Organic Chemistry: Methane to Macromolecules

Written by: John D. Roberts, Marjorie C. Caserio and Stewart Ross

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
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
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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