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

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