1. You can name an alkyl halide correctly using systematic (IUPAC) nomenclature, and can draw a correct structure (including stereochemistry) for an alkyl halide from its name.
  2. You understand the impact of halogen electronegativity on molecular dipole moment, and thus its effect on boiling points compared to the parent hydrocarbon.
  3. You know the mechanism for free-radical halogenation of alkanes, and can write out the mechanism for any choice of specific alkane and halogen (cf., Chapter 3).
  4. You can identify the two new reaction processes introduced in this and the next chapter:  substitution and elimination for alkyl halide reactants.
  5. You know the distinction between a nucleophile and a base (as well as the parallels).
  6. You understand the essential pieces for an SN2 reaction:  a one-step substitution mechanism in which a nucleophile creates a new bond to carbon as the bond from carbon to a leaving group breaks.  You can use electron-pushing arrows to depict the electron flow during this process, and identify nucleophile, substrate, and leaving group.
    Visualization:  Cyanide + MeBr
  7. You can judge the relative nucleophilicity of any two nucleophiles based on charge, polarizability, steric bulk, and solvent interactions.
    Visualization:  Nucleophilicity scale
  8. You understand how to identify likely substrates for SN2 substitution:  methyl or primary; presence of a good leaving group (not alkoxide or hydroxide or hydride), no other steric congestion of the back side of the leaving group. 
    Visualization:  Steric Bulk
  9. You understand that the backside attack of the nucleophile leads to inversion of stereochemistry, and can correctly show the stereochemical outcome for any SN2 reaction.
  10. You can reason out the impact of changing solvent on a given SN2 reaction.
    Solvent properties

Recommended end-of-chapter problems:  6-31, 6-32, 6-38, 6-39, 6-41, 6-42, 6-45, 6-46, 6-57, 6-60.
Worked problems:
Worked Problem 1
Worked Problem 2
Worked Problem 3
Worked Problem 4