Which of the following alkyl halides undergoes solvolysis via an mechanism at the highest rate in aqueous ethanol?
Answer and explanation
Correct answer: C.
- Step 1: Solvolysis via an mechanism involves unimolecular heterolytic cleavage of the carbon-halogen bond to form a carbocation in the rate-determining step.
- Step 2: The reaction rate is directly governed by carbocation stability: .
- Step 3: tert-Butyl chloride dissociates to yield the tertiary tert-butyl carbocation , which is stabilized by nine hyperconjugative hydrogens and three inductive effects, reacting the fastest.
Answer
(tert-butyl chloride).
Why not the others: Isopropyl chloride forms a less stable secondary carbocation; Ethyl chloride forms an unstable primary carbocation; Methyl chloride forms the least stable methyl carbocation and reacts almost exclusively via .
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