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