FUNDAMENTALS OF GENERAL, ORGANIG, AND BLOLOGIGAL CHEMISTRY SIXTH EDITION JOHN R. HOLUM Augsburg College JOHN WILEY & SONS, INC. New York / Ghichester / Weinheim Brisbane / Singapore / Toronto
CONTENTS 1 GOALS, METHODS, AND MEASUREMENTS 1.1 Chemistry and the Molecular Basis of Life 1.2 Facts, Hypotheses, and Theories in Science 3 1.3 Properties and the States of Matter 4 1.4 Physical Quantities, Measurement, and Significant Figures 6 1.5 Scientific Notation 14 1.6 Factor-Label Method in Galculations 19 1.7 Density and Specific Gravity 22 Summary 24 Review Exercises 25 2 MATTER AND ENERGY This Chapter in Gontext 30 2.1 States and Kinds of Matter 30 2.2 Atoms, Chemical Symbols, and Equations 2.3 Kinetic and Potential Energy 38 2.4 Heat 40 2.5 Heat and Molecular Kinetic Energy 43 Summary 45 Review Exercises 46 3 ATOMIG THEORY AND THE PERIODIC TABLE This Chapter in Context 50 3.1 The Nuclear Atom 50 3.2 Periodic Law and Periodic Table 53 3.3 Electron Gonfigurations, an Overview 58 3.4 Electron Configurations and Atomic Orbitals 60 Summary 69 Review Exercises 70 4 CHEMICAL COMPOUNDS AND CHEMICAL BONDS This Chapter in Context 75 4.1 Electron Transfers and Ionic Compounds 4.2 Monatomic Ions and the Octet Rule 81 5 QUANTITATIVE RELATIONSHIPS IN CHEMICAL REACTIONS 117 29 This Chapter in Gontext 118 5.1 Mole Concept 118 5.2 Atomic, Formula, and Molecular Masses 119 33 5.3 Balanced Chemical Equations and Stoichiometry 124 5.4 Reactions in Solution 131 5.5 Molar Concentration 133 5.6 Preparing Dilute Solutions from Goncentrated Solutions 138 Summary 141 Review Exercises 141 75 49 74 4.3 Redox Reactions 85 4.4 Electron Sharing and Molecular Compounds 87 4.5 Lewis Structures and the Octet Rule 89 4.6 Structures of Polyatomic Ions 96 4.7 Writing Lewis Structures of Molecules and Polyatomic Ions 99 4.8 Shapes of Molecules 105 4.9 Polar Molecules 107 Summary 111 Review Exercises 112 6 STATES OF MATTER AND THE KINETIC THEORY 146 This Chapter in Gontext 147 6.1 Gaseous State 147 6.2 Pressure-Volume-Temperature Relationships for a Fixed Amount of Gas 148 6.3 Ideal Gas Law 153 6.4 Dalton's Law of Partial Pressures 156 6.5 Kinetic Theory of Gases Revisited 159 6.6 Liquid State 160 6.7 Vapor Pressure, Dynamic Equilibria, and Ghanges of State 162 6.8 Water and the Hydrogen Bond 165 6.9 Solid State 169 Summary 171 Review Exercises 172
xii CONTENTS 7 SOLUTIONS, AND GOLLOIDS 177 This Chapter in Context 178 7.1 lypes of Homogeneous Mixtures 178 7.2 Aqueous Solutions and How They Form 180 7.3 Solubilities of Gases 185 7.4 Percentage Concentration Expressions 189 7.5 Osmosis and Dialysis 191 7.6 Dialysis and the Bloodstream 195 Summary 198 Review Exercises 198 8 ACIDS, BASES, AND IONIC COMPOUNDS 202 This Chapter in Context 203 8.1 Electrolytes 203 8.2 Acids and Bases as Electrolytes 206 8.3 Chemical Properties of Aqueous Acids and Bases 213 8.4 Strengths of Br0nsted Acids and Bases A Qualitative View 223 8.5 Salts 229 Summary 239 Review Exercises 240 9 REACTION KINETICS AND CHEMICAL EQUILIBRIA. ACID-BASE EQUILIBRIA 246 This Chapter in Context 247 9.1 Factors That Affect Reaction Rates 247 9.2 Kinetic Theory and Chemical Reactions 251 9.3 Chemical Equilibria Revisited 255 9.4 Ion Product Constant of Water 257 9.5 ph Concept 258 9.6 Acid Ionization Constants 264 9i7 Base Ionization Constants 267 9.8 pft a and pk h Concepts 271 9.9 Buffers 273 9.10 Some Quantitative Aspects of Buffers 277 9.11 Acid-Base Titrations 284 Summary 286 Review Exercises 288 10 RADIOACTIVITY AND NUCLEAR CHEMISTRY This Chapter in Context 294 10.1 Atomic Radiation 294 293 10.2 Ionizing Radiation Dangers and Precautions 299 10.3 Units to Describe and Measure Radiation 304 10.4 Synthetic Radionuclides 306 10.5 Radiation Technology in the Food Industry 307 10.6 Radiation Technology in Medicine 309 10.7 Atomic Energy and Radionuclides 312 Summary 318 Review Exercises 319 11 ORGANIC CHEMISTRY. SATURATED HYDROCARBONS 323 This Chapter in Context 324 11.1 Organic and Inorganic Compounds 324 11.2 Some Structural Features of Organic Compounds 325 11.3 Isomerism 334 11.4 Functional Groups 336 11.5 Alkanes and Cycloalkanes 339 11.6 Naming the Alkanes and Cycloalkanes 344 11.7 Chemical Properties of Alkanes 351 Summary 356 Review Exercises 357 12 UNSATURATED HYDROCARBONS 361 This Chapter in Context 362 12.1 Occurrence 362 12.2 Naming the Alkenes 363 12.3 Geometrie Isomers 367 12.4 Addition Reactions of the Double Bond 369 12.5 How Addition Reactions Occur 378 12.6 Addition Polymers 383 12.7 Benzene Ring and Aromatic Properties 386 12.8 Naming Compounds of Benzene 391 Summary 392 Review Exercises 394 13 ALCOHOLS, PHENOLS, ETHERS, AND THIOALCOHOLS This Chapter in Context 400 13.1 Occurrence, Types, and Names of Alcohols 400 13.2 Physical Properties of Alcohols 407 399
CONTENTS xiii 13.3 Chemical Properties of Alcohols 409 13.4 Phenols 415 13.5 Ethers 417 13.6 Thioalcohols and Disulfides 420 Summary 422 Review Exercises 423 14 ALDEHYDES AND KETONES 428 This Chapter in Context 429 14.1 Structures and Physical Properties of Aldehydes and Ketones 429 14.2 Naming Aldehydes and Ketones 430 14.3 Oxidation of Aldehydes and Ketones 434 14.4 Reduction of Aldehydes and Ketones 436 14.5 Reactions of Aldehydes and Ketones with Alcohols 439 Summary 445 Review Exercises 446 17.2 Molecular Chirality 500 17.3 Optical Activity 509 Summary 514 Review Exercises 514 18 GARBOHYDRATES This Chapter in Context 517 18.1 Biochemistry An Overview 517 18.2 18.3 18.4 18.5 Introduction to Monosaccharides 518 D- and L-Families of Carbohydrates 521 Cyclic Forms of Monosaccharides 526 Disaccharides 534 Polysaccharides 537 18.6 Summary 541 Review Exercises 541 516 15 CARBOXYLIC ACIDS AND ESTERS 452 This Chapter in Context 453 15.1 Occurrences, Names, and Physical Properties 15.2 15.3 15.4 15.5 of Carboxylic Acids 453 Acidity of Carboxylic Acids 456 Conversion of Carboxylic Acids to Esters 459 Occurrence, Names, and Physical Properties of Esters 463 Some Reactions of Esters 467 Organophosphate Esters and Anhydrides 470 15.6 Summary 474 Review Exercises 474 16 AMINES AND AMIDES 479 This Chapter in Context 480 16.1 Occurrence, Names, and Physical Properties of Amines 480 16.2 Chemical Properties of Amines 482 16.3 Amides of Carboxylic Acids 487 Summary 493 Review Exercises 493 17 STEREOISOMERISM This Chapter in Context 17.1 Types of Isomerism 499 499 498 19 LlPIDS This Chapter in Context 546 19.1 What Lipids Are 546 19.2 Chemical Properties of Triacylglycerols 19.3 Phospholipids 555 19.4 Steroids 559 19.5 Cell Membranes TheirLipid Gomponents 562 Summary 564 Review Exercises 564 545 552 20 PROTEINS 567 This Chapter in Context 568 20.1 Amino Acids. The Building Blocks of 20.2 20.3 20.4 20.5 20.6 20.7 20.8 Proteins 568 Overview of Protein Structure Primary Structures of Proteins Secondary Structures of Proteins Tertiary Structures of Proteins Quaternary Structures of Proteins 574 575 578 581 582 Common Properties of Proteins 585 Cell Membranes Revisited Glycoprotein Components 590 20.9 Classes of Proteins 596 Summary 597 Review Exercises 598
xiv CONTENTS 21 ENZYMES 601 This Ghapter in Gontext 602 21.1 The Nature of Enzymes 602 21.2 Enzyme-Substrate Complex 606 21.3 Kinetics of Simple Enzyme-Substrate Interactions 608 21.4 Regulation of Enzymes 612 21.5 Enzymes in Medicine 616 Summary 619 Review Exercises 620 Summary 701 Review Exercises 702 25 BlOCHEMICAL ENERGETIGS 705 This Ghapter in Context 706 25.1 Energy for Living An Overview 706 25.2 Gitric Acid Gycle 711 25.3 Respiratory Chain 715 Summary 722 Review Exercises 723 HORMONES AND NEUROTRANSMITTERS 622 This Ghapter in Context 623 22.1 Chemical Communication How It Works 623 22.2 Hormones and Neurotransmitters 627 22.3 Retrograde Messengers 636 Summary 638 Review Exercises 638 23 EXTRACELLULAR FLUIDS OF THE BODY 640 This Chapter in Gontext 641 23.1 Digestive Juices 641 23.2 Blood and the Absorption of Nutrients by Cells 645 23.3 Blood and the Exchange of Respiratory Gases 651 23.4 Acid-Base Balance of the Blood 657 23.5 Blood and the Functions of the Kidneys 662 Summary 663 Review Exercises 664 26 METABOLISM OF GARBOHYDRATES 725 This Chapter in Context 726 26.1 Glycogen Metabolism 726 26.2 Glucose Tolerance 731 26.3 Gatabolism of Glucose 734 26.4 Gluconeogenesis 739 Summary 741 Review Exercises 742 27 METABOLISM OF LIPIDS 744 This Chapter in Context 745 27.1 Absorption and Distribution of Lipids 745 27.2 Storage and Mobilization of Lipids 747 27.3 Oxidation of Fatty Acids 750 27.4 Biosynthesis of Fatty Acids 753 27.5 Biosynthesis of Gholesterol 756 27.6 Ketoacidosis 759 Summary 762 Review Exercises 763 24 NUGLEIC ACIDS 667 This Chapter in Context 668 24.1 Heredity and the Cell 668 24.2 Structure of Nucleic Acids 670 24.3 Ribonucleic Acids 677 24.4 mrna-directed Polypeptide Synthesis 24.5 Viruses 687 24.6 Recombinant DNA Technology and Genetic Engineering 690 24.7 Hereditary Diseases and Genetic Engineering 697 28 METABOLISM OF NITROGEN COMPOUNDS 765 This Ghapter in Gontext 766 28.1 Synthesis of Amino Acids in the Body 682 28.2 Gatabolism of Amino Acids 767 28.3 Formation of Urea 773 28.4 Gatabolism of Other Nitrogen Compounds 775 Summary 778 Review Exercises 778 766
CONTENTS XV 29 NUTRITION This Ghapter in Gontext 781 29.1 General Nutritional Requirements 781 29.2 Protein Requirements 785 29.3 Vitamins 789 29.4 Minerals and Trace Elements in Nutrition 795 Summary 798 Review Exercises 799 C Some Rules for Naming Inorganic Compounds C-l D Three Organic Reaction Mechanisms D-l E Answers to Practice Exercises and Selected Review Exercises E-l GLOSSARY G-l PHOTO GREDITS P-I APPENDIGES A Mathematical Goncepts A-l B Electron Gonfigurations of the Elements B-l INDEX M