Chemistry

Tautomerization under Acidic Conditions (Enol to Carbonyl)

1. Pi bond attacks H3O+

2. H2O attacks OH

Tautomerization under Acidic Conditions (Enol to Carbonyl)

1. O attacks H3O+

2. H2O attacks H

Tautomerization under Basic Conditions (Enol to Carbonyl)

1. OH attacks enol OH

2. Pi bond attacks H2O

Tautomerization under Basic Conditions (Carbonyl to Enol)

1. OH attacks H

2. O attacks H2O

Alpha-Halogenation under Acidic Conditions

Needs: Br2, H3O+

1. O attacks H3O+

2. H2O attacks H

3. Pi bond attacks Br-Br

4. H2O attacks OH

Alpha-Halogenation under Basic Conditions

Needs: Br2 excess, NaOH

1. OH attacks H

2. Pi bond attacks Br-Br

3. OH attacks H

4. Pi bond attacks Br-Br

5. Repeat if needed

Kinetic Alpha Alkylation

Needs: 1.05 equiv LDA, -78 degrees C

1. LDA attacks H

2. Pi bond attacks RX

Thermodynamic Alpha Alkylation

Needs: 0.95 equiv LDA, 0 degrees C

1. LDA attacks H

2. Pi bond attacks H of original reactant

3. Pi bond attacks RX

Self-Aldol Addition

Needs: NaOH, H2O, 0 degrees C

1. OH attacks H

2. Pi bond attacks reactant carbonyl carbon

3. O- attacks H2O

Crossed Aldol Addition Type 1

Needs: LDA, THF, H3O+

1. LDA attacks H

2. Pi bond attacks carbonyl carbon

3. O- attacks H3O+

Crossed Aldol Addition Type 2

Needs: NaOH, H2O, H3O+

1. OH attacks H

2. Pi bond attacks carbonyl carbon

3. O- attacks H3O+

Aldol Condensation

Needs: NaOH, H2O, heat

1. OH attacks H

2. Pi bond attacks carbonyl carbon

3. O- attacks H2O

4. OH attacks H

5. Kick out OH

Intramolecular Aldol Addition

Needs: NaOH, H2O

1. OH attacks H

2. Pi bond attacks carbonyl carbon

3. O- attacks H2O

Intramolecular Aldol Condensation

Needs: NaOH, H2O, heat

1. OH attacks H

2. Pi bond attacks carbonyl carbon

3. O- attacks H2O

4. OH attacks H

5. Kick out OH

Claisen Condensation

Needs: NaOR, HOR (OR must be identical to reactant OR), H2O, HCl

1. OR attacks H

2. Pi bond attacks carbonyl carbon

3. Kick out OR

4. OR attacks H

5. Pi bond attacks H3O+

Intramolecular Claisen Condensation

Needs: NaOR, HOR, H2O, HCl

1. OR attacks H

2. Pi bond attacks carbonyl carbon

3. Kick out OR

4. OR attacks H

5. Pi bond attacks H3O+

Michael Reaction

Needs: OR, HOR

1. OR attacks H

2. Pi bond attacks carbon of pi bond

3. O- attacks H3O+

4. Pi bond attacks H3O+

5. Water attacks OH

Robinson Annulation

Needs: NaOH, H2O, heat

1. OH attacks H

2. Pi bond attacks carbon of pi bond

3. O- attacks H2O

4. OH attacks H

5. Pi bond attacks carbonyl carbon

6. O- attacks H2O

7. OH attacks H

8. Kick out OH

Acid-Catalyzed Ester Hydrolysis

Needs: H2O, HCl, heat

1. O on pi bond attacks H3O+

2. H2O attacks carbonyl carbon

3. H2O attacks H2O+

4. OR attacks H3O+

5. Kick out ROH+

6. H2O attacks OH

Acid-Catalyzed Transesterification

Needs: ROH, HCl, heat

1. O on pi bond attacks ROH+

2. ROH attacks carbonyl carbon

3. ROH attacks ROH+

4. OR attacks ROH+

5. Kick out ROH+

6. ROH attacks OH

Base-Catalyzed Ester Hydrolysis

Needs: H2O, NaOH

1. OH- attacks carbonyl carbon

2. Kick out OR

3. OR- attacks OH

Aminolysis of Ester

Needs: RNH2

1. RNH2 attacks carbonyl carbon

2. RNH2 attacks RNH2+

3. Kick out OR