Chem 35

Course Description: A comprehensive Study of Organic Compounds: Reaction mechanisms

and Spectroscopic Methods of Identification
Prerequisite: Chem 31 and Chem 31.1
Credit: 3 units

I. Organic Reactions and Mechanisms

A. Kinetics, Energetics, and Investigation of Mechanism
B. Review of Typical Organic Reaction and Mechanism
1. Radical Reactions
I.1 Radical Formation
I.2 Radical Stabilization
I.3 Radical Coupling Reaction
I.4 Substitution at Saturated Carbon
I.5 Radical Additions
I.6 Stereochemistry of Radical Reactions
2. Substitution Reactions
2.1 Nucleophilic Substitution at Saturated Carbon
2.2 Nucleophilic Substitution at Unsaturated Carbon
2.3 Electrophilic Aromatic Substitution
3. Elimination Reactions
4. Addition Reactions
4.1 Electrophilic Addition Reaction
4.2 Stereochemistry of Addition Reaction
4.3 Nucleophilic Addition Reaction

II. Redox Reactions

A. Oxidation State
B. Oxidation at a Single Carbon
C. Oxidation at Two Adjacent Carbons
D. Oxidation at Other Atoms
E. Catalytic Hydrogenation
F. Reduction with Hydrides
G. Reduction with Metals

III. Reactions of Carbanions

A. Carbanion and Tautomerism
B. Carbon Nucleophile Addition Reactions
1. Grignard Reaction
2. Reaction of Acetylide
3. Aldol Reactions
4. Perkin Reaction
5. Claisen Ester Condensation Reaction
6. Benzoin Condensation
7. Benzilic acid rearrangement
8. Wittig Reaction
9. Michael Addition
10. Carbonation Reaction
C. Carbanion Elimination Reaction: Decarboxylation Reaction
D. Carbanion Displacement Reaction
1. Malonic Ester Synthesis
2. Wurtz Synthesis
3. Reimer-Tiemann Reaction
E. Halogenation and Alkylation of alpha Carbon of Carbonyl Compounds
1. Haloform Reaction
2. Hell-Volhard-Zelensky Reaction

IV. Molecular Rearrangements

1. General Mechanism
2. Migration to Electron Deficient Carbon, Oxygen, and Nitrogen
3. Anionic Skeletal Rearrangements
4. Rearrangements on an Aromatic Ring

V. Pericyclic Reactions
1. Electrocyclic Reaction
2. Cycloaddition Reaction
3. Sigmatropic Rearrangement

VI. Heterocyclic Reactions

1. Aromaticity and Reactivity
2. Reactions of Five-Membered Heterocycles
3. Reactions of Six-Membered Heterocycles
4. Reactions of Heterocycles with Two or More Heteroatoms

VII. Polymerization Reactions

1. Chain-Growth Polymerization
2. Step-Growth Polymerization

VIII. Organic Synthesis

1. Factors in Design of Synthesis
2. Functional Group Interconversions and Disconnections
3. Carbon-Carbon Bond Formations
4. Synthesis of Some Important Natural Products

IX. Characterization of Organic Compounds

1. Mass Spectroscopy
2. Infrared Spectroscopy
3. NMR Spectroscopy
4. UV/Visible Spectroscopy