Somewhat long-winded, but highly detailed organic chemistry textbook (gosh, I wish I had one of those when I was in school, my textbook was awful) from John D. Roberts and Marjorie C. Caserio, along with Stewart Ross. While professors may complain that this text is too repetitive and wordy, students might find their approach much easier to comprehend than their own assigned textbook.
Table of Contents
- Chapter 1: Introduction
- 1.1 Bonding in Organic Compounds
- 1.2 Methane, Ammonia, Water, and Hydrogen Fluoride
- Chapter 2: The C, and C, hydrocarbons
- 2.1 Molecular Shape of CH4, C2H6, C2H4,and C2H2
- 2.2 Rotational Conformations of Ethane
- 2.3 Space-Filling Models
- Chemical Reactions of the C1 and C2 Hydrocarbons
- 2.4 Combustion
- 2.5 Substitution Reactions of Saturated Hydrocarbons
- 2.6 Addition Reactions of Unsaturated Hydrocarbons
- Chapter 3: Alkanes
- 3.1 Nomenclature
- 3.2 Physical Properties of Alkanes-Concept
- 3.3 Alkanes and Their Chemical Reactions
- 3.4 Cycloalkanes
- Chapter 4: Alkenes
- 4.1 Nomenclature
- 4.2 lsomerism in C,H, Compounds
- 4.3 Cis and Trans Isomers
- 4.4 Chemical Reactions of Alkenes
- Chapter 5: Alkynes
- 5.1 Nomenclature
- 5.2 Physical Properties of Alkynes
- 5.3 Ethyne
- 5.4 Addition Reactions of Alkynes
- 5.5 Alkynes as Acids
- 5.6 Synthesis of Organic Compounds
- Chapter 6: Bonding in conjugated unsaturated systems
- 6.1 Bonding in Benzene
- 6.2 Conjugate Addition
- 6.3 Stabilization of Conjugated Dienes
- 6.4 Stabilization of Cations and Anions
- 6.5 Vinyl Halides and Ethers
- 6.6 Rules for the Resonance Method
- 6.7 Molecular Orbital Method of Huckel
- Chapter 7: Isolation and identification of organic compounds
- 7.1 Isolation and Purification
- 7.2 Identification of Organic Compounds
- Spectroscopy
- 7.3 Absorption of Electromagnetic Radiation
- 7.4 Infrared Spectroscopy
- 7.5 Ultraviolet and Visible Spectroscopy (Electronic Spectroscopy)
- 7.6 Nuclear Magnetic Resonance Spectroscopy
- Chapter 8: Nucleophilic displacement and elimination reactions
- 8.1 Organic Derivatives of Inorganic Compounds
- 8.2 Alcohol Nomenclature
- 8.3 Ether Nomenclature
- 8.4 Carboxylic Acid Nomenclature
- 8.5 The Use of Greek Letters to Denote Substituent Positions
- 8.6 Single- or Multiple-Word Names
- Nucleophilic Displacenzent Reactions
- 8.7 General Considerations
- 8.8 Mechanisms of SN Displacements
- 8.9 Energetics of SN1 and SN2 Reactions
- 8.10 Stereochemistry of SN2 Displacements
- 8.11 Structural and Solvent Effects in SN Reactions
- Elimination Reactions
- 8.12 The E2 Reaction
- 8.13 The E1 Reaction
- Chapter 9: Alkyl halides and organometallic compounds
- 9.1 Physical Properties
- 9.2 Spectra
- 9.3 Preparation of Alkyl Halides
- 9.4 Reaction of Alkyl Halides
- 9.5 Vinyl Halides
- 9.6 Allyl Halides
- 9.7 Polyhalogen Compounds
- 9.8 Fluorinated Alkanes
- 9.9 Organometallic Compounds
- Chapter 10: Alcohols and ethers
- 10.1 Physical Properties of Alcohols
- 10.2 Spectroscopic Properties of Alcohols-Hydrogen Bonding
- 10.3 Preparation of Alcohols
- Chemical Reactions of Alcohols
- 10.4 Reactions Involving the 0-H Bond
- 10.5 Reactions Involving the C-0 Bond of Alcohols
- 10.6 Oxidation of Alcohols
- 10.7 Polyhydroxy Alcohols
- 10.8 Unsaturated Alcohols
- Ethers
- 10.9 Preparation of Ethers
- 10.10 Reactions of Ethers
- 10.11 Cyclic Ethers
- Chapter 11: Aldehydes and ketones I. Reactions at the carbonyl group
- 11.1 Nomenclature of Aldehydes and Ketones
- 11.2 Carbonyl Groups of Aldehydes and Ketones
- 11.3 Preparation of Aldehydes and Ketones
- 11.4 Reactions of Aldehydes and Ketones
- Chapter 12: Aldehydes and ketones 11. Reactions involving substituent
groups. Polycarbonyl compounds - 12.1 Halogenation of Aldehydes and Ketones
- 12.2 Reactions of Enolate Anions
- Unsaturated Carbonyl Compounds
- 12.3 Unsaturated Aldehydes and Ketones
- 12.4 Ketenes
- Polycarbonyl Compounds
- 12.5 1,2-Dicarbonyl Compounds
- 12.6 1,3-Dicarbonyl Compounds
- Chapter 13: Carboxylic acids and derivatives
- 13.1 Physical Properties of Carboxylic Acids
- 13.2 Spectra of Carboxylic Acids
- 13.3 Preparation of Carboxylic Acids
- 13.4 Dissociation of Carboxylic Acids
- 13.5 Reactions at the Carbonyl Carbon of Carboxylic Acids
- 13.6 Decarboxylation of Carboxylic Acids
- 13.7 Reactions at the 2 Positiod of Carboxylic Acids
- Functional Derivatives of Carboxylic Acids
- 13.8 Displacement Reactions of Acid Derivatives
- 13.9 Reactions at the 2 Position (a position) of Carboxylic Acid Derivatives
- 13.10 Reactions of Unsaturated Carboxylic Acids and Their Derivatives
- 13.11 Dicarboxylic Acids
- Chapter 14: Optical isomerism. Enantiomers and diastereomers
- 14.1 Plane-Polarized Light and the Origin of Optical Rotation
- 14.2 Specific Rotation
- 14.3 Optically Active Compounds with Asymmetric Carbon Atoms
- 14.4 Optically Active Compounds Having No Asymmetric Carbon Atoms
- 14.5 Absolute and Relative Configuration
- 14.6 Separation or Resolution of Enantiomers
- 14.7 Asymmetric Synthesis and Asymmetric Induction
- 14.8 Racemization
- 14.9 Inversion of Configuration
- 14.10 Optical Rotatory Dispersion
- Chapter 15: Carbohydrates
- 15.1 Classification of Carbohydrates
- 15.2 Glucose
- 15.3 Cyclic Structures
- 15.4 Mutarotation
- 15.5 Glycosides
- 15.6 Disaccharides
- 15.7 Polysaccharides
- 15.8 Vitamin C
- 15.9 Immunologically Important Carbohydrates
- Chapter 16: Organic nitrogen compounds
- 16.1 Amines
- 16.2 Amides
- 16.3 Nitriles
- 16.4 Nitroso Compounds
- 16.5 Nitro Compounds
- 16.6 Some Compounds with Nitrogen-Nitrogen Bonds
- Chapter 17: Amino acids, proteins, and nucleic acids
- 17.1 Amino Acids
- 17.2 Lactams
- 17.3 Peptides
- 17.4 Protein Structures
- 17.5 Biosynthesis of Proteins
- 17.6 The Structure of DNA
- 17.7 Genetic Control and the Replication of DNA
- 17.8 Chemical Evolution
- Chapter 18: Enzymic processes and metabolism
- 18.1 Catalysis in Organic Systems
- 18.2 Enzymes and Coenzymes
- 18.3 Hydrolytic Enzymes
- 18.4 Oxidative Enzymes
- 18.5 The Energetics of Metabolic Processes
- Chapter 19: Organic compounds of sulfur, phosphorus, silicon and boron
- 19.1 d Orbitals and Chemical Bonds
- 19.2 Types and Nomenclature of Organic Compounds of Sulfur
- 19.3 Phosphorus Compounds
- 19.4 Organosilicon Compounds
- 19.5 Organoboron Compounds
- Chapter 20: Arenes. Electrophilic aromatic substitution
- 20.1 Nomenclature of Arenes
- 20.2 Physical Properties of Arenes
- 20.3 Spectroscopic Properties of Arenes
- 20.4 Reactions of Aromatic Hydrocarbons
- 20.5 Effect of Substituents on Reactivity and Orientation in Electrophilic Aromatic Substitution
- 20.6 Substitution Reactions of Polynuclear Aromatic Hydrocarbons
- 20.7 Nonbenzenoid Conjugated Cyclic Compounds Summary
- Chapter 21: Aryl halogen compounds. Nucleo-philic aromatic substitution
- 21.1 Physical Properties of Aryl Halogen Compounds
- 21.2 Preparation of Aryl Halides
- 21.3 Reactions of Aryl Halides
- 21.4 Organochlorine Pesticides
- Chapter 22: Aryl nitrogen compounds
- Aromatic Nitro Compounds
- 22.1 Synthesis of Nitro Compounds
- 22.2 Reduction of Aromatic Nitro Compounds
- 22.3 Polynitro Compounds
- 22.4 Charge-Transfer and pi Complexes
- Aromatic Amines
- 22.5 General Properties
- 22.6 Aromatic Amines with Nitrous Acid
- Diazonium Salts
- 22.7 Preparation and General Properties
- 22.8 Replacement Reactions of Diazonium Salts
- 22.9 Reactions of Diazonium Compounds that Occur Without Loss of Nitrogen
- Chapter 23: Aryl oxygen compounds
- 23.1 Synthesis and Physical Properties of Phenols
- 23.2 Some Chemical Properties of Phenols
- 23.3 Polyhydric Phenols
- 23.4 Quinones
- 23.5 Tropolones and Related Compounds
- Chapter 24: Aromatic side-chain derivatives
- Preparation of Aromatic Side-Chain Compounds
- 24.1 Aromatic Carboxylic Acids
- 24.2 Preparation of Side-Chain Aromatic Halogen Compounds
- 24.3 Side-Chain Compounds Derived from Arylmethyl Halides
- 24.4 Preparation of Aromatic Side-Chain Compounds by Ring Substitution
- Properties of Aromatic Side-Chain Derivatives
- 24.5 Arylmethyl Halides. Stable Carbonium Ions, Carbanions, and Radicals
- 24.6 Aromatic Aldehydes
- 24.7 Natural Occurrence and Uses of Aromatic Side-Chain Derivatives
- 24.8 Electron Paramagnetic Resonance (epr) Spectroscopy
- 24.9 Linear Free-Energy Relations
- Chapter 25: Heterocyclic compounds
- 25.1 Aromatic Character of Pyrrole, Furan, and Thiophene
- 25.2 Chemical Properties of Pyrrole, Furan, Thiophene, and Pyridine
- 25.3 Polycyclic and Polyhetero Systems
- Heterocyclic Natural Products
- 25.4 Natural Products Related to Pyrrole
- 25.5 Natural Products Related to Indole
- 25.6 Natural Products Related to Pyridine, Quinoline, and Isoquinoline
- 25.7 Natural Products Related to Pyrimidine
- 25.8 Natural Products Related to Purine and Pteridine
- 25.9 Natural Products Related to Pyran
- 25.10 Polyhetero Natural Products
- Chapter 26: Photochemistry
- 26.1 Light Absorption, Fluorescence, and Phosphorescence
- 26.2 Light Absorption and Structure
- 26.3 Photodissociation Reactions
- 26.4 Photochemical Reduction
- 26.5 Photochemical Oxidation
- 26.6 Photochemical Isomerization of Cis- and Trans-Unsaturated Compounds
- 26.7 Photochemical Cycloadditions
- Chapter 27: Cyclization reactions
- 27.1 Cyclization Reactions of Carbonyl Compounds
- 27.2 Cycloaddition Reactions of Carbon-Carbon Multiple Bonds
- 27.3 Fluxional Systems
- 27.4 Annulenes
- 27.5 Orbital Symmetry and Cycloaddition
- Chapter 28: Polymers
- 28.1 Types of Polymers
- Physical Properties of Polymers
- 28.2 Forces Between Polymer Chains
- 28.3 Correlation of Polymer Properties with Structure
- Preparation of Syzthetic Polymers
- 28.4 Condensation Polymers
- 28.5 Addition Polymers
- 28.6 Naturally Occurring Polymers
- 28.7 Dyeing of Fibrous Polymers
- Chapter 29: Some aspects of the chemistry of natural products
- 29.1 Civetone
- 29.2 Spectroscopic Methods in the Determination of the Structures of Natural Products
- 29.3 Terpenes
- 29.4 Steroids
- 29.5 Biogenesis of Terpenes and Steroids
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Organic Chemistry: Methane to Macromolecules