Chemistry. Introduction to General, Organic, and Biological. Robert J. Ouellette MACMILLAN PUBLISHING COMPANY. Maxwell Macmillan, Inc.

Transcription

1 Robert J. Ouellette THE OHIO STATE UNIVERSITY Introduction to General, Organic, and Biological Chemistry THIRD EDITION MACMILLAN PUBLISHING COMPANY NEW YORK Maxwell Macmillan, Inc. TORONTO

2 1 Chemistry l 1.1 Why Am I Studying Chemistry? What Is Science? How Do We Do Science? What Is Chemistry? Where Do We Go from Here? 12 ESSAY What Happened to the Dinosaurs? 5 Summary 13 / Exercises 13 2 Measurements What Is a Measurement? How Reliable Are Measurements? Significant Figures Give the Uncertainty in Measurements Expressing Large and Small Numbers Using Units In Problem Solving The Metrie System Temperature Units 26 ix

3 x Contents Are We the Center of the Universe? 23 International Units (IU) and the U.S. RDA 26 Hyperthermia and Hypothermia 29 Summary 29 / Exercises 30 3 Properties of Matter Matter Exists in Three States Density of Matter Energy Is an Extensive Property Physical and Chemical Properties Mass Is Conserved in Chemical Reactions Energy Is Conserved in Chemical Reactions Mixtures and Pure Substances Elements The Composition of Compounds 50 Specific Gravity as a Diagnostic Tool 37 It Is Calories That We Worry About 38 How Do You Stay Cool? 43 Your Body, Your Elements 49 Summary 51 / Exercises 51 4 Atoms, Molecules, and Ions What Is the Smallest Unit of Matter? The Atom Is Very Small Atoms Contain Subatomic Particles Atomic Number, Mass Number, and Isotopes Molecules and Molecular Formulas Ions Ionic Compounds 66 Calcium Ions and Your Diet 63 Phosphate Supplements Soil for Agriculture 67 Summary 70 / Exercises 70 5 Calculations with Chemical Formulas Matter Submicroscopic and Macroscopic Views Atomic Weights Molecular and Formula Weights of Compounds 75

4 xi 5.4 Percent Composition Avogadro's Number and the Mole Calculations Using Moles Empirical Formula and Molecular Formula 84 How Big 1s Avogadro's Number? 81 Products from the Earth, Sea, and Air 83 Summary 88 / Exercises 88 6 Chemical Equations and Reactions Chemical Equations Represent Chemical Reactions Symbols in Equations Balancing Equations Stoichiometry and the Balanced Equation Solving Stoichiometry Problems Types of Chemical Reactions Combination Reactions Decomposition Reactions Single-Replacement Reactions Double-Replacement Reactions Neutralization Reactions Oxidation-Reduction Reactions 108 What Makes a Rocket Fly? 97 Sulfuric Acid A World Class Chemical 107 Preventing Corrosion, an Unwanted Oxidation 113 Summary 114 / Exercises The Periodic Table and Atomic Structure Organizing the Elements 120 Mendeleev's Classification of Elements 121 The Modern Periodic Table 124 Where Are the Electrons in the Atom? 125 Shells, Subshells, and Orbitals 127 Electron Configuration 131 Electron-Dot Symbols 136 The Periodic Table and Electron Configuration 136 Uses of the Periodic Table 139 Atmospheric Atomic Tests Had to Be Stopped 123 Lighting Our Way with Excited Atoms 126 Silicon Affects Your Life-style 140 Summary 144 / Exercises 144

5 xii Contents 8 Chemical Bonds Bonds and Structure Types of Bonds Ionic Bonds Covalent Bonds Drawing Lewis Structures Polar Covalent Bonds Coordinate Covalent Bonds Resonance Structures Molecular Geometry Polarity of Molecules 165 Ion Radius Affects Cell Composition and Enzyme Reactions 152 Coordinate Covalent Bonds and Respiration 160 Summary 166 / Exercises Gases, Liquids, and Solids The Organization of Matter Pressure The Gas Laws Avogadro's Hypothesis and the Ideal Gas Law Dalton's Law of Partial Pressures Liquids Solids Le Chätelier's Principle and Changes of State Types of Intermolecular Forces 192 Blood Pressure 173 Breathing and Boyle's Law 1 78 Water A Common but Very Unusual Compound 195 Summary 196 / Exercises Solutions Solutions Around Us and in Us Solvents and Solutes Concentration Teils Us the Amount of Solute in Solution Percent Concentration Molarity Dilution of Solutions Electrolytes and Nonelectrolytes 209

6 xiii The Formation of a Solution 210 Factors That Control Solubility 211 Colligative Properties 214 Osmosis 216 Osmosis and Cells 219 Hot Packs and Cold Packs 203 Gas Solubility and the Bends 212 Solubility of Vitamins 214 Osmosis Is a Way to Kill Bacteria 220 Summary 220 / Exercises Reaction Rates and Equilibrium Reactions An Overview Energy and Chemical Reactions Why Do Reactions Occur? Kinetics Activation Energy Chemical Equilibrium Chemical Equilibrium and Le Chätelier's Principle 241 Explosions and Entropy 228 The Effect of Temperature on Organisms 233 Catalysts in Living Systems 234 Summary 244 / Exercises Acid-Base Equilibria General Properties of Acids and Bases Acids and Bases Are Chemical Opposites Reactions of Acids and Bases Conjugate Acids and Conjugate Bases Self-ionization of Water Strengths of Acids and Bases The ph Scale Hydrolysis of Salts Buffers Buffers in the Body Titration 269 Antacids 252 Acid and Tooth Decay 262 Acids and Bases in Agriculture 266 Summary 272 / Exercises 273

7 13 Nuclear Chemistry Radiosotopes and Nuclear Chemistry Radioactivity Units of Radiation Balancing Nuclear Equations Half-lives Biological Effects of Radiation Use of Radioisotopes in Diagnosis Use of Radioisotopes in Therapy Nuclear Transmutations Fission and Fusion Reactions 292 The Radon Problem 286 Positron Emission Tomography 289 Summary 295 / Exercises Introäuction to Organic Chemistry Organic Compounds Orbitals and Molecular Shapes Structural Formulas Structural Models Functional Groups Isomers Organic Reactions and Mechanisms Acid Base Reactions in Organic Chemistry Oxidation-Reduction Reactions 316 ESSAY Organic Compounds in Daily Life 300 Summary 317 / Exercises 318 IS Saturated Hydrocarbons Classes of Hydrocarbons Alkanes Nomenclature of Alkanes Physical Properties of Alkanes Oxidation of Alkanes Halogenation of Alkanes The Mechanism of Chlorination of Alkanes Cycloalkanes 336

8 xv What Are Octane Numbers? 332 Freons, Radicals, and the Ozone Layer 335 Summary 340 / Exercises Unsaturated Hydrocarbons Types of Unsaturated Hydrocarbons Geometrie Isomerism Nomenclature of Alkenes Oxidation and Reduction of Alkenes Addition Reactions of Alkenes Polymerization of Alkenes Alkynes Aromatic Hydrocarbons Nomenclature of Aromatic Hydrocarbons Polycyclic and Heterocyclic Aromatic Hydrocarbons 364 Geometrie Isomers and the Sex Life of Moths 349 Hydrogenation of Oils 352 Summary 365 / Exercises Alcohols, Phenols, and Ethers Compounds of Oxygen Common Alcohols and Phenols Nomenclature and Classification of Alcohols Hydrogen Bonding in Alcohols Acid-Base Reactions Substitution Reactions Dehydration of Alcohols Oxidation of Alcohols Ethers Sulfur Compounds 388 Ethanol An Antidote for Methanol Poisoning 386 Anesthetics 387 Summary 389 / Exercises Aldehydes and Ketones The Carbonyl Group Nomenclature of Aldehydes and Ketones 395

9 xvi Contents 18.3 Physical Properties of Aldehydes and Ketones Oxidation of Carbonyl Compounds Reduction of Carbonyl Compounds Carbonyl Compounds Undergo Addition Reactions Addition of Oxygen Compounds Addition of Nitrogen Compounds Reactivity of the a Carbon Atom The Aldol Condensation 410 Benedict's Test and Diabetes 400 Exercise Aerobic and Anaerobic 401 Isomerism, Addition Reactions, and Vision 407 Summary 411 / Exercises Carboxylic Acids and Esters Carboxylic Acids and Derivatives Nomenclature of Carboxylic Acids Physical Properties of Carboxylic Acids Acidity of Carboxylic Acids Salts of Carboxylic Acids Esters Hydrolysis and Saponification of Esters Nucleophilic Acyl Substitution Esters and Anhydrides of Phosphoric Acid The Claisen Condensation 433 Polyesters 424 Esters as Food Additives 426 Soaps and Detergents 428 Thioesters Are Nature's Active Acyl Compounds 431 Summary 435 / Exercises Amines and Amides Organic Nitrogen Compounds Amines Nomenclature of Amines Physical Properties of Amines Basicity of Amines Reaction of Amines with Nitrous Acid Amides Formation of Amides Hydrolysis of Amides 456 Designer Drugs 440

10 xvii Adrenaline and Amphetamines 448 Barbiturates 452 Bullet-Resistant and Flame-Resistant Polymers 455 Summary 457 / Exercises Biochemistry What Is Biochemistry? Composition of Biochemicals Biochemical Reactions The Cell and Chemical Reactions Configuration of Biochemicals Enantiomers Are Optically Active Perspective Representations of Enantiomers Multiple Chiral Centers How Are Stereoisomers Formed? 482 Biochemistry, Food, and You 467 Chirality and Odor 479 Summary 482 / Exercises Carbohydrates Carbohydrates Sources of Energy Classification of Carbohydrates Configuration of Monosaccharides Glucose A Key Compound Hemiacetals and Hemiketals Glycosides Oxidation of Carbohydrates Disaccharides Polysaccharides 507 Blood Glucose 494 Lactose Intolerance 504 Sweeteners 505 Summary 509 / Exercises Lipids Classification of Lipids Terpenes Steroids 516

11 xviii Contents 23.4 Waxes Fatty Acids Triglycerides Phosphoglycerides Sphingophospholipids Glycosphingolipids Biological Membranes 530 Anabolic Steroids 518 Whale Oil 520 Prostaglandins 523 Triglycerides Store Energy 524 Summary 532 / Exercises Amino Acids and Proteins \ Proteins An Overview Amino Acids Acid-Base Properties of Amino Acids Isolectric Point Peptides Structure of Peptides Bonding in Proteins Structure of Proteins Hydrolysis of Proteins Denaturation of Proteins Classification of Proteins 557 Cholesterol and Lipoproteins 537 Complete Proteins in the Diet 554 Summary 558 / Exercises Nucleic Acids Genes Contain Nucleic Acids Nucleic Acids Are Polymers Polynucleotides The Flow of Genetic Information DNA Replicates Itself DNA Produces Several Types of RNA The Genetic Code Protein Synthesis and Translation Gene Mutations and Genetic Disease Recombinant DNA and Genetic Engineering Viruses 583

12 xix Nucleosides in Medicine 565 Exons and Introns 574 How Do Antibiotics Work? 578 A Gene Defect May Cause Osteoarthritis 581 AIDS Is a Retrovirus Disease 584 Summary 584 / Exercises Enzymes Biological Catalysts Classification of Enzymes Models of Enzyme Action Active Sites Cofactors Kinetics of Enzyme Reactions Enzyme Inhibition Regulatory Enzymes Zymogens 604 Muscle Relaxants 589 Sulfa Drugs as Competitive Inhibitors 600 Mercury and Lead Poisoning 603 Summary 605 / Exercises Biochemical Energy A Free Energy Controls Biochemical Reactions Metabolie Reactions and ATP Coupling of Phosphorylation Substrate Level Phosphorylation Oxidation and Reduction Cellular Respiration Citric Acid Cycle Food and Energy The Mitochondria Regulation of Metabolie Reactions 627 ESSAY Effect of Barbiturates on the Citric Acid Cycle 624 Summary 628 / Exercises 629

13 28 Metabolism of Carbohydrates Digestion of Carbohydrates Glycolysis Pyruvic Acid A Key Compound The ATP Profit from Glucose Gluconeogenesis The Pentose Phosphate Pathway Glycogenolysis and Glycogenesis Regulation of Carbohydrate Metabolism 651 The Marathon and Carbohydrate Loading 634 Alcohol Fermentation 644 Glycogen Storage Diseases 650 Summary 651 / Exercises Metabolism of Triglycerides Fats and Energy Catabolic Reactions of Triglycerides Catabolism of Unsaturated Fatty Acids Ketone Bodies Biosynthesis of Fatty Acids 664 Wouldn't You Rather Be Fat? 661 Essential Fatty Acids 667 Summary 668 / Exercises Metabolism of Proteins Digestion of Proteins Deamination of Amino Acids in Catabolism The Urea Cycle The Fate of the Carbon Skeleton Decarboxylation of Amino Acids Biosynthesis of Amino Acids 681 Transaminases Are Monitored in Medical Diagnosis 673 Hyperammonemia 676 Phenylketonuria 679 Histamine and Antihistamines 680 Summary 682 / Exercises 682

14 xxi Appendix A Scientific Notation and Significant Figur es A*l Appendix B Glossary A*5 Appendix C Answers to Problems A»21 Appendix D Answers to Odd-Numbered Exercises A»25 Index M