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Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction? a) 2-chloro-4-methylpentane b) 2-chloro-2-methylpentane c) cis-1-chloro-2-ethylcyclohexane d) 2-chloro-3-methylpentane e) trans-1 -chloro-2-ethyIcyclohexane

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Answer:

2-chloro-4-methylpentane

Explanation:

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The alkyl chloride that is least likely to undergo rearrangement is 2-chloro-4-methylpentane.

Solvolysis is a type of reaction in which the solvent is a reactant. In such cases, the rate of reaction depends on the substrate concentration since the solvent is present in large excess.

The alkyl chloride that is least likely to undergo rearrangement is 2-chloro-4-methylpentane because such rearrangement involves a 1,3 shift which is not possible in carbocation reactions.

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