Text: Organic Chemistry, Francis A Carey, 3rd and 4th Editions, McGraw-Hill, 1996 and 2000.

Fall 1997
Topics
Chemical Bonding
Alkanes
Conformations of Alkanes and Cycloalkanes
Alcohols and Alkyl Halides
Structure and Preparation of Alkenes. Elimination Reactions
Reactions of Alkenes: Addition Reactions
Stereochemistry
Nucleophilic Substitution
Alkynes
Conjugation in Alkadienes and Allylic Systems
Arenes and Aromaticity
Reactions of Arenes. Electrophilic Aromatic Substitution

Spring 1998
Topics
Spectroscopy
Organometallic Compounds
Alcohols, Diols, and Thiols
Ethers, Epoxides, and Sulfides
Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl Group
Enols and Enolates
Carboxylic Acids
Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution
Ester Enolates
Amines

Fall 1998
Topics
Chemical Bonding
Alkanes Omitted Oxidation Reduction in Organic Chemistry Conformations of Alkanes and Cycloalkanes Omitted Conformational Analysis of Monosubstituted Cyclohexanes
Small Rings: Cyclopropane and Cyclobutane
Cyclopentane
Medium and Large Rings
Conformational Analysis of Disubstituted Cyclohexanes
Polycyclic Ring Systems
Heterocyclic Compounds Alcohols and Alkyl Halides
Structure and Preparation of Alkenes. Elimination Reactions Omitted Rearrangement in Alcohol Dehydration
Anti Elimination in E2 Reactions: Stereoelectronic Effects Reactions of Alkenes: Addition Reactions Omitted Heats of Hydrogenation
Stereochemistry of Alkene Hydrogenation
Carbocation Rearrangement in Hydrogen Halide Addition to Alkenes
Conversion of Alkenes to Vicinal Halohydrins
Epoxidation of Alkenes Stereochemistry
Nucleophilic Substitution Omitted Carbocation Rearrangements in SN1 Reactions
Effect of Solvent on the Rate of Nucleophilic Substitution
Sulfonate Esters as Substrates in Nucleophilic Substitution
A Retrospective Look: Reactions of Alcohols with Hydrogen Halides Arenes and Aromaticity Omitted Polycyclic Aromatic Hydrocarbons
Physical Properties of Arenes
Reactions of Arenes: A Preview
The Birch Reduction
Free-Radical Halogenation of Alkylbenzenes
Oxidation of Alkylbenzenes
Nucleophilic Substitution in Benzylic Halides
Preparation of Alkenylbenzenes
Addition Reactions of Alkenylbenzenes Reactions of Arenes. Electrophilic Aromatic Substitution Omitted Multiple Substituent Effects Alcohols, Diols, and Thiols Omitted Sources of Alcohols
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
Preparation of Alcohols from Epoxides
Preparation of Diols
Esterification
Esters of Inorganic Acids
Biological Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Preparation of Thiols Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl Group Omitted Acetals as Protecting Groups
Reaction with Secondary Amines: Enamines
The Wittig Reaction
Planning as Alkene Synthesis via the Wittig Reaction
Stereoselective Addition to Carbonyl Groups
Baeyer-Villiger Oxidation of Ketones Enols and Enolates Covered The alpha Carbon Atom and Its Hydrogens
Enolization and Enol Content
The Aldol Condensation: Aldehydes Carboxylic Acids Omitted Structure and Bonding
Ionization of Substituted Benzoic Acids
Dicarboxylic Acids
Carbonic Acid
Synthesis of Carbonxylic Acids by the Carboxylation of Grignard Reagents
Reactions of Carboxylic Acids: A Review and a Preview
Mechanism of Acid-Catalyzed Esterification
Intramolecular Ester Formation: Lactones
alpha Halogenation of Carboxylic Acids. The Hell-Volhard-Zelinsky Reaction
Decarboxylic of Malonic Acid and Related Comounds Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Covered Nomenclature of Carboxylic Acid Derivatives
Sources of Esters
Reactions of Esters: A Review and a Preview
Acid-Catalyzed Ester Hydrolysis
Base-Promoted Ester Hydrolysis: Saponification
Preparation of Amides
Hydrolysis of Amides Amines Omitted The Gabriel Synthesis of Primary Alkylamines
Reductive Amination
Reactions of Amines: A Review and a Preview
Electrophilic Aromatic Substitution in Arylamines Spring 1999
Topics
Spectroscopy
Alkynes
Organometallic Compounds
Conformations of Alkanes and Cycloalkanes Covered Conformational Analysis of Monosubstituted Cyclohexanes
Small Rings: Cyclopropane and Cyclobutane
Cyclopentane
Medium and Large Rings
Conformational Analysis of Disubstituted Cyclohexanes
Polycyclic Ring Systems
Heterocyclic Compounds Rearrangements of Carbocations Covered Rearrangement in Alcohol Dehydration
Carbocation Rearrangement in Hydrogen Halide Addition to Alkenes
Carbocation Rearrangements in SN1 Reactions Miscellaneous Covered Oxidation Reduction in Organic Chemistry
Anti Elimination in E2 Reactions: Stereoelectronic Effects
Heats of Hydrogenation
Stereochemistry of Alkene Hydrogenation
Conversion of Alkenes to Vicinal Halohydrins
Epoxidation of Alkenes
Effect of Solvent on the Rate of Nucleophilic Substitution
Sulfonate Esters as Substrates in Nucleophilic Substitution
A Retrospective Look: Reactions of Alcohols with Hydrogen Halides Conjugation in Alkadienes and Allylic Systems
Arenes Covered Polycyclic Aromatic Hydrocarbons
Physical Properties of Arenes
Reactions of Arenes: A Preview
The Birch Reduction
Free-Radical Halogenation of Alkylbenzenes
Oxidation of Alkylbenzenes
Nucleophilic Substitution in Benzylic Halides
Preparation of Alkenylbenzenes
Addition Reactions of Alkenylbenzenes
Multiple Substituent Effects Alcohols, Diols, and Thiols Covered Sources of Alcohols
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
Preparation of Alcohols from Epoxides
Preparation of Diols
Esterification
Esters of Inorganic Acids
Biological Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Preparation of Thiols Ethers, Epoxides, and Sulfides
Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl Group Covered Acetals as Protecting Groups
Reaction with Secondary Amines: Enamines
The Wittig Reaction
Planning as Alkene Synthesis via the Wittig Reaction
Stereoselective Addition to Carbonyl Groups
Baeyer-Villiger Oxidation of Ketones Enols and Enolates Omitted The alpha Carbon Atom and Its Hydrogens
Enolization and Enol Content
The Aldol Condensation: Aldehydes Carboxylic Acids Covered Structure and Bonding
Ionization of Substituted Benzoic Acids
Dicarboxylic Acids
Carbonic Acid
Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
Reactions of Carboxylic Acids: A Review and a Preview
Mechanism of Acid-Catalyzed Esterification
Intramolecular Ester Formation: Lactones
alpha Halogenation of Carboxylic Acids. The Hell-Volhard-Zelinsky Reaction
Decarboxylic of Malonic Acid and Related Comounds Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Omitted Nomenclature of Carboxylic Acid Derivatives
Sources of Esters
Reactions of Esters: A Review and a Preview
Acid-Catalyzed Ester Hydrolysis
Base-Promoted Ester Hydrolysis: Saponification
Preparation of Amides
Hydrolysis of Amides Ester Enolates
Amines Covered The Gabriel Synthesis of Primary Alkylamines
Reductive Amination
Reactions of Amines: A Review and a Preview
Electrophilic Aromatic Substitution in Arylamines Aryl Halides
Phenols

Fall 2001
Topics
Chemical Bonding
Alkanes Omitted Oxidation Reduction in Organic Chemistry Conformations of Alkanes and Cycloalkanes Omitted Conformational Analysis of Monosubstituted Cyclohexanes
Small Rings: Cyclopropane and Cyclobutane
Cyclopentane
Medium and Large Rings
Conformational Analysis of Disubstituted Cyclohexanes
Polycyclic Ring Systems
Heterocyclic Compounds Alcohols and Alkyl Halides
Structure and Preparation of Alkenes. Elimination Reactions Omitted Rearrangement in Alcohol Dehydration
Anti Elimination in E2 Reactions: Stereoelectronic Effects Reactions of Alkenes: Addition Reactions Omitted Heats of Hydrogenation
Stereochemistry of Alkene Hydrogenation
Carbocation Rearrangement in Hydrogen Halide Addition to Alkenes
Conversion of Alkenes to Vicinal Halohydrins
Epoxidation of Alkenes Stereochemistry
Nucleophilic Substitution Omitted Carbocation Rearrangements in SN1 Reactions
Effect of Solvent on the Rate of Nucleophilic Substitution
Sulfonate Esters as Substrates in Nucleophilic Substitution
A Retrospective Look: Reactions of Alcohols with Hydrogen Halides Arenes and Aromaticity Omitted Polycyclic Aromatic Hydrocarbons
Physical Properties of Arenes
Reactions of Arenes: A Preview
The Birch Reduction
Free-Radical Halogenation of Alkylbenzenes
Oxidation of Alkylbenzenes
Nucleophilic Substitution in Benzylic Halides
Preparation of Alkenylbenzenes
Addition Reactions of Alkenylbenzenes
Cyclobutadiene and Cyclooctatetrene
Hückel's Rule: Annulenes
Aromatic Ions
Heterocyclic Aromatic Compounds
Heterocyclic Aromatic Compounds and Hückel's Rule Reactions of Arenes. Electrophilic Aromatic Substitution Omitted Multiple Substituent Effects Alcohols, Diols, and Thiols Omitted Sources of Alcohols
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
Preparation of Alcohols from Epoxides
Preparation of Diols
Esterification
Esters of Inorganic Acids
Biological Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Preparation of Thiols Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl Group Omitted Acetals as Protecting Groups
Reaction with Secondary Amines: Enamines
The Wittig Reaction
Planning as Alkene Synthesis via the Wittig Reaction
Stereoselective Addition to Carbonyl Groups
Baeyer-Villiger Oxidation of Ketones Enols and Enolates Covered The alpha Carbon Atom and Its Hydrogens
Enolization and Enol Content
The Aldol Condensation: Aldehydes Carboxylic Acids Omitted Structure and Bonding
Ionization of Substituted Benzoic Acids
Dicarboxylic Acids
Carbonic Acid
Synthesis of Carbonxylic Acids by the Carboxylation of Grignard Reagents
Reactions of Carboxylic Acids: A Review and a Preview
Mechanism of Acid-Catalyzed Esterification
Intramolecular Ester Formation: Lactones
alpha Halogenation of Carboxylic Acids. The Hell-Volhard-Zelinsky Reaction Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Covered Nomenclature of Carboxylic Acid Derivatives
Sources of Esters
Reactions of Esters: A Review and a Preview
Acid-Catalyzed Ester Hydrolysis
Base-Promoted Ester Hydrolysis: Saponification
Preparation of Amides
Hydrolysis of Amides Amines Omitted The Gabriel Synthesis of Primary Alkylamines
Reductive Amination
Reactions of Amines: A Review and a Preview
Electrophilic Aromatic Substitution in Arylamines
Nitrosation of Alkylamines
Nitrosation of Arylamines
Synthetic Transformations of Aryl Diazonium Salts
Azo Coupling Spring 2002
Topics
Spectroscopy
Alkynes
Organometallic Compounds
Conformations of Alkanes and Cycloalkanes Covered Conformational Analysis of Monosubstituted Cyclohexanes
Small Rings: Cyclopropane and Cyclobutane
Cyclopentane
Medium and Large Rings
Conformational Analysis of Disubstituted Cyclohexanes
Polycyclic Ring Systems
Heterocyclic Compounds Rearrangements of Carbocations Covered Rearrangement in Alcohol Dehydration
Carbocation Rearrangement in Hydrogen Halide Addition to Alkenes
Carbocation Rearrangements in SN1 Reactions Miscellaneous Covered Oxidation Reduction in Organic Chemistry
Anti Elimination in E2 Reactions: Stereoelectronic Effects
Heats of Hydrogenation
Stereochemistry of Alkene Hydrogenation
Conversion of Alkenes to Vicinal Halohydrins
Epoxidation of Alkenes
Effect of Solvent on the Rate of Nucleophilic Substitution
Sulfonate Esters as Substrates in Nucleophilic Substitution
A Retrospective Look: Reactions of Alcohols with Hydrogen Halides Conjugation in Alkadienes and Allylic Systems
Arenes Covered Polycyclic Aromatic Hydrocarbons
Physical Properties of Arenes
Reactions of Arenes: A Preview
The Birch Reduction
Free-Radical Halogenation of Alkylbenzenes
Oxidation of Alkylbenzenes
Nucleophilic Substitution in Benzylic Halides
Preparation of Alkenylbenzenes
Addition Reactions of Alkenylbenzenes
Cyclobutadiene and Cyclooctatetrene
Hückel's Rule: Annulenes
Aromatic Ions
Heterocyclic Aromatic Compounds
Heterocyclic Aromatic Compounds and Hückel's Rule
Multiple Substituent Effects Alcohols, Diols, and Thiols Covered Sources of Alcohols
Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
Preparation of Alcohols from Epoxides
Preparation of Diols
Esterification
Esters of Inorganic Acids
Biological Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Preparation of Thiols Ethers, Epoxides, and Sulfides
Aldehydes and Ketones. Nucleophilic Addition to the Carbonyl Group Covered Acetals as Protecting Groups
Reaction with Secondary Amines: Enamines
The Wittig Reaction
Planning as Alkene Synthesis via the Wittig Reaction
Stereoselective Addition to Carbonyl Groups
Baeyer-Villiger Oxidation of Ketones Enols and Enolates Omitted The alpha Carbon Atom and Its Hydrogens
Enolization and Enol Content
The Aldol Condensation: Aldehydes Carboxylic Acids Covered Structure and Bonding
Ionization of Substituted Benzoic Acids
Dicarboxylic Acids
Carbonic Acid
Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
Reactions of Carboxylic Acids: A Review and a Preview
Mechanism of Acid-Catalyzed Esterification
Intramolecular Ester Formation: Lactones
alpha Halogenation of Carboxylic Acids. The Hell-Volhard-Zelinsky Reaction Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Omitted Nomenclature of Carboxylic Acid Derivatives
Sources of Esters
Reactions of Esters: A Review and a Preview
Acid-Catalyzed Ester Hydrolysis
Base-Promoted Ester Hydrolysis: Saponification
Preparation of Amides
Hydrolysis of Amides Ester Enolates
Amines Covered The Gabriel Synthesis of Primary Alkylamines
Reductive Amination
Reactions of Amines: A Review and a Preview
Electrophilic Aromatic Substitution in Arylamines
Nitrosation of Alkylamines
Nitrosation of Arylamines
Synthetic Transformations of Aryl Diazonium Salts
Azo Coupling Aryl Halides
Phenols