PART I: GENERAL CHEMISTRY. 1. Basic Concepts About Matter. Chemistry: The Study of Matter. Physical States of Matter. Properties of Matter. Changes in Matter. CHEMISTRY AT A GLANCE: Use of the Terms Physical and Chemical. Pure Substances and Mixtures. Elements and Compounds. CHEMISTRY AT A GLANCE: Classes of Matter. Discovery and Abundance of the Elements. Names and Chemical Symbols of the Elements. Atoms and Molecules. Chemical Formulas. CHEMICAL CONNECTIONS: "Good" Versus "Bad" Properties for a Chemical Substance Elemental Composition of the Human Body. 2. Measurements in Chemistry. Measurement Systems. Metric System Units. Exact and Inexact Numbers. Uncertainty in Measurement and Significant Figures. CHEMISTRY AT A GLANCE: Significant Figures. Significant Figures and Mathematical Operations. Scientific Notation. Conversion Factors. Dimensional Analysis. CHEMISTRY AT A GLANCE: Conversion Factors. Density. Temperature Scales. Heat Energy and Specific Heat. CHEMICAL CONNECTIONS: Body Density and Percent Body Fat; Normal Human Body Temperature. 3. Atomic Structure and the Periodic Table. Internal Structure of an Atom. Atomic Number and Mass Number. Isotopes and Atomic Masses. CHEMISTRY AT A GLANCE: Atomic Structure. The Periodic Law and the Periodic Table. Metals and Nonmetals. Electron Arrangements Within Atoms. CHEMISTRY AT A GLANCE: Shell-Subshell-Orbital Interrelationships. Electron Configurations and Orbital Diagrams. The Electronic Basis for the Periodic Law and the Periodic Table. Classification of the Elements. CHEMISTRY AT A GLANCE: Element Classification Schemes and the Periodic Table. CHEMICAL CONNECTIONS: Protium, Deuterium, and Tritium: The Three Isotopes of Hydrogen; Metallic Elements and the Human Body; Iron: The Most Abundant Transition Element in the Human Body. 4. Chemical Bonding: The Ionic Bond Model. Chemical Bonds. Valence Electrons and Lewis Symbols. The Octet Rule. The Ionic Bond Model. The Sign and Magnitude of Ionic Charge. Lewis Structures for Ionic Compounds. Chemical Formulas for Ionic Compounds. The Structure of Ionic Compounds. Recognizing and Naming Binary Ionic Compounds. CHEMISTRY AT A GLANCE: Ionic Bonds and Ionic Compounds. Polyatomic Ions Chemical Formulas and Names for Ionic Compounds Containing Polyatomic Ions. CHEMISTRY AT A GLANCE: Nomenclature of Ionic Compounds. CHEMICAL CONNECTIONS: Fresh Water, Seawater, Hard Water, and Soft Water: A Matter of Ions; Tooth Enamel: A Combination of Monatomic and Polyatomic Ions. 5. Chemical Bonding: The Covalent Bond Model. The Covalent Bond Model. Lewis Structures for Molecular Compounds. Single, Double, and Triple Covalent Bonds. Valence Electrons and Number of Covalent Bonds Formed. Coordinate Covalent Bonds. Systematic Procedures for Drawing Lewis Structures. Bonding in Compounds with Polyatomic Ions Present. Molecular Geometry. CHEMISTRY AT A GLANCE: The Geometry of Molecules. Electronegativity. Bond Polarity. Molecular Polarity. CHEMISTRY AT A GLANCE: Covalent Bonds and Molecular Compounds. Naming Binary Molecular Compounds. CHEMICAL CONNECTIONS: Nitric Oxide: A Molecule Whose Bonding Does Not Follow "The Rules"; The Chemical Senses of Smell and Taste. 6. Chemical Calculations: Formula Masses, Moles, and Chemical Equations. Formula Masses. The Mole: A Counting Unit for Chemists. The Mass of a Mole. Chemical Formulas and the Mole Concept. The Mole and Chemical Calculations. Writing and Balancing Chemical Equations. Chemical Equations and the Mole Concept. CHEMISTRY AT A GLANCE: Relationships Involving the Mole Concept. Chemical Calculations Using Chemical Equations. CHEMICAL CONNECTIONS: Carbon Monoxide Air Pollution: A Case of Combining Ratios Chemical Reactions on an Industrial Scale: Sulfuric Acid. 7. Gases, Liquids, and Solids. The Kinetic Molecular Theory of Matter. Kinetic Molecular Theory and Physical States. Gas Law Variables. Boyle's Law: A Pressure-Volume Relationship. Charles's Law: A Temperature-Volume Relationship. The Combined Gas Law. The Ideal Gas Law. Dalton's Law of Partial Pressures. CHEMISTRY AT A GLANCE: The Gas Laws. Changes of State. Evaporation of Liquids. Vapor Pressure of Liquids. Boiling and Boiling Point. Intermolecular Forces in Liquids. CHEMISTRY AT A GLANCE: Intermolecular Forces. CHEMICAL CONNECTIONS: The Importance of Gas Densities; Blood Pressure and the Sodium Ion/Potassium Ion Ratio; Hydrogen Bonding and the Density of Water. 8. Solutions. Characteristics of Solutions. Solubility. Solution Formation. Solubility Rules. Solution Concentration Units. Dilution. CHEMISTRY AT A GLANCE: Solutions. Colloidal Dispersions and Suspensions. Colligative Properties of Solutions. Osmosis and Osmotic Pressure. CHEMISTRY AT A GLANCE: Summary of Colligative Property Terminology. Dialysis. CHEMICAL CONNECTIONS: Factors Affecting Gas Solubility; Solubility of Vitamins; Controlled-Release Drugs: Regulating Concentration, Rate, and Location of Release; The Artificial Kidney: A Hemodialysis Machine. 9. Chemical Reactions. Types of Chemical Reactions. Redox and Nonredox Chemical Reactions. CHEMISTRY AT A GLANCE: Types of Chemical Reactions. Terminology Associated with Redox Processes. Collision Theory and Chemical Reactions. Exothermic and Endothermic Chemical Reactions. Factors That Influence Chemical Reaction Rates. Chemical Equilibrium. CHEMISTRY AT A GLANCE: Factors That Increase Reaction Rates. Equilibrium Constants. Altering Equilibrium Conditions: Le Châtelier's Principle. CHEMICAL CONNECTIONS: Combustion Reactions, Carbon Dioxide, and Global Warming; "Undesirable" Oxidation-Reduction Processes: Metallic Corrosion; Stratospheric Ozone: An Equilibrium Situation. 10. Acids, Bases, and Salts. Arrhenius Acid-Base Theory. Brønsted-Lowry Acid-Base Theory. Mono-, Di-, and Triprotic Acids. CHEMISTRY AT A GLANCE: Acid-Base Definitions. Strengths of Acids and Bases. Ionization Constants for Acids and Bases. Salts. Acid-Base Neutralization Chemical Reactions. Self-Ionization of Water. The pH Concept. The pKa Method for Expressing Acid Strength. The pH of Aqueous Salt Solutions. CHEMISTRY AT A GLANCE: Acids and Acidic Solutions. Buffers. The Henderson-Hasselbalch Equation. CHEMISTRY AT A GLANCE: Buffer Systems. Electrolytes. Equivalents and Milliequivalents of Electrolytes. Acid-Base Titrations. CHEMICAL CONNECTIONS: Excessive Acidity Within the Stomach: Antacids and Acid Inhibitors; Acid Rain: Excess Acidity; Blood Plasma pH and Hydrolysis; Buffering Action in Human Blood; Electrolytes and Body Fluids. 11. Nuclear Chemistry. Stable and Unstable Nuclides. The Nature of Radioactive Emissions. Equations for Radioactive Decay. Rate of Radioactive Decay. CHEMISTRY AT A GLANCE: Radioactive Decay. Transmutation and Bombardment Reactions. Radioactive Decay Series. Chemical Effects of Radiation. Biochemical Effects of Radiation. Detection of Radiation. Sources of Radiation Exposure. Nuclear Medicine. Nuclear Fission and Nuclear Fusion. CHEMISTRY AT A GLANCE: Characteristics of Nuclear Reactions. Nuclear and Chemical Reactions Compared. CHEMICAL CONNECTIONS: Tobacco Radioactivity and the Uranium-238 Decay Series; Preserving Food Through Food Irradiation; The Indoor Radon-222 Problem. PART II: ORGANIC CHEMISTRY. 12. Saturated Hydrocarbons. Organic and Inorganic Compounds. Bonding Characteristics of the Carbon Atom. Hydrocarbons and Hydrocarbon Derivatives. Alkanes: Acyclic Saturated Hydrocarbons. Structural Formulas. Alkane Isomerism. Conformations of Alkanes. IUPAC Nomenclature for Alkanes. Line-Angle Structural Formulas for Alkanes. CHEMISTRY AT A GLANCE: Structural Representations for Alkane Molecules. Classification of Carbon Atoms. Branched-Chain Alkyl Groups. Cycloalkanes. IUPAC Nomenclature for Cycloalkanes. Isomerism in Cycloalkanes. Sources of Alkanes and Cycloalkanes. Physical Properties of Alkanes and Cycloalkanes. Chemical Properties of Alkanes and Cycloalkanes. CHEMISTRY AT A GLANCE: Properties of Alkanes and Cycloalkanes. Nomenclature and Properties of Halogenated Alkanes. CHEMICAL CONNECTIONS: The Occurrence of Methane; The Physiological Effects of Alkanes; Chlorofluorocarbons and the Ozone Layer. 13. Unsaturated Hydrocarbons. Unsaturated Hydrocarbons. Characteristics of Alkenes and Cycloalkenes. IUPAC Nomenclature for Alkenes and Cycloalkenes. Line-Angle Structural Formulas for Alkenes. Constitutional Isomerism in Alkenes. Cis-Trans Isomerism in Alkenes. Naturally Occurring Alkenes. Physical Properties of Alkenes and Cycloalkenes. Chemical Reactions of Alkenes. Polymerization of Alkenes: Addition Polymers. Alkynes. CHEMISTRY AT A GLANCE: Chemical Reactions of Alkenes 383. CHEMISTRY AT A GLANCE: IUPAC Nomenclature for Alkanes, Alkenes, and Alkynes. Aromatic Hydrocarbons. Names for Aromatic Hydrocarbons. Aromatic Hydrocarbons: Physical Properties and Sources. Chemical Reactions of Aromatic Hydrocarbons. Fused-Ring Aromatic Hydrocarbons. CHEMICAL CONNECTIONS: Ethene: A Plant Hormone and High-Volume Industrial Chemical; Cis-Trans Isomerism and Vision; Carotenoids: A Source of Color; Fused-Ring Aromatic Hydrocarbons and Cancer. 14. Alcohols, Phenols, and Ethers. Bonding Characteristics of Oxygen Atoms in Organic Compounds. Structural Characteristics of Alcohols. Nomenclature for Alcohols. Isomerism for Alcohols. Important Commonly Encountered Alcohols. Physical Properties of Alcohols. Preparation of Alcohols. Classification of Alcohols. Chemical Reactions of Alcohols. CHEMISTRY AT A GLANCE: Summary of Chemical Reactions Involving Alcohols. Polymeric Alcohols. Structural Characteristics of Phenols. Nomenclature for Phenols. Physical and Chemical Properties of Phenols. Occurrence of and Uses for Phenols. Structural Characteristics of Ethers. Nomenclature for Ethers. Isomerism for Ethers. Physical and Chemical Properties of Ethers. Cyclic Ethers. Sulfur Analogs of Alcohols. Sulfur Analogs of Ethers. CHEMICAL CONNECTIONS: Menthol: A Useful Naturally Occurring Terpene Alcohol; Ethers as General Anesthetics; Marijuana: The Most Commonly Used Illicit Drug; Garlic and Onions: Odiferous Medicinal Plants. CHEMISTRY AT A GLANCE: Alcohols, Thiols, Ethers, and Thioethers. 15. Aldehydes and Ketones. The Carbonyl Group. Compounds Containing a Carbonyl Group. The Aldehyde and Ketone Functional Groups. Nomenclature for Aldehydes. Nomenclature for Ketones. Isomerism for Aldehydes and Ketones. Selected Common Aldehydes and Ketones. Physical Properties of Aldehydes and Ketones. Preparation of Aldehydes and Ketones. Oxidation and Reduction of Aldehydes and Ketones. Reaction of Aldehydes and Ketones with Alcohols. CHEMISTRY AT A GLANCE: Summary of Chemical Reactions Involving Aldehydes and Ketones. Formaldehyde-Based Polymers. Sulfur-Containing Carbonyl Groups. CHEMICAL CONNECTIONS: Lachrymatory Aldehydes and Ketones; Melanin: A Hair and Skin Pigment; Diabetes, Aldehyde Oxidation, and Glucose Testing. 16. Carboxylic Acids, Esters, and Other Acid Derivatives. Structure of Carboxylic Acids and Their Derivatives. IUPAC Nomenclature for Carboxylic Acids. Common Names for Carboxylic Acids. Polyfunctional Carboxylic Acids. Metabolic Acids. Physical Properties of Carboxylic Acids. Preparation of Carboxylic Acids. Acidity of Carboxylic Acids. Carboxylic Acid Salts. Structure of Esters. Preparation of Esters. CHEMISTRY AT A GLANCE: Summary of the "H Versus R" Relationship for Pairs of Hydrocarbon Derivatives. Nomenclature for Esters. Selected Common Esters. Isomerism for Carboxylic Acids and Esters. Physical Properties of Esters. Chemical Reactions of Esters. Sulfur Analogs of Esters. CHEMISTRY AT A GLANCE: Summary of Chemical Reactions Involving Carboxylic Acids and Esters. Polyesters. Acid Chlorides and Acid Anhydrides. Esters and Anhydrides of Inorganic Acids. CHEMICAL CONNECTIONS: Nonprescription Pain Relievers Derived from Propanoic Acid Carboxylic Acids and Skin Care; Aspirin; Nitroglycerin: An Inorganic Triester. 17. Amines and Amides. Bonding Characteristics of Nitrogen Atoms in Organic Compounds. Structure and Classifi cation of Amines. Nomenclature for Amines. Isomerism for Amines. Physical Properties of Amines. Basicity of Amines. Amine Salts. Preparation of Amines and Quaternary Ammonium Salts. Heterocyclic Amines. Selected Biochemically Important Amines. Alkaloids. Structure and Classification of Amides. Nomenclature for Amides. Selected Amides and Their Uses. Physical Properties of Amides. Preparation of Amides. Hydrolysis of Amides.Polyamides and Polyurethanes. CHEMISTRY AT A GLANCE: Summary of Chemical Reactions Involving Amines and Amides. CHEMICAL CONNECTIONS: Caffeine: The Most Widely Used Central Nervous System Stimulant; Nicotine Addiction: A Widespread Example of Drug Dependence; Alkaloids Present in Chocolate; Acetaminophen: A Substituted Amide. PART III: BIOLOGICAL CHEMISTRY. 18. Carbohydrates. Biochemistry—An Overview. Occurrence and Functions of Carbohydrates. Classifi cation of Carbohydrates. Chirality: Handedness in Molecules. Stereoisomerism: Enantiomers and Diastereomers. Designating Handedness Using Fischer Projection Formulas. CHEMISTRY AT A GLANCE: Constitutional Isomers and Stereoisomers. Properties of Enantiomers. Classifi cation of Monosaccharides.Biochemically Important Monosaccharides.Cyclic Forms of Monosaccharides. Haworth Projection Formulas. Reactions of Monosaccharides. Disaccharides. CHEMISTRY AT A GLANCE: "Sugar Terminology" Associated with Monosaccharides and Their Derivatives. General Characteristics of Polysaccharides. Storage Polysaccharides. Structural Polysaccharides. CHEMISTRY AT A GLANCE: Types of Glycosidic Linkages for Common Glucose-Containing Diand Polysaccharides. Acidic Polysaccharides. Glycolipids and Glycoproteins: Cell Recognition. Dietary Considerations and Carbohydrates. CHEMICAL CONNECTIONS: Blood Types and Monosaccharides; Lactose Intolerance and Galactosemia; Changing Sugar Patterns: Decreased Sucrose, Increased Fructose; Artificial Sweeteners; "Good and Bad Carbs": The Glycemic Index. 19. Lipids. Structure and Classification of Lipids. Types of Fatty Acids. Physical Properties of Fatty Acids. Energy-Storage Lipids: Triacylglycerols. Dietary Considerations and Triacylglycerols. Chemical Reactions of Triacylglycerols. CHEMISTRY AT A GLANCE: Classification Schemes for Fatty Acid Residues Present in Triacylglycerols. Membrane Lipids: Phospholipids. Membrane Lipids: Sphingoglycolipids. CHEMISTRY AT A GLANCE: Terminology for and Structural Relationships Among Various Types of Fatty-Acid-Containing Lipids. Membrane Lipids: Cholesterol. Cell Membranes. Emulsification Lipids: Bile Acids. Messenger Lipids: Steroid Hormones. Messenger Lipids: Eicosanoids. Protective-Coating Lipids: Biological Waxes. CHEMISTRY AT A GLANCE: Types of Lipids in Terms of How They Function. CHEMICAL CONNECTIONS: The Fat Content of Tree Nuts and Peanuts; Artificial Fat Substitutes; The Cleansing Action of Soap; Trans Fatty Acids and Blood Cholesterol Levels; Steroid Drugs in Sports; The Mode of Action for Anti-Inflammatory Drugs. 20. Proteins. Characteristics of Proteins. Amino Acids: The Building Blocks for Proteins. Chirality and Amino Acids. Acid-Base Properties of Amino Acids. Cysteine: A Chemically Unique Amino Acid. Peptides. Biochemically Important Small Peptides. General Structural Characteristics of Proteins. Primary Structure of Proteins. Secondary Structure of Proteins. Tertiary Structure of Proteins. Quaternary Structure of Proteins. Protein Classification Based on Shape. Protein Classification Based on Function. CHEMISTRY AT A GLANCE: Protein Structure. Protein Hydrolysis. Protein Denaturation. Glycoproteins. Lipoproteins. CHEMICAL CONNECTIONS: The Essential Amino Acids; Substitutes for Human Insulin Protein Structure and the Color of Meat; Denaturation and Human Hair; Cyclosporine: An Antirejection Drug; Lipoproteins and Heart Disease Risk. 21. Enzymes and Vitamins. General Characteristics of Enzymes. Enzyme Structure. Nomenclature and Classifi cation of Enzymes. Models of Enzyme Action. Enzyme Specificity. Factors That Affect Enzyme Activity. CHEMISTRY AT A GLANCE: Enzyme Activity. Enzyme Inhibition. CHEMISTRY AT A GLANCE: Enzyme Inhibition. Regulation of Enzyme Activity. Antibiotics That Inhibit Enzyme Activity. Medical Uses of Enzymes. General Characteristics of Vitamins. Water-Soluble Vitamins. Fat-Soluble Vitamins. CHEMICAL CONNECTIONS: H. pylori and Stomach Ulcers; Enzymatic Browning: Discoloration of Fruits and Vegetables; Heart Attacks and Enzyme Analysis. 22. Nucleic Acids. Types of Nucleic Acids. Nucleotides: Building Blocks of Nucleic Acids. Primary Nucleic Acid Structure. CHEMISTRY AT A GLANCE: Nucleic Acid Structure. The DNA Double Helix. Replication of DNA Molecules. Overview of Protein Synthesis. Ribonucleic Acids. CHEMISTRY AT A GLANCE: DNA Replication. Transcription: RNA Synthesis. The Genetic Code. Anticodons and tRNA Molecules. Translation: Protein Synthesis. Mutations. Nucleic Acids and Viruses. CHEMISTRY AT A GLANCE: Protein Synthesis: Transcription and Translation. Recombinant DNA and Genetic Engineering. The Polymerase Chain Reaction. DNA Sequencing. CHEMICAL CONNECTIONS: Use of Synthetic Nucleic Acid Bases in Medicine; Antibiotics That Inhibit Bacterial Protein Synthesis. 23. Biochemical Energy Production. Metabolism. Metabolism and Cell Structure. Important Intermediate Compounds in Metabolic Pathways. High-Energy Phosphate Compounds. An Overview of Biochemical Energy Production. The Citric Acid Cycle. CHEMISTRY AT A GLANCE: Simplified Summary of the Four Stages of Biochemical Energy Production. CHEMISTRY AT A GLANCE: Summary of the Reactions of the Citric Acid Cycle. The Electron Transport Chain. CHEMISTRY AT A GLANCE: Summary of the Flow of Electrons Through the Four Complexes of the Electron Transport Chain. Oxidative Phosphorylation. CHEMISTRY AT A GLANCE: Summary of the Common Metabolic Pathway. ATP Production for the Common Metabolic Pathway. The Importance of ATP. Non-ETC Oxygen-Consuming Reactions. CHEMICAL CONNECTIONS: Cyanide Poisoning; Brown Fat, Newborn Babies, and Hibernating Animals; Flavonoids: An Important Class of Dietary Antioxidants. 24. Carbohydrate Metabolism. Digestion and Absorption of Carbohydrates. Glycolysis. Fates of Pyruvate. ATP Production for the Complete Oxidation of Glucose. Glycogen Synthesis and Degradation. Gluconeogenesis. Terminology for Glucose Metabolic Pathways. The Pentose Phosphate Pathway. CHEMISTRY AT A GLANCE: Glucose Metabolism. Hormonal Control of Carbohydrate Metabolism. CHEMICAL CONNECTIONS: Lactate Accumulation; Diabetes Mellitus. 25. Lipid Metabolism. Digestion and Absorption of Lipids. Triacylglycerol Storage and Mobilization. Glycerol Metabolism. Oxidation of Fatty Acids. ATP Production from Fatty Acid Oxidation. Ketone Bodies. Biosynthesis of Fatty Acids: Lipogenesis. Relationships Between Lipogenesis and Citric Acid Cycle Intermediates. Biosynthesis of Cholesterol. CHEMISTRY AT A GLANCE: Interrelationships Between Carbohydrate and Lipid Metabolism. Relationships Between Lipid and Carbohydrate Metabolism. CHEMICAL CONNECTIONS: High-Intensity Versus Low-Intensity Workouts; Statins: Drugs That Lower Plasma Levels of Cholesterol. 26. Protein Metabolism. Protein Digestion and Absorption. Amino Acid Utilization. Transamination and Oxidative Deamination. The Urea Cycle. Amino Acid Carbon Skeletons. Amino Acid Biosynthesis. Hemoglobin Catabolism. CHEMISTRY AT A GLANCE: Interrelationships Among Carbohydrate, Lipid, and Protein Metabolism. Interrelationships Among Metabolic Pathways. CHEMICAL CONNECTIONS: The Chemical Composition of Urine Arginine, Citrulline, and the Chemical Messenger Nitric Oxide. Answers to Selected Exercises A-1.