Topics covered in the Semester 1 set:

  • General structure of organic molecules

    • orbital hybridization

    • bond angles

    • bond lengths

    • bond dissociation energies

  • Functional groups and their nomenclature

  • Principles of molecular reactions

    • mechanisms

    • energy diagrams

    • conformational effects

    • A-values

    • acidity, basicity and pKa values

    • behaviors of reactive intermediates (cations, anions, radicals)

  • Stereochemistry

    • chirality

    • configurational assignment

  • Substitution reactions

    • principles and nomenclature

    • mechanisms

    • rates

    • stereochemistry

  • Elimination reactions

    • principles and nomenclature

    • mechanisms

    • rates

    • regiochemistry and stereochemistry

  • Chemistry of alkenes

    • principles and nomenclature

    • mechanisms

    • regiochemistry and stereochemistry

  • Chemistry of alkynes and nitriles

    • principles and nomenclature

    • mechanisms

    • regiochemistry and stereochemistry

  • Oxidation and reduction

    • mechanisms

    • reactions, reagents and limitations

  • Spectroscopy

    • IR spectroscopy absorptions

    • 1H NMR spectroscopy shifts

    • 13C NMR spectroscopy shifts

Topics covered in the Semester 2 set:

  • Concepts of Aromaticity
    • Classifying aromaticity, anti-aromaticity and non-aromaticity
  • Pericyclic Reactions
  • Chemistry of Aromatic Systems
    • Halogenation
    • Nitration
    • Sulfonation
    • Friedel-Crafts Reactions
    • Aromatic diazonium chemistry
    • Reductions of aromatic systems
  • Chemistry of Ketones and Aldehydes
    • Nomenclature
    • pKa values
    • Chemistry of magnesium (Grignard), lithium and copper reagents
    • Oxidation and Reduction
    • Imines, Oximes and Hydrazones
    • Key named reactions of ketones and aldehydes
    • Acetals, ketals and related chemistry
  • Chemistry of Carboxylic Acids and Acid Halides
    • Oxidation and Reduction
    • Synthesis of carboxylic acids
    • Acid halide synthesis
    • Reductions of acid halides
  • Chemistry of Esters
    • Synthesis of esters (Fischer, alkylation, couplings)
    • Hydroysis of esters
    • Reduction of esters
  • Chemistry of Amides
    • Synthesis of amides
    • Reduction
    • Interconversion between nitriles and amides
  • Enolates and Enols
    • Structure and formation
    • Kinetic vs. thermodynamic enolates and their formation
    • Halogenation and alkylation
    • Key named reactions (Aldol, Reformatsky, Claisen, Dieckmann, Knoevenagel, Robinson, etc.)
    • Malonic ester synthesis
    • Micheal reactions
    • Silyl enol ethers
  • Chemistry of Amines
    • pKa values
    • Alkylations of amines
    • Reductive amination
    • Synthesis of amines via reductions
    • Enamines and their chemistry
    • Mannich reaction
    • Elimination reactions of amines
    • Hofmann and Curtius rearrangements
  • Organosulfur Chemistry
    • Oxidations and reductions
    • Couplings of sulfides
    • Corey-Chaykovsky reaction