Isomerism and StereochemistryhardMCQ SINGLE⭐ Must-Do

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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