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Organic Chemistry
First Section
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Chapter 1 Molecular Structure and Bonding
1.1 Molecular Structure and Bonding
1.2 Resonance
Chapter 2 Acids and Bases
2 Acids and Bases
Chapter 3 Nomenclature
3 Nomenclature
Chapter 4 Alkanes
4.1 Intermolecular Forces
4.2 Newman Projections
4.3 Cycloalkanes and Conformations of Cyclohexane
Chapter 5 Isomers and Stereochemistry
5.1 Introduction to Isomers
5.2 Relative and Absolute Configurations of Chiral Centers
5.3 Diastereomers and Meso Compounds
5.4 Atypical Examples in Stereochemistry
Chapter 6 Introduction to Reaction Mechanisms
6 Introduction to Organic Reactions
Chapter 7 Alkenes
7.1 Nomenclature of Alkenes
7.2 Introduction to Electrophilic Addition
7.3 Addition of HBr
7.4 Acid-Catalyzed Addition of Water and Alcohols
7.5 Additon of Br2
7.6 Oxymercuration-Demercuration and Hydroboration-Oxidation
7.7 Catalytic Hydrogenation and Addition of HBr with Peroxide
7.8 Epoxidation, Hydroxylation (Anti and Syn), and Addition of Carbenes
7.9 Ozonolysis
Chapter 8 Alkynes
8.1 Structure, Nomenclature, and Acidity of Alkynes
8.2 Synthesis of Alkynes
8.3 Addition of H2, HBr, Br2, and H2O to Alkynes
8.4 Nucleophilic Addition of Acetylide Ions
Chapter 9 Conjugated Systems
9.1 Addition Reactions to Conjugated Dienes (Thermodynamic vs Kinetic Products)
9.2 Pi Molecular Orbitals
9.3 Diels-Alder Reactions
Chapter 10 Substitution Reactions
10.1 SN1 and SN2 Reactions Part 1
10.2 SN1 and SN2 Reactions Part 2
Chapter 11 Elimination Reactions
11.1 E1 and E2 Reactions
11.2 Distinguishing between SN1, SN2, E1, and E2 Reactions
Chapter 12 Radical Reactions
12.1 Free Radical Halogenation
12.2 Alkene Addition of HBr with Peroxide
Chapter 13 Mass Spectrometry
13.1 Fragmentation Patterns
13.2 Interpreting Mass Spectra
Chapter 14 IR Spectroscopy
14.1 Introduction to IR Spectroscopy
14.2 Interpreting IR Spectra
Chapter 15 NMR Spectroscopy
15.1 Introduction to NMR Spectroscopy
15.2 C13 NMR
15.3 The Number of Signals in Proton NMR (H NMR)
15.4 Integration and Multiplicity (Splitting) in Proton NMR
15.5 Interpreting NMR Spectra
15.6 Interpreting the Combination of All Spectra
Chapter 16 Alcohols, Ethers, and Epoxides
16.1 Nomenclature and Acidity of Alcohols
16.2 Substitution Reactions of Alcohols
16.3 Elimination (Dehydration) Reactions of Alcohols
16.4 Oxidation of Alcohols
16.5 Grignard Reagents
16.6 Retrosynthesis with Grignard Reagents and Acetylide Ions
16.7 Nomenclature of Ethers and Epoxides
16.8 Synthesis and Reactions of Ethers and Epoxides
Chapter 17 Aromatic Compounds
17.1 Nomenclature of Aromatic Compounds
17.2 Aromaticity
17.3 Electrophilic Aromatic Substitution (EAS) Reactions
17.4 EAS Reactions of Substituted Benzenes
17.5 Benzene Side Chain Reactions
17.6 Nucleophilic Aromatic Substitution (NAS) Reactions
17.7 Reactions of Non-benzenoid Aromatics
Chapter 18 Ketones and Aldehydes
18.1 Nomenclature and Synthesis of Ketones and Aldehydes
18.2 Reduction Reactions of Carbonyl Compounds
18.3 Nucleophilic Addition of Acetylides and Grignard Reagents
18.4 Nucleophilic Addition of Amines (Formation of Imines and Enamines)
18.5 Nucleophilic Addition of Water and Alcohols (Formation of Hydrates and Acetals-Ketals)
18.6 Addition to Conjugated Ketones and Aldehydes
18.7 The Wittig Reaction
Chapter 19 Carboxylic Acids and Carboxylic Acid Derivatives
19.1 Nomenclature of Carboxylic Acids and Acid Derivatives
19.2 Synthesis of Carboxylic Acids
19.3 Nuceophilic Acyl Substitution and Trends in Reactivity
19.4 Mechanisms of Nucleophilic Acyl Substitution Reactions
19.5 Gabriel and Baeyer-Villiger Syntheses
Chapter 20 Substitution Reactions at the Alpha Carbon
20.1 Acidity of the Alpha Carbon
20.2 Alpha Halogenation
20.3 Alpha Alkylation and the Michael Reaction
20.4 Aldol Condensation Reactions
20.5 Mechanisms of Aldol Condensation Reactions
20.6 The Robinson Annulation
20.7 Claisen Condensation Reactions
20.8 Beta Decarboxylation and the Malonic Ester and Acetoacetic Ester Syntheses
Chapter 21 Amines
21.1 Nomenclature and Basicity of Amines
21.2 Synthesis of Amines
21.3 Reactions of Amines
21.4 Amino Acids
14.2 Interpreting IR Spectra
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