An optically active tertiary alkyl halide undergoes solvolysis in a polar protic solvent. The produc — Reaction Mechanism Chemistry Question
Question
An optically active tertiary alkyl halide undergoes solvolysis in a polar protic solvent. The product exhibits 55% inversion and 45% retention. This slight preference for inversion indicates:
Answer: C
💡 Solution & Explanation
While $S_N1$ generates a planar carbocation, the departing leaving group sits closely in a solvent cage (intimate ion pair) for a fraction of a second, slightly hindering front-side attack and leading to net inversion.
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