1. You understand the core concept of "chirality" and can describe this in terms of "handedness" or of superimposability of a mirror image.
  2. You can identify objects as "chiral" or "achiral." You can identify an "internal mirror plane" when an object has that intrinsic property.
    Visualization:  Chiral and achiral objects
    Visualization:  Symmetry elements in molecules; explore the difference between rotation axes and mirror planes.
  3. You can apply your understanding of chirality to identify stereogenic atoms in a molecular structure.
    Visualization:  Stereogenic Atoms
  4. You recognize that a stereocenter can be either a "center of chirality" (such as a tetrahedral carbon with 4 different ligands) or an sp2 atom in a double bond capable of E/Z isomerism.
  5. You can specify the amount of spatial information necessary to identify whether an atom is stereogenic, and how much is necessary to define the absolute stereochemistry of that atom.
  6. You can describe the relationship between the presence of one or more center of chirality and the overall chirality of a molecule (or the lack thereof). You can recognize both achiral compounds that contain centers of chirality (meso compounds), and chiral molecules that lack any center of chirality.
    Visualization: Meso Compounds and Chiral Compounds with No Stereocenters
  7. You can use the Cahn-Prelog-Ingold system to identify group priorities around an atom and define whether the absolute stereochemistry is R or S.
    Visualization:  Assigning R and S
  8. You know the definitions of key stereochemical relationships: enantiomers and diastereomers.
    Visualization:  Enantiomers and Diastereomers
  9. You know the impact of chirality on "optical activity" (rotation of the plane of polarization for plane-polarized light). You understand the consequence on optical activity for mixtures of stereoisomers, and can define the terms "racemic" and "racemate" both by structural definition and by physical behavior.
    Visualization: demonstration of the optical rotation of corn syrup
  10. You can use Fischer projections correctly to describe stereochemical properties of compounds with multiple stereogenic atoms.
    Visualization:  the Fischer Projection

Recommended Problems: 5-32, 5-33, 5-36, 5-38, 5-39, 5-41, 5-44, 5-48, 5-57
(and all "in-chapter" problems).

Worked problem:
Worked Problem 1