Fundamentals of General, Organic, and Biological

Chemistry (6th Edition)

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About the Authors
John McMurry, educated at Harvard and Columbia, has taught
approximately 17,000 students in general and organic chemistry over
a 30-year period. A Professor of Chemistry at Cornell University since
1980, Dr. McMurry previously spent 13 years on the faculty at the
University of California at Santa Cruz. He has received numerous
awards, including the Alfred P. Sloan Fellowship (1969 71), the
National Institute of Health Career Development Award (1975 80),
the Alexander von Humboldt Senior Scientist Award (1986 87), and the Max Planck
Research Award (1991).

David S. Ballantine received his B.S. in Chemistry in 1977 from

the College of William and Mary in Williamsburg, VA, and his Ph.D.
in Chemistry in 1983 from the University of Maryland at College
Park. After several years as a researcher at the Naval Research Labs in
Washington, DC, he joined the faculty in the Department of Chemistry
and Biochemistry of Northern Illinois University, where he has been a
professor for the past twenty years. He was awarded the Excellence in
Undergraduate Teaching Award in 1998 and was recently named the departmental
Director of Undergraduate Studies. In addition, he is the faculty advisor to the NIU
Chemistry Club, an American Chemical Society Student Affiliate program.

Carl A. Hoeger received his B.S. in Chemistry from San Diego State
University and his Ph.D. in Organic Chemistry from the University of
Wisconsin, Madison in 1983. After a postdoctoral stint at the Univer-
sity of California, Riverside, he joined the Peptide Biology Laboratory
at the Salk Institute in 1985 where he ran the NIH Peptide Facility
while doing basic research in the development of peptide agonists
and antagonists. During this time he also taught general, organic, and
biochemistry at San Diego City College, Palomar College, and Miramar College.
He joined the teaching faculty at University of Califiornia, San Diego in 1998.
Dr. Hoeger has been teaching chemistry to undergraduates for over 20 years, where
he continues to explore the use of technology in the classroom. In 2004 he won the
Paul and Barbara Saltman Distinguished Teaching Award from UCSD. He is
currently the General Chemistry coordinator at UCSD, where he is also responsible
for the training and guidance of over 100 teaching assistants in the Chemistry and
Biochemistry departments.

Virginia E. Peterson received her B.S. in Chemistry in 1967 from

the University of Washington in Seattle, and her Ph.D. in Bio-
chemistry in 1980 from the University of Maryland at College Park.
Between her undergraduate and graduate years she worked in lipid,
diabetes, and heart disease research at Stanford University. Following
her Ph.D. she took a position in the Biochemistry Department at the
University of Missouri in Columbia and is now an Associate Professor.
Currently she is the Director of Undergraduate Advising for the department and
teaches both senior capstone classes and biochemistry classes for nonscience
majors. Awards include both the college level and the university-wide Excellence in
Teaching Award and, in 2006, the University s Outstanding Advisor Award and the
State of Missouri Outstanding University Advisor Award. Dr. Peterson believes in
public service and in 2003 received the Silver Beaver Award for service from the
Boy Scouts of America.
iii
Brief Contents

Applications xiii
17 Carboxylic Acids and Their
Preface xv Derivatives 516
A Student s Guide to Using This Text xxiv
18 Amino Acids and Proteins 552
1 Matter and Life 2
19 Enzymes and Vitamins 592
2 Measurements in Chemistry 18
20 Chemical Messengers: Hormones,
3 Atoms and the Periodic Table 48 Neurotransmitters, and Drugs 628

4 Ionic Compounds 78 21 The Generation of Biochemical

Energy 658
5 Molecular Compounds 106

6 Chemical Reactions: Classification

22 Carbohydrates 692

and Mass Relationships 142 23 Carbohydrate Metabolism 728

7 Chemical Reactions: Energy, Rates, 24 Lipids 756

and Equilibrium 182
25 Lipid Metabolism 786
8 Gases, Liquids, and Solids 214
26 Nucleic Acids and Protein
9 Solutions 254 Synthesis 808

10 Acids and Bases 292 27 Genomics 840

11 Nuclear Chemistry 332 28 Protein and Amino Acid

Metabolism 860
12 Introduction to Organic Chemistry:
Alkanes 360 29 Body Fluids 878

13 Alkenes, Alkynes, and Aromatic Appendices A-1

Compounds 396
Glossary A-6
14 Some Compounds with Oxygen, Answers to Selected Problems A-13
Sulfur, or a Halogen 434
Photo Credits A-49
15 Amines 464
Index A-51
16 Aldehydes and Ketones 488
iv
Contents

Applications xiii

Preface xv

A Student s Guide to Using This Text xxiv

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
3.5 Some Characteristics of Different Groups 59

2 Measurements in Chemistry 18
Application: The Origin of Chemical
Elements 61
2.1 Physical Quantities 19 3.6 Electronic Structure of Atoms 61
2.2 Measuring Mass 21 3.7 Electron Configurations 64
2.3 Measuring Length and Volume 22 3.8 Electron Configurations and the
2.4 Measurement and Significant Figures 24 Periodic Table 68
2.5 Scientific Notation 26 3.9 Electron-Dot Symbols 71
Application: Powers of 10 28 Application: Atoms and Light 72
2.6 Rounding Off Numbers 29
2.7 Problem Solving: Converting a Quantity from One
Unit to Another 31 4 Ionic Compounds 78
2.8 Problem Solving: Estimating Answers 33 4.1 Ions 79
2.9 Measuring Temperature 35 4.2 Periodic Properties and Ion Formation 81
Application: Temperature-Sensitive 4.3 Ionic Bonds 83
Materials 36 4.4 Some Properties of Ionic Compounds 84
2.10 Energy and Heat 38 4.5 Ions and the Octet Rule 84
2.11 Density 39 Application: Minerals and Gems 85
Application: Obesity and Body Fat 41 4.6 Ions of Some Common Elements 87
2.12 Specific Gravity 42 Application: Salt 89
4.7 Naming Ions 90

3 Atoms and the Periodic Table 48

4.8 Polyatomic Ions 91
Application: Biologically Important Ions 92
3.1 Atomic Theory 49 4.9 Formulas of Ionic Compounds 93
Application: Are Atoms Real? 52 4.10 Naming Ionic Compounds 95
3.2 Elements and Atomic Number 53 4.11 H* and OH+ Ions: An Introduction to Acids
3.3 Isotopes and Atomic Weight 54 and Bases 98
3.4 The Periodic Table 57 Application: Osteoporosis 100

v
vi Contents

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

7 Chemical Reactions: Energy, Rates,

and Equilibrium 182
7.1 Energy and Chemical Bonds 183
5 Molecular Compounds 106
7.2
7.3
Heat Changes during Chemical Reactions 183
Exothermic and Endothermic Reactions 184
5.1 Covalent Bonds 107 7.4 Why Do Chemical Reactions Occur?
5.2 Covalent Bonds and the Periodic Table 110 Free Energy 188
5.3 Multiple Covalent Bonds 113 Application: Energy from Food 189
5.4 Coordinate Covalent Bonds 115 7.5 How Do Chemical Reactions Occur? Reaction
Application: CO and NO: Pollutants or Miracle Rates 193
Molecules? 116 7.6 Effects of Temperature, Concentration,
5.5 Molecular Formulas and Lewis Structures 117 and Catalysts on Reaction Rates 195
5.6 Drawing Lewis Structures 117 7.7 Reversible Reactions and Chemical
5.7 The Shapes of Molecules 122 Equilibrium 198
Application: VERY Big Molecules 127 Application: Regulation of Body Temperature 198
5.8 Polar Covalent Bonds and Electronegativity 128 7.8 Equilibrium Equations and Equilibrium
5.9 Polar Molecules 130 Constants 200
5.10 Naming Binary Molecular Compounds 132 7.9 Le Châtelier s Principle: The Effect of Changing
Conditions on Equilibria 203
5.11 Characteristics of Molecular Compounds 134
Application: Nitrogen Fixation 207
Application: Damascenone by Any Other Name
Would Smell as Sweet 135

8 Gases, Liquids, and Solids 214

6 Chemical Reactions: Classification 8.1 States of Matter and Their Changes 215
8.2 Gases and the Kinetic Molecular Theory 218
and Mass Relationships 142
8.3 Pressure 218
6.1 Chemical Equations 143 8.4 Boyle s Law: The Relation between Volume
6.2 Balancing Chemical Equations 145 and Pressure 222
6.3 Avogadros Number and the Mole 148 Application: Blood Pressure 223
6.4 Gram Mole Conversions 152 8.5 Charles s Law: The Relation between Volume
Application: Did Ben Franklin Have Avogadros and Temperature 225
Number? A Ballpark Calculation 153 8.6 Gay-Lussac s Law: The Relation between Pressure
6.5 Mole Relationships and Chemical Equations 155 and Temperature 226
6.6 Mass Relationships and Chemical 8.7 The Combined Gas Law 228
Equations 156 8.8 Avogadros Law: The Relation between Volume
6.7 Limiting Reagent and Percent Yield 159 and Molar Amount 229
6.8 Classes of Chemical Reactions 161 8.9 The Ideal Gas Law 231
 Contents vii

8.10 Partial Pressure and Daltons Law 233 10.11 Buffer Solutions 312
8.11 Intermolecular Forces 235 10.12 Buffers in the Body 315
Application: Greenhouse Gases and Global Application: Buffers in the Body: Acidosis
Warming 236 and Alkalosis 317
8.12 Liquids 240 10.13 Acid and Base Equivalents 318
8.13 Water: A Unique Liquid 242 10.14 Some Common Acid Base Reactions 320
8.14 Solids 243 10.15 Titration 321
8.15 Changes of State 244 Application: Acid Rain 324
Application: Biomaterials for Joint 10.16 Acidity and Basicity of Salt Solutions 325
Replacement 246
Application: CO2 as an Environmentally Friendly
Solvent 248 11 Nuclear Chemistry 332
11.1 Nuclear Reactions 333
11.2 The Discovery and Nature of Radioactivity 334
9 Solutions 254 11.3 Stable and Unstable Isotopes 335
9.1 Mixtures and Solutions 255 11.4 Nuclear Decay 336
9.2 The Solution Process 257 11.5 Radioactive Half-Life 341
9.3 Solid Hydrates 259 Application: Medical Uses of Radioactivity 342
9.4 Solubility 260 11.6 Radioactive Decay Series 344
9.5 The Effect of Temperature on Solubility 261 11.7 Ionizing Radiation 345
9.6 The Effect of Pressure on Solubility: 11.8 Detecting Radiation 347
Henry s Law 262 11.9 Measuring Radiation 348
9.7 Units of Concentration 265 Application: Irradiated Food 349
Application: Breathing and Oxygen Transport 266 11.10 Artificial Transmutation 350
9.8 Dilution 273 Application: Body Imaging 352
9.9 Ions in Solution: Electrolytes 275 11.11 Nuclear Fission and Nuclear Fusion 352
9.10 Electrolytes in Body Fluids: Equivalents Application: Archaeological Radiocarbon
and Milliequivalents 276 Dating 355
9.11 Properties of Solutions 278
Application: Electrolytes, Fluid Replacement,
and Sports Drinks 279 12 Introduction to Organic Chemistry:
9.12 Osmosis and Osmotic Pressure 282 Alkanes 360
9.13 Dialysis 285
12.1 The Nature of Organic Molecules 361
Application: Timed-Release Medications 286
12.2 Families of Organic Molecules: Functional
Groups 363
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
viii Contents

12.3 The Structure of Organic Molecules: 13.10 Naming Aromatic Compounds 423
Alkanes and Their Isomers 368 13.11 Reactions of Aromatic Compounds 426
12.4 Drawing Organic Structures 370 Application: Why We See Color 428
12.5 The Shapes of Organic Molecules 376
12.6 Naming Alkanes 378
Application: Displaying Molecular 14 Some Compounds with Oxygen,
Shapes 379 Sulfur, or a Halogen 434
12.7 Properties of Alkanes 385
14.1 Alcohols, Phenols, and Ethers 435
12.8 Reactions of Alkanes 386
14.2 Some Common Alcohols 437
12.9 Cycloalkanes 387
14.3 Naming Alcohols 438
Application: Petroleum 388
14.4 Properties of Alcohols 441
12.10 Drawing and Naming Cycloalkanes 389
14.5 Reactions of Alcohols 442
Application: Ethyl Alcohol as a Drug and
13 Alkenes, Alkynes, and Aromatic a Poison 447
14.6 Phenols 448
Compounds 396
14.7 Acidity of Alcohols and Phenols 449
13.1 Alkenes and Alkynes 397 Application: Phenols as Antioxidants 450
13.2 Naming Alkenes and Alkynes 398 14.8 Ethers 451
13.3 The Structure of Alkenes: Cis Trans 14.9 Thiols and Disulfides 453
Isomerism 401 Application: Inhaled Anesthetics 454
13.4 Properties of Alkenes and Alkynes 405 14.10 Halogen-Containing Compounds 455
13.5 Types of Organic Reactions 405 Application: Chlorofluorocarbons and the Ozone
Application: The Chemistry of Vision 406 Hole 457
13.6 Reactions of Alkenes and Alkynes 409
13.7 How Alkene Addition Reactions Occur 415
13.8 Alkene Polymers 416 15 Amines 464
Application: Polymer Applications Currency 420 15.1 Amines 465
13.9 Aromatic Compounds and the Structure Application: Chemical Information 468
of Benzene 420 15.2 Properties of Amines 471
Application: Polycyclic Aromatic Hydrocarbons 15.3 Heterocyclic Nitrogen Compounds 473
and Cancer 422
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

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
 Contents ix

16.6 Reduction of Aldehydes and Ketones 500

Application: How Toxic Is Toxic? 503
16.7 Addition of Alcohols: Hemiacetals and
Acetals 504

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 19.3 Enzyme Classification 596
17.6 Hydrolysis of Esters and Amides 538 Application: Biocatalysis: Industrial
17.7 Polyamides and Polyesters 541 Biochemistry 600
Application: Kevlar: A Life-Saving Polymer 542 19.4 How Enzymes Work 600
17.8 Phosphoric Acid Derivatives 543 19.5 Effect of Concentration on Enzyme Activity 603
19.6 Effect of Temperature and pH on Enzyme
Activity 604
18 Amino Acids and Proteins 552 19.7 Enzyme Regulation: Feedback and Allosteric
18.1 An Introduction to Biochemistry 553 Control 606
18.2 Protein Structure and Function: Application: Extremozymes Enzymes from the
An Overview 555 Edge 607
18.3 Amino Acids 556 Application: Enzymes in Medical Diagnosis 608
18.4 Acid Base Properties of Amino Acids 559 19.8 Enzyme Regulation: Inhibition 610
Application: Nutrition in Health and Disease 560 Application: Enzyme Inhibitors as Drugs 613
18.5 Handedness 561 19.9 Enzyme Regulation: Covalent Modification and
Genetic Control 614
18.6 Molecular Handedness and Amino Acids 562
19.10 Vitamins 615
18.7 Primary Protein Structure 565
Application: Vitamins, Minerals, and Food
Application: Proteins in the Diet 569
Labels 621
18.8 Shape-Determining Interactions in Proteins 570
Application: Protein Analysis by
Electrophoresis 573
18.9 Secondary Protein Structure 574
20 Chemical Messengers: Hormones,
18.10 Tertiary Protein Structure 576
Neurotransmitters, and Drugs 628
18.11 Quaternary Protein Structure 579 20.1 Messenger Molecules 629
Application: Collagen A Tale of Two Diseases 581 20.2 Hormones and the Endocrine System 630
18.12 Chemical Properties of Proteins 583 Application: Homeostasis 631
Application: Prions: Proteins that Cause 20.3 How Hormones Work: Epinephrine and
Disease 584 Fight-or-Flight 634
20.4 Amino Acid Derivatives and Polypeptides as
Hormones 636
19 Enzymes and Vitamins 592 20.5 Steroid Hormones 638
19.1 Catalysis by Enzymes 593 Application: Plant Hormones 641
19.2 Enzyme Cofactors 595 20.6 Neurotransmitters 641
x Contents

21.10 Harmful Oxygen By-Products and Antioxidant

Vitamins 685
Application: Plants and Photosynthesis 686

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
20.7 How Neurotransmitters Work: Acetylcholine, 22.9 Some Important Polysaccharides 717
Its Agonists and Antagonists 643 Application: Cell-Surface Carbohydrates and
20.8 Histamine and Antihistamines 646 Blood Type 720
Application: And from This Little Frog ... 647 Application: Dietary Fiber 722
20.9 Serotonin, Norepinephrine, and Dopamine 648
20.10 Neuropeptides and Pain Relief 650 23 Carbohydrate Metabolism 728
20.11 Drug Discovery and Drug Design 651
23.1 Digestion of Carbohydrates 729
23.2 Glucose Metabolism: An Overview 730
21 The Generation of Biochemical 23.3
23.4
Glycolysis 732
Entry of Other Sugars into Glycolysis 736
Energy 658
Application: Tooth Decay 737
21.1 Energy and Life 659 23.5 The Fate of Pyruvate 738
21.2 Energy and Biochemical Reactions 660 23.6 Energy Output in Complete Catabolism of
Application: Life without Sunlight 663 Glucose 740
21.3 Cells and Their Structure 664 Application: Microbial Fermentations: Ancient and
21.4 An Overview of Metabolism and Energy Modern 741
Production 666 23.7 Regulation of Glucose Metabolism and Energy
21.5 Strategies of Metabolism: ATP and Energy Production 741
Transfer 669 23.8 Metabolism in Fasting and Starvation 742
21.6 Strategies of Metabolism: Metabolic Pathways 23.9 Metabolism in Diabetes Mellitus 744
and Coupled Reactions 671 Application: Diagnosis and Monitoring
Application: Basal Metabolism 673 of Diabetes 744
21.7 Strategies of Metabolism: Oxidized and Reduced 23.10 Glycogen Metabolism: Glycogenesis and
Coenzymes 674 Glycogenolysis 746
21.8 The Citric Acid Cycle 677 Application: The Biochemistry of Running 748
21.9 The Electron-Transport Chain and ATP 23.11 Gluconeogenesis: Glucose from
Production 680 Noncarbohydrates 749
Application: Energy Undone: Blockers and Application: Polysaccharides What Are They
Uncouplers of Oxidative Phosphorylation 683 Good For? 751
 Contents xi

26.9 The Genetic Code 829

24 Lipids 756
26.10 Translation: Transfer RNA and Protein
24.1 Structure and Classification of Lipids 757 Synthesis 830
24.2 Fatty Acids and Their Esters 759 Application: Bird Flu : The Next Epidemic? 834
24.3 Properties of Fats and Oils 762
Application: Lipids in the Diet 763
24.4 Chemical Reactions of Triacylglycerols 766 27 Genomics 840
Application: Detergents 767 27.1 Mapping the Human Genome 841
24.5 Cell Membrane Lipids: Phospholipids and 27.2 A Trip Along a Chromosome 843
Glycolipids 768 Application: Whose Genome Is It? 844
24.6 Cell Membrane Lipids: Cholesterol 774 27.3 Mutations and Polymorphisms 846
Application: Butter and Its Substitutes 774 27.4 Recombinant DNA 849
24.7 Structure of Cell Membranes 775 Application: Serendipity and the Polymerase Chain
Application: Liposomes for Health Reaction 850
and Beauty 775 Application: DNA Fingerprinting 852
24.8 Transport Across Cell Membranes 778 27.5 Genomics: Using What We Know 853
24.9 Eicosanoids: Prostaglandins and
Leukotrienes 780
28 Protein and Amino Acid
25 Lipid Metabolism 786 Metabolism 860

25.1 Digestion of Triacylglycerols 787 28.1 Digestion of Protein 861

25.2 Lipoproteins for Lipid Transport 789 28.2 Amino Acid Metabolism: An Overview 862
Application: Lipids and Atherosclerosis 791 28.3 Amino Acid Catabolism: The Amino Group 864
25.3 Triacylglycerol Metabolism: An Overview 792 28.4 The Urea Cycle 866
Application: Fat Storage: A Good Thing Application: Gout: When Biochemistry
or Not? 794 Goes Awry 869
25.4 Storage and Mobilization of Triacylglycerols 794 Application: The Importance of Essential Amino
Acids and Effects of Deficiencies 870
25.5 Oxidation of Fatty Acids 796
28.5 Amino Acid Catabolism: The Carbon Atoms 871
25.6 Energy from Fatty Acid Oxidation 797
28.6 Biosynthesis of Nonessential Amino Acids 872
25.7 Ketone Bodies and Ketoacidosis 799
Application: The Liver, Clearinghouse for
Metabolism 801
25.8 Biosynthesis of Fatty Acids 802

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
xii Contents

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

Appendices A-1

Glossary A-6

Answers to Selected Problems A-13

Photo Credits A-49

Index A-51
29 Body Fluids 878
29.1 Body Water and Its Solutes 879
29.2 Fluid Balance 882
 Contents xiii

Applications

Aspirin A Case Study 9 Toxicology 482

Mercury and Mercury Poisoning 14 Chemical Warfare among the Insects 493
Powers of 10 28 Vanilla: Which Kind Is Best? 496
Temperature-Sensitive Materials 36 How Toxic Is Toxic? 503
Obesity and Body Fat 41 Acids for the Skin 530
Are Atoms Real? 52 Acid Salts as Food Additives 531
The Origin of Chemical Elements 61 Kevlar: A Life-Saving Polymer 542
Atoms and Light 72 Nutrition in Health and Disease 560
Minerals and Gems 85 Proteins in the Diet 569
Salt 89 Protein Analysis by Electrophoresis 573
Biologically Important Ions 92 Collagen A Tale of Two Diseases 581
Osteoporosis 100 Prions: Proteins that Cause Disease 584
CO and NO: Pollutants or Miracle Molecules? 116 Biocatalysis: Industrial Biochemistry 600
VERY Big Molecules 127 Extremozymes Enzymes from the Edge 607
Damascenone by Any Other Name Would Smell as Sweet 135 Enzymes in Medical Diagnosis 608
Did Ben Franklin Have Avogadro s Number? A Ballpark Enzyme Inhibitors as Drugs 613
Calculation 153 Vitamins, Minerals, and Food Labels 621
Anemia A Limiting Reagent Problem? 162 Homeostasis 631
Gout and Kidney Stones: Problems in Solubility 165 Plant Hormones 641
Batteries 171 And from This Little Frog . . . 647
Energy from Food 189 Life without Sunlight 663
Regulation of Body Temperature 198 Basal Metabolism 673
Nitrogen Fixation 207 Energy Undone: Blockers and Uncouplers
Blood Pressure 223 of Oxidative Phosphorylation 683
Greenhouse Gases and Global Warming 236 Plants and Photosynthesis 686
Biomaterials for Joint Replacement 246 Chirality and Drugs 699
CO2 as an Environmentally Friendly Solvent 248 Carbohydrates in the Diet 704
Breathing and Oxygen Transport 266 Cell Walls: Rigid Defense Systems 714
Electrolytes, Fluid Replacement, and Sports Drinks 279 Cell-Surface Carbohydrates and Blood Type 720
Timed-Release Medications 286 Dietary Fiber 722
GERD Too Much Acid or Not Enough? 302 Tooth Decay 737
pH of Body Fluids 311 Microbial Fermentations: Ancient and Modern 741
Buffers in the Body: Acidosis and Alkalosis 317 Diagnosis and Monitoring of Diabetes 744
Acid Rain 324 The Biochemistry of Running 748
Medical Uses of Radioactivity 342 Polysaccharides What Are They Good For? 751
Irradiated Food 349 Lipids in the Diet 763
Body Imaging 352 Detergents 767
Archaeological Radiocarbon Dating 355 Butter and Its Substitutes 774
Displaying Molecular Shapes 379 Liposomes for Health and Beauty 775
Petroleum 388 Lipids and Atherosclerosis 791
The Chemistry of Vision 406 Fat Storage: A Good Thing or Not? 794
Polymer Applications Currency 420 The Liver, Clearinghouse for Metabolism 801
Polycyclic Aromatic Hydrocarbons and Viruses and AIDS 820
Cancer 422 It's a Ribozyme! 826
Why We See Color 428 Bird Flu : The Next Epidemic? 834
Ethyl Alcohol as a Drug and a Poison 447 Whose Genome Is It? 844
Phenols as Antioxidants 450 Serendipity and the Polymerase Chain Reaction 850
Inhaled Anesthetics 454 DNA Fingerprinting 852
Chlorofluorocarbons and the Ozone Hole 457 Gout: When Biochemistry Goes Awry 869
Chemical Information 468 The Importance of Essential Amino Acids and Effects
NO: A Small Molecule with Big Responsibilities 475 of Deficiencies 870
Organic Compounds in Body Fluids and the The Blood Brain Barrier 888
Solubility Switch 478 Automated Clinical Laboratory Analysis 897

xiii
Preface

his textbook is primarily designed to provide students in the allied health

T sciences with an appropriate background in chemistry and biochemistry.

But it also provides a general context for many of the chemical concepts
so that students in other disciplines will gain a better appreciation of
the importance of chemistry in everyday life. The coverage in this sixth edition
includes sufficient breadth and depth to ensure adequate context and to provide
students with opportunities to expand their knowledge.
To teach chemistry all the way from What is an atom? to How do we get
energy from glucose? is a challenge. Throughout our general chemistry and organic
chemistry coverage, the focus is on concepts fundamental to the chemistry of living
things and everyday life. In our biochemistry coverage we strive to meet the further
challenge of providing a context for the application of those concepts in biological sys-
tems. Our goal is to provide enough detail for thorough understanding while avoiding
so much detail that students are overwhelmed. Many practical and relevant examples
are included to illustrate the concepts and enhance student learning.
The material covered is ample for a two-term introduction to general, organic, and
biological chemistry. While the general and early organic chapters contain concepts
that are fundamental to understanding the material in biochemistry, the later chapters
can be covered individually and in an order that can be adjusted to meet the needs of
the students and the duration of the course.
The writing style is clear and concise and punctuated with practical and familiar
examples from students personal experience. Art work, diagrams, and molecular
models are used extensively to provide graphical illustration of concepts to enhance
student understanding. Since the true test of knowledge is the ability to apply that
knowledge appropriately, we include numerous worked examples that incorporate
consistent problem-solving strategies.
Regardless of their career paths, all students will be citizens in an increasingly
technological society. When they recognize the principles of chemistry at work not just
in their careers but in their daily lives, they are prepared to make informed decisions
on scientific issues based on a firm understanding of the underlying concepts.

Organization
GENERAL CHEMISTRY: CHAPTERS 1 11 The introduction to elements, atoms, the
periodic table, and the quantitative nature of chemistry (Chapters 1 3) is followed
by chapters that individually highlight the nature of ionic and molecular com-
pounds (Chapters 4 and 5). The next two chapters discuss chemical reactions and
their stoichiometry, energies, rates, and equilibria (Chapters 6 and 7). Topics rele-
vant to the chemistry of life follow: Gases, Liquids, and Solids (Chapter 8); Solu-
tions (Chapter 9); and Acids and Bases (Chapter 10). Nuclear Chemistry (Chapter 11)
closes the general chemistry sequence.

ORGANIC CHEMISTRY: CHAPTERS 12 17 These chapters concisely focus on what

students must know in order to understand biochemistry. The introduction to
hydrocarbons (Chapters 12 and 13) includes the basics of nomenclature, which is
thereafter kept to a minimum. Discussion of functional groups with single bonds to
oxygen, sulfur, or a halogen (Chapter 14) is followed by a short chapter on amines,
which are so important to the chemistry of living things and drugs (Chapter 15).
After introducing aldehydes and ketones (Chapter 16), the chemistry of carboxylic
acids and their derivatives (including amides) is covered (Chapter 17), with a focus
on similarities among the derivatives.
xv
xvi Preface

BIOLOGICAL CHEMISTRY: CHAPTERS 18 29 Rather than proceed through the com-

plexities of protein, carbohydrate, lipid, and nucleic acid structure before getting to
the roles of these compounds in the body, structure and function are integrated in
this text. Protein structure (Chapter 18) is followed by enzyme and coenzyme
chemistry (Chapter 19). After that we cover the function of hormones and neuro-
transmitters, and the action of drugs (Chapter 20). With enzymes introduced, the
central pathways and themes of biochemical energy production can be described
(Chapter 21). If the time you have available to cover biochemistry is limited, stop
with Chapter 21 and your students will have an excellent preparation in the essen-
tials of metabolism. The following chapters cover carbohydrate chemistry (Chap-
ters 22 and 23), then lipid chemistry (Chapters 24 and 25). Next we discuss nucleic
acids and protein synthesis (Chapter 26) and genomics (Chapter 27). The last two
chapters cover protein and amino acid metabolism (Chapter 28) and provide an
overview of the chemistry of body fluids (Chapter 29).

Changes to This Edition

COVERAGE OF GENERAL CHEMISTRY
Once again, there is a major emphasis in this edition on problem-solving strategies.
This is reflected in expanded solutions in the Worked Example problems and the
addition of more Key Concept Problems that focus on conceptual understanding.
The most significant change in the Worked Example problems is the addition of a
Ballpark Estimate at the beginning of many problems. The Ballpark Estimate pro-
vides an opportunity for students to evaluate the relationships involved in the
problem and allows them to use an intuitive approach to arrive at a first approxi-
mation of the final answer. The ability to think through a problem before attempt-
ing a mathematical solution is a skill that will be particularly useful on exams, or
when solving real world problems.
Other specific changes to chapters are provided below:

Chapter 1
The Scientific Method is introduced in the text and reinforced in Applications
presented in the chapter.

Chapter 3
Discussion of the critical experiments of Thomson, Millikan, and Rutherford are
included in the Application Are Atoms Real to provide historical perspective
on the development of our understanding of atomic structure.
Electron dot structures are introduced in Chapter 3 to emphasize the impor-
tance of the valence shell electronic configurations with respect to chemical
behavior of the elements.

Chapter 4
Electron dot structures are used to reinforce the role of valence shell electronic
configurations in explaining periodic behavior and the formation of ions.

Chapter 5
The two methods for drawing Lewis dot structures (the general method and
the streamlined method for molecules containing C, N, O, X, and H) are dis-
cussed back-to-back to highlight the underlying principle of the octet rule com-
mon to both methods.

Chapter 6
The concept of limiting reagents is incorporated in Section 6.7 in the discussion
of reaction stoichiometry and percent yields.
 Preface xvii

Chapter 7
The discussion of free energy and entropy in Section 7.4 has been revised to
help students develop a more intuitive understanding of the role of entropy in
spontaneous processes.
Section 7.8 includes more discussion of how the equilibrium constant is calcu-
lated and what it tells us about the extent of reaction.
Chapter 8
Sections 8.3 8.10 include more emphasis on use of the kinetic molecular theory
to understand the behavior of gases described by the gas laws.
Section 8.15 includes more discussion on the energetics of phase changes to
help students understand the difference between heat transfer associated with
a temperature change and heat transfer associated with the phase change of
a substance.
Chapter 9
Discussion of equivalents in Section 9.10 has been revised to emphasize the
relationship between ionic charge and equivalents of ionic compounds.
Discussion of osmotic pressure (Section 9.12) now includes the osmotic pres-
sure equation and emphasizes the similarity with the ideal gas law.
Chapter 10
Both the algebraic and logarithmic forms of Kw are presented in Section 10.8 to
give students another approach to solving pH problems.
The discussion of buffer systems now introduces the Henderson-Hasselbalch
equation. This relationship makes it easier to identify the factors that affect the
pH of a buffer system and is particularly useful in biochemical applications in
later chapters.
Discussion of common acid-base reactions has been moved back in the chapter
to provide a more logical segue into titrations in Section 10.15.
Chapter 11
Treatment of half-life in Section 11.5 now includes a generic equation to allow
students to determine the fraction of isotope remaining after an integral or
non-integral number of half-lives, which is more consistent with real world
applications.
The Applications in this chapter have been expanded to include discussion of
new technologies such as Boron Neutron-Capture Therapy (BNCT), or to clear
up misconceptions about current methods such as MRI.

COVERAGE OF ORGANIC CHEMISTRY

A major emphasis in this edition was placed on making the fundamental reactions
organic molecules undergo much clearer to the reader, with particular vision
toward those reactions encountered again in biochemical transformations. Also
new to this edition is the expanded use and evaluation of line-angle structure for
organic molecules, which are so important when discussing biomolecules. Most of
the Applications have been updated to reflect current understanding and research.
Other specific changes to chapters are provided below:
Chapter 12
This chapter has been significantly rewritten to provide the student with a
stronger foundation for the organic chemistry chapters that follow.
A clearer description of what a functional group is, as well as a more systematic
approach to drawing alkane isomers have been made.
xviii Preface

The topic of how to draw and interpret line structures for organic molecules has
been added, along with worked examples of such.
The discussion of conformations has been expanded.

Chapter 13
A more general discussion of cis and trans isomers has been added.
The discussion of organic reaction types, particularly rearrangement reactions,
have been simplified.

Chapter 14
The topic of oxidation in organic molecules has been clarified.

Chapter 15
The role of NO in human biology has been updated to reflect current research.

Chapter 16
A more detailed discussion of what is meant by toxic or poisonous has been
added.

Chapter 17
A discussion of ibuprofen has been added.

COVERAGE OF BIOLOGICAL CHEMISTRY

New topics, such as the use of anabolic steroids in sports, have been added to many
of these chapters to highlight the relevance of biochemistry in modern society.
In this text, nutrition is not treated as a separate subject but is integrated with the
discussion of each type of biomolecule.

Chapter 18
The discussion of sickle cell anemia has been expanded and the role of an
amino acid substitution on hemoglobin structure clarified.
The Application Prions Proteins That Cause Disease has been updated to reflect
current research.

Chapter 19
Incorporated the information about lead poisoning into the discussion of
enzyme inhibition.

Chapter 20
The discussion of anabolic steroids has been updated.
The discussion of drugs and their interaction with the neurotransmitter acetyl-
choline has been expanded.

Chapter 21
The discussion of ATP energy production has been revised.

Chapter 22
An explanation of the chair conformation of glucose has been included to
enhance understanding of the shape of cyclic sugars.
The Application Chirality and Drugs has been updated.
The Application Cell Surface Carbohydrates and Blood Type has been revised.
 Preface xix

Chapter 23
The explanation of substrate level phosphorylation has been expanded for clarity.
The emerging medical condition referred to as Metabolic Syndrome has been
added to the text discussion of diabetes.
The Application Diagnosis and Monitoring of Diabetes has been updated to include
metabolic syndrome.
Section 23.11 now contains an expanded discussion of gluconeogenesis.
The discussion of polysaccharides has been updated.

Chapter 24
The description of the cell membrane has been expanded.
A discussion of some inhibitors of Cox 1 and Cox 2 enzymes, important in
inflammation, has been added.

Chapter 25
The discussion of triacylglycerol synthesis has been expanded.
The discussion of ketone body formation has been expanded.
A thorough explanation of the biosynthesis of fatty acids has been added.

Chapter 26
The Application Viruses and AIDS has been updated.
Information about the 1918 influenza pandemic was included in the Applica-
tion Bird Flu : The Next Epidemic?

Chapter 27
A discussion of the problems associated with using recombinant DNA for
commercial protein manufacture has been added.
In Section 27.5, new bioethical issues are pointed out to reflect modern
concerns.
The discussion of recombinant DNA and polymerase chain reactions has been
moved to this chapter from Chapter 26.

Focus on Learning
WORKED EXAMPLES Most Worked Examples, both quantitative and not quantita-
tive, include an Analysis section that precedes the Solution. The Analysis lays out
the approach to solving a problem of the given type. When appropriate, a Ballpark
Estimate gives students an overview of the relationships needed to solve the prob-
lem, and provides an intuitive approach to arrive at a rough estimate of the answer.
The Solution presents the worked-out example using the strategy laid out in the
Analysis and, in many cases, includes expanded discussion to enhance student
understanding. The use of the two-column format introduced in the fifth edition for
quantitative problems has been applied to more Worked Examples throughout the
text. Following the Solution there is a Ballpark Check that compares the calculated
answer to the Ballpark Estimate, when appropriate, and verifies that the answer
makes chemical and physical sense.

KEY CONCEPT PROBLEMS are integrated throughout the chapters to focus attention
on the use of essential concepts, as do the Understanding Key Concepts problems at
the end of each chapter. Understanding Key Concepts problems are designed to test
students mastery of the core principles developed in the chapter. Students thus
xx Preface

have an opportunity to ask Did I get it? before they proceed. Most of these Key
Concept Problems use graphics or molecular-level art to illustrate the core princi-
ples and will be particularly useful to visual learners.

PROBLEMS The problems within the chapters, for which brief answers are given
in an appendix, cover every skill and topic to be understood. One or more prob-
lems, many of which are new to this edition, follow each Worked Example and
others stand alone at the ends of sections.

MORE COLOR-KEYED, LABELED EQUATIONS It is entirely too easy to skip looking at

a chemical equation while reading. We have extensively used color to call attention
to the aspects of chemical equations and structures under discussion, a continuing
feature of this book that has been judged very helpful.

MOLECULAR MODELS Additional computer-generated molecular models have

been introduced, including the use of electrostatic-potential maps for molecular
models.

KEY WORDS Every key term is boldfaced on its first use, fully defined in the mar-
gin adjacent to that use, and listed at the end of the chapter. These are the terms
students must understand to get on with the subject at hand. Definitions of all Key
Words are collected in the Glossary.

END-OF-CHAPTER SUMMARIES Here, the answers to the questions posed at the

beginning of the chapter provide a summary of what is covered in that chapter.
Where appropriate, the types of chemical reactions in a chapter are also summarized.

Focus on Relevancy
Chemistry is often considered to be a difficult and tedious subject. But when stu-
dents make a connection between a concept in class and an application in their
daily lives the chemistry comes alive, and they get excited about the subject. The
applications in this book strive to capture student interest and emphasize the rele-
vance of the scientific concepts. The use of relevant applications makes the concepts
more accessible and increases understanding.
Applications are both integrated into the discussions in the text and set off
from the text in Application boxes. Each boxed application provides sufficient
information for reasonable understanding and, in many cases, extends the con-
cepts discussed in the text in new ways. The boxes end with a cross-reference to
end-of-chapter problems that can be assigned by the instructor. Some well-
received Applications from previous editions that have been retained include
Breathing and Oxygen Transport, Buffers in the Body, Prions, Protein Analysis by
Electrophoresis, The Biochemistry of Running, and DNA Fingerprinting.
New Applications in this edition include Aspirin A Case Study, Temperature-
Sensitive Materials, Anemia A Limiting Reagent Problem, GERD: Too Much Acid or
Not Enough, and It s a Ribozyme!

FOCUS ON MAKING CONNECTIONS AMONG GENERAL, ORGANIC, AND BIOLOGICAL

CHEMISTRY This can be a difficult course to teach. Much of what students are
interested in lies in the last part of the course, but the material they need to under-
stand the biochemistry is found in the first two-thirds. It is easy to lose sight of the
connections among general, organic, and biological chemistry so we use a feature,
Concepts to Review, to call attention to these connections. From Chapter 4 on, the
Concepts to Review section at the beginning of the chapter lists topics covered in
earlier chapters that form the basis for what is discussed in the current chapter.
 Preface xxi

We have also retained the successful concept link icons and Looking Ahead notes.
Concept link icons are used extensively to indicate places where previ-
ously covered material is relevant to the discussion at hand. These links pro-
vide for cross-references and also serve to highlight important chemical themes
as they are revisited.
Looking Ahead notes call attention to connections between just-covered mate-
rial and discussions in forthcoming chapters. These notes are designed to illus-
trate to the students why what they are learning will be useful in what lies
ahead.

Making It Easier to Teach:

Supplements for Instructors
MasteringChemistry (www.masteringchemistry.com) MasteringChemistry is the
first adaptive-learning online homework system. It provides selected end-of-chapter
problems from the text, as well as hundreds of tutorials with automatic grading,
immediate answer-specific feedback, and simpler questions on request. Based on
extensive research of precise concepts students struggle with, MasteringChemistry
uniquely responds to your immediate needs, thereby optimizing your study time.

Instructor Resource Manual (0-32-161241-8) Features lecture outlines with presen-

tation suggestions, teaching tips, suggested in-class demonstrations, and topics for
classroom discussion.

Test Item File (0-32-161514-X) Updated to reflect the revisions in this text and con-
tains questions in a bank of more than 2,000 multiple-choice questions.

Transparency Pack (0-32-161513-1) More than 225 full-color transparencies chosen

from the text put principles into visual perspective and save you time while you are
preparing for your lectures.

Instructor Resource Center on CD/DVD (0-32-161242-6) This CD/DVD provides

an intergrated collection of resources designed to help you make efficient and effec-
tive use of your time. This CD/DVD features most art from the text, including fig-
ures and tables in PDF format for high-resolution printing, as well as four pre-built
PowerPoint presentations. The first presentation contains the images/
figures/tables embedded within the PowerPoint slides, while the second includes a
complete modifiable lecture outline. The final two presentations contain worked
in chapter sample exercises and questions to be used with Classroom Response
Systems. This CD/DVD also contains movies and animations, as well as the
TestGen version of the Test Item File, which allows you to create and tailor exams to
your needs.

BlackBoard® and WebCT ® Practice and assessment materials are available upon
request in these course management platforms.

Making It Easier to Learn:

Supplements for Students
Study Guide and Full Solutions Manual (0-32-161238-8) and Study Guide and
Selected Solutions Manual (0-32-161239-6), both by Susan McMurry. The selected
version provides solutions only to those problems that have a short answer in the
xxii Preface

text s Selected Answer Appendix (problems numbered in blue in the text). Both ver-
sions explain in detail how the answers to the in-text and end-of-chapter problems
are obtained. They also contain chapter summaries, study hints, and self-tests for
each chapter.

For the Laboratory

Exploring Chemistry: Laboratory Experiments in General, Organic and Biologi-
cal Chemistry, 2nd Edition (0-13-047714-1) by Julie R. Peller of Indiana University.
Written specifically to accompany Fundamentals of General, Organic and Biologi-
cal Chemistry, this manual contains 34 fresh and accessible experiments specifically
for GOB students.

Catalyst: The Prentice Hall Custom Laboratory Program for Chemistry. This pro-
gram allows you to custom-build a chemistry lab manual that matches your content
needs and course organization. You can either write your own labs using the Lab
Authoring Kit tool, or select from the hundreds of labs available at www.
prenhall.com/catalyst. This program also allows you to add your own course
notes, syllabi, or other materials.

Acknowledgments
From conception to completion, the development of a modern textbook requires
both a focused attention on the goals and the coordinated efforts of a diverse team.
We have been most fortunate to have had the services of many talented and dedi-
cated individuals whose efforts have contributed greatly to the overall quality of
this text.
First and foremost, we are grateful to Kent Porter Hamann who, as senior edi-
tor of this text through many past revisions, provided exemplary leadership and
encouragement to the team in the early stages of this project. Very special apprecia-
tion goes to Ray Mullaney, editor in chief of book development, who mentored the
new team members and managed to coordinate the many and varied details. Irene
Nunes, our developmental editor, worked closely with the authors to ensure
accuracy and consistency. We also are grateful for the services of Wendy Perez,
project manager; Laurie Varites, assistant editor; Lia Tarabokjia, and Jill Traut and
Robert Walters, production project managers. Finally, special thanks also to Susan
McMurry and Margaret Trombley, whose efforts on the Solutions Manuals and
MasteringChemistry tutorial software, respectively, have added value to the overall
package.
Finally, many instructors and students who have used the fifth edition have
provided valuable insights and feedback and improved the accuracy of the current
edition. We gratefully acknowledge the following reviewers for their contributions
to the sixth edition:
Sheikh Ahmed, West Virgina University Karen L. Ericson, Indiana University-Purdue
Stanley Bajue, CUNY-Medgar Evers College University, Fort Wayne
Daniel Bender, Sacramento City College Charles P. Gibson, University of Wisconsin,
Dianne A. Bennett, Sacramento City Oshkosh
College Clifford Gottlieb, Shasta College
Alfredo Castro, Felician College Mildred V. Hall, Clark State Community
Gezahegn Chaka, Louisiana State University, College
Alexandria Meg Hausman, University of Southern Maine
Michael Columbia, Indiana University- Ronald Hirko, South Dakota State University
Purdue University, Fort Wayne L. Jaye Hopkins, Spokane Community
Rajeev B. Dabke, Columbus State University College
Danae R. Quirk-Dorr, Minnesota State Margaret Isbell, Sacramento City College
University, Mankato James T. Johnson, Sinclair Community
Pamela S. Doyle, Essex County College College
Marie E. Dunstan, York College of Margaret G. Kimble, Indiana University-
Pennsylvania Purdue University Fort Wayne
 Preface xxiii

Grace Lasker, Lake Washington Technical Douglas E. Raynie, South Dakota State
College University
Ashley Mahoney, Bethel University Paul D. Root, Henry Ford Community College
Matthew G. Marmorino, Indiana University, Victor V. Ryzhov, Northern Illinois University
South Bend Karen Sanchez, Florida Community College,
Diann Marten, South Central College, Mankato Jacksonville-South
Barbara D. Mowery, York College of Mir Shamsuddin, Loyola University, Chicago
Pennsylvania Jeanne A. Stuckey, University of Michigan
Tracey Arnold Murray, Capital University John Sullivan, Highland Community College
Andrew M. Napper, Shawnee State Deborah E. Swain, North Carolina Central
University University
Lisa Nichols, Butte Community College Susan T. Thomas, University of Texas, San
Glenn S. Nomura, Georgia Perimeter Antonio
College Yakov Woldman, Valdosta State University

The authors are committed to maintaining the highest quality and accuracy and
look forward to comments from students and instructors regarding any aspect of
this text and supporting materials. Questions or comments should be directed to
the lead co-author.
David S. Ballantine
dballant@niu.edu
Concise, Accessible, and Unique
QUANTITATIVE AND CONCEPTUAL

Worked Examples
These examples have been modified to
emphasize both problem-solving strategies
and conceptual understanding.
Analysis
Most Worked Examples include an Analysis section
that precedes the solution. The Analysis lays out the
approach to solving a problem of the given type.
NEW! Ballpark Estimates
Ballpark Estimates help students arrive at a rough
estimate of the final answer based on an intuitive
approach to the problem.
Solution
The Solution shows students how to apply the
appropriate problem-solving strategy and guides them
through the steps to follow in obtaining the answer.
Ballpark Check
Many of the Worked Examples culminate with a
Ballpark Check that helps students quickly check
whether the answer they have calculated in numerical
Worked Examples is reasonable.

Key Concept Problems

These problems are integrated within the chapter,
appearing at the end of a Worked Example or after the
discussion of an important concept. These problems
immediately focus students attention on essential
concepts and help them to test their understanding.

Looking Ahead
Looking Ahead Notes provide students with a preview
of how the material being presented connects to the
discussion in forthcoming chapters.

Concept Links
These links indicate where concepts in the text build on
material from earlier chapters. This chain link icon
provides a quick visual reminder that new material being
discussed relates to a concept introduced previously.