Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?
A) cyclohexyl bromide
B) methyl iodide
C) isopropyl chloride
D) 3-chloropentane
E) 3-iodo-3-methylpentane

Question

Quizplus · Accepted Answer

3-iodo-3-methylpentane undergoes solvolysis most rapidly due to the formation of a more stable tertiary carbocation intermediate. The tertiary carbon adjacent to the leaving group (iodide) stabilizes the carbocation through inductive and hyperconjugative effects, making the solvolysis process faster compared to the other options which form less stable primary or secondary carbocations.

Which of the Compounds Below Undergoes Solvolysis in Aqueous Ethanol