Conformational stability generally dictates that bulky groups reside as far apart as possible (Anti — Isomerism and Stereochemistry Chemistry Question
Question
Conformational stability generally dictates that bulky groups reside as far apart as possible (Anti conformation). However, the most stable conformation of 2,3-butanediol is NOT the Anti form. Which form is the most stable and why?
Answer: B
💡 Solution & Explanation
While the Anti conformer ($180^\circ$) minimizes steric repulsion, 2,3-butanediol possesses two adjacent hydroxyl ($-OH$) groups. In the Gauche conformation ($60^\circ$), these polar $-OH$ groups are positioned perfectly to engage in highly stabilizing intramolecular hydrogen bonding, forming a chelate ring that thermodynamically overrules standard steric repulsion.
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