1. You can name substituted cycloalkanes.
  2. You recognize the formal impact of a ring structure on molecular formula as an "unsaturation."
  3. You understand the different sources of strain in a molecule: angle deformation (primarily), but also bond stretching, torsional strain from eclipsing interactions, and steric compression.
  4. You can rank C3 to C7 rings in order of increasing strain.
    Visualization: Cycloalkanes and strain
  5. You know the distinction between conformations (different structures that can interconvert by rotating about single bonds) and configurations (different structures that would require breaking and remaking at least one bond to interconvert).
  6. You understand the terms cis and trans and how they apply to pairs of substituents on a ring.
  7. You know that the chair conformation of cyclohexane is the most stable, can correctly draw a chair cyclohexane with all its substituents, and can identify equatorial and axial positions.
    Visualization: Drawing a chair cyclohexane
  8. You can recognize less stable conformers: twist-boat, half-chair, and boat, and can place these on a potential energy diagram for a chair-to-chair ring flip.
    Visualization: Animation of Figure 4-9 from the text.
  9. You can identify axial-axial interactions that determine which ring flip conformer is more stable for any substituted (or multiply-substituted) cyclohexane.
    Visualization: Steric interactions in axial vs. equatorial cyclohexane substituents

Recommended problems:
4-23, 4-24, 4-27, 4-29, 4-30, 4-32, 4-34, 4-50.
(as well as all "in-chapter" problems).

Worked problem:
Worked problem