TY - BOOK AU - Denniston,K.J. AU - Topping,Joseph J. AU - Caret,Robert L. TI - General, organic, and biochemistry SN - 9780072828474 (hbk.) U1 - 547 22 PY - 2007/// CY - Boston PB - McGraw-Hill Higher Education KW - Chemistry, Organic KW - Textbooks KW - Biochemistry N1 - Includes index; Contents Preface xxi Supplementary Materials xxiv Acknowledgments xxv Media System xxvii Learning System xxviii General Chemistry 1 Chemistry: Methods and Measurement 1 CHEMISTRY CONNECTION: Chance Favors the Prepared Mind 2 1.1 The Discovery Process 3 Chemistry 3 Major Areas of Chemistry 3 The Scientific Method 3 A HUMAN PERSPECTIVE: The Scientific Method 4 Models in Chemistry 5 1.2 Matter and Properties 5 Matter and Physical Properties 5 Matter and Chemical Properties 6 Intensive and Extensive Properties 7 Classification of Matter 8 1.3 Measurement in Chemistry 10 Data, Results, and Units 10 English and Metric Units 10 Unit Conversion: English and Metric Systems 12 Conversion of Units within the Same System 12 Conversion of Units from One System to Another 14 1.4 Significant Figures and Scientific Notation 15 Significant Figures 15 Recognition of Significant Figures 16 Scientific Notation 17 Significant Figures in Calculation of Results 18 Rounding Off Numbers 20 1.5 Experimental Quantities 21 Mass 21 Length 22 Volume 22 Time 23 Temperature 23 Energy 24 Concentration 26 Density and Specific Gravity 26 A HUMAN PERSPECTIVE: Food Calories 25 A CLINICAL PERSPECTIVE: Diagnosis Based on Waste 29 Summary 29 Key Terms 30 Questions and Problems 31 Critical Thinking Problems 32 2 The Composition and Structure of the Atom 33 CHEMISTRY CONNECTION: Curiosity, Science, and Medicine 34 2.1 Matter and Structure 34 An Overview 34 Atomic Structure 35 2.2 Composition of the Atom 35 Electrons, Protons, and Neutrons 36 Isotopes 37 Ions 40 2.3 Development of Atomic Theory 41 Dalton's Theory 41 Evidence for Subatomic Particles: Electrons, Protons, and Neutrons 42 Evidence for the Nucleus 43 2.4 The Relationship between Light and Atomic Structure 44 2.5 The Bohr Atom 46 2.6 Modern Atomic Theory 47 A HUMAN PERSPECTIVE: Atomic Spectra and the Fourth of July 47 AN ENVIRONMENTAL PERSPECTIVE: Electromagnetic Radiation and Its Effects on Our Everyday Lives 48 Summary 50 Key Terms 50 Questions and Problems 51 Critical Thinking Problems 52 3 Elements, Atoms, Ions, and the Periodic Table 53 CHEMISTRY CONNECTION: Managing Mountains of Information 54 3.1 The Periodic Law and the Periodic Table 54 Numbering Groups in the Periodic Table 56 Periods and Groups 57 Metals and Nonmetals 57 Atomic Number and Atomic Mass 57 A MEDICAL PERSPECTIVE: Copper Deficiency and Wilson's Disease 58 3.2 Electron Arrangement and the Periodic Table 59 Valence Electrons 59 The Quantum Mechanical Atom 62 Energy Levels and Sublevels 62 Electron Configuration and the Aufbau Principle 64 Abbreviated Electron Configurations 66 3.3 The Octet Rule 67 Ion Formation and the Octet Rule 67 A CLINICAL PERSPECTIVE: Dietary Calcium 69 3.4 Trends in the Periodic Table 70 Atomic Size 70 Ion Size 70 Ionization Energy 70 Electron Affinity 72 Summary 73 Key Terms 73 Questions and Problems 73 Critical Thinking Problems 75 4 Structure and Properties of Ionic and Covalent Compounds 77 CHEMISTRY CONNECTION: Magnets and Migration 78 4.1 Chemical Bonding 78 Lewis Symbols 79 Principal Types of Chemical Bonds: Ionic and Covalent 79 Polar Covalent Bonding and Electronegativity 81 4.2 Naming Compounds and Writing Formulas of Compounds 83 Ionic Compounds 83 Covalent Compounds 88 A HUMAN PERSPECTIVE: Origin of the Elements 91 4.3 Properties of Ionic and Covalent Compounds 91 Physical State 91 Melting and Boiling Points 91 Structure of Compounds in the Solid State 92 Solutions of Ionic and Covalent Compounds 92 4.4 Drawing Lewis Structures of Molecules and Polyatomic Ions 92 Lewis Structures of Molecules 92 A CLINICAL PERSPECTIVE: Blood Pressure and the Sodium Ion/Potassium Ion Ratio 93 Lewis Structures of Polyatomic Ions 96 Lewis Structure, Stability, Multiple Bonds, and Bond Energies 98 Lewis Structures and Resonance 99 Lewis Structures and Exceptions to the Octet Rule 101 Lewis Structures and Molecular Geometry; VSEPR Theory 102 Lewis Structures and Polarity 107 4.5 Properties Based on Electronic Structure and Molecular Geometry 109 Solubility 110 Boiling Points of Liquids and Melting Points of Solids 110 Summary 111 Key Terms 112 Questions and Problems 113 Critical Thinking Problems 114 5 Calculations and the Chemical Equation 115 CHEMISTRY CONNECTION: The Chemistry of Automobile Air Bags 116 5.1 The Mole Concept and Atoms 117 The Mole and Avogadro's Number 117 Calculating Atoms, Moles, and Mass 118 5.2 Compounds 121 The Chemical Formula 121 5.3 The Mole Concept Applied to Compounds 122 5.4 The Chemical Equation and the Information It Conveys 124 A Recipe for Chemical Change 124 Features of a Chemical Equation 125 The Experimental Basis of a Chemical Equation 125 5.5 Balancing Chemical Equations 126 A CLINICAL PERSPECTIVE: Carbon Monoxide Poisoning: A Case of Combining Ratios 130 5.6 Calculations Using the Chemical Equation 131 General Principles 131 Use of Conversion Factors 131 Theoretical and Percent Yield 137 A MEDICAL PERSPECTIVE: Pharmaceutical Chemistry: The Practical Significance of Percent Yield 138 Summary 139 Key Terms 140 Questions and Problems 140 Critical Thinking Problems 142 6 States of Matter: Gases, Liquids, and Solids 143 CHEMISTRY CONNECTION: The Demise of the Hindenburg 144 6.1 The Gaseous State 145 Ideal Gas Concept 145 Measurement of Gases 145 Boyle's Law 146 Charles's Law 148 Combined Gas Law 150 A CLINICAL PERSPECTIVE: Autoclaves and the Gas Laws 151 Avogadro's Law 153 Molar Volume of a Gas 154 Gas Densities 154 The Ideal Gas Law 154 AN ENVIRONMENTAL PERSPECTIVE: The Greenhouse Effect and Global Warming 157 Dalton's Law of Partial Pressures 157 Kinetic Molecular Theory of Gases 158 Ideal Gases Versus Real Gases 158 6.2 The Liquid State 159 Compressibility 159 Viscosity 159 A CLINICAL PERSPECTIVE: Blood Gases and Respiration 160 Surface Tension 160 Vapor Pressure of a Liquid 161 Van der Waals Forces 162 Hydrogen Bonding 162 6.3 The Solid State 163 Properties of Solids 164 Types of Crystalline Solids 164 Summary 165 Key Terms 166 Questions and Problems 166 Critical Thinking Problems 167 7 Reactions and Solutions 169 CHEMISTRY CONNECTION: Seeing a Thought 170 7.1 Writing Chemical Reactions 171 Combination Reactions 171 Decomposition Reactions 171 Replacement Reactions 171 7.2 Types of Chemical Reactions 172 Precipitation Reactions 172 Reactions with Oxygen 174 Acid-Base Reactions 174 Oxidation-Reduction Reactions 174 7.3 Properties of Solutions 175 General Properties of Liquid Solutions 175 Solutions and Colloids 176 Degree of Solubility 177 Solubility and Equilibrium 177 Solubility of Gases: Henry's Law 177 7.4 Concentration of Solutions: Percentage 178 Weight/Volume Percent 178 A HUMAN PERSPECTIVE: Scuba Diving: Nitrogen and the Bends 179 Weight/Weight Percent 180 7.5 Concentration of Solutions: Moles and Equivalents 181 Molarity 181 Dilution 183 Representation of Concentration of Ions in Solution 185 7.6 Concentration-Dependent Solution Properties 185 Vapor Pressure Lowering 186 Freezing Point Depression and Boiling Point Elevation 186 Osmotic Pressure 187 A CLINICAL PERSPECTIVE: Oral Rehydration Therapy 191 7.7 Water as a Solvent 192 7.8 Electrolytes in Body Fluids 193 A HUMAN PERSPECTIVE: An Extraordinary Molecule 194 A CLINICAL PERSPECTIVE: Hemodialysis 195 Summary 196 Key Terms 198 Questions and Problems 198 Critical Thinking Problems 199 8 Chemical and Physical Change: Energy, Rate, and Equilibrium 201 CHEMISTRY CONNECTION: The Cost of Energy? More Than You Imagine 202 8.1 Thermodynamics 202 The Chemical Reaction and Energy 203 Exothermic and Endothermic Reactions 203 Enthalpy 204 Spontaneous and Nonspontaneous Reactions 205 Entropy 205 Free Energy 206 A HUMAN PERSPECTIVE: Triboluminescence: Sparks in the Dark with Candy 207 8.2 Experimental Determination of Energy Change in Reactions 208 8.3 Kinetics 211 The Chemical Reaction 212 Activation Energy and the Activated Complex 212 A CLINICAL PERSPECTIVE: Hot and Cold Packs 214 Factors That Affect Reaction Rate 214 Mathematical Representation of Reaction Rate 216 8.4 Equilibrium 219 Rate and Reversibility of Reactions 219 Physical Equilibrium 219 Chemical Equilibrium 221 The Generalized Equilibrium-Constant Expression for a Chemical Reaction 222 LeChatelier's Principle 226 Summary 229 Key Terms 230 Questions and Problems 230 Critical Thinking Problems 231 9 Charge-Transfer Reactions: Acids and Bases and Oxidation-Reduction 233 CHEMISTRY CONNECTION: Drug Delivery 234 9.1 Acids and Bases 235 Arrhenius Theory of Acids and Bases 235 Bronsted-Lowry Theory of Acids and Bases 235 Conjugate Acids and Bases 236 Acid-Base Properties of Water 237 Acid and Base Strength 237 The Dissociation of Water 239 9.2 pH: A Measurement Scale for Acids and Bases 240 A Definition of pH 240 Measuring pH 241 Calculating pH 241 The Importance of pH and pH Control 245 9.3 Reactions between Acids and Bases 245 Neutralization 245 AN ENVIRONMENTAL PERSPECTIVE: Acid Rain 248 Polyprotic Substances 249 9.4 Acid-Base Buffers 250 The Buffer Process 250 Addition of Base (OH_) to a Buffer Solution 251 Addition of Acid (H3O_) to a Buffer Solution 251 Preparation of a Buffer Solution 252 The Henderson-Hasselbalch Equation 254 A CLINICAL PERSPECTIVE: Control of Blood pH 255 9.5 Oxidation-Reduction Processes 255 A CLINICAL PERSPECTIVE: Oxidizing Agents for Chemical Control of Microbes 256 Oxidation and Reduction 256 Applications of Oxidation and Reduction 257 A CLINICAL PERSPECTIVE: Electrochemical Reactions in the Statue of Liberty and in Dental Fillings 258 Biological Processes 259 Voltaic Cells 259 A MEDICAL PERSPECTIVE: Turning the Human Body into a Battery 261 Electrolysis 262 Summary 263 Key Terms 263 Questions and Problems 264 Critical Thinking Problems 265 10 The Nucleus, Radioactivity, and Nuclear Medicine 267 CHEMISTRY CONNECTION: An Extraordinary Woman in Science 268 10.1 Natural Radioactivity 269 Alpha Particles 270 Beta Particles 270 Gamma Rays 270 Properties of Alpha, Beta, and Gamma Radiation 270 10.2 Writing a Balanced Nuclear Equation 271 Alpha Decay 271 Beta Decay 271 Gamma Production 272 Predicting Products of Nuclear Decay 272 10.3 Properties of Radioisotopes 273 Nuclear Structure and Stability 273 Half-Life 274 10.4 Nuclear Power 275 Energy Production 275 Nuclear Fission 276 Nuclear Fusion 276 Breeder Reactors 278 10.5 Radiocarbon Dating 278 10.6 Medical Applications of Radioactivity 278 AN ENVIRONMENTAL PERSPECTIVE: Nuclear Waste Disposal 279 Cancer Therapy Using Radiation 280 Nuclear Medicine 280 Making Isotopes for Medical Applications 282 10.7 Biological Effects of Radiation 283 Radiation Exposure and Safety 283 A CLINICAL PERSPECTIVE: Magnetic Resonance Imaging 284 10.8 Measurement of Radiation 286 Nuclear Imaging 286 Computer Imaging 286 The Geiger Counter 287 Film Badges 287 Units of Radiation Measurement 287 AN ENVIRONMENTAL PERSPECTIVE: Radon and Indoor Air Pollution 288 Summary 289 Key Terms 290 Questions and Problems 290 Critical Thinking Problems 291 Organic Chemistry 11 An Introduction to Organic Chemistry: The Saturated Hydrocarbons 293 CHEMISTRY CONNECTION: The Origin of Organic Compounds 294 11.1 The Chemistry of Carbon 295 Important Differences between Organic and Inorganic Compounds 296 AN ENVIRONMENTAL PERSPECTIVE: Frozen Methane: Treasure or Threat? 297 Families of Organic Compounds 298 11.2 Alkanes 300 Structure and Physical Properties 300 Alkyl Groups 303 Nomenclature 303 Constitutional or Structural Isomers 307 AN ENVIRONMENTAL PERSPECTIVE: Oil-Eating Bacteria 309 11.3 Cycloalkanes 309 cis-trans Isomerism in Cycloalkanes 311 11.4 Conformations of Alkanes and Cycloalkanes 313 AN ENVIRONMENTAL PERSPECTIVE: The Petroleum Industry and Gasoline Production 314 11.5 Reactions of Alkanes and Cycloalkanes 315 Combustion 315 A MEDICAL PERSPECTIVE: Polyhalogenated Hydrocarbons Used as Anesthetics 316 A MEDICAL PERSPECTIVE: Chloroform in Your Swimming Pool? 317 Halogenation 317 Summary of Reactions 319 Summary 319 Key Terms 320 Questions and Problems 320 Critical Thinking Problems 323 12 The Unsaturated Hydrocarbons: Alkenes, Alkynes, and Aromatics 325 CHEMISTRY CONNECTION: A Cautionary Tale: DDT and Biological Magnification 326 12.1 Alkenes and Alkynes: Structure and Physical Properties 327 12.2 Alkenes and Alkynes: Nomenclature 328 A MEDICAL PERSPECTIVE: Killer Alkynes in Nature 330 12.3 Geometric Isomers: A Consequence of Unsaturation 333 12.4 Alkenes in Nature 336 12.5 Reactions Involving Alkenes 337 Hydrogenation: Addition of H2 to an Alkene 339 Halogenation: Addition of X2 to an Alkene 340 Hydration: Addition of H2O to an Alkene 342 A HUMAN PERSPECTIVE: Folklore, Science, and Technology 343 Hydrohalogenation: Addition of HX to an Alkene 345 Addition Polymers of Alkenes 346 A HUMAN PERSPECTIVE: Life without Polymers? 347 AN ENVIRONMENTAL PERSPECTIVE: Plastic Recycling 348 12.6 Aromatic Hydrocarbons 350 Structure and Properties 351 Nomenclature 352 Reactions Involving Benzene 354 A HUMAN PERSPECTIVE: Aromatic Compounds and Carcinogenesis 355 12.7 Heterocyclic Aromatic Compounds 356 Summary of Reactions 357 Summary 358 Key Terms 359 Questions and Problems 359 Critical Thinking Problems 362 13 Alcohols, Phenols, Thiols, and Ethers 363 CHEMISTRY CONNECTION: Polyols for the Sweet Tooth 364 13.1 Alcohols: Structure and Physical Properties 366 13.2 Alcohols: Nomenclature 367 I.U.P.A.C. Names 367 Common Names 368 13.3 Medically Important Alcohols 369 A MEDICAL PERSPECTIVE: Fetal Alcohol Syndrome 370 13.4 Classification of Alcohols 370 13.5 Reactions Involving Alcohols 372 Preparation of Alcohols 372 Dehydration of Alcohols 374 Oxidation Reactions 377 13.6 Oxidation and Reduction in Living Systems 379 A HUMAN PERSPECTIVE: Alcohol Consumption and the Breathalyzer Test 380 13.7 Phenols 381 13.8 Ethers 382 13.9 Thiols 384 Summary of Reactions 386 Summary 387 Key Terms 388 Questions and Problems 388 Critical Thinking Problems 391 14 Aldehydes and Ketones 393 CHEMISTRY CONNECTION: Genetic Complexity from Simple Molecules 394 14.1 Structure and Physical Properties 395 14.2 I.U.P.A.C. Nomenclature and Common Names 396 Naming Aldehydes 396 Naming Ketones 399 14.3 Important Aldehydes and Ketones 401 14.4 Reactions Involving Aldehydes and Ketones 403 Preparation of Aldehydes and Ketones 403 A CLINICAL PERSPECTIVE: Medical Applications of Aldehydes 403 Oxidation Reactions 404 Reduction Reactions 407 A MEDICAL PERSPECTIVE: That Golden Tan Without the Fear of Skin Cancer 408 Addition Reactions 410 Keto-Enol Tautomers 412 Aldol Condensation 413 A HUMAN PERSPECTIVE: The Chemistry of Vision 415 Summary of Reactions 416 Summary 417 Key Terms 417 Questions and Problems 417 Critical Thinking Problems 420 15 Carboxylic Acids and Carboxylic Acid Derivatives 421 CHEMISTRY CONNECTION: Wake Up, Sleeping Gene 422 15.1 Carboxylic Acids 423 Structure and Physical Properties 423 Nomenclature 424 Some Important Carboxylic Acids 429 Reactions Involving Carboxylic Acids 429 AN ENVIRONMENTAL PERSPECTIVE: Garbage Bags from Potato Peels 430 15.2 Esters 433 Structure and Physical Properties 433 Nomenclature 433 A HUMAN PERSPECTIVE: The Chemistry of Flavor and Fragrance 434 Reactions Involving Esters 435 15.3 Acid Chlorides and Acid Anhydrides 441 Acid Chlorides 441 Acid Anhydrides 444 15.4 Nature's High-Energy Compounds: Phosphoesters and Thioesters 447 A HUMAN PERSPECTIVE: Carboxylic Acid Derivatives of Special Interest 449 Summary of Reactions 450 Summary 451 Key Terms 451 Questions and Problems 451 Critical Thinking Problems 454 16 Amines and Amides 457 CHEMISTRY CONNECTION: The Nicotine Patch 458 16.1 Amines 459 Structure and Physical Properties 459 Nomenclature 463 A CLINICAL PERSPECTIVE: Medically Important Amines 465 Reactions Involving Amines 466 A MEDICAL PERSPECTIVE: Secondary Amines and Cancer 469 Quaternary Ammonium Salts 470 16.2 Heterocyclic Amines 470 16.3 Amides 472 Structure and Physical Properties 473 Nomenclature 473 A MEDICAL PERSPECTIVE: Semisynthetic Penicillins 474 Reactions Involving Amides 475 A CLINICAL PERSPECTIVE: Medically Important Amides 475 16.4 A Preview of Amino Acids, Proteins, and Protein Synthesis 478 16.5 Neurotransmitters 478 Catecholamines 479 Serotonin 479 Histamine 480 Aminobutyric Acid and Glycine 481 Acetylcholine 481 Nitric Oxide and Glutamate 482 Summary of Reactions 483 Summary 484 Key Terms 484 Questions and Problems 484 Critical Thinking Problems 487 Biochemistry 17 Carbohydrates 489 CHEMISTRY CONNECTION: Chemistry Through the Looking Glass 490 17.1 Types of Carbohydrates 491 A HUMAN PERSPECTIVE: Tooth Decay and Simple Sugars 493 17.2 Monosaccharides 494 17.3 Stereoisomers and Stereochemistry 495 Stereoisomers 495 Rotation of Plane-Polarized Light 496 The Relationship between Molecular Structure and Optical Activity 497 Fischer Projection Formulas 498 The D- and L-System of Nomenclature 498 17.4 Biologically Important Monosaccharides 500 Glucose 500 Fructose 504 Galactose 505 Ribose and Deoxyribose, Five-Carbon Sugars 505 Reducing Sugars 506 17.5 Biologically Important Disaccharides 508 Maltose 508 Lactose 509 Sucrose 511 A HUMAN PERSPECTIVE: Blood Transfusions and the Blood Group Antigens 510 17.6 Polysaccharides 512 Starch 512 Glycogen 512 Cellulose 514 A CLINICAL PERSPECTIVE: The Bacterial Cell Wall 514 A MEDICAL PERSPECTIVE: Monosaccharide Derivatives and Heteropolysaccharides of Medical Interest 516 Summary 518 Key Terms 518 Questions and Problems 519 Critical Thinking Problems 520 18 Lipids and Their Functions in Biochemical Systems 521 CHEMISTRY CONNECTION: Lifesaving Lipids 522 18.1 Biological Functions of Lipids 522 18.2 Fatty Acids 524 Structure and Properties 524 Chemical Reactions of Fatty Acids 527 A HUMAN PERSPECTIVE: Mummies Made of Soap 528 Eicosanoids: Prostaglandins, Leukotrienes, and Thromboxanes 530 18.3 Glycerides 531 Neutral Glycerides 531 Phosphoglycerides 533 18.4 Nonglyceride Lipids 535 Sphingolipids 535 A CLINICAL PERSPECTIVE: Disorders of Sphingolipid Metabolism 537 Steroids 538 A HUMAN PERSPECTIVE: Anabolic Steroids and Athletics 539 A CLINICAL PERSPECTIVE: Steroids and the Treatment of Heart Disease 541 Waxes 542 18.5 Complex Lipids 542 18.6 The Structure of Biological Membranes 546 Fluid Mosaic Structure of Biological Membranes 547 Membrane Transport 549 A CLINICAL PERSPECTIVE: Liposome Delivery Systems 550 A CLINICAL PERSPECTIVE: Antibiotics That Destroy Membrane Integrity 552 Energy Requirements for Transport 555 Summary 556 Key Terms 557 Questions and Problems 557 Critical Thinking Problems 558 19 Protein Structure and Function 559 CHEMISTRY CONNECTION: Angiogenesis Inhibitors: Proteins That Inhibit Tumor Growth 560 19.1 Cellular Functions of Proteins 561 19.2 The _-Amino Acids 561 A CLINICAL PERSPECTIVE: Proteins in the Blood 562 19.3 The Peptide Bond 565 A HUMAN PERSPECTIVE: The Opium Poppy and Peptides in the Brain 568 19.4 The Primary Structure of Proteins 570 19.5 The Secondary Structure of Proteins 570 Helix 571 Pleated Sheet 572 19.6 The Tertiary Structure of Proteins 574 A HUMAN PERSPECTIVE: Collagen: A Protein That Holds Us Together 575 19.7 The Quaternary Structure of Proteins 577 19.8 An Overview of Protein Structure and Function 577 19.9 Myoglobin and Hemoglobin 579 Myoglobin and Oxygen Storage 579 Hemoglobin and Oxygen Transport 579 Oxygen Transport from Mother to Fetus 581 Sickle Cell Anemia 581 A MEDICAL PERSPECTIVE: Immunoglobulins: Proteins That Defend the Body 582 19.10 Denaturation of Proteins 584 19.11 Dietary Protein and Protein Digestion 587 Summary 588 Key Terms 589 Questions and Problems 589 Critical Thinking Problems 591 20 Enzymes 593 CHEMISTRY CONNECTION: Super Hot Enzymes and the Origin of Life 594 20.1 Nomenclature and Classification 595 Classification of Enzymes 595 Nomenclature of Enzymes 599 20.2 The Effect of Enzymes on the Activation Energy of a Reaction 600 20.3 The Effect of Substrate Concentration on Enzyme-Catalyzed Reactions 600 20.4 The Enzyme-Substrate Complex 601 20.5 Specificity of the Enzyme-Substrate Complex 602 20.6 The Transition State and Product Formation 603 A MEDICAL PERSPECTIVE: HIV Protease Inhibitors and Pharmaceutical Drug Design 604 20.7 Cofactors and Coenzymes 606 20.8 Environmental Effects 608 Effect of pH 608 Effect of Temperature 610 A MEDICAL PERSPECTIVE: 1-Antitrypsin and Familial Emphysema 611 20.9 Regulation of Enzyme Activity 612 Allosteric Enzymes 612 Feedback Inhibition 613 Zymogens 614 Protein Modification 614 20.10 Inhibition of Enzyme Activity 615 Irreversible Inhibitors 615 Reversible, Competitive Inhibitors 615 A CLINICAL PERSPECTIVE: Enzymes, Nerve Transmission, and Nerve Agents 616 Reversible, Noncompetitive Inhibitors 618 20.11 Proteolytic Enzymes 618 A CLINICAL PERSPECTIVE: Enzymes, Isoenzymes, and Myocardial Infarction 620 20.12 Uses of Enzymes in Medicine 622 Summary 624 Key Terms 625 Questions and Problems 625 Critical Thinking Problems 626 21 Carbohydrate Metabolism 629 CHEMISTRY CONNECTION: The Man Who Got Tipsy from Eating Pasta 630 21.1 ATP: The Cellular Energy Currency 631 21.2 Overview of Catabolic Processes 634 Stage I: Hydrolysis of Dietary Macromolecules into Small Subunits 635 Stage II: Conversion of Monomers into a Form That Can Be Completely Oxidized 636 Stage III: The Complete Oxidation of Nutrients and the Production of ATP 637 21.3 Glycolysis 637 A MEDICAL PERSPECTIVE: Genetic Disorders of Glycolysis 638 An Overview 637 Reactions of Glycolysis 640 Regulation of Glycolysis 645 21.4 Fermentations 646 A HUMAN PERSPECTIVE: Fermentations: The Good, the Bad, and the Ugly 648 Lactate Fermentation 646 Alcohol Fermentation 647 21.5 The Pentose Phosphate Pathway 649 21.6 Gluconeogenesis: The Synthesis of Glucose 650 21.7 Glycogen Synthesis and Degradation 652 The Structure of Glycogen 653 Glycogenolysis: Glycogen Degradation 653 Glycogenesis: Glycogen Synthesis 655 Compatibility of Glycogenesis and Glycogenolysis 658 A CLINICAL PERSPECTIVE: Diagnosing Diabetes 659 A HUMAN PERSPECTIVE: Glycogen Storage Diseases 660 Summary 661 Key Terms 661 Questions and Problems 661 Critical Thinking Problems 663 22 Aerobic Respiration and Energy Production 665 CHEMISTRY CONNECTION: Mitochondria from Mom 666 22.1 The Mitochondria 667 Structure and Function 667 Origin of the Mitochondria 667 A HUMAN PERSPECTIVE: Exercise and Energy Metabolism 668 22.2 Conversion of Pyruvate to Acetyl CoA 668 22.3 An Overview of Aerobic Respiration 671 22.4 The Citric Acid Cycle (The Krebs Cycle) 672 Reactions of the Citric Acid Cycle 672 22.5 Control of the Citric Acid Cycle 675 22.6 Oxidative Phosphorylation 676 Electron Transport Systems and the Hydrogen Ion Gradient 676 ATP Synthase and the Production of ATP 677 Summary of the Energy Yield 680 A HUMAN PERSPECTIVE: Brown Fat: The Fat That Makes You Thin? 678 22.7 The Degradation of Amino Acids 681 Removal of -Amino Groups: Transamination 681 Removal of -Amino Groups: Oxidative Deamination 683 The Fate of Amino Acid Carbon Skeletons 683 22.8 The Urea Cycle 685 Reactions of the Urea Cycle 685 A MEDICAL PERSPECTIVE: Pyruvate Carboxylase Deficiency 688 22.9 Overview of Anabolism: The Citric Acid Cycle as a Source of Biosynthetic Intermediates 689 Summary 691 Key Terms 691 Questions and Problems 692 Critical Thinking Problems 693 23 Fatty Acid Metabolism 695 CHEMISTRY CONNECTION: Obesity: A Genetic Disorder? 696 23.1 Lipid Metabolism in Animals 697 Digestion and Absorption of Dietary Triglycerides 697 Lipid Storage 698 23.2 Fatty Acid Degradation 700 An Overview of Fatty Acid Degradation 700 A HUMAN PERSPECTIVE: Losing Those Unwanted Pounds of Adipose Tissue 702 The Reactions of Oxidation 704 23.3 Ketone Bodies 707 Ketosis 707 Ketogenesis 708 A CLINICAL PERSPECTIVE: Diabetes Mellitus and Ketone Bodies 710 23.4 Fatty Acid Synthesis 712 A Comparison of Fatty Acid Synthesis and Degradation 712 23.5 The Regulation of Lipid and Carbohydrate Metabolism 714 The Liver 714 Adipose Tissue 715 Muscle Tissue 715 The Brain 716 23.6 The Effects of Insulin and Glucagon on Cellular Metabolism 716 Summary 718 Key Terms 718 Questions and Problems 718 Critical Thinking Problems 719 24 Introduction to Molecular Genetics 721 CHEMISTRY CONNECTION: Molecular Genetics and Detection of Human Genetic Disease 722 24.1 The Structure of the Nucleotide 723 Chemical Composition of DNA and RNA 723 Nucleotide Structure 723 24.2 The Structure of DNA and RNA 726 DNAStructure: The Double Helix 726 A CLINICAL PERSPECTIVE: Fooling the AIDS Virus with "Look-Alike" Nucleotides 728 Chromosomes 729 RNA Structure 732 24.3 DNA Replication 732 24.4 Information Flow in Biological Systems 734 Classes of RNA Molecules 734 Transcription 734 Post-transcriptional Processing of RNA 736 24.5 The Genetic Code 738 24.6 Protein Synthesis 741 The Role of Transfer RNA 741 The Process of Translation 742 24.7 Mutation, Ultraviolet Light, and DNA Repair 743 The Nature of Mutations 743 The Results of Mutations 745 Mutagens and Carcinogens 747 Ultraviolet Light Damage and DNA Repair 747 A CLINICAL PERSPECTIVE: The Ames Test for Carcinogens 746 Consequences of Defects in DNA Repair 748 24.8 Recombinant DNA 748 Tools Used in the Study of DNA 748 Genetic Engineering 750 A HUMAN PERSPECTIVE: DNA Fingerprinting 751 24.9 Polymerase Chain Reaction 754 A MEDICAL PERSPECTIVE: A Genetic Approach to Familial Emphysema 754 24.10 The Human Genome Project 755 Genetic Strategies for Genome Analysis 756 DNASequencing 756 Summary 757 Key Terms 758 Questions and Problems 759 Critical Thinking Problems 760 Appendix A: A Review of Mathematics Applied to Problem Solving in Chemistry 761 Appendix B: Table of Formula Weights 772 Appendix C: Determination of Composition and Formulas of Compounds 773 Appendix D: Stereochemistry and Stereoisomers Revisited 777 Appendix E: Lipid-Soluble Vitamins 783 Appendix F: Water-Soluble Vitamins 788 Appendix G: Energy Yields from Aerobic Respiration: Some Alternatives 795 Appendix H: Minerals and Cellular Function 797 Glossary 801 Answers to Odd-Numbered Problems 817 Credits 853 Index 855 Chemistry Connections and Perspectives Chemistry Connection Chance Favors the Prepared Mind 2 Curiosity, Science, and Medicine 34 Managing Mountains of Information 54 Magnets and Migration 78 The Chemistry of Automobile Air Bags 116 The Demise of the Hindenburg 144 Seeing a Thought 170 The Cost of Energy? More Than You Imagine 202 Drug Delivery 234 An Extraordinary Woman in Science 268 The Origin of Organic Compounds 294 A Cautionary Tale: DDT and Biological Magnification 326 Polyols for the Sweet Tooth 364 Genetic Complexity from Simple Molecules 394 Wake Up, Sleeping Gene 422 The Nicotine Patch 458 Chemistry Through the Looking Glass 490 Lifesaving Lipids 522 Angiogenesis Inhibitors: Proteins That Inhibit Tumor Growth 560 Super Hot Enzymes and the Origin of Life 594 The Man Who Got Tipsy from Eating Pasta 630 Mitochondria from Mom 666 Obesity: A Genetic Disorder? 696 Molecular Genetics and Detection of Human Genetic Disease 722 A Human Perspective The Scientific Method 4 Food Calories 25 Atomic Spectra and the Fourth of July 47 Origin of the Elements 91 Scuba Diving: Nitrogen and the Bends 179 An Extraordinary Molecule 194 Triboluminescence: Sparks in the Dark with Candy 207 Folklore, Science, and Technology 343 Life without Polymers? 347 Aromatic Compounds and Carcinogenesis 355 Alcohol Consumption and the Breathalyzer Test 380 The Chemistry of Vision 415 The Chemistry of Flavor and Fragrance 434 Carboxylic Acid Derivatives of Special Interest 449 Tooth Decay and Simple Sugars 493 Blood Transfusions and the Blood Group Antigens 510 Mummies Made of Soap 528 Anabolic Steroids and Athletics 539 The Opium Poppy and Peptides in the Brain 568 Collagen: A Protein That Holds Us Together 575 Fermentations: The Good, the Bad, and the Ugly 648 Glycogen Storage Diseases 660 Exercise and Energy Metabolism 668 Brown Fat: The Fat That Makes You Thin? 678 Losing Those Unwanted Pounds of Adipose Tissue 702 DNAFingerprinting 751 A Clinical Perspective Diagnosis Based on Waste 29 Dietary Calcium 69 Blood Pressure and the Sodium Ion/Potassium Ion Ratio 93 Carbon Monoxide Poisoning: A Case of Combining Ratios 130 Autoclaves and the Gas Laws 151 Blood Gases and Respiration 160 Oral Rehydration Therapy 191 Hemodialysis 195 Hot and Cold Packs 214 Control of Blood pH 255 Oxidizing Agents for Chemical Control of Microbes 256 Electrochemical Reactions in the Statue of Liberty and in Dental Fillings 258 Magnetic Resonance Imaging 284 Medical Applications of Aldehydes 403 Medically Important Amines 465 Medically Important Amides 475 The Bacterial Cell Wall 514 Disorders of Sphingolipid Metabolism 537 Steroids and the Treatment of Heart Disease 541 Liposome Delivery Systems 550 Antibiotics That Destroy Membrane Integrity 552 Proteins in the Blood 562 Enzymes, Nerve Transmission, and Nerve Agents 616 Enzymes, Isoenzymes, and Myocardial Infarction 620 Diagnosing Diabetes 659 Diabetes Mellitus and Ketone Bodies 710 Fooling the AIDS Virus with "Look-Alike" Nucleotides 728 The Ames Test for Carcinogens 746 A Medical Perspective Copper Deficiency and Wilson's Disease 58 Pharmaceutical Chemistry: The Practical Significance of Percent Yield 138 Turning the Human Body into a Battery 261 Polyhalogenated Hydrocarbons Used as Anesthetics 316 Chloroform in Your Swimming Pool? 317 Killer Alkynes in Nature 330 Fetal Alcohol Syndrome 370 That Golden Tan Without the Fear of Skin Cancer 408 Secondary Amines and Cancer 469 Semisynthetic Penicillins 474 Monosaccharide Derivatives and Heteropolysaccharides of Medical Interest 516 Immunoglobulins: Proteins That Defend the Body 582 HIV Protease Inhibitors and Pharmaceutical Drug Design 604 1-Antitrypsin and Familial Emphysema 611 Genetic Disorders of Glycolysis 638 Pyruvate Carboxylase Deficiency 688 A Genetic Approach to Familial Emphysema 754 An Environmental Perspective Electromagnetic Radiation and Its Effects on Our Everyday Lives 48 The Greenhouse Effect and Global Warming 157 Acid Rain 248 Nuclear Waste Disposal 279 Radon and Indoor Air Pollution 288 Frozen Methane: Treasure or Threat? 297 Oil-Eating Bacteria 309 The Petroleum Industry and Gasoline Production 314 Plastic Recycling 348 Garbage Bags from Potato Peels 430 UR - http://www.loc.gov/catdir/toc/ecip0515/2005018776.html ER -