Introduction - Review of Organic Chemistry I Concepts

1. Examples of Organic Compounds
   1. Line-Angle Drawings
   2. Functional Groups
2. Isomers
3. Reactions
   1. Preparations of Alkyl Halides
   2. Preparations of Alcohols
   3. Preparations of Alkenes
4. Reaction Mechanisms
   1. Arrows in Organic Chemistry
   2. Reactive Intermediates
   3. Examples
5. Organometallic Reagents
   1. Carbanion-Like (Gilman, Grignard)
   2. Carbene-Like (Simmons-Smith)

Chapter 13. Nuclear Magnetic Resonance (NMR) Spectroscopy

1. Physical Basis
2. Chemical Shift
3. Spin-Spin Splitting
4. Integration
5. Interpreting Proton NMR Spectra
6. Effect of Stereocenters
   1. Example
   2. Topicity of Atoms or Groups
7. Instrumentation
8. 13-C NMR

Ch 13 section not covered: The DEPT Method (section 13.12).

Chapter 12. Infrared (IR) Spectroscopy

1. Physical Basis for IR Spectroscopy
2. Vibrational Modes
   1. Examples
   2. Signal Intensity
   3. Frequency Trends
3. Group Frequencies

Chapter 16. Aldehydes and Ketones

1. Nomenclature
2. Structure and Bonding
3. Preparation of Aldehydes and Ketones
4. Reactions
   1. Addition Reactions
   2. The Wittig Reaction
   3. Reactions alpha to the Carbonyl Carbon
   4. Oxidations
   5. Reductions

Ch 16 section not covered: The stereochemistry of the Wittig reaction and the Horner-Emmons-Wadsworth modification (pp 598-599).

Chapter 17. Carboxylic Acids

1. Structure and Bonding
2. Nomenclature
3. Properties
4. Preparations of Carboxylic Acids
   1. Oxidation of Alcohols
   2. Haloform Reactions
   3. Grignard Reactions
5. Reactions
   1. Reductions
   2. Esterification
   3. Acid Chloride Formation
   4. Decarboxylation

Ch 17 section not covered: 17.5 part B (Industrial Synthesis of Acetic Acid)

Chapter 18. Carboxylic Acid Derivatives

1. Nomenclature and Examples
2. Nucleophilic Acyl Substitution Reactions
3. Preparations and Reactions
   1. Acid Chlorides
   2. Acid Anhydrides
   3. Esters
   4. Amides
   5. Nitriles
4. IR Spectroscopy

Chapter 19. Enolate Anions and Enamines (Carbonyl Condensation Reactions and Rections of alpha-beta-Unsaturated Carbonyl Compounds)

1. Enolates and Enamines
2. Aldol Reaction
   1. Mechanism
   2. Use in Synthesis
3. Condensations with Esters
   1. Claisen Condensation
   2. Diekmann Condensation
4. Reactions with Enamines
5. Acetoacetic Ester Synthesis and Malonic Ester Synthesis
6. Conjugate Additions to alpha-beta-Unsaturated Carbonyl Compounds

Chapter 14. Mass Spectrometry

1. Principles and Instrumentation
2. Analysis of Mass Spectra
   1. Molecular Ion
   2. Fragmentation Patterns
   3. Isotope Patterns

Chapter 20. Conjugated Systems (and UV-Visible Spectroscopy)

1. Special Stability
   1. Resonance View
   2. Molecular Orbital Picture
   3. Evidence from Heats of Reaction
2. Special Reactivity: 1,2 and 1,4 Additions
   1. Reaction and Mechanism
   2. Kinetic vs. Thermodynamyic Control
3. UV-Visible Spectroscopy
   1. Physical Basis / Alkene Examples
   2. Other Examples
   3. Typical Uses

Chapter 21. Benzene and the Concept of Aromaticity

1. Examples of Aromatic Compounds
2. Benzene
   1. Structure and Bonding Issues
   2. Bonding Models
3. Huckel's Criteria for Aromaticity
   1. The Rules
   2. Why 4n+2?
   3. Heterocyclic Examples
4. Nomenclature
   1. Monosubstituted Benzenes
   2. Disubstituted Benzenes
5. Selected Reactions of Phenols and Reactions at Benzylic Positions
   1. Reactions of Phenols
   2. Reactions at Benzylic Positions
6. NMR Spectroscopy of Benzene Derivatives

Chapter 22. Reactions of Benzene and its Derivatives

1. Electrophilic Aromatic Substitution Reactions
   1. Reactions of Benzene
   2. Mechanisms
   3. Directing Effects
2. Nucleophilic Aromatic Substitution Reactions
   1. Addition-Elimination Mechanism
   2. Benzyne Intermediate Mechanism
3. Other Useful Reactions

Chapter 23. Amines

1. Nomenclature and Examples
   1. Aliphatic Amines
   2. Aromatic Amines
   3. Alkaloids
2. Properties
3. Preparations of Amines
   1. From Epoxides
   2. From Reductions of Amides, Nitriles, and Imines
   3. From Reductions of Azides
   4. Preparation of Aniline
   5. SN2 Reactions with Amines
4. Reactions of Amines
   1. Acid/Base Reactions
   2. Alkylation Reactions
   3. Reactions with Nitrous Acid
   4. Two Special Elimination Reactions

Chapter 24. Carbon-Carbon Bond Forming Reactions

1. Pericyclic Reactions
   1. Diels-Alder Reaction
   2. Claisen and Cope Rearrangements
2. Palladium-Catalyzed Coupling Reactions
   1. Heck Reaction
   2. Suzuki Coupling
3. Alkene Metathesis