GENERAL, ORGANIC AND BIOLOGICAL CHEMISTRY. JOHN R. AMEND Montana State University. BRADFORD P. MUNDY Colby College
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1 GENERAL, ORGANIC AND BIOLOGICAL CHEMISTRY JOHN R. AMEND Montana State University BRADFORD P. MUNDY Colby College MELVIN T. ARMOLD Adams State College # Saunders Golden Sunburst Series SAUNDERS COLLEGE PUBLISHING Harcourt Brace Jovanovich College Publishers Forth Worth Philadelphia San Diego New York Orlando Austin San Antonio Toronto Montreal London Sydney Tokyo
2 BRIEF CONTENTS PARTI General Chemistry CHAPTER 1 Measurement: The Basic Science 5 CHAPTER 2 Some Basic Principles of Chemistry 36 CHAPTER 3 An Atomic Mystery: Discovery of The Structure of Atoms 67 CHAPTER 4 Electrons and Chemical Periodicity 88 CHAPTER 5 The Chemical Bond 113 CHAPTER 6 Shapes and Polarities of Covalent Molecules 143 CHAPTER 7 Chemical Formulas and Equations 165 CHAPTER 8 Chemical Arithmetic: Mass Relationships in Chemical Reactions 201 CHAPTER 9 The Behavior of Gases 226 CHAPTER 10 Solutions, Colloids, and Suspensions 248 CHAPTER 11 Energy: The Driving Force in Chemical Reactions 269 CHAPTER 12 Acids and Bases 295 CHAPTER 13 Nuclear Chemistry 336 PART II Organic and Biological Chemistry CHAPTER 14 An Introduction to Organic Chemistry 377 CHAPTER 15 Alkanes and Cycloalkanes: Single-Bonded Hydrocarbons 393 CHAPTER 16 Unsaturated Hydrocarbons 438 CHAPTER 17 Aromatic Hydrocarbons 474 CHAPTER 18 Alcohols, Phenols, Ethers, and Thiols 498 CHAPTER 19 Carbonyl Group and Its Compounds: Aldehydes and Ketones 532 Xlll
3 xiv BRIEF CONTENTS CHAPTER 20 Carboxylic Acids and Their Derivatives 563 CHAPTER 21 Amines and Amides 594 CHAPTER 22 Introduction to Biochemistry 622 CHAPTER 23 Carbohydrates 641 CHAPTER 24 Lipids 668 CHAPTER 25 Amino Acids, Peptides and Proteins 698 CHAPTER 26 Molecular Basis of Heredity 728 CHAPTER 27 Enzymes 766 CHAPTER 28 Bioenergetics and Catabolism 792 CHAPTER 29 Anabolism 829 CHAPTER 30 Blood: The Constant Internal Environment 854
4 CONTENTS PARTI General Chemistry CHAPTER 1 Measurement: The Basic Science 5 CHAPTER Measurement Systems Units of Length Dimensional Analysis Units of Volume Mass and Weight Density and Specific Gravity Calculators, Significant Figures, and Scientific Notation Energy, Heat, and Temperature Calories and Specific Heat 28 Electrons and Chemical Periodicity The Behavior of Electrons in Atoms Light, Color, and Energy The Bohr Atom: Electrons May Behave Like Planets Orbitals Electron-Filling Series Electrons and the Periodic Table 107 CHAPTER 2 Some Basic Principles of Chemistry Physical Properties of Matter Physical and Chemical Change and the Conservation of Matter Mixtures, Compounds, and Elements Before It Was a Science: The Discovery of Order Chemical Periodicity and Classification of the Elements 52 CHAPTER 3 An Atomic Mystery: Discovery of the Structure of Atoms Discovery of the Electron A Plum Pudding Model of the Atom Discovery of X-Rays Discovery of Natural Radioactivity Discovery of the Atomic Nucleus 77
5 xvi CONTENTS CHAPTER 6 Shapes and Polarities of Covalent Molecules Shapes of Covalent Molecules Molecular Dipoles: A Consequence of Molecular Shape and Electronegativity Behavior of Polar Molecules Hydrogen Bonding Water: A Very Special Molecule 158 CHAPTER 7 Chemical Formulas and Equations Naming Chemical Compounds Balanced Formulas Names of Simple Binary Compounds Compounds Involving More Than Two Elements: Polyatomic Ions Additional Systems for Naming Compounds Writing and Balancing Chemical Equations Electron-Transfer Reactions 191 CHAPTER 5 The Chemical Bond Electron Configuration of the Inert Gases Ionic Bonding: Electron Transfer as a Route to Chemical Stability Properties of Ionic Compounds Factors Involved in Transfer of Electrons Covalent Bonding: Electron Sharing as a Route to Chemical Stability Electronegativity: A Way to Predict Bond Type Electron Dots: A Way to Show Chemical Bonds Coordinate Covalent Bonding Metallic Bonding 137 CHAPTER 8 Chemical Arithmetic: Mass Relationships in Chemical Reactions An Introduction to Chemical Arithmetic: Percentage Composition The Mole: A "Chemist's Dozen" Empirical Formulas Mass Relationships in Chemical Reactions (Stoichiometry) 213
6 Contents CHAPTER 9 The Behavior of Gases Kinetic Molecular Theory Relationship of Volume to Temperature and Pressure Combined Gas Laws The Ideal Gas Law Partial Pressure 240 CHAPTER 10 Acids and Bases Acids: Hydrogen Ion Donors 296 Bases: Hydrogen Ion Acceptors 300 Streng and Weak Acids and Bases 305 The ph Scale and Equilibrium 306 Acid-Base Reactions and Volumetrie Analysis Buffers and Equilibrium: The Hydrogen Ion in Biological Systems Lewis Acids and Bases 329 Solutions, Colloids, and Suspensions Characteristics of Solutions, Colloids, and Suspensions Solution Concentration Colligative Properties of Solutions 259 CHAPTER 11 CHAPTER 12 xvii Energy: The Driving Force in Chemical Reactions The Chemical Reaction: It Starts with a Collision Effect of Concentration on Reaction Rate Effect of Temperature on Reaction Rate Hypothermia: A Reaction Rate Problem Effect of Catalysts on Reaction Rate Effect of Molecular Complexity on Reaction Rate Equilibrium: Reactions That Go in Both Directions The Equilibrium Constant: A Useful Chemical Tool 287 CHAPTER 13 Nuclear Chemistry Nuclear Decay: Transmutation and Half-Life Interaction of Radiation with Matter Detection of Nuclear Radiation Radiation Biology and Nuclear Medicine Nuclear Power 358
7 xviii CONTENTS PART II Organic and Biological Chemistry An Introduction to Organic Chemistry Introduction Carbon's Electronegativity Makes It Unique 14.3 Introduction to Functional Croups Alkanes and Cycloalkanes: Slngle- Bonded Hydrocarbons Unsaturated Hydrocarbons 438 Introduction to the Unsaturated Hydrocarbons 439 Structure and Physical Properties 440 Nomenclature 444 Chemical Reactivity of Alkenes 448 Chemical Reactivity of Alkynes 460 Polyunsaturated Alkenes 462 Interesting Unsaturated Compounds Structure and Physical Properties Alkanes and Their Nomenclature Alkyl Groups and Nomenclature Cycloalkanes Conformations of Alkanes and Cycloalkanes 15.6 Chemical Reactivity of Alkanes and Cycloalkanes Health-Related Products Based on Hydrocarbon Structures CHAPTER 17 Aromatic Hydrocarbons Structure: Resonance and Electron Delocalization Nomenclature Aromatic Reactions: A Consequence of Overlapping Pi Bonds Fused-Ring Aromatic Systems Important Aromatic Hydrocarbons 489 Alcohols, Phenols, Ethers, and Thiols Alcohols Phenols Ethers Thiols: Sulfur Equivalents of Alcohols 520
8 Contents CHAPTER 19 Carbonyl Group and Its Compounds: Aldehydes and Ketones Structure and Properties of the Carbonyl Group Nomenclature of Carbonyl Compounds Reactions of Carbonyl Compounds Natural Examples of Acetals Preparation Reactions of Carbonyl Compounds Oxidation of Hydroquinones to Quinones 551 CHAPTER 20 Carboxylic Acids and Their Derivatives Carboxylic Acids: Structure, Properties, and Nomenclature Reactions and Preparations of Carboxylic Acids Esters Acid Anhydrides Important Organic Acids and Acid Derivatives 587 CHAPTER 21 Amines and Amides Amines: Structure, Properties, and Nomenclature Reactions of Amines Amides Special Amines 608 CHAPTER 22 Introduction to Biochemistry Introduction to Cells Procaryotic Cells Eucaryotic Cells Biomolecules General Principles of Nutrition 636 CHAPTER 23 Carbohydrates Classification of Carbohydrates Monosaccharides Properties and Reactions of Sugars Oligosaccharides Polysaccharides 658 CHAPTER 24 Lipids Classification of Lipids Fatty Acids Triacylglycerols Saponifiable Lipids of Membranes 24.5 Nonsaponifiable Lipids Liposomes and Membranes
9 xx CONTENTS CHAPTER 28 Bioenergetics and Catabolism Bioenergetics Digestion, Absorption, and Transport Carbohydrate Catabolism Tricarboxylic Acid Cycle Electron Transport and Oxidative Phosphorylation Lipid Catabolism Amino Acid Catabolism 822 CHAPTER 29 Anabolism 829 CHAPTER 25 Amino Acids, Peptides, and Proteins Protein Function Alpha Amino Acids Peptide Bonds and Peptides Protein Structure Properties and Classification of Proteins 721 HAPTER 26 Molecular Basis of Heredity Search for the Molecular Basis of Heredity 26.2 Nucleotides Structure and Replication of DNA RNA Transcription Translation Mutagenesis Regulation of Gene Expression Genetic Engineering Introduction to Anabolism Photosynthesis Biosynthesis of Carbohydrates Biosynthesis of Lipids Biosynthesis of Amino Acids Biosynthesis of Nucleotides 850 CHAPTER 30 Blood: The Constant Internal Environment Gas Exchange Removal of Wastes from the Blood Regulation of ph Circulation of Hormones and Their Role in Nutrient Maintenance Blood and Immunity 868 Solutions to Odd-Numbered Exercises S.l Glossary G.l Photo Credits PCI Index 1.1 CHAPTER 27 Enzymes The Roles of Enzymes in Metabolism Enzymes Enzyme Specificity and Activity Rates of Enzyme-Catalyzed Reactions Regulation of Enzyme Activity 784
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