Organic Chemistry

  1. Alpha-Carbon Chemistry: Enols and Enolates
    1. Acidity of Alpha Hydrogens
      1. Factors Affecting Acidity
        1. pKa Values
          1. Stabilization of Enolate Anions
          2. Keto-Enol Tautomerism
            1. Equilibrium
              1. Acid-Catalyzed Tautomerization
                1. Base-Catalyzed Tautomerization
                  1. Factors Affecting Equilibrium
                  2. Enolate Formation
                    1. Base Selection
                      1. Kinetic vs Thermodynamic Enolates
                        1. Regioselectivity
                        2. Alkylation of Enolates
                          1. SN2 Mechanism
                            1. Limitations
                              1. Malonic Ester Synthesis
                                1. Acetoacetic Ester Synthesis
                                2. Aldol Reactions
                                  1. Aldol Addition
                                    1. Mechanism
                                      1. Stereochemistry
                                      2. Aldol Condensation
                                        1. Dehydration
                                          1. Driving Force
                                          2. Crossed Aldol Reactions
                                            1. Successful Combinations
                                              1. Directed Aldol Reactions
                                              2. Intramolecular Aldol Reactions
                                              3. Claisen Condensation
                                                1. Mechanism
                                                  1. Requirements
                                                    1. Crossed Claisen Condensation
                                                      1. Dieckmann Condensation
                                                      2. Michael Addition
                                                        1. Mechanism
                                                          1. Michael Acceptors
                                                            1. Michael Donors
                                                              1. Robinson Annulation

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                                                            12. Carbonyl Chemistry: Carboxylic Acids and Derivatives

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                                                            14. Special Topics in Organic Chemistry