Introduction to General, Organic, and Biochemistry, Twelfth Edition
By Frederick A. Bettelheim, William H. Brown, Mary K. Ca mpbell, Shaw n O. Farrell, Omar J. Torres and Sara Madsen
Contents:
Chapter 1 Matter, Energy, and
Measurement 1
1.1 Chemistry and the Study of Matter 1
1.2 The Scientific Method 3
1.3 Reporting Numbers in Science 5
How To Determine the Number of Significant Figures in
a Number 6
1.4 Making Measurements 7
1.5 Unit Conversions 12
How To Do Unit Conversions by the Factor-Label
Method 13
1.6 States of Matter 17
1.7 Density and Specific Gravity 18
1.8 Describing the Various Forms of Energy 20
Chapter Summary 21
Problems 22
CHEMICAL CONNECTIONS
1A Drug Dosage and Body Mass 11
Chapter 2 Atoms 26
2.1 Composition of Matter 26
2.2 Classifying Matter 27
2.3 Postulates of Dalton’s Atomic Theory 30
2.4 Composition of Atoms 33
2.5 The Periodic Table 38
2.6 Arrangement of Electrons in an Atom 44
2.7 Electron Configuration and the Periodic Table 51
2.8 Periodic Properties 52
Chapter Summary 55
Problems 56
CHEMICAL CONNECTIONS
2A Elements Necessary for Human Life 28
2B Abundance of Elements Present in the Human Body
and in the Earth’s Crust 32
2C Strontium-90 42
2D The Use of Metals as Historical Landmarks 43
Chapter 3 Chemical Bonds 63
3.1 The Octet Rule 63
3.2 Naming Anions and Cations 66
3.3 The Two Major Types of Chemical Bonds 68
3.4 An Ionic Bond 70
3.5 Naming Ionic Compounds 72
3.6 A Covalent Bond 74
How To Draw Lewis Structures 77
3.7 Naming Binary Covalent Compounds 82
3.8 Resonance 82
How To Draw Curved Arrows and Push Electrons 84
3.9 Predicting Bond Angles in Covalent Molecules 87
3.10 Determining If a Molecule Is Polar 91
Chapter Summary 93
Problems 94
CHEMICAL CONNECTIONS
3A Coral Chemistry and Broken Bones 68
3B Ionic Compounds in Medicine 75
3C Nitric Oxide: Air Pollutant and Biological
Messenger 83
Chapter 4 Chemical
Reactions and Energy
Calculations 104
4.1 The Chemical Reaction 104
4.2 Balancing Chemical
Equations 104
How To Balance a Chemical
Equation 105
4.3 Predicting Whether Ions in
Aqueous Solution Will React
with Each Other 108
4.4 Oxidation and Reduction Reactions 112
4.5 Formula Weights and Molecular Weights 117
4.6 The Mole and Calculating Mass Relationships 117
4.7 Calculating Mass Relationships in Chemical
Reactions 121
4.8 Describing Heat and the Ways in Which It Is
Transferred 128
4.9 Heat of Reaction 131
Chapter Summary 132
Problems 133
CHEMICAL CONNECTIONS
4A Solubility and Tooth Decay 112
4B Voltaic Cells 115
4C Artificial Pacemakers and Redox 116
Chapter 5 Gases, Liquids, and Solids 140
5.1 Introduction to the Three States of Matter 140
5.2 Gas Pressure and Measurements 141
5.3 The Behavior of Gases 142
5.4 Avogadro’s Law and the Ideal Gas Law 146
5.5 Dalton’s Law of Partial Pressures 148
5.6 The Kinetic Molecular Theory 150
5.7 Types of Intermolecular Attractive Forces 151
5.8 The Behavior of Liquids at the Molecular
Level 155
Chapter Summary 161
Problems 162
CHEMICAL CONNECTIONS
5A Breathing and Boyle’s Law 143
5B Hyperbaric Medicine 149
5C Blood Pressure Measurement 157
5D The Densities of Ice and Water 160
Chapter 6 Solutions and Colloids 168
6.1 Introduction to Mixtures 168
6.2 The Most Common Types of Solutions 169
6.3 The Distinguishing Characteristics of
Solutions 169
6.4 Factors Affecting Solubility 171
6.5 The Most Common Units for Concentration 174
6.6 Water as a Good Solvent 180
6.7 Colloids 185
6.8 Colligative Properties 187
Chapter Summary 194
Problems 194
CHEMICAL CONNECTIONS
6A Acid Rain 170
6B The Bends 173
6C Electrolyte Solutions in Body and Intravenous
Fluids 181
6D Hydrates and Air Pollution: The Decay of Buildings
and Monuments 184
6E Emulsions and Emulsifying Agents 186
6F Reverse Osmosis and Desalinization 191
6G Hemodialysis 193
Chapter 7 Reaction Rates and
Chemical Equilibrium 200
7.1 Measuring Reaction Rates 200
7.2 Molecular Collisions and Reactions 202
7.3 Activation Energy and Reaction Rate 204
7.4 Rate of a Chemical Reaction 206
7.5 Equilibrium 210
7.6 The Equilibrium Constant 213
How To Interpret the Value of the Equilibrium
Constant, K 216
7.7 Le Chatelier’s Principle 218
Chapter Summary 223
Problems 224
CHEMICAL CONNECTIONS
7A Why High Fever Is Dangerous 209
7B The Effects of Lowering Body Temperature 211
7C Timed-Release Medication 212
7D Sunglasses and Le Chatelier’s Principle 221
7E The Haber Process 223
Chapter 8 Acids and Bases 229
8.1 Acids and Bases 229
8.2 Defining the Strength of Acids
and Bases 231
8.3 Conjugate Acid–Base
Pairs 233
How To Name Common Acids 235
8.4 The Position of Equilibrium in
an Acid–Base Reaction 236
8.5 Acid Ionization
Constants 238
How To Use Logs and
Antilogs 239
8.6 Properties of Acids and Bases 241
8.7 Acidic and Basic Properties of Pure Water 244
8.8 pH and pOH 246
8.9 Using Titrations to Calculate Concentration 249
8.10 Buffers 251
8.11 Calculating the pH of a Buffer 255
8.12 TRIS, HEPES, and Other Biochemical Buffers 257
Chapter Summary 260
Problems 261
Chemical Connections
8A Some Important Acids and Bases 232
8B Drugstore Antacids 245
8C Respiratory and Metabolic Acidosis 258
8D Alkalosis and the Sprinter’s Trick 260
Chapter 9 Nuclear Chemistry 266
9.1 Discovery of Radioactivity 266
9.2 Defining Radioactivity 267
9.3 Nucleus and Radioactivity 268
How To Balance a Nuclear Equation 270
9.4 Nuclear Half-Life 273
9.5 Detecting and Measuring Nuclear Radiation 276
9.6 Radiation Dosimetry and Human Health 279
9.7 Nuclear Medicine 282
9.8 Nuclear Fusion 287
9.9 Nuclear Fission and Atomic Energy 289
Chapter Summary 291
Summary of Key Reactions 292
Problems 292
CHEMICAL CONNECTIONS
9A Radioactive Dating 275
9B The Indoor Radon Problem 281
9C How Radiation Damages Tissues: Free Radicals 283
9D Magnetic Resonance Imaging 285
9E Radioactive Fallout from Nuclear Accidents 291
Chapter 10 Organic Chemistry 298
10.1 Introduction to Organic Chemistry 298
10.2 Obtaining Organic Compounds 300
10.3 Writing Structural Formulas of Organic Compounds 302
10.4 Functional Groups 304
Chapter Summary 310
Problems 310
CHEMICAL CONNECTIONS
10A Taxol: A Story of Search and Discovery 301
Chapter 11 Alkanes 316
11.1 Introduction to Alkanes 316
11.2 Writing Structural Formulas of Alkanes 317
11.3 Constitutional Isomers 318
11.4 Naming Alkanes 321
11.5 Obtaining Alkanes 325
11.6 Cycloalkanes 325
11.7 Shapes of Alkanes and Cycloalkanes 327
How To Draw Alternative Chair Conformations of
Cyclohexane 329
11.8 Cis-Trans Isomerism in Cycloalkanes 331
11.9 Physical Properties of Alkanes and
Cycloalkanes 333
11.10 Characteristic Reactions of Alkanes 336
11.11 Some Important Haloalkanes 338
Chapter Summary 339
Summary of Key Reactions 340
Problems 341
CHEMICAL CONNECTIONS
11A The Poisonous Puffer Fish 330
11B Octane Rating: What Those Numbers at the Pump Mean 336
11C The Environmental Impact of Freons 338
Chapter 12 Alkenes, Alkynes, and Aromatic
Compounds 347
12.1 Introduction to Alkenes and Alkynes 347
12.2 Structures of Alkenes and Alkynes 348
12.3 Naming Alkenes and Alkynes 349
12.4 Physical Properties of Alkenes and Alkynes 354
12.5 Characteristic Reactions of Alkenes 355
12.6 Important Polymerization Reactions of Ethylene
and Substituted Ethylenes 364
12.7 Structure of Benzene 368
12.8 Naming Aromatic Compounds 370
12.9 Reactions of Benzene and Its Derivatives 372
12.10 Phenols 374
Chapter Summary 377
Summary of Key Reactions 378
Problems 379
Chemical Connections
12A Cis-Trans Isomerism in Vision 355
12B Recycling Plastics 366
12C DDT: A Boon and a Curse 372
12D Iodide Ion and Goiter 373
12E Capsaicin, for Those Who Like It Hot 376
Chapter 13 Alcohols, Ethers, and
Thiols 388
13.1 Structures, Names, and Physical Properties of
Alcohols 389
13.2 Characteristic Reactions of
Alcohols 393
13.3 Structures, Names, and Physical
Properties of Ethers 398
13.4 Structures, Names, and Physical
Properties of Thiols 402
13.5 Commercially Important
Alcohols 404
Chapter Summary 406
Summary of Key
Reactions 407
Problems 407
CHEMICAL CONNECTIONS
13A The Importance of Hydrogen Bonding in Drug-
Receptor Interactions 394
13B Breath-Alcohol Screening 399
13C Ethylene Oxide: A Chemical Sterilant 400
13D Ethers and Anesthesia 401
Chapter 14 Chirality: The Handedness of
Molecules 413
14.1 Enantiomerism 413
How To Draw Enantiomers 417
14.2 Specifying the Configuration of a Stereocenter 419
14.3 Possible Stereoisomers for Molecules with Two or
More Stereocenters 423
14.4 Optical Activity and Chirality in the Laboratory 427
14.5 Significance of Chirality in the Biological
World 428
Chapter Summary 430
Problems 430
Chemical Connections
14A Chiral Drugs 427
Chapter 15 Amines 436
15.1 Structure of Amines 436
15.2 Names of Amines 439
15.3 Physical Properties of Amines 442
15.4 Basicity of Amines 442
15.5 Characteristic Reactions of Amines 445
Chapter Summary 449
Summary of Key Reactions 449
Problems 449
CHEMICAL CONNECTIONS
15A Amphetamines (Pep Pills) 437
15B Alkaloids 438
15C Tranquilizers 443
15D The Solubility of Drugs in Body Fluids 446
15E Epinephrine: A Prototype for the Development of
New Bronchodilators 448
Chapter 16 Aldehydes and Ketones 455
16.1 Aldehydes and Ketones 455
16.2 Naming Aldehydes and Ketones 456
16.3 Physical Properties of Aldehydes and Ketones 459
16.4 Characteristic Reactions of Aldehydes and
Ketones 460
16.5 Keto-Enol Tautomerism 467
Chapter Summary 468
Summary of Key Reactions 468
Problems 469
Chemical Connections
16A From Moldy Clover to a Blood Thinner 459
Chapter 17 Carboxylic Acids 476
17.1 Carboxylic Acids 476
17.2 Names of Carboxylic Acids 476
17.3 Physical Properties of Carboxylic Acids 480
17.4 Soaps and Detergents 481
17.5 Characteristic Reactions of Carboxylic Acids 486
Chapter Summary 494
Summary of Key Reactions 494
Problems 495
CHEMICAL CONNECTIONS
17A Trans Fatty Acids: What Are They and How Do You
Avoid Them? 483
17B Esters as Flavoring Agents 491
17C Ketone Bodies and Diabetes 493
Chapter 18 Carboxylic
Anhydrides, Esters, and
Amides 502
18.1 Carboxylic Anhydrides,
Esters, and Amides 502
18.2 Preparation of Esters 506
18.3 Preparation of Amides 507
18.4 Characteristic Reactions
of Anhydrides, Esters, and
Amides 507
18.5 Phosphoric Anhydrides and
Phosphoric Esters 515
18.6 Step-Growth Polymerization 515
Chapter Summary 518
Summary of Key Reactions 519
Problems 520
Chemical Connections
18A The Pyrethrins—Natural Insecticides of Plant
Origin 504
18B The Penicillins and Cephalosporins: b-Lactam
Antibiotics 505
18C From Willow Bark to Aspirin and Beyond 506
18D Ultraviolet Sunscreens and Sunblocks 510
18E Barbiturates 514
18F Stitches That Dissolve 518
Chapter 19 Carbohydrates 525
19.1 Monosaccharides: The Simplest
Carbohydrates 525
19.2 Cyclic Structures of Monosaccharides 531
19.3 Characteristic Reactions of Monosaccharides 534
19.4 Disaccharides and Oligosaccharides 539
19.5 Polysaccharides 544
19.6 Acidic Polysaccharides 546
Chapter Summary 548
Summary of Key Reactions 549
Problems 550
Chemical Connections
19A Galactosemia 531
19B Testing for Glucose 537
19C A, B, AB, and O Blood Types 540
19D Is There a Connection Between Carbohydrates and
Obesity? 546
Chapter 20 Lipids 555
20.1 Importance of Lipids 555
20.2 Fatty Acids 556
20.3 Triglyceride Structure 559
20.4 Properties of Triglycerides 560
20.5 Structures of Complex Lipids 564
17B Esters as Flavoring Agents 491
17C Ketone Bodies and Diabetes 493
Chapter 18 Carboxylic
Anhydrides, Esters, and
Amides 502
18.1 Carboxylic Anhydrides,
Esters, and Amides 502
18.2 Preparation of Esters 506
18.3 Preparation of Amides 507
18.4 Characteristic Reactions
of Anhydrides, Esters, and
Amides 507
18.5 Phosphoric Anhydrides and
Phosphoric Esters 515
18.6 Step-Growth Polymerization 515
Chapter Summary 518
Summary of Key Reactions 519
Problems 520
Chemical Connections
18A The Pyrethrins—Natural Insecticides of Plant
Origin 504
18B The Penicillins and Cephalosporins: b-Lactam
Antibiotics 505
18C From Willow Bark to Aspirin and Beyond 506
18D Ultraviolet Sunscreens and Sunblocks 510
18E Barbiturates 514
18F Stitches That Dissolve 518
Chapter 19 Carbohydrates 525
19.1 Monosaccharides: The Simplest
Carbohydrates 525
19.2 Cyclic Structures of Monosaccharides 531
19.3 Characteristic Reactions of Monosaccharides 534
19.4 Disaccharides and Oligosaccharides 539
19.5 Polysaccharides 544
19.6 Acidic Polysaccharides 546
Chapter Summary 548
Summary of Key Reactions 549
Problems 550
Chemical Connections
19A Galactosemia 531
19B Testing for Glucose 537
19C A, B, AB, and O Blood Types 540
19D Is There a Connection Between Carbohydrates and
Obesity? 546
Chapter 20 Lipids 555
20.1 Importance of Lipids 555
20.2 Fatty Acids 556
20.3 Triglyceride Structure 559
20.4 Properties of Triglycerides 560
20.5 Structures of Complex Lipids 564
20.6 Lipids and Membrane Structure 565
20.7 Glycerophospholipids 566
20.8 Sphingolipids 568
20.9 Glycolipids 570
20.10 Steroids 571
20.11 Physiological Roles of Steroid Hormones 578
20.12 Bile Salts 583
20.13 Prostaglandins, Thromboxanes, and
Leukotrienes 584
20.14 Molecular Transport Across Membranes 589
Chapter Summary 594
Problems 596
Chemical Connections
20A Butter vs. Margarine – Which is healthier? 562
20B Lipid Storage Diseases 572
20C Anabolic Steroids 580
20D Oral Contraception 584
20E Action of Anti-inflammatory Drugs 586
20F Why Should We Eat More Salmon? 587
Chapter 21 Proteins 600
21.1 The Many Functions of Proteins 600
21.2 Amino Acids 601
21.3 Amino Acids Exist as Zwitterions 607
21.4 Amino Acids Combine to Form Proteins 610
21.5 Amino Acid Characteristics 613
21.6 Uncommon Amino Acids 615
21.7 Protein Properties 616
21.8 Protein Primary Structure 618
21.9 Protein Secondary Structure 623
21.10 Protein Tertiary Structure 625
21.11 Protein Quaternary Structure 630
21.12 Protein Denaturation 634
Chapter Summary 636
Problems 637
Chemical Connections
21A Aspartame, the Sweet Peptide 612
21B AGE and Aging 616
21C Peptide Hormones—Small Molecules with Big
Effects 620
21D Sickle Cell Anemia 622
21E Protein/Peptide Conformation–Dependent
Diseases 632
21F Laser Surgery and Protein Denaturation 635
Chapter 22 Enzymes 641
22.1 Enzymes are Biological Catalysts 641
22.2 Enzyme Nomenclature 643
22.3 Enzyme Activity 644
22.4 Enzyme Mechanisms 647
22.5 Enzyme Regulation 655
22.6 Enzymes in Medicine 659
Chapter Summary 661
Problems 662
Chemical Connections
22A Enzymes Allow Us to Enjoy Champagne 643
22B Enzymes and Memory 649
22C Medical Uses of Inhibitors 652
22D Case Study in Enzyme Regulation 660
Chapter 23 Chemical
Communications:
Neurotransmitters and
Hormones 667
23.1 Cells Communicate in Many
Ways 667
23.2 Neurotransmitters and
Hormones 668
23.3 Cholinergic Messengers 671
23.4 Amino Acid Neurotransmitters 677
23.5 Adrenergic Messengers 679
23.6 Peptides in Chemical Communications 684
23.7 Steroid Hormone Messengers 689
23.8 Drugs Affect Chemical Communications 690
Chapter Summary 693
Problems 694
Chemical Connections
23A Zebrafish, Synapses, and Sleep 672
23B Alzheimer’s Disease and Chemical
Communication 674
23C Parkinson’s Disease: Depletion of Dopamine 683
23D Diabetes 687
23E Depression—An Epidemic In Modern Times 691
Chapter 24 Nucleotides, Nucleic Acids,
and Heredity 697
24.1 DNA and RNA are the Molecules
of Heredity 697
24.2 Nucleic Acids 698
24.3 The Structure of DNA and RNA 703
24.4 RNA Types 710
24.5 Genes 714
24.6 Medical Applications of RNA 715
24.7 DNA Replication 717
24.8 DNA Amplification 721
Chapter Summary 727
Problems 728
Chemical Connections
24A Who Owns Your Genes? 701
24B DNA Fingerprinting 709
24C Telomeres, Telomerase, and Immortality 722
24D Synthetic Genome Created 722
24E Did the Neandertals Go Extinct? 725
Chapter 25 Gene Expression and Protein
Synthesis 731
25.1 DNA Leads to RNA and Protein 731
25.2 Transcription of DNA 733
25.3 Translation of RNA 735
25.4 The Genetic Code 736
25.5 Protein Synthesis 738
25.6 Gene Regulation 746
25.7 DNA Mutations 751
25.8 DNA Manipulation 755
25.9 Gene Therapy 756
25.10 Epigenetics 760
Chapter Summary 762
Problems 763
Chemical Connections
25A Breaking the Dogma: The Twenty-First Amino
Acid 744
25B Protein Synthesis Makes Memories 744
25C Mutations and Biochemical Evolution 752
25D Silent Mutations 753
25E p53: A Central Tumor Suppressor Protein 754
25F Twenty Years of Cystic Fibrosis Trials and
Tribulations 758
25G How Cancer and Aging Are Related to Epigenetic
States 761
Chapter 26 Bioenergetics: How the Body
Converts Food to Energy 766
26.1 The Nature of Metabolism 766
26.2 Mitochondria and Their Role in Metabolism 767
26.3 The Principal Compounds of Catabolic
Pathways 770
26.4 The Citric Acid Cycle and in Metabolism 773
26.5 Electron and H1 Transport 777
26.6 The Chemiosmotic Pump and ATP Production 781
26.7 Energy Yield from Aerobic Metabolism 782
26.8 Conversion of Chemical Energy to Other
Forms 783
Chapter Summary 786
Problems 787
Chemical Connections
26A Uncoupling and Obesity 780
26B ATP in Cell Signaling 785
Chapter 27 Specific Catabolic Pathways:
Carbohydrate, Lipid, and Protein
Metabolism 790
27.1 The General Outline of Catabolic Pathway 790
27.2 The Reactions of Glycolysis 793
27.3 The Energy Yield from Glucose Catabolism 798
27.4 Glycerol Catabolism 801
27.5 b-Oxidation of Fatty Acids 802
27.6 The Energy Yield from Stearic Acid
Catabolism 805
27.7 Ketone Bodies 806
27.8 Nitrogen Processing in Amino Acid
Catabolism 809
27.9 Carbon Skeleton Processing in Amino Acid
Catabolsim 814
Chapter Summary 816
Problems 817
Chemical Connections
27A Lactate Accumulation 796
27B Treating Obesity—Changing Carbohydrate
Metabolism 800
27C Ketoacidosis in Diabetes 808
27D Hereditary Defects in Amino Acid Catabolism:
PKU 813
Chapter 28 Biosynthetic
Pathways 820
28.1 The General Outline of
Biosynthetic Pathways 820
28.2 Biosynthesis of
Carbohydrates 822
28.3 Biosynthesis of Fatty
Acids 827
28.4 Biosynthesis of Membrane Lipids 829
28.5 Biosynthesis of Amino Acids 832
Chapter Summary 835
Problems 835
Chemical Connections
28A Photosynthesis 823
28B Acetyl-CoA Carboxylase—A New Target in the Fight
Against Obesity 828
28C Statin Drugs as Inhibitors of Cholesterol
Biosynthesis 831
28D Essential Amino Acids 833
Chapter 29 Nutrition 838
29.1 Nutritional Guidelines 838
29.2 Counting Calories 843
29.3 Carbohydrate Digestion 845
29.4 Fat Digestion 847
29.5 Protein Digestion 848
29.6 The Importance of Vitamins, Minerals, and
Water 850
Chapter Summary 860
Problems 861
Chemical Connections
29A The New Food Guide 841
29B Why Is It So Hard to Lose Weight? 844
29C Do Hormones or Overeating Cause Obesity? 846
29D Iron: An Example of a Mineral Requirement 856
29E Food for Performance Enhancement 857
29F Depression in America—Don’t Worry; Be
Happy 858
29G Is Gluten-Freedom a Fad? 859
Chapter 30 Immunochemistry 864
30.1 The Body’s Defense against Invasion 864
30.2 Organs and Cells of the Immune System 866
30.3 Antigens Stimulate the Immune System 870
30.4 Immunoglobulins 872
30.5 T Cells and T-Cell Receptors 878
30.6 Immunization 880
30.7 Distinguishing “Self” from “Nonself” 884
30.8 The Human Immunodeficiency Virus and
AIDS 888
Chapter Summary 898
Problems 899
Chemical Connections
30A Monoclonal Antibodies Wage War on Breast
Cancer 876
30B Antibiotics: A Double-Edged Sword 885
30C A Little Swine Goes a Long Way 894
30D Inflammation 896
Chapter 31 Body Fluids 902
To access this online-only chapter, search for
ISBN 978-1-337-57135-7 at www.cengage.com
and visit this book’s companion website.
Appendix I Exponential Notation A-1
Appendix II Significant Figures A-5
Answers To In-Text And Odd-Numbered
End-Of-Chapter Problems A-8
Glossary G-1
Index I-1