The product obtained in the following solvolysis reaction is Enantiomerically pure compound · ABC26OR0657
Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Medium
The product obtained in the following solvolysis reaction is 
Enantiomerically pure compound
Enantiomerically pure compound(a)a racemic mixture of trans 1,2-diacetoxycyclohexane
(b)enantiomerically pure trans 1,2-diacetoxycyclohexane
(c)racemic cis 1,2-diacetoxycyclohexane
(d)a mixture of cis and trans 1,2-diacetoxycyclohexane
Answer
Answer (as printed): A
Explanation
The trans-2-acetoxy group participates as the tosylate leaves (anti neighbouring-group participation), forming a cis-fused 1,3-dioxolan-2-ylium (acetoxonium) ion. This cation has a mirror plane and is achiral, so acetate attacks either ring carbon equally, each time with inversion. Both pathways give trans-1,2-diacetoxycyclohexane, as its two enantiomers in equal amounts. The product is the racemic trans diacetate, option (a).
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