OrgoChem I

Cycloalkanes

Chair flips axial vs equatorial and stability rules

Summary

Focus on chair mastery and stability predictions. Full reference is on the external link.

What you need to know:

This topic covers cycloalkanes. Focus on mastering the key concepts in the "Must know checklist" below. Follow the study steps systematically, and use practice problems to reinforce your understanding. The external reference provides comprehensive coverage of all concepts.

Video Tutorial

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Cyclohexane Chair Conformations and Ring Flips

Click to watch on YouTube →

Must know checklist

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Chair conformationalternating axial (up/down) and equatorial (around ring) positions; equatorial is more stable
Cycloalkanes and Cyclohexane Chair Conformations - Axial and Equatorial→
Chair flipall axial become equatorial and vice versa; up substituents stay up, down stay down
Cyclohexane Chair Conformations and Ring Flips→
1,3-diaxial interactionsaxial substituents clash with axial H's 3 carbons away; bulky groups prefer equatorial
1,3-Diaxial Interactions and Steric Strain in Cyclohexane→
Cis/trans in ringscis = both up or both down; trans = one up one down; relate to wedge/dash notation
Cis and Trans Isomers in Cyclohexane - Chair Conformations→
Stabilitymono-substituted prefers equatorial; trans-1,4-disubstituted prefers diequatorial conformation
Energy Ranking of Substituted Cyclohexanes - Stability Analysis→

Common mistakes

Thinking chair flip changes up down stereochemistry

Leaving a bulky group axial and not checking the flip

Confusing cis trans on a ring with wedge dash on a flat drawing