Chair conformation (most stable):
- 6 axial H's (3 up, 3 down, alternating) and 6 equatorial H's
- Ring flip interconverts axial ↔ equatorial (all positions switch)
- Equatorial position preferred for bulky groups (less 1,3-diaxial strain)
Boat conformation (less stable by ~30 kJ/mol):
- Flagpole interactions (steric strain between H atoms)
- Eclipsing strain along the sides
- Twist-boat is slightly more stable than perfect boat
1,3-Diaxial strain: Axial substituent interacts sterically with other axial H's on the same face. Larger groups have greater preference for equatorial position.
A-value = -DeltaG for axial → equatorial conversion. Larger A-value = stronger equatorial preference.
- tert-butyl: ~22 kJ/mol (essentially locks the ring)
- CH3: ~7.1 kJ/mol
- Cl: ~2.2 kJ/mol