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
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
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
CONTENTS PARTI General Chemistry CHAPTER 1 Measurement: The Basic Science 5 CHAPTER 4 1.1 Measurement Systems 6 1.2 Units of Length 6 1.3 Dimensional Analysis 7 1.4 Units of Volume 11 1.5 Mass and Weight 15 1.6 Density and Specific Gravity 17 1.7 Calculators, Significant Figures, and Scientific Notation 19 1.8 Energy, Heat, and Temperature 24 1.9 Calories and Specific Heat 28 Electrons and Chemical Periodicity 88 4.1 The Behavior of Electrons in Atoms 89 4.2 Light, Color, and Energy 90 4.3 The Bohr Atom: Electrons May Behave Like Planets 96 4.4 Orbitals 99 4.5 Electron-Filling Series 102 4.6 Electrons and the Periodic Table 107 CHAPTER 2 Some Basic Principles of Chemistry 36 2.1 Physical Properties of Matter 37 2.2 Physical and Chemical Change and the Conservation of Matter 45 2.3 Mixtures, Compounds, and Elements 47 2.4 Before It Was a Science: The Discovery of Order 49 2.5 Chemical Periodicity and Classification of the Elements 52 CHAPTER 3 An Atomic Mystery: Discovery of the Structure of Atoms 67 3.1 Discovery of the Electron 68 3.2 A Plum Pudding Model of the Atom 71 3.3 Discovery of X-Rays 73 3.4 Discovery of Natural Radioactivity 74 3.5 Discovery of the Atomic Nucleus 77
xvi CONTENTS CHAPTER 6 Shapes and Polarities of Covalent Molecules 143 6.1 Shapes of Covalent Molecules 145 6.2 Molecular Dipoles: A Consequence of Molecular Shape and Electronegativity 150 6.3 Behavior of Polar Molecules 152 6.4 Hydrogen Bonding 157 6.5 Water: A Very Special Molecule 158 CHAPTER 7 Chemical Formulas and Equations 165 7.1 Naming Chemical Compounds 166 7.2 Balanced Formulas 167 7.3 Names of Simple Binary Compounds 175 7.4 Compounds Involving More Than Two Elements: Polyatomic Ions 176 7.5 Additional Systems for Naming Compounds 181 7.6 Writing and Balancing Chemical Equations 183 7.7 Electron-Transfer Reactions 191 CHAPTER 5 The Chemical Bond 113 5.1 Electron Configuration of the Inert Gases 114 5.2 Ionic Bonding: Electron Transfer as a Route to Chemical Stability 115 5.3 Properties of Ionic Compounds 119 5.4 Factors Involved in Transfer of Electrons 123 5.5 Covalent Bonding: Electron Sharing as a Route to Chemical Stability 128 5.6 Electronegativity: A Way to Predict Bond Type 129 5.7 Electron Dots: A Way to Show Chemical Bonds 134 5.8 Coordinate Covalent Bonding 135 5.9 Metallic Bonding 137 CHAPTER 8 Chemical Arithmetic: Mass Relationships in Chemical Reactions 201 8.1 An Introduction to Chemical Arithmetic: Percentage Composition 202 8.2 The Mole: A "Chemist's Dozen" 205 8.3 Empirical Formulas 209 8.4 Mass Relationships in Chemical Reactions (Stoichiometry) 213
Contents CHAPTER 9 The Behavior of Gases 226 9.1 Kinetic Molecular Theory 227 9.2 Relationship of Volume to Temperature and Pressure 230 9.3 Combined Gas Laws 235 9.4 The Ideal Gas Law 237 9.5 Partial Pressure 240 CHAPTER 10 Acids and Bases 295 12.1 12.2 12.3 12.4 12.5 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 313 12.6 Buffers and Equilibrium: The Hydrogen Ion in Biological Systems 321 12.7 Lewis Acids and Bases 329 Solutions, Colloids, and Suspensions 248 10.1 Characteristics of Solutions, Colloids, and Suspensions 249 10.2 Solution Concentration 254 10.3 Colligative Properties of Solutions 259 CHAPTER 11 CHAPTER 12 xvii Energy: The Driving Force in Chemical Reactions 269 11.1 The Chemical Reaction: It Starts with a Collision 270 11.2 Effect of Concentration on Reaction Rate 274 11.3 Effect of Temperature on Reaction Rate 275 11.4 Hypothermia: A Reaction Rate Problem 278 11.5 Effect of Catalysts on Reaction Rate 280 11.6 Effect of Molecular Complexity on Reaction Rate 282 11.7 Equilibrium: Reactions That Go in Both Directions 285 11.8 The Equilibrium Constant: A Useful Chemical Tool 287 CHAPTER 13 Nuclear Chemistry 336 13.1 Nuclear Decay: Transmutation and Half-Life 337 13.2 Interaction of Radiation with Matter 347 13.3 Detection of Nuclear Radiation 348 13.4 Radiation Biology and Nuclear Medicine 351 13.5 Nuclear Power 358
xviii CONTENTS PART II Organic and Biological Chemistry An Introduction to Organic Chemistry 377 14.1 Introduction 378 14.2 Carbon's Electronegativity Makes It Unique 14.3 Introduction to Functional Croups 382 378 Alkanes and Cycloalkanes: Slngle- Bonded Hydrocarbons 393 16.1 16.2 16.3 16.4 16.5 16.6 16.7 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 463 15.1 Structure and Physical Properties 394 15.2 Alkanes and Their Nomenclature 396 15.3 Alkyl Groups and Nomenclature 402 15.4 Cycloalkanes 411 15.5 Conformations of Alkanes and Cycloalkanes 15.6 Chemical Reactivity of Alkanes and Cycloalkanes 420 15.7 Health-Related Products Based on Hydrocarbon Structures 429 416 CHAPTER 17 Aromatic Hydrocarbons 474 17.1 Structure: Resonance and Electron Delocalization 475 17.2 Nomenclature 478 17.3 Aromatic Reactions: A Consequence of Overlapping Pi Bonds 483 17.4 Fused-Ring Aromatic Systems 489 17.5 Important Aromatic Hydrocarbons 489 Alcohols, Phenols, Ethers, and Thiols 498 18.1 Alcohols 499 18.2 Phenols 511 18.3 Ethers 516 18.4 Thiols: Sulfur Equivalents of Alcohols 520
Contents CHAPTER 19 Carbonyl Group and Its Compounds: Aldehydes and Ketones 532 19.1 Structure and Properties of the Carbonyl Group 533 19.2 Nomenclature of Carbonyl Compounds 535 19.3 Reactions of Carbonyl Compounds 540 19.4 Natural Examples of Acetals 546 19.5 Preparation Reactions of Carbonyl Compounds 546 19.6 Oxidation of Hydroquinones to Quinones 551 CHAPTER 20 Carboxylic Acids and Their Derivatives 563 20.1 Carboxylic Acids: Structure, Properties, and Nomenclature 564 20.2 Reactions and Preparations of Carboxylic Acids 569 20.3 Esters 576 20.4 Acid Anhydrides 585 20.5 Important Organic Acids and Acid Derivatives 587 CHAPTER 21 Amines and Amides 594 21.1 Amines: Structure, Properties, and Nomenclature 595 21.2 Reactions of Amines 598 21.3 Amides 605 21.4 Special Amines 608 CHAPTER 22 Introduction to Biochemistry 622 22.1 Introduction to Cells 623 22.2 Procaryotic Cells 625 22.3 Eucaryotic Cells 627 22.4 Biomolecules 629 22.5 General Principles of Nutrition 636 CHAPTER 23 Carbohydrates 641 23.1 Classification of Carbohydrates 642 23.2 Monosaccharides 645 23.3 Properties and Reactions of Sugars 653 23.4 Oligosaccharides 657 23.5 Polysaccharides 658 CHAPTER 24 Lipids 668 24.1 Classification of Lipids 669 24.2 Fatty Acids 670 24.3 Triacylglycerols 675 24.4 Saponifiable Lipids of Membranes 24.5 Nonsaponifiable Lipids 682 24.6 Liposomes and Membranes 689 679
xx CONTENTS CHAPTER 28 Bioenergetics and Catabolism 792 28.1 Bioenergetics 793 28.2 Digestion, Absorption, and Transport 797 28.3 Carbohydrate Catabolism 805 28.4 Tricarboxylic Acid Cycle 810 28.5 Electron Transport and Oxidative Phosphorylation 813 28.6 Lipid Catabolism 817 28.7 Amino Acid Catabolism 822 CHAPTER 29 Anabolism 829 CHAPTER 25 Amino Acids, Peptides, and Proteins 698 25.1 Protein Function 699 25.2 Alpha Amino Acids 699 25.3 Peptide Bonds and Peptides 707 25.4 Protein Structure 711 25.5 Properties and Classification of Proteins 721 HAPTER 26 Molecular Basis of Heredity 728 26.1 Search for the Molecular Basis of Heredity 26.2 Nucleotides 731 26.3 Structure and Replication of DNA 735 26.4 RNA 744 26.5 Transcription 745 26.6 Translation 748 26.7 Mutagenesis 752 26.8 Regulation of Gene Expression 757 26.9 Genetic Engineering 761 729 29.1 Introduction to Anabolism 830 29.2 Photosynthesis 831 29.3 Biosynthesis of Carbohydrates 836 29.4 Biosynthesis of Lipids 841 29.5 Biosynthesis of Amino Acids 848 29.6 Biosynthesis of Nucleotides 850 CHAPTER 30 Blood: The Constant Internal Environment 854 30.1 Gas Exchange 855 30.2 Removal of Wastes from the Blood 859 30.3 Regulation of ph 860 30.4 Circulation of Hormones and Their Role in Nutrient Maintenance 863 30.5 Blood and Immunity 868 Solutions to Odd-Numbered Exercises S.l Glossary G.l Photo Credits PCI Index 1.1 CHAPTER 27 Enzymes 766 27.1 The Roles of Enzymes in Metabolism 767 27.2 Enzymes 767 27.3 Enzyme Specificity and Activity 772 27.4 Rates of Enzyme-Catalyzed Reactions 777 27.5 Regulation of Enzyme Activity 784