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Fundamentals of General, Organic, and Biological Chemistry, Sixth Edition

by John McMurry; Mary Castellion; David S. Ballantine; Carl A. Hoeger; Virginia E. Peterson

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Copyright, ii
About the Authors, iii
Applications, xiii
Preface, xv
Concise, Accessible, and Unique, xxiv
Chapter 1. Matter and Life, 2
1.1. Chemistry: The Central Science, 3
1.2. States of Matter, 5
1.3. Classification of Matter, 6
1.4. An Example of a Chemical Reaction, 8
1.5. Chemical Elements and Symbols, 8
Application: Aspirin—A Case Study, 9
1.6. Elements and the Periodic Table, 11
Application: Mercury and Mercury Poisoning, 14
Chapter 2. Measurements in Chemistry, 18
2.1. Physical Quantities, 19
2.2. Measuring Mass, 21
2.3. Measuring Length and Volume, 22
2.4. Measurement and Significant Figures, 24
2.5. Scientific Notation, 26
Application: Powers of 10, 28
2.6. Rounding Off Numbers, 29
2.7. Problem Solving: Converting a Quantity from One Unit to Another, 31
2.8. Problem Solving: Estimating Answers, 33
2.9. Measuring Temperature, 35
Application: Temperature-Sensitive Materials, 36
2.10. Energy and Heat, 38
2.11. Density, 39
Application: Obesity and Body Fat, 41
2.12. Specific Gravity, 42
Chapter 3. Atoms and the Periodic Table, 48
3.1. Atomic Theory, 49
Application: Are Atoms Real?, 52
3.2. Elements and Atomic Number, 53
3.3. Isotopes and Atomic Weight, 54
3.4. The Periodic Table, 57
3.5. Some Characteristics of Different Groups, 59
Application: The Origin of Chemical Elements, 61
3.6. Electronic Structure of Atoms, 61
3.7. Electron Configurations, 64
3.8. Electron Configurations and the Periodic Table, 68
3.9. Electron-Dot Symbols, 71
Application: Atoms and Light, 72
Chapter 4. Ionic Compounds, 78
4.1. Ions, 79
4.2. Periodic Properties and Ion Formation, 81
4.3. Ionic Bonds, 83
4.4. Some Properties of Ionic Compounds, 84
4.5. Ions and the Octet Rule, 84
Application: Minerals and Gems, 85
4.6. Ions of Some Common Elements, 87
Application: Salt, 89
4.7. Naming Ions, 90
4.8. Polyatomic Ions, 91
Application: Biologically Important Ions, 92
4.9. Formulas of Ionic Compounds, 93
4.10. Naming Ionic Compounds, 95
4.11. H^+ and OH^- Ions: An Introduction to Acids and Bases, 98
Application: Osteoporosis, 100
Chapter 5. Molecular Compounds, 106
5.1. Covalent Bonds, 107
5.2. Covalent Bonds and the Periodic Table, 110
5.3. Multiple Covalent Bonds, 113
5.4. Coordinate Covalent Bonds, 115
Application: CO and NO: Pollutants or Miracle Molecules?, 116
5.5. Molecular Formulas and Lewis Structures, 117
5.6. Drawing Lewis Structures, 117
5.7. The Shapes of Molecules, 122
Application: VERY Big Molecules, 127
5.8. Polar Covalent Bonds and Electronegativity, 128
5.9. Polar Molecules, 130
5.10. Naming Binary Molecular Compounds, 132
5.11. Characteristics of Molecular Compounds, 134
Application: Damascenone by Any Other Name Would Smell as Sweet, 135
Chapter 6. Chemical Reactions: Classification and Mass Relationships, 142
6.1. Chemical Equations, 143
6.2. Balancing Chemical Equations, 145
6.3. Avogadro’s Number and the Mole, 148
6.4. Gram–Mole Conversions, 152
Application: Did Ben Franklin Have Avogadro’s Number? A Ballpark Calculation, 153
6.5. Mole Relationships and Chemical Equations, 155
6.6. Mass Relationships and Chemical Equations, 156
6.7. Limiting Reagent and Percent Yield, 159
6.8. Classes of Chemical Reactions, 161
Application: Anemia – A Limiting Reagent Problem?, 162
6.9. Precipitation Reactions and Solubility Guidelines, 163
Application: Gout and Kidney Stones: Problems in Solubility, 165
6.10. Acids, Bases, and Neutralization Reactions, 165
6.11. Redox Reactions, 166
Application: Batteries, 171
6.12. Recognizing Redox Reactions, 172
6.13. Net Ionic Equations, 174
Chapter 7. Chemical Reactions: Energy, Rates, and Equilibrium, 182
7.1. Energy and Chemical Bonds, 183
7.2. Heat Changes during Chemical Reactions, 183
7.3. Exothermic and Endothermic Reactions, 184
7.4. Why Do Chemical Reactions Occur? Free Energy, 188
Application: Energy from Food, 189
7.5. How Do Chemical Reactions Occur? Reaction Rates, 193
7.6. Effects of Temperature, Concentration, and Catalysts on Reaction Rates, 195
7.7. Reversible Reactions and Chemical Equilibrium, 198
Application: Regulation of Body Temperature, 198
7.8. Equilibrium Equations and Equilibrium Constants, 200
7.9. Le Châtelier’s Principle: The Effect of Changing Conditions on Equilibria, 203
Application: Nitrogen Fixation, 207
Chapter 8. Gases, Liquids, and Solids, 214
8.1. States of Matter and Their Changes, 215
8.2. Gases and the Kinetic–Molecular Theory, 218
8.3. Pressure, 218
8.4. Boyle’s Law: The Relation between Volume and Pressure, 222
Application: Blood Pressure, 223
8.5. Charles’s Law: The Relation between Volume and Temperature, 225
8.6. Gay-Lussac’s Law: The Relation between Pressure and Temperature, 226
8.7. The Combined Gas Law, 228
8.8. Avogadro’s Law: The Relation between Volume and Molar Amount, 229
8.9. The Ideal Gas Law, 231
8.10. Partial Pressure and Dalton’s Law, 233
8.11. Intermolecular Forces, 235
Application: Greenhouse Gases and Global Warming, 236
8.12. Liquids, 240
8.13. Water: A Unique Liquid, 242
8.14. Solids, 243
8.15. Changes of State, 244
Application: Biomaterials for Joint Replacement, 246
Application: CO_2 as an Environmentally Friendly Solvent, 248
Chapter 9. Solutions, 254
9.1. Mixtures and Solutions, 255
9.2. The Solution Process, 257
9.3. Solid Hydrates, 259
9.4. Solubility, 260
9.5. The Effect of Temperature on Solubility, 261
9.6. The Effect of Pressure on Solubility: Henry’s Law, 262
9.7. Units of Concentration, 265
Application: Breathing and Oxygen Transport, 266
9.8. Dilution, 273
9.9. Ions in Solution: Electrolytes, 275
9.10. Electrolytes in Body Fluids: Equivalents and Milliequivalents, 276
9.11. Properties of Solutions, 278
Application: Electrolytes, Fluid Replacement, and Sports Drinks, 279
9.12. Osmosis and Osmotic Pressure, 282
9.13. Dialysis, 285
Application: Timed-Release Medications, 286
Chapter 10. Acids and Bases, 292
10.1. Acids and Bases in Aqueous Solution, 293
10.2. Some Common Acids and Bases, 294
10.3. The Brønsted–Lowry Definition of Acids and Bases, 295
10.4. Water as Both an Acid and a Base, 298
10.5. Acid and Base Strength, 299
Application: GERD—Too Much Acid or Not Enough?, 302
10.6. Acid Dissociation Constants, 303
10.7. Dissociation of Water, 304
10.8. Measuring Acidity in Aqueous Solution: pH, 306
10.9. Working with pH, 308
10.10. Laboratory Determination of Acidity, 310
Application: pH of Body Fluids, 311
10.11. Buffer Solutions, 312
10.12. Buffers in the Body, 315
Application: Buffers in the Body: Acidosis and Alkalosis, 317
10.13. Acid and Base Equivalents, 318
10.14. Some Common Acid–Base Reactions, 320
10.15. Titration, 321
Application: Acid Rain, 324
10.16. Acidity and Basicity of Salt Solutions, 325
Chapter 11. Nuclear Chemistry, 332
11.1. Nuclear Reactions, 333
11.2. The Discovery and Nature of Radioactivity, 334
11.3. Stable and Unstable Isotopes, 335
11.4. Nuclear Decay, 336
11.5. Radioactive Half-Life, 341
Application: Medical Uses of Radioactivity, 342
11.6. Radioactive Decay Series, 344
11.7. Ionizing Radiation, 345
11.8. Detecting Radiation, 347
11.9. Measuring Radiation, 348
Application: Irradiated Food, 349
11.10. Artificial Transmutation, 350
Application: Body Imaging, 352
11.11. Nuclear Fission and Nuclear Fusion, 352
Application: Archaeological Radiocarbon Dating, 355
Chapter 12. Introduction to Organic Chemistry: Alkanes, 360
12.1. The Nature of Organic Molecules, 361
12.2. Families of Organic Molecules: Functional Groups, 363
12.3. The Structure of Organic Molecules: Alkanes and Their Isomers, 368
12.4. Drawing Organic Structures, 370
12.5. The Shapes of Organic Molecules, 376
12.6. Naming Alkanes, 378
Application: Displaying Molecular Shapes, 379
12.7. Properties of Alkanes, 385
12.8. Reactions of Alkanes, 386
12.9. Cycloalkanes, 387
Application: Petroleum, 388
12.10. Drawing and Naming Cycloalkanes, 389
Chapter 13. Alkenes, Alkynes, and Aromatic Compounds, 396
13.1. Alkenes and Alkynes, 397
13.2. Naming Alkenes and Alkynes, 398
13.3. The Structure of Alkenes: Cis–Trans Isomerism, 401
13.4. Properties of Alkenes and Alkynes, 405
13.5. Types of Organic Reactions, 405
Application: The Chemistry of Vision, 406
13.6. Reactions of Alkenes and Alkynes, 409
13.7. How Alkene Addition Reactions Occur, 415
13.8. Alkene Polymers, 416
Application: Polymer Applications—Currency, 420
13.9. Aromatic Compounds and the Structure of Benzene, 420
Application: Polycyclic Aromatic Hydrocarbons and Cancer, 422
13.10. Naming Aromatic Compounds, 423
13.11. Reactions of Aromatic Compounds, 426
Application: Why We See Color, 428
Chapter 14. Some Compounds with Oxygen, Sulfur, or a Halogen, 434
14.1. Alcohols, Phenols, and Ethers, 435
14.2. Some Common Alcohols, 437
14.3. Naming Alcohols, 438
14.4. Properties of Alcohols, 441
14.5. Reactions of Alcohols, 442
Application: Ethyl Alcohol as a Drug and a Poison, 447
14.6. Phenols, 448
14.7. Acidity of Alcohols and Phenols, 449
Application: Phenols as Antioxidants, 450
14.8. Ethers, 451
14.9. Thiols and Disulfides, 453
Application: Inhaled Anesthetics, 454
14.10. Halogen-Containing Compounds, 455
Application: Chlorofluorocarbons and the Ozone Hole, 457
Chapter 15. Amines, 464
15.1. Amines, 465
Application: Chemical Information, 468
15.2. Properties of Amines, 471
15.3. Heterocyclic Nitrogen Compounds, 473
Application: NO: A Small Molecule with Big Responsibilities, 475
15.4. Basicity of Amines, 476
Application: Organic Compounds in Body Fluids and the “Solubility Switch”, 478
15.5. Amine Salts, 479
15.6. Amines in Plants: Alkaloids, 481
Application: Toxicology, 482
Chapter 16. Aldehydes and Ketones, 488
16.1. The Carbonyl Group, 489
16.2. Naming Aldehydes and Ketones, 492
Application: Chemical Warfare among the Insects, 493
16.3. Properties of Aldehydes and Ketones, 494
Application: Vanilla: Which Kind Is Best?, 496
16.4. Some Common Aldehydes and Ketones, 497
16.5. Oxidation of Aldehydes, 499
16.6. Reduction of Aldehydes and Ketones, 500
Application: How Toxic Is Toxic?, 503
16.7. Addition of Alcohols: Hemiacetals and Acetals, 504
Chapter 17. Carboxylic Acids and Their Derivatives, 516
17.1. Carboxylic Acids and Their Derivatives: Properties and Names, 517
17.2. Some Common Carboxylic Acids, 527
17.3. Acidity of Carboxylic Acids, 528
Application: Acids for the Skin, 530
Application: Acid Salts as Food Additives, 531
17.4. Reactions of Carboxylic Acids: Ester and Amide Formation, 532
17.5. Aspirin and Other Over-the-Counter Carboxylic Acid Derivatives, 535
17.6. Hydrolysis of Esters and Amides, 538
17.7. Polyamides and Polyesters, 541
Application: Kevlar: A Life-Saving Polymer, 542
17.8. Phosphoric Acid Derivatives, 543
Chapter 18. Amino Acids and Proteins, 552
18.1. An Introduction to Biochemistry, 553
18.2. Protein Structure and Function: An Overview, 555
18.3. Amino Acids, 556
18.4. Acid–Base Properties of Amino Acids, 559
Application: Nutrition in Health and Disease, 560
18.5. Handedness, 561
18.6. Molecular Handedness and Amino Acids, 562
18.7. Primary Protein Structure, 565
Application: Proteins in the Diet, 569
18.8. Shape-Determining Interactions in Proteins, 570
Application: Protein Analysis by Electrophoresis, 573
18.9. Secondary Protein Structure, 574
18.10. Tertiary Protein Structure, 576
18.11. Quaternary Protein Structure, 579
Application: Collagen—A Tale of Two Diseases, 581
18.12. Chemical Properties of Proteins, 583
Application: Prions: Proteins that Cause Disease, 584
Chapter 19. Enzymes and Vitamins, 592
19.1. Catalysis by Enzymes, 593
19.2. Enzyme Cofactors, 595
19.3. Enzyme Classification, 596
Application: Biocatalysis: Industrial Biochemistry, 600
19.4. How Enzymes Work, 600
19.5. Effect of Concentration on Enzyme Activity, 603
19.6. Effect of Temperature and pH on Enzyme Activity, 604
19.7. Enzyme Regulation: Feedback and Allosteric Control, 606
Application: Extremozymes—Enzymes from the Edge, 607
Application: Enzymes in Medical Diagnosis, 608
19.8. Enzyme Regulation: Inhibition, 610
Application: Enzyme Inhibitors as Drugs, 613
19.9. Enzyme Regulation: Covalent Modification and Genetic Control, 614
19.10. Vitamins, 615
Application: Vitamins, Minerals, and Food Labels, 621
Chapter 20. Chemical Messengers: Hormones, Neurotransmitters, and Drugs, 628
20.1. Messenger Molecules, 629
20.2. Hormones and the Endocrine System, 630
Application: Homeostasis, 631
20.3. How Hormones Work: Epinephrine and Fight-or-Flight, 634
20.4. Amino Acid Derivatives and Polypeptides as Hormones, 636
20.5. Steroid Hormones, 638
Application: Plant Hormones, 641
20.6. Neurotransmitters, 641
20.7. How Neurotransmitters Work: Acetylcholine, Its Agonists and Antagonists, 643
20.8. Histamine and Antihistamines, 646
Application: And from This Little Frog ..., 647
20.9. Serotonin, Norepinephrine, and Dopamine, 648
20.10. Neuropeptides and Pain Relief, 650
20.11. Drug Discovery and Drug Design, 651
Chapter 21. The Generation of Biochemical Energy, 658
21.1. Energy and Life, 659
21.2. Energy and Biochemical Reactions, 660
Application: Life without Sunlight, 663
21.3. Cells and Their Structure, 664
21.4. An Overview of Metabolism and Energy Production, 666
21.5. Strategies of Metabolism: ATP and Energy Transfer, 669
21.6. Strategies of Metabolism: Metabolic Pathways and Coupled Reactions, 671
Application: Basal Metabolism, 673
21.7. Strategies of Metabolism: Oxidized and Reduced Coenzymes, 674
21.8. The Citric Acid Cycle, 677
21.9. The Electron-Transport Chain and ATP Production, 680
Application: Energy Undone: Blockers and Uncouplers of Oxidative Phosphorylation, 683
21.10. Harmful Oxygen By-Products and Antioxidant Vitamins, 685
Application: Plants and Photosynthesis, 686
Chapter 22. Carbohydrates, 692
22.1. An Introduction to Carbohydrates, 693
22.2. Handedness of Carbohydrates, 695
22.3. The D and L Families of Sugars: Drawing Sugar Molecules, 697
Application: Chirality and Drugs, 699
22.4. Structure of Glucose and Other Monosaccharides, 700
Application: Carbohydrates in the Diet, 704
22.5. Some Important Monosaccharides, 705
22.6. Reactions of Monosaccharides, 709
22.7. Disaccharides, 711
Application: Cell Walls: Rigid Defense Systems, 714
22.8. Variations on the Carbohydrate Theme, 715
22.9. Some Important Polysaccharides, 717
Application: Cell-Surface Carbohydrates and Blood Type, 720
Application: Dietary Fiber, 722
Chapter 23. Carbohydrate Metabolism, 728
23.1. Digestion of Carbohydrates, 729
23.2. Glucose Metabolism: An Overview, 730
23.3. Glycolysis, 732
23.4. Entry of Other Sugars into Glycolysis, 736
Application: Tooth Decay, 737
23.5. The Fate of Pyruvate, 738
23.6. Energy Output in Complete Catabolism of Glucose, 740
Application: Microbial Fermentations: Ancient and Modern, 741
23.7. Regulation of Glucose Metabolism and Energy Production, 741
23.8. Metabolism in Fasting and Starvation, 742
23.9. Metabolism in Diabetes Mellitus, 744
Application: Diagnosis and Monitoring of Diabetes, 744
23.10. Glycogen Metabolism: Glycogenesis and Glycogenolysis, 746
Application: The Biochemistry of Running, 748
23.11. Gluconeogenesis: Glucose from Noncarbohydrates, 749
Application: Polysaccharides—What Are They Good For?, 751
Chapter 24. Lipids, 756
24.1. Structure and Classification of Lipids, 757
24.2. Fatty Acids and Their Esters, 759
24.3. Properties of Fats and Oils, 762
Application: Lipids in the Diet, 763
24.4. Chemical Reactions of Triacylglycerols, 766
Application: Detergents, 767
24.5. Cell Membrane Lipids: Phospholipids and Glycolipids, 768
24.6. Cell Membrane Lipids: Cholesterol, 774
Application: Butter and Its Substitutes, 774
24.7. Structure of Cell Membranes, 775
Application: Liposomes for Health and Beauty, 775
24.8. Transport Across Cell Membranes, 778
24.9. Eicosanoids: Prostaglandins and Leukotrienes, 780
Chapter 25. Lipid Metabolism, 786
25.1. Digestion of Triacylglycerols, 787
25.2. Lipoproteins for Lipid Transport, 789
Application: Lipids and Atherosclerosis, 791
25.3. Triacylglycerol Metabolism: An Overview, 792
Application: Fat Storage: A Good Thing or Not?, 794
25.4. Storage and Mobilization of Triacylglycerols, 794
25.5. Oxidation of Fatty Acids, 796
25.6. Energy from Fatty Acid Oxidation, 797
25.7. Ketone Bodies and Ketoacidosis, 799
Application: The Liver, Clearinghouse for Metabolism, 801
25.8. Biosynthesis of Fatty Acids, 802
Chapter 26. Nucleic Acids and Protein Synthesis, 808
26.1. DNA, Chromosomes, and Genes, 809
26.2. Composition of Nucleic Acids, 810
26.3. The Structure of Nucleic Acid Chains, 815
26.4. Base Pairing in DNA: The Watson–Crick Model, 817
26.5. Nucleic Acids and Heredity, 819
Application: Viruses and AIDS, 820
26.6. Replication of DNA, 822
26.7. Structure and Function of RNA, 825
Application: It’s a Ribozyme!, 826
26.8. Transcription: RNA Synthesis, 826
26.9. The Genetic Code, 829
26.10. Translation: Transfer RNA and Protein Synthesis, 830
Application: “Bird Flu”: The Next Epidemic?, 834
Chapter 27. Genomics, 840
27.1. Mapping the Human Genome, 841
27.2. A Trip Along a Chromosome, 843
Application: Whose Genome Is It?, 844
27.3. Mutations and Polymorphisms, 846
27.4. Recombinant DNA, 849
Application: Serendipity and the Polymerase Chain Reaction, 850
Application: DNA Fingerprinting, 852
27.5. Genomics: Using What We Know, 853
Chapter 28. Protein and Amino Acid Metabolism, 860
28.1. Digestion of Protein, 861
28.2. Amino Acid Metabolism: An Overview, 862
28.3. Amino Acid Catabolism: The Amino Group, 864
28.4. The Urea Cycle, 866
Application: Gout: When Biochemistry Goes Awry, 869
Application: The Importance of Essential Amino Acids and Effects of Deficiencies, 870
28.5. Amino Acid Catabolism: The Carbon Atoms, 871
28.6. Biosynthesis of Nonessential Amino Acids, 872
Chapter 29. Body Fluids, 878
29.1. Body Water and Its Solutes, 879
29.2. Fluid Balance, 882
29.3. Blood, 884
29.4. Plasma Proteins, White Bloods Cells, and Immunity, 886
Application: The Blood–Brain Barrier, 888
29.5. Blood Clotting, 890
29.6. Red Blood Cells and Blood Gases, 891
29.7. The Kidney and Urine Formation, 895
29.8. Urine Composition and Function, 895
Application: Automated Clinical Laboratory Analysis, 897
Appendix A. Scientific Notation, A-1
Appendix B. Conversion Factors, A-5
Glossary, A-6
Answers to Selected Problems, A-13
Photo Credits, A-49
Index, A-51
End Papers, EP-1

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