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For 2-fluoroethanol, which sequence correctly represents the increasing order of stability of its three principal conformations—eclipsed, anti, and gauche?
- Eclipsed, anti, gauche
- Anti, gauche, eclipsed
- Eclipsed, gauche, anti
- Gauche, eclipsed, anti
Correct answer: Eclipsed, anti, gauche
Solution
In 2-fluoroethanol the gauche conformer is stabilized by an intramolecular O-H...F hydrogen bond (and the gauche effect), making it the most stable; the eclipsed form is the least stable. Increasing stability: eclipsed < anti < gauche.
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