1. Structure and properties of organic compounds. Structure of organic compounds. Properties of organic compounds. Bond in organic compounds. Tetrahedral carbon geometry. Isomerism. Functional groups. Nomenclature. Molecular structure. Acids and Bases, Polar and Nonpolar Molecules. Deeper look: Organic Foods. Alkaloids
2. Alkanes and cicloalkanes. Physical properties. Bond-Dissociation Energies. Substituted alkanes. Structure of Alkyl Radicals: Hyperconjugation. Reactions of Alkanes. Stability and conformations of Cycloalkanes: Ring Strain. Conformations of Cyclohexane: Axial and Equatorial Bonds. Combustion. Deeper look: Petroleum. Cyclohexane, Adamantane, and Diamandoids.
3. Stereochemistry at Tetrahedral Centers. Enantiomers and the Tetrahedral Carbon, Chirality. Optical Activity. Sequence Rules for
Specifying Configuration. Diastereomers. Meso Compounds. Racemic Mixtures and the Resolution of Enantiomers. Deep looks: Chiral Drugs
4. Alkyl halides. Halogenation. Nucleophilic bimolecular and unimolecular substitution: SN2 and SN1 reactions. Preparation of alkenes: unimolecular and bimolecular elimination reactions: E1 and E2.
5. Alkenes, dienes and alkynes. Structure and reactivity of alkenes: physical properties of alkenes; Cis¿Trans Isomerism in alkenes and stereochemistry; stability of alkenes; reactions of alkenes: electrophilic addition reactions, reduction and oxidation; radical additions to alkenes: Radical Additions: anti-Markovnikov product formation, chain-growth polymers. Radical mechanism substitution reactions. Preparation of alkenes. Dienes: Stability of Conjugated Dienes. Diels-Alder reactions. Deeper look: Terpenes: Naturally Occurring. Biological Additions of Radicals to Alkenes. Synthesis of Antitumor Drugs. Polymers and natural and synthetic rubbers. The Diels-Alder Reaction is ¿Green¿. Properties of alkynes; Preparation of alkynes; Reactions of alkynes: electrophilic addition reactions and anti-Markovnikov Additions reactions. Deep look: Ethyne as an Industrial Starting Material. Alkynes in Nature and in Medicine.
6. Spectroscopy. Radiation-matter interaction. UV-Visible Spectroscopy. UV-Visible and conjugation: color. Fluorescence. Infrared spectroscopy. Nuclear magnetic resonance. Chemical shift. 1H-NMR and 13C-NMR. Spin¿spin splitting: coupling constant.
7. Aromatic Compounds. Sources and Names of Aromatic Compounds. Structure and Stability of Benzene. Aromaticity. Aromatic Heterocycles: Pyridine and Pyrrole. Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution: Bromination, Alkylation, Acylation and Other Aromatic Substitutions. Deeper look: Compounds Made of Pure Carbon: Graphite, Graphene, Diamond, and Fullerenes. Explosive Nitroarenes: TNT and Picric Acid
8. Alcohols, phenols, and ethers. Naming alcohols and phenols. Properties of alcohols and phenols. Preparation of alcohols: from carbonyl compounds: Reduction, Grignard Reaction. Reactions of alcohols: Dehydration of alcohols. Oxidation of alcohols and phenols and their uses. Reactions of phenols. Deeper look: Ethanol: Chemical, Drug, Poison. Alcohol oxidation in the body. Names and Properties of Ethers. Synthesis of Ethers. Reactions of Ethers. Reactions of Epoxides: Ring-Opening. Thiols and Sulfides. Deeper Look: Epoxy Resins and Adhesives
9. Adehydes and ketones. Structure of the Carbonyl Group. Naming the Aldehydes and Ketones. Preparation of Aldehydes and Ketones. Reactivity of the Carbonyl Group: Mechanisms of Addition: addition of water to form hydrates, addition of alcohols to form hemiacetals and acetals, nucleophilic addition of ammonia and its derivatives. Deoxygenation of the carbonyl group. Addition of hydrogen cyanide to give cyanohydrins. Addition of phosphorus Ylides: the Wittig Reaction. Enols, enolates and the aldol condensation. alpha-beta- Unsaturated Aldehydes and Ketones. Oxidative Chemical Tests for Aldehydes. Worked Examples: Integrating the Concepts. Reactions in Nature and in the Laboratory.
10. Carboxylic acids and derivatives Naming the Carboxylic Acids. Structural and Physical Properties of Carboxylic Acids. Acidic and Basic Character of Carboxylic Acids. Carboxylic Acid Synthesis in Industry. Methods for Introducing the Carboxy Functional Group. Substitution at the Carboxy Carbon: The Addition¿Elimination Mechanism. Carboxylic Acid Derivatives: Acyl Halides and Anhydrides. Esters. Esters in Nature: Waxes, Fats, Oils, and Lipids. Amides. Reduction of Carboxylic Acids by Lithium Aluminum Hydride. Biological Activity of Carboxylic Acids. Deeper look: Long-Chain Carboxylates and Sulfonates Make Soaps and Detergents. Green Plastics, Fibers, and Energy from Biomass-Derived Hydroxyesters.
11. Amines Naming Amines. Structure and properties of amines. Basicity of amines and arylamines. Biological Amines . Synthesis of Amines. Reactions of Amines and Arylamines. Heterocyclic Amines. Deeper Look: Green Chemistry II: Ionic Liquids.
12. Biomolecules. Carbohydrates. Lipids. Amino acids, proteins and enzymes. Nucleic acids and protein synthesis. Metabolic processes and energy production. Deeper look: Saturated Fats, Cholesterol, and Heart Disease. Statin Drugs