Table of Contents

Chemical Compounds
• Introduction
• GENERAL CONSIDERATIONS
  • The periodic table.
  • Trends in the chemical properties of the elements.
• CLASSIFICATION OF COMPOUNDS
• INORGANIC COMPOUNDS
  • Nomenclature of inorganic compounds
    • BINARY COMPOUNDS
      • Binary ionic compounds.
      • Binary molecular (covalent) compounds.
    • NONBINARY COMPOUNDS
      • Ionic compounds containing polyatomic ions.
      • Acids.
      • Compounds with complex ions.
  • Water
    • SIGNIFICANCE OF WATER
    • STRUCTURE OF WATER
      • Structures of ice.
      • Significance of the structure of liquid water.
    • BEHAVIOUR AND PROPERTIES
      • Water at high temperatures and pressures.
      • Physical properties.
      • Chemical properties.
        • Acid-base reactions.
        • Oxidation-reduction reactions.
  • Oxides
    • METAL OXIDES
    • NONMETAL OXIDES
      • Oxides of nitrogen.
      • Oxides of phosphorus.
      • Oxides of carbon.
        • Carbon monoxide.
        • Carbon dioxide.
        • Carbon suboxide.
      • Oxides of sulfur.
    • PEROXIDES
      • Hydrogen peroxide.
      • Superoxides.
  • Oxyacids and their salts
    • OXYACIDS OF NITROGEN AND THEIR SALTS
      • Nitric acid and its salts.
      • Nitrous acid and its salts.
    • OXYACIDS OF PHOSPHORUS AND THEIR SALTS
      • Orthophosphoric acid and its salts.
      • Phosphorous acid and its salts.
      • Hypophosphorous acid and its salts.
    • OXYACIDS OF SULFUR AND THEIR SALTS
      • Sulfuric acid.
        • Preparation.
        • Formation of salts.
        • Reactions and uses.
      • Sulfurous acid.
    • CARBONIC ACID AND ITS SALTS
      • Carbonate and hydrogen carbonate salts.
      • Other carbonic acids.
  • Carbides, nitrides, phosphides, and sulfides
    • CARBIDES
      • Preparation.
      • Classification.
        • Saltlike carbides.
        • Interstitial carbides.
        • Covalent carbides.
    • NITRIDES
      • Preparation.
      • Ionic nitrides.
      • Interstitial nitrides.
        • Covalent nitrides.
        • Boron nitride.
        • Cyanogen.
        • Sulfur nitrides.
    • PHOSPHIDES
    • SULFIDES
  • Hydrides
    • Saline hydrides.
    • Metallic hydrides.
    • Covalent hydrides.
    • Ammonia.
      • Preparation.
      • Physical properties.
      • Chemical reactivity.
      • Industrial uses.
      • Derivatives of ammonia.
  • Inorganic polymers
    • GENERAL CHARACTERISTICS
    • MAJOR CLASSES OF INORGANIC POLYMERS
      • Borates.
      • Silicates.
      • Silicones.
      • Silanes.
  • Boranes and carboranes
    • BORANES
      • Structure and bonding.
      • Reactions and synthesis.
    • CARBORANES
      • Structure and bonding.
      • Reactions and synthesis.
  • Coordination compounds
    • GENERAL CONSIDERATIONS
      • Coordination number.
      • Ligands and chelates.
        • Mononuclear, monodentate.
        • Polydentate.
        • Polynuclear.
      • Nomenclature.
    • HISTORICAL REVIEW
    • STRUCTURE AND BONDING
      • Valence bond theory.
      • Crystal field, ligand field, and molecular orbital theories.
      • Isomerism.
        • Ionization isomerism.
        • Coordination isomerism.
        • Ligand isomerism.
        • Linkage isomerism.
        • Geometric isomerism.
        • Optical isomerism.
      • Geometry of compounds of various coordination numbers.
    • PRINCIPAL TYPES
      • Aqua complexes.
      • Halide complexes.
      • Metal carbonyls.
      • Metal nitrosyls.
      • Metal cyanides and isocyanides.
      • Metal clusters.
      • Isopoly and heteropoly anions.
      • Organometallic complexes.
    • REACTIONS
      • Lability and inertness.
      • Principal types.
        • Substitution.
        • Isomerization.
        • Oxidation-reduction.
    • SYNTHESIS
    • USES
      • Dyes and pigments.
      • Extraction and separation of metals.
      • Chemical analysis.
      • Sequestering.
      • Catalysis.
      • Biology.
  • Organometallic compounds
    • GENERAL CONSIDERATIONS
      • Defining characteristics.
      • Historical developments.
    • s- AND p-BLOCK ORGANOMETALLIC COMPOUNDS
      • The stability and reactivity of organometallic compounds.
      • The synthesis of s- and p-block organometallic compounds.
        • Formation of alkyllithium and Grignard reagents.
        • Double displacement.
        • Redistribution.
        • Hydrometallation.
        • Reduction.
        • Carbanion character.
        • -hydrogen elimination.
    • d- AND f-BLOCK ORGANOMETALLIC COMPOUNDS
      • Metal carbonyls.
        • The structure of metal carbonyls.
        • Zero-oxidation-state metal carbonyls.
        • Metal carbonyl anions.
      • Compounds with metal-carbon bonds.
        • Simple alkyl ligands.
        • Alkylidene ligands.
        • Alkylidyne ligands.
        • Alkene and alkyne ligands.
        • Polyene ligands.
        • Cyclic polyene ligands.
    • METAL CLUSTERS
    • ORGANOMETALLIC COMPOUNDS IN CATALYSIS
      • Hydrogenation.
      • Hydroformylation.
      • Alkene polymerization.
• ORGANIC COMPOUNDS
  • General considerations
    • HISTORICAL DEVELOPMENTS
    • CARBON BONDING
    • FUNCTIONAL GROUPS
      • Alkanes.
      • Alkenes.
      • Alkynes.
      • Aromatics.
      • Alcohols, phenols, and ethers.
      • Aldehydes and ketones.
      • Carboxylic acids and their derivatives.
      • Amines and thiols.
      • Halides.
      • Polyfunctional compounds.
    • CHEMICAL SYNTHESIS
      • General considerations.
      • General approach to synthesis.
      • Evaluation of a synthetic method.
      • Isolation and purification of products.
    • SPECTROSCOPY OF ORGANIC COMPOUNDS
      • Ultraviolet and visible (UV-visible) spectroscopy.
      • Infrared (IR) spectroscopy.
      • Nuclear magnetic resonance (NMR) spectroscopy.
      • Proton magnetic resonance spectroscopy.
      • Carbon-13 magnetic resonance spectroscopy.
      • Mass spectrometry.
    • REACTION TYPES
      • Substitution reactions.
      • Elimination reactions.
      • Addition reactions.
      • Hydrolysis.
      • Condensation.
      • Acid-base reactions.
  • Hydrocarbons
    • ALIPHATIC HYDROCARBONS
      • Alkanes.
        • Nomenclature.
        • Three-dimensional structures.
        • Cycloalkanes.
        • Stereoisomerism.
        • Physical properties.
        • Sources and occurrence.
        • Chemical reactions.
      • Alkenes and alkynes.
        • Bonding in alkenes and alkynes.
        • Natural occurrence.
        • Synthesis.
        • Physical properties.
        • Chemical properties.
        • Polymerization.
    • AROMATIC HYDROCARBONS
      • Arenes.
        • Structure and bonding.
        • Nomenclature.
        • Physical properties.
        • Source and synthesis.
        • Reactions.
      • Nonbenzenoid aromatic compounds.
        • Annulenes and the Hückel rule.
        • Polycyclic nonaromatic compounds.
  • Alcohols, phenols, and ethers
    • ALCOHOLS
      • Structure and classification.
      • Nomenclature.
        • Common names.
      • Physical properties.
        • The effect of hydrogen bonding on boiling points.
        • Solubility properties.
      • Commercially important alcohols.
        • Methanol.
        • Ethanol.
        • 2-Propanol.
      • Sources.
        • Reduction of carbonyl compounds.
        • Hydration of alkenes.
        • Displacement of halides.
        • Using Grignard and organolithium reagents.
      • Reactions.
        • Oxidation.
        • Biological oxidation.
        • Dehydration to alkenes.
        • Substitution to form alkyl halides.
        • Esterification.
        • Acidity of alcohols: formation of alkoxides.
    • PHENOLS
      • Nomenclature.
      • Physical properties.
      • Natural sources.
      • Synthesis.
        • Hydrolysis of chlorobenzene (the Dow process).
        • Oxidation of isopropylbenzene.
        • General synthesis of phenols.
      • Reactions.
        • Acidity of phenols.
        • Oxidation.
        • Electrophilic aromatic substitution.
        • Formation of phenol-formaldehyde resins.
    • ETHERS
      • Nomenclature.
      • Physical properties.
      • Complexes of ethers with reagents.
      • Synthesis.
        • Williamson ether synthesis.
        • Bimolecular dehydration.
      • Reactions.
        • Cleavage.
        • Autoxidation.
      • Epoxides.
  • Aldehydes and ketones
    • STRUCTURE
    • NOMENCLATURE
      • Aldehydes.
      • Ketones.
    • PROPERTIES
      • Physical properties.
      • Tautomerism.
    • SYNTHESIS
    • PRINCIPAL CATEGORIES OF REACTIONS
      • Oxidation-reduction reactions.
      • Nucleophilic addition.
        • Addition of noncarbon nucleophiles.
        • Addition of carbon nucleophiles.
      • Displacement at the alpha carbon.
        • Alpha halogenation.
        • Aldol reaction.
      • Conjugate addition.
    • USES OF ALDEHYDES AND KETONES
      • Formaldehyde.
      • Acetone.
      • Other carbonyl compounds of industrial use.
  • Carboxylic acids and their derivatives
    • NOMENCLATURE OF CARBOXYLIC ACIDS AND THEIR SALTS
    • PROPERTIES OF CARBOXYLIC ACIDS
      • Acidity.
      • Solubility.
      • Boiling point.
      • Odour.
    • CLASSES OF CARBOXYLIC ACIDS
      • Saturated aliphatic acids.
      • Unsaturated aliphatic acids.
      • Aromatic acids.
      • Polycarboxylic acids.
      • Hydroxy and keto acids.
      • Amino acids.
    • SYNTHESIS OF CARBOXYLIC ACIDS
      • Hydrolysis of acid derivatives.
      • Oxidation.
      • Other synthetic methods.
    • PRINCIPAL REACTIONS OF CARBOXYLIC ACIDS
      • Conversion to acid derivatives.
      • Reduction.
      • Other reactions.
    • DERIVATIVES OF CARBOXYLIC ACIDS
      • Carboxylic esters.
        • Nomenclature.
        • Synthesis.
        • Properties.
      • Reactions.
        • Lactones.
        • Polyesters.
      • Amides.
        • Nomenclature.
        • Synthesis.
        • Properties.
        • Reactions.
        • Polyamides.
        • Related compounds.
      • Acyl halides.
        • Nomenclature and synthesis.
        • Reactions.
      • Anhydrides.
        • Nomenclature and synthesis.
        • Reactions.
      • Nitriles.
        • Nomenclature.
        • Synthesis.
        • Reactions.
  • Amines
    • NOMENCLATURE
    • PROPERTIES
      • Physical properties.
      • Molecular shape and configuration.
    • OCCURRENCE AND SOURCES
    • REACTIVITY
      • Addition.
      • Substitution.
      • Oxidation.
      • Elimination.
    • USES
  • Organic sulfur compounds
    • The sulfur atom.
    • Analysis of organosulfur compounds.
    • ORGANIC COMPOUNDS OF BIVALENT SULFUR
      • Thiols.
        • Preparation.
        • Reactions.
      • Sulfides.
        • Preparation.
        • Reactions.
      • Disulfides and polysulfides and their oxidized products.
        • Preparation.
      • Reactions.
      • Thiocarbonyl compounds.
        • Preparation.
        • Reactions.
    • ORGANIC COMPOUNDS OF POLYVALENT SULFUR
      • Sulfoxides and sulfones.
        • Occurrence and preparation.
        • Reactions.
      • Other sulfinyl and sulfonyl compounds.
      • Sulfonium and oxosulfonium salts; sulfur ylides.
      • Sulfuranes: hypervalent organosulfur compounds.
  • Heterocyclic compounds
    • GENERAL ASPECTS OF HETEROCYCLIC SYSTEMS
      • Comparison with carbocyclic compounds.
      • Nomenclature.
    • MAJOR CLASSES OF HETEROCYCLIC COMPOUNDS
      • Three-membered rings.
      • Four-membered rings.
      • Five-membered rings with one heteroatom.
      • Six-membered rings with one heteroatom.
      • Five- and six-membered rings with two or more hetero-atoms.
      • Rings with seven or more members.
      • Rings with uncommon heteroatoms.
        • Selenium and tellurium.
        • Phosphorus, arsenic, and antimony.
        • Boron.
  • Organohalogen compounds
    • Nomenclature.
    • Carbon-halogen bond strengths and reactivity.
    • ALKYL HALIDES
      • Structure and physical properties.
      • Natural occurrence.
      • Synthesis.
      • Reactions.
        • Nucleophilic substitution.
        • Elimination.
        • Preparation of Grignard reagents.
    • VINYLIC HALIDES
      • Natural occurrence.
      • Preparation.
        • Dehydrohalogenation of a dihalide.
        • Addition of a hydrogen halide to an alkyne.
      • Reactions.
    • ARYL HALIDES
      • Natural occurrence.
      • Preparation.
        • Halogenation.
        • Diazonium salts.
      • Reactions.
  • Coloured compounds and dyes
    • HISTORICAL DEVELOPMENTS
      • Natural dyes.
      • Development of the synthetic dye industry.
    • CHROMOGENS AND COLOUR
    • GENERAL FEATURES OF DYES AND DYEING
      • Fibre structure.
      • Fibre porosity.
      • Dye retention.
        • Fastness.
        • Attractive forces.
      • Dyeing techniques.
        • Vat dyeing.
        • Disperse dyeing.
        • Azo dyeing techniques.
      • Classifications of dyes.
    • DEVELOPMENT OF SYNTHETIC DYES
      • Triphenylmethane dyes.
      • Anthraquinone dyes.
      • Xanthene and related dyes.
      • Azo dyes.
      • Phthalocyanine compounds.
      • Quinacridone compounds.
      • Reactive dyes.
      • Optical brighteners.
      • Food dyes.
      • Current dye-industry research.
      • Standardization tests and identification of dyes.
  • Carbohydrates
    • MONOSACCHARIDES
    • DISACCHARIDES
    • POLYSACCHARIDES
  • Amino acids, peptides, and proteins
    • AMINO ACIDS
      • Structure.
      • Sources.
    • PEPTIDES AND PROTEINS
      • Structure.
      • Biosynthesis.
      • Laboratory synthesis.
        • Use of -halo acid chlorides.
        • The carbobenzoxy protecting group.
        • The Boc protecting group.
        • Solid-phase methods.
  • Lipids
    • GENERAL DESCRIPTION AND STRUCTURAL FEATURES
    • TRIGLYCERIDES, PHOSPHOLIPIDS, AND SPHINGOLIPIDS
      • Fatty acids.
      • Triglycerides.
        • Structure.
        • Occurrence.
        • Selected examples.
        • Biosynthesis.
        • Synthesis.
      • Phospholipids.
        • Definition and structural features.
        • Occurrence.
        • Selected examples.
        • Biosynthesis.
      • Sphingolipids.
        • Definition.
        • Structural features.
        • Occurrence.
        • Selected examples.
        • Biosynthesis.
        • Biosynthesis of gangliosides.
        • Biosynthesis of long-chain glycosphingolipids.
        • Biosynthesis of lacto-phospholipids.
    • PROSTAGLANDINS AND RELATED COMPOUNDS: THE EICOSANOIDS
      • Structures of prostaglandins.
      • Biosynthesis.
      • The action of anti-inflammatory drugs on eicosanoids.
    • ISOPRENOIDS
      • Chemistry of isoprenoids.
        • Structural features.
        • Classification.
        • Tail-to-tail coupling.
        • Natural sources.
        • Biological functions.
        • Uses.
        • Isolation and identification.
        • Purification.
        • Analysis.
        • Determination of structure.
        • Biosynthesis.
      • Comparative survey of isoprenoid compounds.
        • Monoterpenes.
        • Sesquiterpenes.
        • Diterpenes.
        • Triterpenes.
        • Tetraterpenes.
        • Polyterpenes.
    • STEROIDS
      • Historical background.
      • Chemistry of steroids.
        • Steroid numbering system and nomenclature.
        • Methods of isolation.
        • Determination of structure and methods of analysis.
        • Total synthesis of steroids.
        • Partial synthesis of steroids.
      • Natural distribution and functions.
        • Sterols and bile acids.
        • Sex hormones.
        • Adrenal hormones.
        • Steroids of lower organisms.
      • Biosynthesis and metabolism of steroids.
        • Cholesterol.
        • Steroid hormones.
        • Steroid metabolism in plants.
      • Structural relationships of the principal categories of steroids.
        • Sterols.
        • Bile acids and alcohols.
        • Estrogens.
        • Progestational steroids (gestogens, progestins).
        • Androgens.
        • Adrenal cortical hormones.
        • Ecdysones.
        • Cardiac glycosides and aglycones.
        • Toad poisons.
        • Sapogenins and saponins.
      • Pharmacological actions of steroids.
        • Androgens and anabolic steroids.
        • Antiandrogens.
        • Synthetic estrogens and gestogens: steroid contraceptives.
        • Antiestrogens.
        • Adrenal hormones.
        • Cardiotonic steroids.
        • The general biological significance of steroids.
• Bibliography
  • General works.
  • Inorganic compounds.
  • Boranes and carboranes:
  • Coordination compounds:
  • Organometallic compounds:
  • Organic compounds.
  • Hydrocarbons:
  • Alcohols, phenols, and ethers:
  • Aldehydes and ketones:
  • Carboxylic acids and their derivatives:
  • Amines:
  • Organic sulfur compounds:
  • Heterocyclic compounds:
  • Organohalogen compounds:
  • Coloured compounds and dyes:
  • Carbohydrates:
  • Amino acids, peptides, and proteins:
  • Lipids: