies that, a tertiary alkyl halide is better able to undergo nucleophilic substitution by SN1 mechanism compared to a secondary, primary or methyl.

This is because, the transition state leading to the formation of an SN1 product involves a carbocation. The order of stability of carbocations is; tertiary > secondary > primary > methyl.

Hence a tertiary alkyl halide such as 3-chloro-3-methylpentane leads to a more stable transition state and undergoes SN1 reaction at a faster rate.

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