TY - BOOK AU - Denniston,Katherine J. AU - Joseph J.Topping AU - Robert L.Caret TI - General, organic, and biochemistry / SN - 9780071278744 U1 - 547 PY - 2008/// CY - Boston PB - McGraw-Hill, KW - Biochemistry--Textbooks KW - Chemistry, Organic--Textbooks KW - Chemistry N1 - Includes index; Chemistry Connections and Perspectives xvii Preface xix G E N E R A L C H E M I S T R Y 1 Chemistry: Methods and Measurement.....1 2 The Structure of the Atom and the Periodic Table ......37 3 Structure and Properties of Ionic and Covalent Compounds ...... 77 4 Calculations and the Chemical Equation .... 117 5 States of Matter: Gases, Liquids, and Solids .......151 6 Solutions ......177 7 Energy, Rate, and Equilibrium ........207 8 Acids and Bases and Oxidation-Reduction ........239 9 The Nucleus, Radioactivity, and Nuclear Medicine ........275 O R G A N I C C H E M I S T R Y 10 An Introduction to Organic Chemistry: The Saturated Hydrocarbons ....... 303 11 The Unsaturated Hydrocarbons: Alkenes, Alkynes, and Aromatics ......339 12 Alcohols, Phenols, Thiols, and Ethers ........381 13 Aldehydes and Ketones ......415 14 Carboxylic Acids and Carboxylic Acid Derivatives .....447 15 Amines and Amides ......487 B I O C H E M I S T R Y 16 Carbohydrates .......523 17 Lipids and Their Functions in Biochemical Systems .....555 18 Protein Structure and Function .....595 19 Enzymes ......629 20 Introduction to Molecular Genetics ..... 667 21 Carbohydrate Metabolism .....711 22 Aerobic Respiration and Energy Production ...... ...... 745 23 Fatty Acid Metabolism .......777 Glossary G-1 Answers to Selected Problems AP-1 Credits C-1 Index I-1 Contents Chemisty Connections and Perspectives xvii Preface xix G E N E R A L C H E M I S T R Y 1 Chemistry: Methods and Measurements 1 Chemistry Connection: Chance Favors the Prepared Mind 2 1.1 The Discovery Process 3 Chemistry 3 Major Areas of Chemistry 3 The Scienti?c Method 3 A Human Perspective: The Scienti?c Method 4 Models in Chemistry 5 A Medical Perspective: Curiosity, Science, and Medicine 5 1.2 Matter and Properties 7 Matter and Physical Properties 7 Matter and Chemical Properties 8 Intensive and Extensive Properties 8 Classi?cation of Matter 9 1.3 Measurement in Chemistry 11 Data, Results, and Units 11 English and Metric Units 11 Unit Conversion: English and Metric Systems 13 Conversion of Units Within the Same System 13 Conversion of Units from One System to Another 15 1.4 Signi?cant Figures and Scienti?c Notation 16 Signi?cant Figures 16 Recognition of Signi?cant Figures 17 Scienti?c Notation 18 Error, Accuracy, Precision, and Uncertainty 19 Signi?cant Figures in Calculation of Results 20 Exact (Counted) and Inexact Numbers 22 Rounding Off Numbers 22 1.5 Experimental Quantities 23 Mass 23 Length 24 Volume 24 Time 25 Temperature 25 Energy 27 Concentration 27 Density and Speci?c Gravity 28 A Human Perspective: Food Calories 28 A Medical Perspective: Diagnosis Based on Waste 31 Summary 32 Key Terms 33 Questions and Problems 33 Critical Thinking Problems 35 2 The Structure of the Atom and the Periodic Table 37 Chemistry Connection: Managing Mountains of Information 38 2.1 Composition of the Atom 39 Electrons, Protons, and Neutrons 39 Isotopes 40 Ions 43 2.2 Development of Atomic Theory 44 Dalton?s Theory 44 Evidence for Subatomic Particles: Electrons, Protons, and Neutrons 45 Evidence for the Nucleus 45 2.3 Light, Atomic Structure, and the Bohr Atom 46 Light and Atomic Structure 46 An Environmental Perspective: Electromagnetic Radiation and Its Effects on Our Everyday Lives 48 The Bohr Atom 49 Modern Atomic Theory 51 2.4 The Periodic Law and the Periodic Table 52 A Human Perspective: Atomic Spectra and the Fourth of July 52 Numbering Groups in the Periodic Table 54 Periods and Groups 55 Metals and Nonmetals 55 Atomic Number and Atomic Mass 55 2.5 Electron Arrangement and the Periodic Table 56 A Medical Perspective: Copper De?ciency and Wilson?s Disease 57 Valence Electrons 58 The Quantum Mechanical Atom 60 Energy Levels and Sublevels 61 Electron Con?guration and the Aufbau Principle 62 Shorthand Electron Con?gurations 64 2.6 The Octet Rule 65 Ion Formation and the Octet Rule 65 A Medical Perspective: Dietary Calcium 67 2.7 Trends in the Periodic Table 68 Atomic Size 68 Ion Size 68 Ionization Energy 69 Electron Af?nity 70 Summary 71 Key Terms 72 Questions and Problems 72 Critical Thinking Problems 75 3 Structure and Properties of Ionic and Covalent Compounds 77 3.1 Chemical Bonding 78 Chemistry Connection: Magnets and Migration 78 Lewis Symbols 79 Principal Types of Chemical Bonds: Ionic and Covalent 79 Polar Covalent Bonding and Electronegativity 82 3.2 Naming Compounds and Writing Formulas of Compounds 84 Ionic Compounds 84 Covalent Compounds 89 3.3 Properties of Ionic and Covalent Compounds 92 Physical State 92 A Human Perspective: Origin of the Elements 92 Melting and Boiling Points 93 Structure of Compounds in the Solid State 93 Solutions of Ionic and Covalent Compounds 93 3.4 Drawing Lewis Structures of Molecules and Polyatomic Ions 93 Lewis Structures of Molecules 93 A Medical Perspective: Blood Pressure and the Sodium Ion/Potassium Ion Ratio 94 Lewis Structures of Polyatomic Ions 97 Lewis Structure, Stability, Multiple Bonds, and Bond Energies 100 Lewis Structures and Resonance 101 Lewis Structures and Exceptions to the Octet Rule 103 Lewis Structures and Molecular Geometry; VSEPR Theory 104 Lewis Structures and Polarity 109 3.5 Properties Based on Electronic Structure and Molecular Geometry 111 Solubility 111 Boiling Points of Liquids and Melting Points of Solids 112 Summary 113 Key Terms 114 Questions and Problems 115 Critical Thinking Problems 116 4 Calculations and the Chemical Equation 117 Chemistry Connection: The Chemistry of Automobile Air Bags 118 4.1 The Mole Concept and Atoms 119 The Mole and Avogadro?s Number 119 Calculating Atoms, Moles, and Mass 121 4.2 The Chemical Formula, Formula Weight, and Molar Mass 123 The Chemical Formula 123 Formula Weight and Molar Mass 124 4.3 The Chemical Equation and the Information It Conveys 126 A Recipe for Chemical Change 126 Features of a Chemical Equation 127 T The Experimental Basis of a Chemical Equation 127 Writing Chemical Reactions 128 Types of Chemical Reactions 129 4.4 Balancing Chemical Equations 132 4.5 Calculations Using the Chemical Equation 136 General Principles 136 A Medical Perspective: Carbon Monoxide Poisoning: A Case of Combining Ratios 136 Use of Conversion Factors 137 Theoretical and Percent Yield 143 A Medical Perspective: Pharmaceutical Chemistry: The Practical Signi?cance of Percent Yield 144 Summary 145 Key Terms 146 Questions and Problems 146 Critical Thinking Problems 149 Chemistry Connection: The Demise of the Hindenburg 152 5.1 The Gaseous State 153 Ideal Gas Concept 153 Measurement of Gases 153 K Kinetic Molecular Theory of Gases 154 Boyle?s Law 155 Charles?s Law 157 Combined Gas Law 160 Avogadro?s Law 161 Molar Volume of a Gas 163 Gas Densities 163 The Ideal Gas Law 163 Dalton?s Law of Partial Pressures 166 An Environmental Perspective: The Greenhouse Effect and Global Warming 166 Ideal Gases Versus Real Gases 167 5.2 The Liquid State 167 Compressibility 167 Viscosity 167 Surface Tension 168 A Medical Perspective: Blood Gases and Respiration 168 Vapor Pressure of a Liquid 169 Van der Waals Forces 170 Hydrogen Bonding 170 5.3 The Solid State 171 Properties of Solids 171 Types of Crystalline Solids 172 Summary 173 Key Terms 174 Questions and Problems 174 Critical Thinking Problems 176 6 Solutions 177 6.1 Properties of Solutions 178 Chemistry Connection: Seeing a Thought 178 General Properties of Liquid Solutions 179 Solutions and Colloids 179 Degree of Solubility 180 Solubility and Equilibrium 181 Solubility of Gases: Henry?s Law 181 6.2 Concentration Based on Mass 182 Weight/Volume Percent 182 A Human Perspective: Scuba Diving: Nitrogen and the Bends 183 Weight/Weight Percent 185 Parts Per Thousand (ppt) and Parts Per Million (ppm) 185 6.3 Concentration of Solutions: Moles and Equivalents 187 Molarity 187 Dilution 188 Representation of Concentration of Ions in Solution 190 6.4 Concentration-Dependent Solution Properties 191 Vapor Pressure Lowering 192 Freezing Point Depression and Boiling Point Elevation 192 Osmotic Pressure 193 A Medical Perspective: Oral Rehydration Therapy 197 6.5 Water as a Solvent 198 A Human Perspective: An Extraordinary Molecule 199 6.6 Electrolytes in Body Fluids 200 A Medical Perspective: Hemodialysis 201 Summary 202 Key Terms 203 Questions and Problems 204 Critical Thinking Problems 205 7 Energy, Rate, and Equilibrium 207 7.1 Thermodynamics 208 Chemistry Connection: The Cost of Energy? More Than You Imagine 208 The Chemical Reaction and Energy 209 Exothermic and Endothermic Reactions 209 Enthalpy 211 Spontaneous and Nonspontaneous Reactions 211 Entropy 211 A Human Perspective: Triboluminescence: Sparks in the Dark with Candy 213 Free Energy 214 7.2 Experimental Determination of Energy Change in Reactions 215 Kinetics 218 The Chemical Reaction 219 Activation Energy and the Activated Complex 220 Factors That Affect Reaction Rate 221 A Medical Perspective: Hot and Cold Packs 221 Mathematical Representation of Reaction Rate 224 7.4 Equilibrium 226 Rate and Reversibility of Reactions 226 Physical Equilibrium 226 Chemical Equilibrium 227 The Generalized Equilibrium-Constant Expression for a Chemical Reaction 228 LeChatelier?s Principle 232 Summary 235 Key Terms 236 Questions and Problems 236 Critical Thinking Problems 237 8 Acids and Bases and Oxidation-Reduction 239 Chemistry Connection: Drug Delivery 240 8.1 Acids and Bases 241 Arrhenius Theory of Acids and Bases 241 Br?nsted-Lowry Theory of Acids and Bases 241 Acid-Base Properties of Water 242 Acid and Base Strength 242 Conjugate Acids and Bases 243 The Dissociation of Water 246 8.2 pH: A Measurement Scale for Acids and Bases 246 A De?nition of pH 246 Measuring pH 247 Calculating pH 247 The Importance of pH and pH Control 252 8.3 Reactions Between Acids and Bases 252 Neutralization 252 Polyprotic Substances 255 8.4 Acid-Base Buffers 256 An Environmental Perspective: Acid Rain 256 The Buffer Process 257 Addition of Base (OH?) to a Buffer Solution 258 Addition of Acid (H3O+) to a Buffer Solution 258 Preparation of a Buffer Solution 259 T The Henderson-Hasselbalch Equation 261 A Medical Perspective: Control of Blood pH 262 8.5 Oxidation-Reduction Processes 263 Oxidation and Reduction 263 A Medical Perspective: Oxidizing Agents for Chemical Control of Microbes 264 Applications of Oxidation and Reduction 265 A Medical Perspective: Electrochemical Reactions in the Statue of Liberty and in Dental Fillings 266 Biological Processes 267 Voltaic Cells 267 Electrolysis 269 A Medical Perspective: Turning the Human Body into a Battery 270 Summary 271 Key Terms 272 Questions and Problems 272 Critical Thinking Problems 274 9 The Nucleus, Radioactivity, and Nuclear Medicine 275 Chemistry Connection: An Extraordinary Woman in Science 276 9.1 Natural Radioactivity 277 Alpha Particles 278 Beta Particles 278 Gamma Rays 278 Properties of Alpha, Beta, and Gamma Radiation 2799.2 Writing a Balanced Nuclear Equation 279 Alpha Decay 280 Beta Decay 280 Position Emission 280 Gamma Production 280 Predicting Products of Nuclear Decay 2819.3 Properties of Radioisotopes 282 Nuclear Structure and Stability 282 Half-Life 2829.4 Nuclear Power 284 Energy Production 284 An Environmental Perspective: Nuclear Waste Disposal 285 Nuclear Fission 286 Nuclear Fusion 287 Breeder Reactors 2879.5 Radiocarbon Dating 2889.6 Medical Applications of Radioactivity 288 Cancer Therapy Using Radiation 289 Nuclear Medicine 289 Making Isotopes for Medical Applications 291 A Medical Perspective: Magnetic Resonance Imaging 292 9.7 Biological Effects of Radiation 293 Radiation Exposure and Safety 293 9.8 Measurement of Radiation 295 An Environmental Perspective: Radon and Indoor Air Pollution 295 Nuclear Imaging 296 Computer Imaging 296 The Geiger Counter 296 Film Badges 296 Units of Radiation Measurement 297 Summary 298 Key Terms 299 Questions and Problems 299 Critical Thinking Problems 301 ORGANIC CHEMISTRY 10 An Introduction to Organic Chemistry: The Saturated Hydrocarbons 303 Chemistry Connection: The Origin of Organic Compounds 304 10.1 The Chemistry of Carbon 305 Important Differences Between Organic and Inorganic Compounds 306 An Environmental Perspective: Frozen Methane: Treasure or Threat? 307 Families of Organic Compounds 308 10.2 Alkanes 310 Structure and Physical Properties 310 Alkyl Groups 313 Nomenclature 315 An Environmental Perspective: Oil-Eating Microbes 317 Constitutional or Structural Isomers 319 10.3 Cycloalkanes 321 cis-trans Isomerism in Cycloalkanes 322 10.4 Conformations of Alkanes and Cycloalkanes 325 Alkanes 325 Cycloalkanes 325 A n Environmental Perspective: The Petroleum Industry and Gasoline Production 326 10.5 Reactions of Alkanes and Cycloalkanes 327 Combustion 327 A Medical Perspective: Polyhalogenated Hydrocarbons Used as Anesthetics 328 Halogenation 329 A Medical Perspective: Chloroform in Your Swimming Pool? 331 Summary of Reactions 332 Summary 332 Key Terms 332 Questions and Problems 333 Critical Thinking Problems 337 11 The Unsaturated Hydrocarbons: Alkenes, Alkynes, and Aromatics 339 Chemistry Connection: A Cautionary Tale: DDT and Biological Magni?cation 340 11.1 Alkenes and Alkynes: Structure and Physical Properties 342 11.2 Alkenes and Alkynes: Nomenclature 343 11.3 Geometric Isomers: A Consequence of Unsaturation 346 A Medical Perspective: Killer Alkynes in Nature 346 11.4 Alkenes in Nature 352 11.5 Reactions Involving Alkenes and Alkynes 354 Hydrogenation: Addition of H2 354 Halogenation: Addition of X2 356 Hydration: Addition of H2O 358 Hydrohalogenation: Addition of HX 361 A Human Perspective: Folklore, Science, and Technology 362 Addition Polymers of Alkenes 364 A Human Perspective: Life Without Polymers? 364 11.6 Aromatic Hydrocarbons 366 An Environmental Perspective: Plastic Recycling 366 Structure and Properties 368 Nomenclature 368 Polynuclear Aromatic Hydrocarbons 371 Reactions Involving Benzene 372 11.7 Heterocyclic Aromatic Compounds 373 Summary of Reactions 374 Summary 375 Key Terms 375 Questions and Problems 375 Critical Thinking Problems 379 12 Alcohols, Phenols, Thiols, and Ethers 381 Chemistry Connection: Polyols for the Sweet Tooth 382 12.1 Alcohols: Structure and Physical Properties 384 12.2 Alcohols: Nomenclature 385 I.U.P.A.C. Names 385 Common Names 386 12.3 Medically Important Alcohols 387 A Medical Perspective: Fetal Alcohol Syndrome 388 12.4 Classi?cation of Alcohols 389 12.5 Reactions Involving Alcohols 391 Preparation of Alcohols 391 Dehydration of Alcohols 394 Oxidation Reactions 397 12.6 Oxidation and Reduction in Living Systems 400 A Human Perspective: Alcohol Consumption and the Breathalyzer Test 401 12.7 Phenols 402 12.8 Ethers 403 12.9 Thiols 405 Summary of Reactions 409 Summary 409 Key Terms 410 Questions and Problems 410 Critical Thinking Problems 413 13 Aldehydes and Ketones 415 Chemistry Connection: Genetic Complexity from Simple Molecules 416 13.1 Structure and Physical Properties 417 13.2 I.U.P.A.C. Nomenclature and Common Names 419 Naming Aldehydes 419 Naming Ketones 422 13.3 Important Aldehydes and Ketones 424 13.4 Reactions Involving Aldehydes and Ketones 424 Preparation of Aldehydes and Ketones 424 A Medical Perspective: Formaldehyde and Methanol Poisoning 426 Oxidation Reactions 427 A Human Perspective: Alcohol Abuse and Antabuse 430 Reduction Reactions 431 A Medical Perspective: That Golden T an Without the Fear of Skin Cancer 432 Addition Reactions 434 Keto-Enol Tautomers 436 Aldol Condensation 438 A Human Perspective: The Chemistry of Vision 440 Summary of Reactions 440 Summary 442 Key Terms 443 Questions and Problems 443 Critical Thinking Problems 445 14 Carboxylic Acids and Carboxylic Acid Derivatives 447 Chemistry Connection: Wake Up, Sleeping Gene 448 14.1 Carboxylic Acids 449 Structure and Physical Properties 449 Nomenclature 451 Some Important Carboxylic Acids 455 An Environmental Perspective: Garbage Bags from Potato Peels 456 Reactions Involving Carboxylic Acids 457 14.2 Esters 461 Structure and Physical Properties 461 Nomenclature 461 Reactions Involving Esters 462 A Human Perspective: The Chemistry of Flavor and Fragrance 464 14.3 Acid Chlorides and Acid Anhydrides 470 Acid Chlorides 470 Acid Anhydrides 473 14.4 Nature?s High-Energy Compounds: Phosphoesters and Thioesters 476 A Human Perspective: Carboxylic Acid Derivatives of Special Interest 478 Summary of Reactions 480 Summary 481 Key Terms 481 Questions and Problems 481 Critical Thinking Problems 485 15 Amines and Amides 487 Chemistry Connection: The Nicotine Patch 488 15.1 Amines 489 Structure and Physical Properties 489 Nomenclature 493 Medically Important Amines 495 Reactions Involving Amines 497 A Human Perspective: Methamphetamine 500 Quaternary Ammonium Salts 501 15.2 Heterocyclic Amines 502 15.3 Amides 504 Structure and Physical Properties 504 Nomenclature 505 Medically Important Amides 505 Reactions Involving Amides 506 A Medical Perspective: Semisynthetic Penicillins 507 15.4 A Preview of Amino Acids, Proteins, and Protein Synthesis 510 15.5 Neurotransmitters 511 Catecholamines 511 Serotonin 511 A Medical Perspective: Opiate Biosynthesis and the Mutant Poppy 512 Histamine 514 g-Aminobutyric Acid and Glycine 515 Acetylcholine 515 Nitric Oxide and Glutamate 516 Summary of Reactions 517 Summary 518 Key Terms 518 Questions and Problems 518 Critical Thinking Problems 521 B I O C H E M I S T R Y 16 Carbohydrates 523 Chemistry Connection: Chemistry Through the Looking Glass 524 16.1 Types of Carbohydrates 526 16.2 Monosaccharides 527 A Human Perspective: Tooth Decay and Simple Sugars 528 16.3 Stereoisomers and Stereochemistry 529 Stereoisomers 529 Rotation of Plane-Polarized Light 530 The Relationship Between Molecular Structure and Optical Activity 532 Fischer Projection Formulas 532 The D- and L- System of Nomenclature 534 16.4 Biologically Important Monosaccharides 535 Glucose 535 Fructose 539 Galactose 540 Ribose and Deoxyribose, Five-Carbon Sugars 541 Reducing Sugars 541 16.5 Biologically Important Disaccharides 543 Maltose 543 Lactose 544 Sucrose 545 A Human Perspective: Blood Transfusions and the Blood Group Antigens 546 16.6 Polysaccharides 548 Starch 548 Glycogen 548 Cellulose 549 A Medical Perspective: Monosaccharide Derivatives and Heteropolysaccharides of Medical Interest 550 Summary 552 Key Terms 552 Questions and Problems 553 Critical Thinking Problems 554 17 Lipids and Their Functions in Biochemical Systems 555 Chemistry Connection: Lifesaving Lipids 556 17.1 Biological Functions of Lipids 557 17.2Fatty Acids 558 Structure and Properties 558 Chemical Reactions of Fatty Acids 561 A Human Perspective: Mummies Made of Soap 563 Eicosanoids: Prostaglandins, Leukotrienes, and Thromboxanes 564 17.3Glycerides 567 Neutral Glycerides 567 Phosphoglycerides 568 17.4 Nonglyceride Lipids 570 Sphingolipids 570 Steroids 572 A Medical Perspective: Disorders of Sphingolipid Metabolism 573 A Medical Perspective: Steroids and the Treatment of Heart Disease 574 Waxes 577 17.5 Complex Lipids 577 17.6 The Structure of Biological Membranes 581 Fluid Mosaic Structure of Biological Membranes 582 Membrane Transport 583 A Medical Perspective: Liposome Delivery Systems 586 A Medical Perspective: Antibiotics That Destroy Membrane Integrity 588 Energy Requirements for Transport 590 Summary 591 Key Terms 591 Questions and Problems 592 Critical Thinking Problems 593 18 Protein Structure and Function 595 Chemistry Connection: Angiogenesis Inhibitors: Proteins That Inhibit Tumor Growth 596 18.1 Cellular Functions of Proteins 597 18.2 The a-Amino Acids 597 Structure of Amino Acids 597 Stereoisomers of Amino Acids 598 A Medical Perspective: Proteins in the Blood 599 Classes of Amino Acids 600 18.3 The Peptide Bond 602 A Human Perspective: The Opium Poppy and Peptides in the Brain 604 18.4 The Primary Structure of Proteins 606 18.5 The Secondary Structure of Proteins 606 a-Helix 607 b-Pleated Sheet 609 18.6 The Tertiary Structure of Proteins 609 18.7 The Quaternary Structure of Proteins 611 A Human Perspective: Collagen: A Protein That Holds Us Together 612 18.8 An Overview of Protein Structure and Function 613 18.9 Myoglobin and Hemoglobin 615 Myoglobin and Oxygen Storage 615 Hemoglobin and Oxygen Transport 616 Oxygen Transport from Mother to Fetus 616 Sickle Cell Anemia 617 18.10 Denaturation of Proteins 617 A Medical Perspective: Immunoglobulins: Proteins That Defend the Body 618 Temperature 618 pH 620 Organic Solvents 621 Detergents 621 Heavy Metals 622 Mechanical Stress 622 18.11 Dietary Protein and Protein Digestion 622 Summary 624 Key Terms 625 Questions and Problems 625 Critical Thinking Problems 627 19 Enzymes 629 Chemistry Connection: Super Hot Enzymes and the Origin of Life 630 19.1 Nomenclature and Classi?cation 631 Classi?cation of Enzymes 631 Nomenclature of Enzymes 635 19.2 The Effect of Enzymes on the Activation Energy of a Reaction 636 19.3 The Effect of Substrate Concentration on Enzyme-Catalyzed Reactions 637 19.4 The Enzyme-Substrate Complex 637 19.5 Speci?city of the Enzyme-Substrate Complex 639 19.6 The Transition State and Product Formation 639 A Medical Perspective: HIV Protease Inhibitors and Pharmaceutical Drug Design 641 19.7 Cofactors and Coenzymes 643 19.8 Environmental Effects 646 Effect of pH 646 Effect of Temperature 647 A Medical Perspective: a1-Antitrypsin and Familial Emphysema 648 19.9 Regulation of Enzyme Activity 649 Allosteric Enzymes 649 Feedback Inhibition 650 Proenzymes 651 Protein Modi?cation 651 19.10 Inhibition of Enzyme Activity 652 Irreversible Inhibitors 652 Reversible, Competitive Inhibitors 652 Reversible, Noncompetitive Inhibitors 653 A Medical Perspective: Enzymes, Nerve Transmission, and Nerve Agents 654 19.11 Proteolytic Enzymes 656 A Medical Perspective: Enzymes, Isoenzymes, and Myocardial Infarction 658 19.12 Uses of Enzymes in Medicine 660 Summary 661 Key Terms 662 Questions and Problems 663 Critical Thinking Problems 665 20 Introduction to Molecular Genetics 667 Chemistry Connection: Molecular Genetics and Detection of Human Genetic Disease 668 20.1 The Structure of the Nucleotide 669 Nucleotide Structure 669 20.2 The Structure of DNA and RNA 671 DNA Structure: The Double Helix 671 Chromosomes 673 RNA Structure 674 20.3 DNA Replication 674 A Medical Perspective: Fooling the AIDS Virus with ?Look-Alike? Nucleotides 676 Bacterial DNA Replication 677 Eukaryotic DNA Replication 681 20.4 Information Flow in Biological Systems 681 Classes of RNA Molecules 681 Transcription 682 Post-transcriptional Processing of RNA 684 20.5 The Genetic Code 685 20.6 Protein Synthesis 687 The Role of Transfer RNA 688 The Process of Translation 690 20.7 Mutation, Ultraviolet Light, and DNA Repair 692 The Nature of Mutations 692 The Results of Mutations 692 Mutagens and Carcinogens 693 Ultraviolet Light Damage and DNA Repair 694 A Medical Perspective: The Ames Test for Carcinogens 694 Consequences of Defects in DNA Repair 695 20.8 Recombinant DNA 696 Tools Used in the Study of DNA 696 Genetic Engineering 699 20.9 Polymerase Chain Reaction 701 A Human Perspective: DNA Fingerprinting 702 20.10 The Human Genome Project 703 Genetic Strategies for Genome Analysis 704 DNA Sequencing 704 A Medical Perspective: A Genetic Approach to Familial Emphysema 705 Summary 706 Key Terms 707 Questions and Problems 707 Critical Thinking Problems 709 21 Carbohydrate Metabolism 711 Chemistry Connection: The Man Who Got Tipsy from Eating Pasta 712 21.1 ATP: The Cellular Energy Currency 713 21.2 Overview of Catabolic Processes 715 Stage I: Hydrolysis of Dietary Macromolecules into Small Subunits 715 Stage II: Conversion of Monomers into a Form That Can Be Completely Oxidized 717 Stage III: The Complete Oxidation of Nutrients and the Production of ATP 718 21.3 Glycolysis 719 An Overview 719 Reactions of Glycolysis 721 A Medical Perspective: Genetic Disorders of Glycolysis 722 Regulation of Glycolysis 726 21.4 Fermentations 726 Lactate Fermentation 727 Alcohol Fermentation 727 A Human Perspective: Fermentations: The Good, the Bad, and the Ugly 728 21.5 The Pentose Phosphate Pathway 730 21.6 Gluconeogenesis: The Synthesis of Glucose 730 21.7 Glycogen Synthesis and Degradation 733 The Structure of Glycogen 733 Glycogenolysis: Glycogen Degradation 733 Glycogenesis: Glycogen Synthesis 735 A Medical Perspective: Diagnosing Diabetes 738 Compatibility of Glycogenesis and Glycogenolysis 739 A Human Perspective: Glycogen Storage Diseases 740 Summary 741 Key Terms 742 Questions and Problems 742 Critical Thinking Problems 744 22 Aerobic Respiration and Energy Production 745 Chemistry Connection: Mitochondria from Mom 746 22.1 The Mitochondria 747 Structure and Function 747 Origin of the Mitochondria 747 A Human Perspective: Exercise and Energy Metabolism 748 22.2 Conversion of Pyruvate to Acetyl CoA 750 22.3 An Overview of Aerobic Respiration 752 22.4 The Citric Acid Cycle (The Krebs Cycle) 753 Reactions of the Citric Acid Cycle 753 22.5 Control of the Citric Acid Cycle 756 22.6 Oxidative Phosphorylation 757 A Human Perspective: Brown Fat: The Fat That Makes You Thin? 758 Electron Transport Systems and the Hydrogen Ion Gradient 760 ATP Synthase and the Production of ATP 760 Summary of the Energy Yield 761 22.7 The Degradation of Amino Acids 762 Removal of a-Amino Groups: Transamination 762 Removal of a-Amino Groups: Oxidative Deamination 764 The Fate of Amino Acid Carbon Skeletons 766 22.8 The Urea Cycle 766 Reactions of the Urea Cycle 766 A Medical Perspective: Pyruvate Carboxylase De?ciency 769 22.9 Overview of Anabolism: The Citric Acid Cycle as a Source of Biosynthetic Intermediates 770 Summary 772 Key Terms 773 Questions and Problems 773 Critical Thinking Problems 775 23 Fatty Acid Metabolism 777 Chemistry Connection: Obesity: A Genetic Disorder? 778 23.1 Lipid Metabolism in Animals 779 Digestion and Absorption of Dietary Triglycerides 779 Lipid Storage 781 23.2 Fatty Acid Degradation 782 An Overview of Fatty Acid Degradation 782 A Human Perspective: Losing Those Unwanted Pounds of Adipose Tissue 784 The Reactions of b-Oxidation 786 23.3 Ketone Bodies 789 Ketosis 789 Ketogenesis 789 23.4 Fatty Acid Synthesis 791 A Comparison of Fatty Acid Synthesis and Degradation 791 23.5 The Regulation of Lipid and Carbohydrate Metabolism 793 The Liver 793 A Medical Perspective: Diabetes Mellitus and Ketone Bodies 794 Adipose Tissue 796 Muscle Tissue 796 The Brain 796 23.6 The Effects of Insulin and Glucagon on Cellular Metabolism 797 Summary 799 Key Terms 799 Questions and Problems 799 Critical Thinking Problems 801 Glossary G-1 Answers to Odd-Numbered Problems AP-1 Credits C-1 Index I-1 Chemistry Connections and Perspectives A Human Perspective Chemistry Connection Chance Favors the Prepared Mind 2 Managing Mountains of Information 38 Magnets and Migration 78 The Chemistry of Automobile Air Bags 118 The Demise of the Hindenburg 152 Seeing a Thought 178 The Cost of Energy? More Than You Imagine 208 Drug Delivery 240 An Extraordinary Woman in Science 276 The Origin of Organic Compounds 304 A Cautionary Tale: DDT and Biological Magni?cation 340 Polyols for the Sweet Tooth 382 Genetic Complexity from Simple Molecules 416 Wake Up, Sleeping Gene 448 The Nicotine Patch 488 Chemistry Through the Looking Glass 524 Lifesaving Lipids 556 Angiogenesis Inhibitors: Proteins That Inhibit Tumor Growth 596 Super Hot Enzymes and the Origin of Life 630 Molecular Genetics and Detection of Human Genetic Disease 668 The Man Who Got Tipsy from Eating Pasta 712 Mitochondria from Mom 746 Obesity: A Genetic Disorder? 778 The Scienti?c Method 4 Food Calories 28 Atomic Spectra and the Fourth of July 52 Origin of the Elements 92 Scuba Diving: Nitrogen and the Bends 183 An Extraordinary Molecule 199 Triboluminescence: Sparks in the Dark with Candy 213 Folklore, Science, and Technology 362 Life Without Polymers? 364 Alcohol Consumption and the Breathalyzer Test 401 Alcohol Abuse and Antabuse 430 The Chemistry of Vision 440 The Chemistry of Flavor and Fragrance 464 Carboxylic Acid Derivatives of Special Interest 478 Methamphetamine 500 Tooth Decay and Simple Sugars 528 Blood Transfusions and the Blood Group Antigens 546 Mummies Made of Soap 563 The Opium Poppy and Peptides in the Brain 604 Collagen: A Protein That Holds Us Together 612 DNA Fingerprinting 702 Fermentations: The Good, the Bad, and the Ugly 728 Glycogen Storage Diseases 740 Exercise and Energy Metabolism 748 Brown Fat: The Fat That Makes You Thin? 758 Losing Those Unwanted Pounds of Adipose Tissue 784 Steroids and the Treatment of Heart Disease 574 Liposome Delivery Systems 586 Antibiotics That Destroy Membrane Integrity 588 Proteins in the Blood 599 Immunoglobulins: Proteins That Defend the Body 618 HIV Protease Inhibitors and Pharmaceutical Drug Design 641 a1-Antitrypsin and Familial Emphysema 648 Enzymes, Nerve Transmission, and Nerve Agents 654 Enzymes, Isoenzymes, and Myocardial Infarction 658 Fooling the AIDS Virus with ?Look-Alike? Nucleotides 676 The Ames Test for Carcinogens 694 A Genetic Approach to Familial Emphysema 705 Genetic Disorders of Glycolysis 722 Diagnosing Diabetes 738 Pyruvate Carboxylase De?ciency 769 Diabetes Mellitus and Ketone Bodies 794 An Environmental Perspective Electromagnetic Radiation and Its Effects on Our Everyday Lives 48 The Greenhouse Effect and Global Warming 166 Acid Rain 256 Nuclear Waste Disposal 285 Radon and Indoor Air Pollution 295 Frozen Methane: Treasure or Threat? 307 Oil-Eating Microbes 317 The Petroleum Industry and Gasoline Production 326 Plastic Recycling 366 Garbage Bags from Potato Peels 456 A Medical Perspective Curiosity, Science, and Medicine 5 Diagnosis Based on Waste 31 Copper De?ciency and Wilson?s Disease 57 Dietary Calcium 67 Blood Pressure and the Sodium Ion/Potassium Ion Ratio 94 Carbon Monoxide Poisoning: A Case of Combining Ratios 136 Pharmaceutical Chemistry: The Practical Signi?cance of Percent Yield 144 Blood Gases and Respiration 168 Oral Rehydration Therapy 197 Hemodialysis 201 Hot and Cold Packs 221 Control of Blood pH 262 Oxidizing Agents for Chemical Control of Microbes 264 Electrochemical Reactions in the Statue of Liberty and in Dental Fillings 266 Turning the Human Body into a Battery 270 Magnetic Resonance Imaging 292 Polyhalogenated Hydrocarbons Used as Anesthetics 328 Chloroform in Your Swimming Pool? 331 Killer Alkynes in Nature 346 Fetal Alcohol Syndrome 388 Formaldehyde and Methanol Poisoning 426 That Golden Tan Without the Fear of Skin Cancer 432 Semisynthetic Penicillins 507 Opiate Biosynthesis and the Mutant Poppy 512 Monosaccharide Derivatives and Heteropolysaccharides of Medical Interest 550 Disorders of Sphingolipid Metabolism 573 ER -