General, organic, and biochemistry / Katherine J. Denniston, Joseph J. Topping, Robert L. Caret

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