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STANDARD ATOMIC WEIGHTS OF THE ELEMENTS 2010 Based on relative atomic mass of 12C 5 12, where 12C is a neutral
atom in its nuclear and electronic ground state.†
Atomic Atomic Atomic Atomic

Name Symbol Number Weight Name Symbol Number Weight
Actinium* Ac 89 (227) Mendelevium* Md 101 (258)

Aluminum Al 13 26.9815386(8) Mercury Hg 80 200.59(2)
Americium* Am 95 (243) Molybdenum Mo 42 95.96(2)
Antimony Sb 51 121.760(1) Moscovium MC 115 (289)
Argon Ar 18 39.948(1) Neodymium Nd 60 144.22(3)
Arsenic As 33 74.92160(2) Neon Ne 10 20.1797(6)
Astatine* At 85 (210) Neptunium* Np 93 (237)
Barium Ba 56 137.327(7) Nickel Ni 28 58.6934(4)
Berkelium* Bk 97 (247) Niobium Nb 41 92.90638(2)
Beryllium Be 4 9.012182(3) Nitrogen N 7 14.0067(2)
Bismuth Bi 83 208.98040(1) Nihonium Nh 113 (286)
Bohrium Bh 107 (264) Nobelium* No 102 (259)
Boron B 5 10.811(7) Oganesson Og 118 (294)
Bromine Br 35 79.904(1) Osmium Os 76 190.23(3)
Cadmium Cd 48 112.411(8) Oxygen O 8 15.9994(3)
Cesium Cs 55 132.9054519(2) Palladium Pd 46 106.42(1)
Calcium Ca 20 40.078(4) Phosphorus P 15 30.973762(2)
Californium* Cf 98 (251) Platinum Pt 78 195.084(9)
Carbon C 6 12.0107(8) Plutonium* Pu 94 (244)
Cerium Ce 58 140.116(1) Polonium* Po 84 (209)
Chlorine Cl 17 35.453(2) Potassium K 19 39.0983(1)
Chromium Cr 24 51.9961(6) Praseodymium Pr 59 140.90765(2)
Cobalt Co 27 58.933195(5) Promethium* Pm 61 (145)
Copernicium* Cn 112 (285) Protactinium* Pa 91 231.03588(2)
Copper Cu 29 63.546(3) Radium* Ra 88 (226)
Curium* Cm 96 (247) Radon* Rn 86 (222)
Darmstadtium Ds 110 (271) Rhenium Re 75 186.207(1)
Dubnium Db 105 (262) Rhodium Rh 45 102.90550(2)
Dysprosium Dy 66 162.500(1) Roentgenium Rg 111 (272)
Einsteinium* Es 99 (252) Rubidium Rb 37 85.4678(3)
Erbium Er 68 167.259(3) Ruthenium Ru 44 101.07(2)
Europium Eu 63 151.964(1) Rutherfordium Rf 104 (261)
Fermium* Fm 100 (257) Samarium Sm 62 150.36(2)
Flerovium Fl 114 (289) Scandium Sc 21 44.955912(6)
Fluorine F 9 18.9984032(5) Seaborgium Sg 106 (266)
Francium* Fr 87 (223) Selenium Se 34 78.96(3)
Gadolinium Gd 64 157.25(3) Silicon Si 14 28.0855(3)
Gallium Ga 31 69.723(1) Silver Ag 47 107.8682(2)
Germanium Ge 32 72.64(1) Sodium Na 11 22.9896928(2)
Gold Au 79 196.966569(4) Strontium Sr 38 87.62(1)
Hafnium Hf 72 178.49(2) Sulfur S 16 32.065(5)
Hassium Hs 108 (277) Tantalum Ta 73 180.9488(2)
Helium He 2 4.002602(2) Technetium* Tc 43 (98)
Holmium Ho 67 164.93032(2) Tellurium Te 52 127.60(3)
Hydrogen H 1 1.00794(7) Tennessine Ts 117 (293)
Indium In 49 114.818(3) Terbium Tb 65 158.92535(2)
Iodine I 53 126.90447(3) Thallium Tl 81 204.3833(2)
Iridium Ir 77 192.217(3) Thorium* Th 90 232.03806(2)
Iron Fe 26 55.845(2) Thulium Tm 69 168.93421(2)
Krypton Kr 36 83.798(2) Tin Sn 50 118.710(7)
Lanthanum La 57 138.90547(7) Titanium Ti 22 47.867(1)
Lawrencium* Lr 103 (262) Tungsten W 74 183.84(1)
Lead Pb 82 207.2(1) Uranium* U 92 238.02891(3)
Lithium Li 3 6.941(2) Vanadium V 23 50.9415(1)
Livermorium Lv 116 (292) Xenon Xe 54 131.293(6)
Lutetium Lu 71 174.9668(1) Ytterbium Yb 70 173.54(5)
Magnesium Mg 12 24.3050(6) Yttrium Y 39 88.90585(2)
Manganese Mn 25 54.938045(5) Zinc Zn 30 65.38(2)
Meitnerium Mt 109 (268) Zirconium Zr 40 91.224(2)
†The atomic weights of many elements can vary depending on the origin *Elements with no stable nuclide; the value given in parentheses is the
and treatment of the sample. This is particularly true for Li; commercially atomic mass number of the isotope of longest known half-life. However,
available lithium-containing materials have Li atomic weights in the three such elements (Th, Pa, and U) have a characteristic terrestial isoto-
range of 6.939 and 6.996. The uncertainties in atomic weight values are pic composition, and the atomic weight is tabulated for these. http://www
given in parentheses following the last significant figure to which they are .chem.qmw.ac.uk/iupac/AtWt/
attributed.
Introduc tion to
General,
Organic, and
Biochemistry
T welfth Edition
Introduc tion to
General,
Organic, and
Biochemistry
T welfth Edition
Frederick A. Bettelheim
William H. Brown
Beloit College
Mary K. Campbell
Shawn O. Farrell
Omar J. Torres
College of the Canyons
Sara Madsen
South Dakota State University
Australia ● Brazil ● Mexico ● Singapore ● United Kingdom ● United States
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Printed in the United States of America

Print Number: 01 Print Year: 2019
To Carolyn, with whom life is a joy. —WB
To my family and friends, without whose support this would not have
been possible, and to all of my students, past and future, especially the
non-traditional ones, who have inspired me to try to be the best teacher
I can be —SF
To my loving family and friends who have supported me through
this journey: Mom, Dad, Lisa, Abuela, René, Ryan,
and Dianne. I could not have made it without your urging
and support. I am truly blessed to have each of
you in my life. — OT
To my family who have supported me from the beginning:
Theo, Mom, Dad, Koeen, and Mark. All of you have helped
me find everlasting creativity and confidence. I love you
very much. —SKM
Contents in Brief
General Chemistry
Chapter 1 Matter, Energy, and Measurement 1
Chapter 2 Atoms 26
Chapter 3 Chemical Bonds 63
Chapter 4 Chemical Reactions and Energy Calculations 104
Chapter 5 Gases, Liquids, and Solids 140
Chapter 6 Solutions and Colloids 168
Chapter 7 Reaction Rates and Chemical Equilibrium 200
Chapter 8 Acids and Bases 229
Chapter 9 Nuclear Chemistry 266
Organic Chemistry
Chapter 10 Organic Chemistry 298
Chapter 11 Alkanes 316
Chapter 12 Alkenes, Alkynes, and Aromatic Compounds 347
Chapter 13 Alcohols, Ethers, and Thiols 388
Chapter 14 Chirality: The Handedness of Molecules 413
Chapter 15 Amines 436
Chapter 16 Aldehydes and Ketones 455
Chapter 17 Carboxylic Acids 476
Chapter 18 Carboxylic Anhydrides, Esters, and Amides 502
Biochemistry
Chapter 19 Carbohydrates 525
Chapter 20 Lipids 555
Chapter 21 Proteins 600
Chapter 22 Enzymes 641
vi
Chapter 23 Chemical Communications: Neurotransmitters
and Hormones 667
Chapter 24 Nucleotides, Nucleic Acids, and Heredity 697
Chapter 25 Gene Expression and Protein Synthesis 731
Chapter 26 Bioenergetics: How the Body Converts
Food to Energy 766
Chapter 27 Specific Catabolic Pathways: Carbohydrate,
Lipid, and Protein Metabolism 790
Chapter 28 Biosynthetic Pathways 820
Chapter 29 Nutrition 838
Chapter 30 Immunochemistry 864
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.
vii
Contents
Chapter 1 Matter, Energy, and How To Draw Lewis Structures 77

Measurement 1 3.7 Naming Binary Covalent Compounds 82
3.8 Resonance 82
1.1 Chemistry and the Study of Matter 1
How To Draw Curved Arrows and Push Electrons 84
1.2 The Scientific Method 3
1.3 Reporting Numbers in Science 5 3.9 Predicting Bond Angles in Covalent Molecules 87
3.10 Determining If a Molecule Is Polar 91
How To Determine the Number of Significant Figures in
a Number 6 Chapter Summary 93
1.4 Making Measurements 7 Problems 94
1.5 Unit Conversions 12 CHEMICAL CONNECTIONS
How To Do Unit Conversions by the Factor-Label 3A Coral Chemistry and Broken Bones 68
Method 13 3B Ionic Compounds in Medicine 75
3C Nitric Oxide: Air Pollutant and Biological
1.6 States of Matter 17
Messenger 83
1.7 Density and Specific Gravity 18
1.8 Describing the Various Forms of Energy 20
Chapter Summary 21 Chapter 4 Chemical
Problems 22 Reactions and Energy
CHEMICAL CONNECTIONS Calculations 104
1A Drug Dosage and Body Mass 11 4.1 The Chemical Reaction 104
4.2 Balancing Chemical
Chapter 2 Atoms 26 Equations 104
How To Balance a Chemical
2.1 Composition of Matter 26
Equation 105
2.2 Classifying Matter 27
2.3 Postulates of Dalton’s Atomic Theory 30 4.3 Predicting Whether Ions in
2.4 Composition of Atoms 33 Aqueous Solution Will React
2.5 The Periodic Table 38 with Each Other 108
2.6 Arrangement of Electrons in an Atom 44 4.4 Oxidation and Reduction Reactions 112
2.7 Electron Configuration and the Periodic Table 51 4.5 Formula Weights and Molecular Weights 117
2.8 Periodic Properties 52 4.6 The Mole and Calculating Mass Relationships 117
4.7 Calculating Mass Relationships in Chemical
Chapter Summary 55 Reactions 121
Problems 56 4.8 Describing Heat and the Ways in Which It Is
CHEMICAL CONNECTIONS Transferred 128
2A Elements Necessary for Human Life 28 4.9 Heat of Reaction 131
2B Abundance of Elements Present in the Human Body Chapter Summary 132
and in the Earth’s Crust 32
Problems 133
2C Strontium-90 42
CHEMICAL CONNECTIONS
2D The Use of Metals as Historical Landmarks 43
4A Solubility and Tooth Decay 112
4B Voltaic Cells 115
Chapter 3 Chemical Bonds 63 4C Artificial Pacemakers and Redox 116
3.1 The Octet Rule 63
3.2 Naming Anions and Cations 66
3.3 The Two Major Types of Chemical Bonds 68
Chapter 5 Gases, Liquids, and Solids 140
3.4 An Ionic Bond 70 5.1 Introduction to the Three States of Matter 140
3.5 Naming Ionic Compounds 72 5.2 Gas Pressure and Measurements 141
3.6 A Covalent Bond 74 5.3 The Behavior of Gases 142
viii
5.4 Avogadro’s Law and the Ideal Gas Law 146 How To Interpret the Value of the Equilibrium
5.5 Dalton’s Law of Partial Pressures 148 Constant, K 216
5.6 The Kinetic Molecular Theory 150 7.7 Le Chatelier’s Principle 218
5.7 Types of Intermolecular Attractive Forces 151
Chapter Summary 223
5.8 The Behavior of Liquids at the Molecular
Problems 224
Level 155
Chapter Summary 161
7A Why High Fever Is Dangerous 209
Problems 162
7B The Effects of Lowering Body Temperature 211
CHEMICAL CONNECTIONS 7C Timed-Release Medication 212
5A Breathing and Boyle’s Law 143 7D Sunglasses and Le Chatelier’s Principle 221
5B Hyperbaric Medicine 149 7E The Haber Process 223
5C Blood Pressure Measurement 157
5D The Densities of Ice and Water 160
Chapter 8 Acids and Bases 229
Chapter 6 Solutions and Colloids 168 8.1 Acids and Bases 229
8.2 Defining the Strength of Acids
6.1 Introduction to Mixtures 168 and Bases 231
6.2 The Most Common Types of Solutions 169 8.3 Conjugate Acid–Base
6.3 The Distinguishing Characteristics of Pairs 233
Solutions 169 How To Name Common
6.4 Factors Affecting Solubility 171 Acids 235
6.5 The Most Common Units for Concentration 174
8.4 The Position of Equilibrium in
6.6 Water as a Good Solvent 180
an Acid–Base Reaction 236
6.7 Colloids 185
8.5 Acid Ionization
6.8 Colligative Properties 187
Constants 238
Chapter Summary 194
How To Use Logs and
Problems 194
Antilogs 239
8.6 Properties of Acids and Bases 241
6A Acid Rain 170 8.7 Acidic and Basic Properties of Pure Water 244
6B The Bends 173 8.8 pH and pOH 246
6C Electrolyte Solutions in Body and Intravenous 8.9 Using Titrations to Calculate Concentration 249
Fluids 181
8.10 Buffers 251
6D Hydrates and Air Pollution: The Decay of Buildings
8.11 Calculating the pH of a Buffer 255
and Monuments 184
8.12 TRIS, HEPES, and Other Biochemical Buffers 257
6E Emulsions and Emulsifying Agents 186
6F Reverse Osmosis and Desalinization 191 Chapter Summary 260
6G Hemodialysis 193 Problems 261
Chemical Connections
8A Some Important Acids and Bases 232
Chapter 7 Reaction Rates and 8B Drugstore Antacids 245
Chemical Equilibrium 200 8C Respiratory and Metabolic Acidosis 258
7.1 Measuring Reaction Rates 200 8D Alkalosis and the Sprinter’s Trick 260
7.2 Molecular Collisions and Reactions 202
7.3 Activation Energy and Reaction Rate 204
7.4 Rate of a Chemical Reaction 206
Chapter 9 Nuclear Chemistry 266
7.5 Equilibrium 210 9.1 Discovery of Radioactivity 266
7.6 The Equilibrium Constant 213 9.2 Defining Radioactivity 267
ix
x | Contents
9.3 Nucleus and Radioactivity 268 Chapter 12 Alkenes, Alkynes, and Aromatic
How To Balance a Nuclear Equation 270 Compounds 347
9.4 Nuclear Half-Life 273
12.1 Introduction to Alkenes and Alkynes 347
9.5 Detecting and Measuring Nuclear Radiation 276
12.2 Structures of Alkenes and Alkynes 348
9.6 Radiation Dosimetry and Human Health 279
12.3 Naming Alkenes and Alkynes 349
9.7 Nuclear Medicine 282
12.4 Physical Properties of Alkenes and Alkynes 354
9.8 Nuclear Fusion 287
12.5 Characteristic Reactions of Alkenes 355
9.9 Nuclear Fission and Atomic Energy 289
12.6 Important Polymerization Reactions of Ethylene
Chapter Summary 291 and Substituted Ethylenes 364
Summary of Key Reactions 292 12.7 Structure of Benzene 368
Problems 292 12.8 Naming Aromatic Compounds 370
CHEMICAL CONNECTIONS 12.9 Reactions of Benzene and Its Derivatives 372
9A Radioactive Dating 275 12.10 Phenols 374
9B The Indoor Radon Problem 281 Chapter Summary 377
9C How Radiation Damages Tissues: Free Radicals 283 Summary of Key Reactions 378
9D Magnetic Resonance Imaging 285 Problems 379
9E Radioactive Fallout from Nuclear Accidents 291 Chemical Connections
12A Cis-Trans Isomerism in Vision 355
Chapter 10 Organic Chemistry 298 12B Recycling Plastics 366
12C DDT: A Boon and a Curse 372
10.1 Introduction to Organic Chemistry 298 12D Iodide Ion and Goiter 373
10.2 Obtaining Organic Compounds 300 12E Capsaicin, for Those Who Like It Hot 376
10.3 Writing Structural Formulas of Organic
Compounds 302
10.4 Functional Groups 304
Chapter 13 Alcohols, Ethers, and
Chapter Summary 310 Thiols 388
Problems 310
13.1 Structures, Names, and Physical Properties of
Alcohols 389
10A Taxol: A Story of Search and Discovery 301
13.2 Characteristic Reactions of
Alcohols 393
Chapter 11 Alkanes 316 13.3 Structures, Names, and Physical
Properties of Ethers 398
11.1 Introduction to Alkanes 316 13.4 Structures, Names, and Physical
11.2 Writing Structural Formulas of Alkanes 317 Properties of Thiols 402
11.3 Constitutional Isomers 318 13.5 Commercially Important
11.4 Naming Alkanes 321 Alcohols 404
11.5 Obtaining Alkanes 325
11.6 Cycloalkanes 325
Chapter Summary 406
11.7 Shapes of Alkanes and Cycloalkanes 327
Summary of Key
Reactions 407
How To Draw Alternative Chair Conformations of
Problems 407
Cyclohexane 329
11.8 Cis-Trans Isomerism in Cycloalkanes 331
13A The Importance of Hydrogen Bonding in Drug-
11.9 Physical Properties of Alkanes and
Receptor Interactions 394
Cycloalkanes 333
13B Breath-Alcohol Screening 399
11.10 Characteristic Reactions of Alkanes 336
13C Ethylene Oxide: A Chemical Sterilant 400
11.11 Some Important Haloalkanes 338
13D Ethers and Anesthesia 401
Chapter Summary 339
Summary of Key Reactions 340
Problems 341 Chapter 14 Chirality: The Handedness of
CHEMICAL CONNECTIONS Molecules 413
11A The Poisonous Puffer Fish 330
14.1 Enantiomerism 413
11B Octane Rating: What Those Numbers at the Pump
Mean 336 How To Draw Enantiomers 417
11C The Environmental Impact of Freons 338 14.2 Specifying the Configuration of a Stereocenter 419
Contents | xi
14.3 Possible Stereoisomers for Molecules with Two or 17B Esters as Flavoring Agents 491
More Stereocenters 423 17C Ketone Bodies and Diabetes 493
14.4 Optical Activity and Chirality in the Laboratory 427
14.5 Significance of Chirality in the Biological
World 428
Chapter 18 Carboxylic
Anhydrides, Esters, and
Chapter Summary 430
Amides 502
Problems 430
Chemical Connections 18.1 Carboxylic Anhydrides,
Esters, and Amides 502
14A Chiral Drugs 427
18.2 Preparation of Esters 506
18.3 Preparation of Amides 507
Chapter 15 Amines 436 18.4 Characteristic Reactions
of Anhydrides, Esters, and
15.1 Structure of Amines 436
Amides 507
15.2 Names of Amines 439
18.5 Phosphoric Anhydrides and
15.3 Physical Properties of Amines 442
Phosphoric Esters 515
15.4 Basicity of Amines 442
18.6 Step-Growth Polymerization 515
15.5 Characteristic Reactions of Amines 445
Chapter Summary 518
Chapter Summary 449
Problems 520
Problems 449
18A The Pyrethrins—Natural Insecticides of Plant
15A Amphetamines (Pep Pills) 437
Origin 504
15B Alkaloids 438
18B The Penicillins and Cephalosporins: b-Lactam
15C Tranquilizers 443
Antibiotics 505
15D The Solubility of Drugs in Body Fluids 446
18C From Willow Bark to Aspirin and Beyond 506
15E Epinephrine: A Prototype for the Development of
18D Ultraviolet Sunscreens and Sunblocks 510
New Bronchodilators 448
18E Barbiturates 514
18F Stitches That Dissolve 518
Chapter 16 Aldehydes and Ketones 455
16.1 Aldehydes and Ketones 455 Chapter 19 Carbohydrates 525
16.2 Naming Aldehydes and Ketones 456
19.1 Monosaccharides: The Simplest
16.3 Physical Properties of Aldehydes and Ketones 459
Carbohydrates 525
16.4 Characteristic Reactions of Aldehydes and
19.2 Cyclic Structures of Monosaccharides 531
Ketones 460
19.3 Characteristic Reactions of Monosaccharides 534
16.5 Keto-Enol Tautomerism 467
19.4 Disaccharides and Oligosaccharides 539
Chapter Summary 468 19.5 Polysaccharides 544
Summary of Key Reactions 468 19.6 Acidic Polysaccharides 546
Problems 469
Chapter Summary 548
Chemical Connections Summary of Key Reactions 549
16A From Moldy Clover to a Blood Thinner 459 Problems 550
Chapter 17 Carboxylic Acids 476 19A Galactosemia 531
19B Testing for Glucose 537
17.1 Carboxylic Acids 476 19C A, B, AB, and O Blood Types 540
17.2 Names of Carboxylic Acids 476 19D Is There a Connection Between Carbohydrates and
17.3 Physical Properties of Carboxylic Acids 480 Obesity? 546
17.4 Soaps and Detergents 481
17.5 Characteristic Reactions of Carboxylic Acids 486
Chapter Summary 494 Chapter 20 Lipids 555
Summary of Key Reactions 494 20.1 Importance of Lipids 555
Problems 495 20.2 Fatty Acids 556
CHEMICAL CONNECTIONS 20.3 Triglyceride Structure 559
17A Trans Fatty Acids: What Are They and How Do You 20.4 Properties of Triglycerides 560
Avoid Them? 483 20.5 Structures of Complex Lipids 564
xii | Contents
20.6 Lipids and Membrane Structure 565 Chapter Summary 661

20.7 Glycerophospholipids 566 Problems 662
20.8 Sphingolipids 568 Chemical Connections
20.9 Glycolipids 570 22A Enzymes Allow Us to Enjoy Champagne 643
20.10 Steroids 571 22B Enzymes and Memory 649
20.11 Physiological Roles of Steroid Hormones 578 22C Medical Uses of Inhibitors 652
20.12 Bile Salts 583 22D Case Study in Enzyme Regulation 660
20.13 Prostaglandins, Thromboxanes, and
Leukotrienes 584
20.14 Molecular Transport Across Membranes 589
Chapter 23 Chemical
Chapter Summary 594 Communications:
Problems 596 Neurotransmitters and
Chemical Connections Hormones 667
20A Butter vs. Margarine – Which is healthier? 562
23.1 Cells Communicate in Many
20B Lipid Storage Diseases 572
Ways 667
20C Anabolic Steroids 580
23.2 Neurotransmitters and
20D Oral Contraception 584
Hormones 668
20E Action of Anti-inflammatory Drugs 586
23.3 Cholinergic Messengers 671
20F Why Should We Eat More Salmon? 587
23.4 Amino Acid Neurotransmitters 677
23.5 Adrenergic Messengers 679
Chapter 21 Proteins 600 23.6 Peptides in Chemical Communications 684
23.7 Steroid Hormone Messengers 689
21.1 The Many Functions of Proteins 600 23.8 Drugs Affect Chemical Communications 690
21.2 Amino Acids 601
Chapter Summary 693
21.3 Amino Acids Exist as Zwitterions 607
Problems 694
21.4 Amino Acids Combine to Form Proteins 610
21.5 Amino Acid Characteristics 613 Chemical Connections
21.6 Uncommon Amino Acids 615 23A Zebrafish, Synapses, and Sleep 672
21.7 Protein Properties 616 23B Alzheimer’s Disease and Chemical
21.8 Protein Primary Structure 618 Communication 674
21.9 Protein Secondary Structure 623 23C Parkinson’s Disease: Depletion of Dopamine 683
21.10 Protein Tertiary Structure 625 23D Diabetes 687
21.11 Protein Quaternary Structure 630 23E Depression—An Epidemic In Modern Times 691
21.12 Protein Denaturation 634
Chapter Summary 636
Chapter 24 Nucleotides, Nucleic Acids,
Problems 637
and Heredity 697
21A Aspartame, the Sweet Peptide 612 24.1 DNA and RNA are the Molecules
21B AGE and Aging 616 of Heredity 697
21C Peptide Hormones—Small Molecules with Big 24.2 Nucleic Acids 698
Effects 620 24.3 The Structure of DNA and RNA 703
21D Sickle Cell Anemia 622 24.4 RNA Types 710
21E Protein/Peptide Conformation–Dependent 24.5 Genes 714
Diseases 632 24.6 Medical Applications of RNA 715
21F Laser Surgery and Protein Denaturation 635 24.7 DNA Replication 717
24.8 DNA Amplification 721
Chapter Summary 727
Chapter 22 Enzymes 641 Problems 728
22.1 Enzymes are Biological Catalysts 641 Chemical Connections
22.2 Enzyme Nomenclature 643 24A Who Owns Your Genes? 701
22.3 Enzyme Activity 644 24B DNA Fingerprinting 709
22.4 Enzyme Mechanisms 647 24C Telomeres, Telomerase, and Immortality 722
22.5 Enzyme Regulation 655 24D Synthetic Genome Created 722
22.6 Enzymes in Medicine 659 24E Did the Neandertals Go Extinct? 725
Contents | xiii
Chapter 25 Gene Expression and Protein 27.6 The Energy Yield from Stearic Acid
Synthesis 731 Catabolism 805
27.7 Ketone Bodies 806
25.1 DNA Leads to RNA and Protein 731 27.8 Nitrogen Processing in Amino Acid
25.2 Transcription of DNA 733 Catabolism 809
25.3 Translation of RNA 735 27.9 Carbon Skeleton Processing in Amino Acid
25.4 The Genetic Code 736 Catabolsim 814
25.5 Protein Synthesis 738
Chapter Summary 816
25.6 Gene Regulation 746
Problems 817
25.7 DNA Mutations 751
25.8 DNA Manipulation 755 Chemical Connections
25.9 Gene Therapy 756 27A Lactate Accumulation 796
25.10 Epigenetics 760 27B Treating Obesity—Changing Carbohydrate
Metabolism 800
Chapter Summary 762
27C Ketoacidosis in Diabetes 808
Problems 763
27D Hereditary Defects in Amino Acid Catabolism:
Chemical Connections PKU 813
25A Breaking the Dogma: The Twenty-First Amino
Acid 744
25B Protein Synthesis Makes Memories 744 Chapter 28 Biosynthetic
25C Mutations and Biochemical Evolution 752 Pathways 820
25D Silent Mutations 753 28.1 The General Outline of
25E p53: A Central Tumor Suppressor Protein 754 Biosynthetic Pathways 820
25F Twenty Years of Cystic Fibrosis Trials and 28.2 Biosynthesis of
Tribulations 758
Carbohydrates 822
25G How Cancer and Aging Are Related to Epigenetic
28.3 Biosynthesis of Fatty
States 761
Acids 827
28.4 Biosynthesis of Membrane Lipids 829
Chapter 26 Bioenergetics: How the Body 28.5 Biosynthesis of Amino Acids 832
Converts Food to Energy 766 Chapter Summary 835
Problems 835
26.1 The Nature of Metabolism 766
26.2 Mitochondria and Their Role in Metabolism 767
28A Photosynthesis 823
26.3 The Principal Compounds of Catabolic
28B Acetyl-CoA Carboxylase—A New Target in the Fight
Pathways 770
Against Obesity 828
26.4 The Citric Acid Cycle and in Metabolism 773
28C Statin Drugs as Inhibitors of Cholesterol
26.5 Electron and H1 Transport 777
Biosynthesis 831
26.6 The Chemiosmotic Pump and ATP Production 781
28D Essential Amino Acids 833
26.7 Energy Yield from Aerobic Metabolism 782
26.8 Conversion of Chemical Energy to Other
Forms 783 Chapter 29 Nutrition 838
Chapter Summary 786 29.1 Nutritional Guidelines 838
Problems 787 29.2 Counting Calories 843
Chemical Connections 29.3 Carbohydrate Digestion 845
26A Uncoupling and Obesity 780 29.4 Fat Digestion 847
26B ATP in Cell Signaling 785 29.5 Protein Digestion 848
29.6 The Importance of Vitamins, Minerals, and
Water 850
Chapter 27 Specific Catabolic Pathways: Chapter Summary 860
Carbohydrate, Lipid, and Protein Problems 861
Metabolism 790 Chemical Connections
27.1 The General Outline of Catabolic Pathway 790 29A The New Food Guide 841
27.2 The Reactions of Glycolysis 793 29B Why Is It So Hard to Lose Weight? 844
27.3 The Energy Yield from Glucose Catabolism 798 29C Do Hormones or Overeating Cause Obesity? 846
27.4 Glycerol Catabolism 801 29D Iron: An Example of a Mineral Requirement 856
27.5 b-Oxidation of Fatty Acids 802 29E Food for Performance Enhancement 857
xiv | Contents
29F Depression in America—Don’t Worry; Be Chapter 31 Body Fluids 902

Happy 858
29G Is Gluten-Freedom a Fad? 859 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.
Chapter 30 Immunochemistry 864
30.1 The Body’s Defense against Invasion 864 Appendix I Exponential Notation A-1
30.2 Organs and Cells of the Immune System 866
30.3 Antigens Stimulate the Immune System 870
30.4 Immunoglobulins 872 Appendix II Significant Figures A-5
30.5 T Cells and T-Cell Receptors 878
30.6 Immunization 880 Answers To In-Text And Odd-Numbered
30.7 Distinguishing “Self ” from “Nonself ” 884 End-Of-Chapter Problems A-8
30.8 The Human Immunodeficiency Virus and
AIDS 888 Glossary G-1
Chapter Summary 898
Problems 899 Index I-1
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
Preface
W
elcome to the 12th edition of Introduction to General, Organic, and
Biochemistry. We wish to sincerely thank our colleagues who not
only adopted the previous editions for their courses but also offered
sage advice on suggested changes and updates to this edition.
With all the continuous advances in the field, this edition emphasizes the
inclusion of new relevant concepts and examples in this fast-growing disci-
pline, especially in the biochemistry chapters. Based on valuable feedback
from reviewers, we also strive to consolidate content in a more meaningful
and manageable manner while preserving an integrated view of chemistry.
This new edition continues with the tradition of providing a solid foundation
on which instructors can build upon, and chapter resources are conceived
and written with flexibility in mind, affording instructors the opportunity
to seamlessly select applicable topics for discussion with their students. The
wealth of problems, both practical and challenging, provide students with
numerous ways to test their knowledge from a variety of viewpoints.
From the very beginning of the book, we include organic compounds and
biochemical substances to illustrate relevant and overlapping principles.
This progression ascends from the simple to the complex. We encourage our
colleagues to advance to the chapters of biochemistry as quickly as possible,
because there lies most of the material that is relevant to the future profes-
sions of our students.
Audience and Unified Approach

This book is intended for non-chemistry majors, mainly those entering
health sciences and related fields, such as nursing, medical technology,
physical therapy, and nutrition. In its entirety, it can be used for a one-year
(two-semester or three-quarter) course in chemistry, or
parts of the book can be used in a one-term chemistry
course.
We assume that the students using this book have
little or no background in chemistry. Therefore, we in-
troduce the basic concepts slowly at the beginning and
increase the tempo and the level of sophistication as we
go on. We progress from the basic tenets of general chem-
istry to organic and then to biochemistry. Throughout, we
integrate the parts by keeping a unified view of chemis-
try. For example, we frequently use organic and biological
© michaeljung/ShutterStock.com
substances to illustrate general principles.

While teaching the chemistry of the human body is
our ultimate goal, we try to show that each subsection
of chemistry is important in its own right, besides being
necessary for understanding future topics.
xv
xvi | Preface
Chemical Connections (Medical and Other

Applications of Chemical Principles)
The Chemical Connections boxes contain applications of the principles dis-
cussed in the text. Comments from users of earlier editions indicate that
these boxes have been especially well received, and provide a much-requested
relevance to the text. For example, in Chapter 1, students can see how cold
116 | Chapter 4 Chemical Reactions and Energy Calculations
compresses relate to waterbeds and to lake temper-
CHeMICAL ConneCtIons 4C Artificial Pacemakers and Redox atures (Chemical Connections 1C). New up-to-date
An artificial pacemaker is a small electrical device that The zinc atom is oxidized to Zn , and Hg is reduced 21 21topics include coverage of omega-3 fatty acids and
uses electrical impulses, delivered by electrodes con- to Hg. Many contemporary artificial pacemakers con-
tacting the heart muscles, to regulate the beating of the tain a lithium-iodine battery, which has a longer bat-
heart disease (Chemical Connections 21F), and the
heart. The primary purpose of a pacemaker is to maintain tery life (10 years or more). Consider the unbalanced
an adequate heart rate, either because the heart’s native redox reaction for the lithium-iodine battery:
search for treatments for cystic fibrosis (Chemical
pacemaker does not beat fast enough, or perhaps there
is a blockage in the heart’s electrical conduction system. Li 1 I h LiI 2
Connections 26F).
When a pacemaker detects The lithium atom is ox- The inclusion of Chemical Connections allows for
that the heart is beating idized to Li , and the I
a considerable degree of flexibility. If an instructor
1
2
too slowly, it sends an molecule is reduced to I . 2
elec trical signal to the
heart, generated via a
When the pacemaker fails
to sense a heartbeat within wants to assign only the main text, the Chemical
redox reaction, so that the
heart muscle beats faster.
a normal beat-to-beat time
period, an electrical signal
Connections do not interrupt continuity, and the es-
Modern pacemakers are
externally programmable
produced from these reac-
tions is initiated, stimu-
sential material will be covered. However, because
and allow a cardiologist
to select the optimum pac-
lating the ventricle of the
heart. This sensing and
they enhance the core material, most instructors
ing modes for individual
patients.
stimulating activity contin-
ues on a beat-by-beat ba-
will probably wish to assign at least some of the
Early pacemakers gen-
erated an electrical im-
sis. More complex systems Chemical Connections. In our experience, students
include the ability to stim-
pulse via the following
redox reaction:
A pacemaker is a medical device that uses electrical impulses, ulate both the atrial and are eager to read the relevant Chemical Connec-
delivered by electrodes contacting the heart muscles, to regulate ventricular chambers. ■
Zn 1 Hg h Zn 1 Hg the beating of the heart.
21 21 tions, without assignments, and they do with dis-
Test your knowledge with Problem 69. crimination. From such a large number of boxes, an
instructor can select those that best fit the partic-
2. Respiration Humans and animals get their energy by respiration. The ular needs of the course. So that students can test
oxygen in the air we breathe oxidizes carbon-containing compounds in
our cells to produce CO and their
H O. Noteknowledge,
2 that respiration we
2 provide problems at the end of each chapter for all of the
is equivalent
to combustion, except that it takes place more slowly and at a much
lower temperature. We discuss Chemicalrespiration Connections;
more fully in Chapter 26. these problems are now identified within the boxes.
The important product of respiration is not CO2 (which the body elimi-
nates) or H2O, but energy.
3. Rusting We all know that when iron or steel objects are left out in the
Metabolism: Color Code

open air, they eventually rust (steel is mostly iron but contains certain
other elements as well). In rusting, iron is oxidized to a mixture of iron
oxides. We can represent the main reaction by the following equation:
The biological functions of chemical compounds are explained in each of
4Fessd 1 3O2sgd b 2Fe2O3ssd
the biochemistry chapters and in many of the organic chapters. Emphasis

4. Bleaching Most bleaching involves oxidation, and common bleaches
are oxidizing agents. The colored compounds being bleached are
is placed on chemistry rather than physiology. Positive feedback about the
usually organic compounds; oxidation converts them to colorless
Cassiohabib/Shutterstock.com
compounds.
▲
organization
5. Batteries A voltaic cell (Chemical Connections 4B)of is a the metabolism
device in which chapters has encouraged us to maintain the
order (Chapters 26–27).
electricity is generated from a chemical reaction. Such cells are often
called batteries (Figure 4.5). We are all familiar with batteries in our
Household bleaches are oxidizing First, weplace

introduce
in the battery the
cars and in such portable devices as radios, flashlights, cell phones, and
computers. In all cases, the reaction that takes is a common metabolic pathway through which all food
agents.
redox reaction.
is utilized (the citric acid cycle and oxidative phosphorylation), and only after
that do we discuss the specific pathways leading to the common pathway. We
find this a useful pedagogic device, and it enables us to sum the caloric values
of each type of food because its utilization through the c ommon p athway has
already been learned. Finally, we separate the catabolic pathways from the
anabolic pathways by treating them in different chapters, emphasizing the
different ways the body breaks down and builds up different molecules.
The topic of metabolism is a difficult one for most students, and we have
tried to explain it as clearly as possible. We enhance the clarity of presenta-
tion by the use of a color code for the most important biological compounds.
Each type of compound is screened in a specific color, which remains the
same throughout the three chapters. These colors are as follows:
ATP and other nucleoside triphosphates
ADP and other nucleoside diphosphates
The oxidized coenzymes NAD+ and FAD
The reduced coenzymes NADH and FADH2
Acetyl coenzyme A
Preface | xvii
In figures showing metabolic pathways, we display the numbers of the

various steps in yellow. In addition to this main use of a color code, other
figures in various parts of the book are color coded so that the same color is
used for the same entity throughout. For example, in all figures that show
enzyme–substrate interactions, enzymes are always shown in blue and sub-
strates in orange.
Features
●● Problem-Solving Strategies The in-text examples include a description of
the strategy used to arrive at a solution. This will help students orga-
nize the information in order to solve the problem.
●● Visual Impact We have introduced illustrations with heightened
pedagogical impact. Some of these show the microscopic and macro-
scopic aspects of a topic under discussion, such as Figures 6-3 (Henry’s
Law) and 6-10 (electrolytic conductance). The Chemical Connections es-
says have been enhanced further with more photos to illustrate each
topic.
●● [UPDATED] Chemical Connections Over 150 essays describe applica-
tions of chemical concepts presented in the text, linking the chemis-
try to their real uses. Many new application boxes on diverse topics
were added.
●● Summary of Key Reactions In each organic chemistry chapter (10–18)
there is an annotated summary of all the new reactions introduced.
Keyed to sections in which they are introduced, there is also an example
of each reaction.
●● Chapter Summaries Summaries reflect the Chapter contents. At the end
of each chapter, summary paragraphs highlight the concepts.
●● Looking Ahead Problems At the end of most chapters, the challenge
problems are designed to show the application of principles in the chap-
ter to material in the following chapters.
●● Tying-It-Together and Challenge Problems At the end of most chapters,
these problems build on past material to test students’ knowledge of
these concepts. In the Challenge Problems, associated chapter refer-
ences are given.
●● How To Boxes These boxes emphasize the skills students need to master
the material. They include topics such as, “How to Determine the Num-
ber of Significant Figures in a Number” (Chapter 1) and “How to Draw
Enantiomers” (Chapter 14).
●● Molecular Models Ball-and-stick models, space-filling models, and
electron-density maps are used throughout the text as appropriate
aids for visualizing molecular properties and interactions.
●● Margin Definitions Many terms are also defined in the margin to help
students learn terminology. By skimming the chapter for these defini-
tions, students will have a quick summary of its contents.
●● Answers to all in-text and odd-numbered end-of-chapter problems
Answers to selected problems are provided at the end of the book. De-
tailed worked-out solutions to these same problems are provided in the
Student Solutions Manual.
●● Glossary The glossary at the back of the book gives a definition of each
new term along with the number of the section in which the term is
introduced.
xviii | Preface
Organization and Updates

General Chemistry (Chapters 1–9)
●● Chapter 1, Matter, Energy, and Measurement, serves as a general intro-
duction to the text and introduces the pedagogical elements that are
new to this edition, with an emphasis on solving conversion problems
related to a clinical setting. Concepts of heat from prior editions were
moved to a later chapter. New problems were added.
●● In Chapter 2, Atoms, we introduce four of the five ways used to represent
molecules throughout the text: we show water as a molecular formula,
a structural formula, a ball-and-stick model, and a space-filling model.
Seventeen new problems were added.
●● Chapter 3, Chemical Bonds, begins with a discussion of ionic compounds,
followed by a discussion of molecular compounds. Fourteen new prob-
lems were added.
●● Chapter 4, Chemical Reactions, and Energy Calculations introduces the
various intricacies in writing and balancing chemical reactions before
stoichiometry is introduced. This chapter includes the How To box,
“How to Balance a Chemical Equation,” which illustrates a step-by-step
method for balancing an equation. This chapter also incorporates and
expands the discussion on heat of reaction with sample problems.
●● In Chapter 5, Gases, Liquids, and Solids, we present intermolecular
forces of attraction in order of increasing energy, namely London disper-
sion forces, dipole–dipole interactions, and hydrogen bonding. Ten new
problems were added.
●● Chapter 6, Solutions and Colloids, opens with a listing of the most com-
mon types of solutions, followed by a discussion of the factors that affect
solubility and the most common units for concentration, and closes with
an enhanced discussion of colligative properties. Seven new problems
were added.
●● Chapter 7, Reaction Rates and Chemical Equilibrium, shows how these
two important topics are related to one another. A How To box shows
how to interpret the value of the equilibrium constant, K. In addition,
eight new problems were added.
●● Chapter 8, Acids and Bases, introduces the use of curved arrows to show
the flow of electrons in organic reactions. Specifically, we use them here
to show the flow of electrons in proton-transfer reactions. The major
theme in this chapter is the discussion of acid–base buffers and the
Henderson–Hasselbalch equation. Information was added on solving
problems using the activity series, along with eleven new problems.
●● Chapter 9, Nuclear Chemistry, highlights nuclear applications in medi-
cine. Four new problems were added.
Organic Chemistry (Chapters 10–18)

●● Chapter 10, Organic Chemistry, is an introduction to the characteristics
of organic compounds and to the most important organic functional
groups. Eight new problems were added.
●● In Chapter 11, Alkanes, we introduce the concept of a line-angle formula,
which we will continue to use throughout the organic chapters. These
are easier to draw than the usual condensed structural formulas and
are easier to visualize. The discussion on the conformation of alkanes
Preface | xix
has been reduced and instead concentrates on the conformations of cy-

cloalkanes. Fifteen new problems were added, including concepts from
prior chapters.
●● In Chapter 12, Alkenes, Alkynes, and Aromatic Compounds we introduce
a new, simple way of looking at reaction mechanisms: add a proton, take
a proton away, break a bond, and make a bond. The purpose of this in-
troduction to reaction mechanisms is to demonstrate to students that
chemists are interested not only in what happens in a chemical reac-
tion, but also in how it happens. Content on aromatic compounds was
also added to this chapter and condensed from previous editions. We
refined the discussion of these reaction mechanisms in this edition and
added a new problem to the end-of-chapter exercise about a compound
once used as a flame retardant in polystyrene-foam building insulation
and why its use is now prohibited.
While aromatic compounds are seemingly similar to alkenes via
the presence of the carbon-carbon double bond, they do have different
reactions. For instance, aromatic compounds can undergo substitution.
In contrast to alkenes that can do addition reactions. The 11th edition
Chapter 13 was consolidated into the 12th edition Chapter 12. The close
proximity of the content in one chapter will better contrast similarities
and differences between alkenes/alkynes and aromatic compounds.
●● Chapter 13, Alcohols, Ethers, and Thiols, discusses the structures, names,
and properties of alcohols first, and then gives a similar treatment to
ethers, and finally thiols. The chapter opener was changed to contrast
the chemical and physical differences between the alcohol, ether, and
thiol functional groups. Each functional group’s reactions were com-
pared in a real-world application. In addtion, through out the chapter
figures and examples, more colors were implemented to better reference
and contrast with the text. In a simple example of this, using red for ox-
ygen, blue/green for partial positive charges and red for partial negative
charges was implemented in to various figures. Also, all hydrogen bond-
ing interactions are now shown consistently in each figure with blue
dots.
●● In Chapter 14, Chirality: The Handedness of Molecules, the concept of a
stereocenter and enantiomerism is slowly introduced, using 2-butanol
as a prototype. We then treat molecules with two or more stereocenters
and show how to predict the number of stereoisomers possible for a par-
ticular molecule. We also explain R,S convention for assigning absolute
configuration to a tetrahedral stereocenter. Twenty new problems were
added to reinforce new content and address concepts from previous
chapters.
●● In Chapter 15, Amines, the initial introductory example problem opens
using the central nervous stimulant nicotine. This molecule is used to
assist students in the stepwise classification of amines. In addtion to
this chapter, the tranquilizer Chemical Connection was expanded to in-
clude a small data portion on opioid use.
●● Chapter 16, Aldehydes and Ketones, has a discussion of NaBH4 as a car-
bonyl-reducing agent with emphasis on its use as a hydride-transfer
reagent. We then make the parallel to NADH as a carbonyl-reducing
agent and hydride-transfer agent. Nine new problems were added.
●● Chapter 17, Carboxylic Acids, focuses on the chemistry and physical
properties of carboxylic acids. To continue the discussion on trans fatty
acids from the previous edition, the chapter opener shows products that
have that might have low levels of trans fatty acids. In addition, this
xx | Preface
leads into the trans fatty acid Chemical Connection. Then, this chapter
implements more acid base terminology.
●● Chapter 18, Carboxylic Anhydrides, Esters, and Amides, describes the
chemistry of these three important functional groups with emphasis on
their acid-catalyzed and base-promoted hydrolysis and reactions with
amines and alcohols. A short presentation about Green Chemistry is
presented in this chapter. In the section about characteristic reactions
of esters, the 12 Principles of Green Chemistry are introduced.
Biochemistry (Chapters 19–30)

●● Chapter 19, Carbohydrates, begins with the structure and nomenclature
of monosaccharides, including their oxidation, reduction, and the for-
mation of glycosides, then concludes with a discussion of the structure
of disaccharides, polysaccharides, and acidic polysaccharides. The de-
scriptions of these structures, especially glucose stereochemistry, have
been clarified in this edition. Three new example problems are offered
in the chapter, as well as 5 new end of chapter problems. A new section
was added to help students learn how to convert Fisher projections to
Haworth projections
●● Chapter 20, Lipids, covers the most important features of lipid biochem-
istry, including membrane structure and the structures and functions
of steroids. In this edition, we have stressed the need for students to re-
call material from earlier chapters, especially structure and reactions of
carboxylic acids. The chapter also has an increased emphasis on mem-
brane transport and an update on possible classification of trans fatty
acids as food additives. A new section on fatty acid basics was added
using some material from previous chapters so that this chapter can be
read more easily on its own. A new Chemical Connections box on Butter
and Margarine was added, along with 7 new example problems and 10
end of chapter problems
●● Chapter 21, Proteins, covers the many facets of protein structure and
function. It gives an overview of how proteins are organized, beginning
with the nature of individual amino acids and how this organization leads
to their many functions. This supplies the student with the basics needed
to lead into the sections on enzymes and metabolism. Points causing dif-
ficulty for students in the last edition, mostly pertaining to the roles of
amino acids in proteins and bonding in transition-metal complexes, have
been clarified. This chapter also has 7 new example problems, including
sections on how to remember amino acid abbreviations. There is a new
section on myoglobin and hemoglobin structure, and a new Chemical
Connections box about peptide hormones
●● Chapter 22, Enzymes, covers the important topic of enzyme catalysis
and regulation. This discussion has been modified for a stronger cor-
relation with pathways to be discussed in Chapter 28. Specific medical
applications of enzyme inhibition are included, A new Chemical Con-
nections box describes how enzymes are involved with our perception of
taste. A new section on enzyme inhibition was added. Five new example
problems were added along with 3 end of chapter problems.
●● In Chapter 23, Chemical Communications, we see the biochemistry of
hormones and neurotransmitters. This chapter has been reorganized for
better flow in introducing the different ways of classifying neurotrans-
mitters. The health-related implications of how these substances act in
the body is the main focus of this chapter. Along with a new Chemical
Preface | xxi
Connections box focusing on Alzheimer’s disease and diabetes, the sec-

tion on depression was expanded to include new information on deep
brain stimulation. Seven new example problems were added.
●● Chapter 24, Nucleotides, Nucleic Acids, and Heredity, introduces DNA
and the processes encompassing its replication and repair. How nucleo-
tides are linked together and the flow of genetic information due to the
unique properties of these molecules is emphasized. An exciting new
section on the medical application of RNA has been added, including
a focus on the hottest topic today - CRISPR technology. Eight example
problems and 8 end of chapter problems have also been added.
●● Chapter 25, Gene Expression and Protein Synthesis, shows how the
information contained in the DNA blueprint of a cell is used to pro-
duce RNA and, eventually, protein. The focus is on how organisms
control the expression of genes through transcription and transla-
tion. Five new example problems were added, along with 10 new end
of chapter problems
●● Chapter 26, Bioenergetics, is an introduction to metabolism that focuses
strongly on the central pathways, namely the citric acid cycle, electron
transport, and oxidative phosphorylation. Eight example problems and
8 end of chapter problems were added.
●● In Chapter 27, Specific Catabolic Pathways, we address the details of car-
bohydrate, lipid, and protein breakdown, concentrating on energy yield.
A new section was added to better explain the shuttle mechanisms
and how carnitine is used to carry fatty acids across the mitochondrial
membrane. Nine new example problems were included.
●● Chapter 28, Biosynthetic Pathways, starts with a general consideration
of anabolism and proceeds to carbohydrate biosynthesis in both plants
and animals. Lipid biosynthesis is linked to the production of mem-
branes, and the chapter concludes with an account of amino-acid bio-
synthesis. New material has been added to aid the student with the big
picture concepts of tying metabolism together. A new Chemical Connec-
tions box about the enzyme Acetyl-CoA Carboxylase and its relation-
ship to obesity was added, along with 5 new example problems and 4
end of chapter problems
●● In Chapter 29, Nutrition, we take a biochemical approach to under-
standing nutrition concepts. Along the way, we look at a revised version
of the Food Guide Pyramid and debunk some of the myths about car-
bohydrates and fats. A new Chemical Connection was added about one
of the hottest topics in nutrition—gluten sensitivity. Six new example
problems and 4 end of chapter problems were added.
●● Chapter 30, Immunochemistry, covers the basics of our immune system
and how we protect ourselves from foreign invading organisms. Consid-
erable time is spent on the acquired immunity system. No chapter on
immunology would be complete without a description of the Human Im-
munodeficiency Virus. New sections were written to cover some hot top-
ics, such as miniature antibodies, regulatory T cells, and new material
on the search for an antibody against HIV. A new Chemical Connection
was written about one of the biggest topics in medicine—inflammation.
Eight new example problems were added, along with 24 new end of
chapter problems.
●● Chapter 31, Body Fluids
To access this online-only chapter, search for ISBN 978-1-337-57135-7 at
www.cengagebrain.com and visit this book’s companion website.
xxii | Preface
Supporting Materials
Please visit http://www.cengage.com/chemistry/bettelheim/gob12e
for information about the student and instructor resources for this text.
Acknowledgments
The publication of a book such as this requires the efforts of many more
people than merely the authors. We would like to thank the following pro-
fessors who offered many valuable suggestions for this new edition:
We are especially grateful for Jordan Fantini, Denison University, who
read page proofs with eyes for accuracy.
Thank you to everyone at Cengage for their support through this revi-
sion process: Learning Designer Peter McGahey, Content Manager Teresa
L. Trego, and Subject Matter Expert Dakin Sharum. Thank you to MPS
Limited for their work on this project.
We so appreciate the time and expertise of our reviewers who have read
our manuscript and given us helpful comments. They include:
Reviewers of the 12th Edition:

Stephen Z. Goldberg, Professor of Chemistry, Adelphi University
David E. Binkley, Jr., MS/MA Ed, Adjunct Professor, Departments of
Chemistry and Education, Baldwin Wallace University
Billy Samulak, PhD, Fitchburg State University
Dr. Amanda R. Knapp, Mars Hill University
Dr. Radhika Venkatraman Kumar, Adelphi University
Thomas Ott, PhD, Oakland University
Dr. Pradyumna Kumar Pradhan, UNC Greensboro
Dr. Michael Staude, Trine University
Dick Trent, Elgin Community College
Steven M. Socol
Matthew Marmorino, Indiana University South Bend
Deborah Heyl-Clegg, Eastern Michigan University
Regan Silvestri, Lorain County Community College, Elyria, Ohio
Daniel A. Barr, PhD, University of Mary
Dr. David Baker, Delta College
Betty Owen, Northeast Mississippi Community College
Ashley N. Lamm, Assistant Professor, Eastern Washington University
Corey P. Causey
Kristi Mock, University of Toledo
Kateri Ahrendt
Nathan S. Werner, Southern Utah University
D. David Nowack
Luna Zhang, Immaculata University
Riham Mahfouz, Associate Professor of Chemistry, Thomas Nelson
Community College
Polina Pine, PhD, Loyola University Chicago
Preface | xxiii

Jennifer Barber, Atlanta Metropolitan State College
Ling Chen, Borough of Manhattan Community College
Kyle Craig, Walla Walla University
Sidnee-Marie Dunn, South Puget Sound Community College
Timothy Marshall, Pima Community College
Lynda Peebles, Texas Woman’s University
Rill Reuter, Winona State University
Susan Sawyer, Kellogg Community College
Theresa Thewes, Edinboro University of Pennsylvania

Julian Davis, University of the Incarnate Word
Robert Keil, Moorpark College
Margaret Kimble, Indiana University–Purdue University Fort Wayne
Bette Kruez, University of Michigan, Dearborn
Timothy Marshall, Pima Community College
Donald Mitchell, Delaware Technical and Community College
Paul Root, Henry Ford Community College
Ahmed Sheikh, West Virginia University
Steven Socol, McHenry County College
Susan Thomas, University of Texas–San Antonio
Holly Thompson, University of Montana
Janice Webster, Ivy Tech Community College
About the Cover
F
rom the “nanoworld” to the macroworld, chemistry and biochemistry
allow us to understand how living things work. The initial chapters of
this book help us learn about atoms, what they are, what they do, and
how they form molecules like the glucose-6-phosphate shown in the upper
left of the figure. Molecules then undergo thousands of reactions in the
body, forming new molecules and using or releasing energy. Some of these
reactions can be organized into pathways, like glycogenesis shown by the
glucose-6-phosphate forming glycogen, or like glycolysis shown by the glu-
cose-6-phosphate forming pyruvic acid or lactic acid. These pathways work
to allow tissues to function correctly. As a goose takes off from the lake, it
will need energy produced from some of these pathways to fuel its flight
muscles.
xxiv
Health-Related Topics
Key Basal Caloric Requirement Sect. 29-2

Bends, the ChemConn 6B
ChemConn = Chemical Connections Box number
Bile Salts Sect. 20-12
Sect. = Section number
Blood Alcohol Screening ChemConn 13B
Prob. = Problem number
Blood Buffers Sect. 8-10D
Blood pH ChemConn 8C
A, B, AB, and O Blood Types ChemConn 19C
Blood Pressure Measurement Sect. 31-8, Probs. 31-32–31-39
Abundance of Elements in the Human
ChemConn 5C
Body and in the Earth’s Crust ChemConn 2B
Bone, Artificial ChemConn 3A
Acetaminophen (Tylenol) Probs. 1-33, 1-86
Bone Density and Solubility Equilibrium Sect. 7-6
Acid Rain ChemConn 6A
Breath Alcohol Screening ChemConn 13B
Acidic Polysaccharides Sect. 19-6
Breathing and Boyle’s Law ChemConn 5A
Acidosis ChemConn 8C
Bronchodilators and Asthma ChemConn 15E
Acquired Immunity Sect. 30-1B
Brown Fat and Hibernation ChemConn 26A
Advanced Glycation End Products ChemConn 21B
Buffers Sect. 8-10
AGE and Aging ChemConn 21B
Caffeine Prob. 4-93
AIDS Sect. 30-8
Calcium as a Signaling Agent Sect. 23-3C
Alkaloids ChemConn 15B
Calorie Counting Sect. 29-2
Alkalosis and the Sprinter’s Trick ChemConn 8D
Cancer Cell Growth and Metabolic State Sect. 26-1
Alzheimer’s Disease ChemConn 23B
Cancer Therapy Antibodies ChemConn 30A
Amoxicillin Prob. 14-32
Cannabinoid Receptors ChemConn 29F
Amphetamines ChemConn 15A, Prob. 23-50
Captopril and ACE Inhibitors Prob. 14-27
Anabolic Steroids ChemConn 20C
Capsaicin, for Those Who Like It Hot ChemConn 12E
Androstenedione Prob. 3-110
Carcinogens ChemConn 12B, Sect. 25-7
Antacids ChemConn 8B
b-Carotene Prob. 12-85
Antibiotics ChemConn 30B
Cephalosporins ChemConn 18B
Antibodies and Cancer Therapy ChemConn 30A
Cetylpyridinium Chloride Prob. 17-22
Antidepressants Probs. 24-73, 24-74, Sect. 23.8
Chiral Drugs ChemConn 14A
Antigens Sect. 30-3C
Chirality in the Biological World Sect. 14-5
Antihistamines Sect. 23-5G
Chlorine Dioxide Probs. 3-86, 4-43
Anti-inflammatory Drugs ChemConn 20E
Cholera Sect. 23-5E
Anticoagulants ChemConn 16A
Cholesterol Sect. 20-10A
Artificial Pacemakers and Redox ChemConn 4C
Cis-Trans Isomerism in
Aspartame Prob. 18-10, ChemConn 21A
Vision ChemConn 12A
Aspirin and Other NSAIDs ChemConn 18C
Cocaine ChemConn 15B
Asthma Sect. 20-13
Chondroitin Sulfate Prob. 19-66
Atherosclerosis: Levels of LDL and HDL Sect. 20-14C
Coniine ChemConn 15B
Atomic Energy Sect. 9-9
Connection between Carbohydrates and Obesity ChemConn 19D
Atropine Prob. 15-49
Coral Chemistry and Broken Bones ChemConn 3A
Attention Deficit Disorder (ADD) ChemConn 23C
COX-2 Inhibitor Drugs ChemConn 20E
Autoimmune Diseases Sect. 30-7C
Creatine: Performance Enhancement ChemConn 29E
Automobile Air Bags Prob. 5-44
Crenation Sect. 6-8C
Azithromycin Prob. 17-51
Cystic Fibrosis ChemConn 25F
B Cells Sect. 30-1B
Cytokines Sect. 30–2A
Barbiturates ChemConn 18E
DDT ChemConn 12C
xxv
xxvi | Health-Related Topics
DEET Prob. 18-40 Hyperbaric Medicine ChemConn 5B

Depression ChemConn 23E, 29G Immune System Sect. 30.2
Diabetes ChemConn 23C Immunization Sect. 30-6
Dialysis Sect. 6-8D Immunoglobin Sect. 30-4D
Dietary Protein Prob. 20-83 Immunosuppressant FK-506 Probs. 14-41, 16-46
Dietary Reference Intake Sect. 29-1 Indoor Radon Problem ChemConn 9B
Dieting and Weight Loss Prob. 19-52, Sect. 29-2 Innate Immunity Sect. 30-1A
2,4-Dinitrophenol as an Uncoupling Agent ChemConn 26A Insulin Sect. 21-8
DNA Fingerprinting ChemConn 42B Insulin, Structure Sect. 21-8
Drug Dosage and Body Mass Prob. 1-34, ChemConn 1A Iodide Ion and Goiter ChemConn 12D
Emulsions and Emulsifying Agents ChemConn 6E Ionic Compounds in Medicine ChemConn 3B
Enantiomers of Ibuprofen Sect. 14-2 Ionizing Radiation Sect. 9-5
Environmental Impact of Freons ChemConn 11C Iron and Mineral Requirements ChemConn 29D
Enzyme Regulation ChemConn 22D, Sect. 22-5 Ketoacidosis in Diabetes ChemConn 27C
Enzymes in Medical Diagnosis Sect. 22-6 Ketone Bodies ChemConn 17C, Sect. 27-7
Enzymes in Therapy Sect. 22-6 Lactate Accumulation ChemConn 27A
Ephedrine Probs. 3-91, 14-22 Laetrile Prob. 19-59
Epigenetics and DNA Sect. 25-10 Laser In Situ Keratomileusis (LASIK) ChemConn 21F
Epigenetics, Cancer, and Aging ChemConn 25G Laser Surgery and Protein Denaturation ChemConn 21F
Epinephrine ChemConn 15E Librium ChemConn 15C
Erythromycin A Prob. 13-55 Lipid Storage Diseases ChemConn 20B
Essential Amino Acids Sect. 29-5, ChemConn 28D Local Anesthetics for Dentistry Prob. 18-41
Esters, as Flavoring Agents ChemConn 17B Lowering Body Temperature ChemConn 7B
Ethers and Anesthesia ChemConn 13D Lunesta Prob. 14-43
Ethylene Oxide, as a Chemical Sterilant ChemConn 13C Lycopene Prob. 12-84
Fatty Acids Sect. 17-4A Mad Cow Disease ChemConn 21E
Fever, as a Protective Mechanism ChemConn 7A Magnetic Resonance Imaging ChemConn 9D
Fever, Dangers of ChemConn 7A Medical Uses of Inhibitors ChemConn 22C
Fluid Mosaic, Model of Membranes Sect. 20.6 Memory and Protein Synthesis ChemConn 25B
Fluoride Ion in Dental Decay ChemConn 4A Menstrual Cycle Sect. 20-11B
Fish in Diet – Health Benefits ChemConn 20F Metformin (Glucophage) Prob. 15-23
Food for Performance ChemConn 29E Methadone ChemConn 15D
Food Guide Pyramid ChemConn 29A Methamphetamine ChemConn 15A
Free Radicals ChemConn 9C, Methylparaben Prob. 17-44
Galactosemia ChemConn 19A Milk of Magnesia ChemConn 8A
Gallstones Sect. 20-10A Monoclonal Antibodies ChemConn 30-4E
Gene Patents ChemConn 24A Morphine and Enkephalins Sect. 23-6A
Gene Therapy Sect. 25-9 Morphine and Morphine Analogs Prob. 15- 5 4
Genetic Code Sect. 25-4 Mutagens Sect. 25-7
Gout Sect. 6-6B Mutations and Biochemical Evolution ChemConn 25C
G-protein/cAMP Cascade Sect. 23-5C Naproxen Sects. 14-2, 14-5B
Haber Process ChemConn 7E Neurotransmitters Sect. 21-5, Sect. 23-2
Heavy Metal Poisoning Sect. 21-12 Nicotine ChemConn 15B
Hemodialysis ChemConn 6G Nitric Oxide ChemConn 3C, 23E
Hemoglobin Sect. 21-7 Nitrous Oxide (“Laughing Gas”) Prob. 3-62
Hemolysis Sect. 6-8C NMDA Receptors Sect. 23-4B
Heparin Sect. 19-6B, Prob. 19-58 Nuclear Medicine Sect. 9-7
High Fever ChemConn 7A Nutritional Causes of Depression ChemConn 29F
HIV Protease Inhibitors ChemConn 22C Nutritional Daily Values Sect. 29-1
Hormones Sect. 23-2 Obesity ChemConn 27B, 29C, Sect. 29-2
How Soap Cleans Sect. 17-4C Omega-3 Fatty Acids ChemConn 20F
Human Insulin Sect. 21-8 Oncogenes and Cancer ChemConn 25E
Hyaluronic Acid Sect. 19-6A Oral Contraception ChemConn 20D
Health-Related Topics | xxvii
Oseltamivir (Tamiflu) Prob. 14-42 Statins ChemConn 28C

Osmotic Pressure Sect. 6-8C Stem Cells Sect. 30-2C
Parkinson’s Disease ChemConn 23C, Sect. 21-5 Stitches That Dissolve ChemConn 18F
Paroxetine Prob. 14-31 Strontium-90 ChemConn 2C
Paternity Testing ChemConn 24B Sunglasses and Le Chatelier’s Principle
Penicillins ChemConn 18B ChemConn 7D
Peramivir for Influenza A (H1N1) and Swine Flu Prob. 18-43 Sunscreens and Sunblocks ChemConn 18D
Phencyclidine (PCP) Sect. 23-4B Swine Flu ChemConn 30C
Phenylketonuria (PKU) ChemConn 27D Synapses and Sleep ChemConn 23A
Photorefractive Keratectomy (PRK) ChemConn 21F Synthetic Genome ChemConn 24D
Photosynthesis ChemConn 28A T Cells Sect. 30-2C
Poison Ivy Sect. 12-10A Tamoxifen and Breast Cancer Prob. 15-27
Poisonous Puffer Fish ChemConn 11A Taxol ChemConn 10A
Positron Emission Tomography (PET) Sect. 9-7A Tears ChemConn 31E, Probs. 31-47–31-50
Prion Disease ChemConn 21E Telomeres and Immortality ChemConn 24C
Pyrethrins ChemConn 18A Terpin Hydrate Prob. 12-42
Radiation Sect. 9-2 Testing for Glucose ChemConn 19B
Radiation Dosimetry Sect. 9-6 Tetrodotoxin ChemConn 11A
Radiation Sickness Sect. 9-6 Timed-Released Medication ChemConn 7C
Radioactive Dating ChemConn 9A Tranquilizers ChemConn 15C
Radioactive Fallout from Nuclear Trans Fatty Acids Sect. 20.2, ChemConn 17A
Accidents ChemConn 9E Transport Across Cell Membranes Sect. 20.14
Radioactive Isotopes, in Nuclear Imaging Sect. 9-7A Tumor Suppressors ChemConn 25E
Radioactive Isotopes, in Medical Therapy Sect. 9-7B Urinometer Sect. 1-7B
Recommended Daily Allowances (RDA) Sect. 29-1 Vaccines Sect. 30-6
Relative Sweetness Sect. 19-4D Valium ChemConn 15C
Reverse Osmosis and Desalinization ChemConn 6F Viagra ChemConn 22C
Roentgens, Rads, and Rems Sect. 9-6 Viagra and Blood Vessel Dilation ChemConn 22C
SCID Sect. 25-9 Viruses Sect. 25-1
SCUBA Diving Prob. 5-83 Vitamin A and Vision ChemConn 12A
Sickle Cell Anemia ChemConn 21D Vitamin Excess Sect. 29-6
Significance of Chirality in the Biological World Sect. 14-5 Vitamins and Depression ChemConn 29F
Solubility of Drugs in Body Fluids ChemConn 15D Vitamins and Minerals Sect. 29-6
Solubility and Tooth Decay ChemConn 4A Vitamins, in Diet Sect. 29-6
Sports Drinks Sect. 20.12, ChemConn 29E Zebrafish Synapses ChemConn 23A
Matter, Energy, and Measurement
Contents
1
1.1 Chemistry and the Study of
Matter
1.2 The Scientific Method
1.3 Reporting Numbers in
Science
How To . . . Determine the
Number of Significant Figures
in a Number
1.4 Making Measurements
1.5 Unit Conversions
How To . . . Do Unit
Conversions by the Factor-
Label Method
1.6 States of Matter
© Gorodenkoff/Shutterstock.com
1.7 Density and Specific Gravity

1.8 Describing the Various Forms
of Energy
Scientists in action in the laboratory, investigating the phenomena of chemistry.
1.1 Chemistry and the Study of Matter

The world around us is made of chemicals. Our food, our clothing, the build-
ings in which we live are all made of chemicals. While it is easy to be-
lieve that chemistry occurs in the laboratory, it also occurs in our daily lives.
Think about why the sky is blue, why washing with soap cleans our hands,
why we may cry while cutting onions, why meals are cooked faster in a
pressure cooker, and why ice floats in a glass of water. These phenomena all
occur because of chemistry that we witness every day.
Our bodies are made of chemicals too. To understand the human body,
its diseases, and its cures, we must know all we can about those chemicals.
There was a time—only a few hundred years ago—when physicians were
powerless to treat many diseases. Cancer, tuberculosis, smallpox, typhus,
plague, and many other sicknesses struck people seemingly at random. Doc-
tors, who had no idea what caused any of these diseases, could do little or
nothing about them. Doctors treated them with magic or by such measures
as bleeding, laxatives, hot plasters, and pills made from powdered stag-
horn, saffron, or gold. None of these treatments were effective, and the doc-
tors, because they came into direct contact with highly contagious diseases,
died at a much higher rate than the general public.
Medicine has made great strides since those times. We live much lon-
ger, and many once-feared diseases have been essentially eliminated or are
curable. Smallpox has been eradicated, and polio, typhus, bubonic plague,
diphtheria, and other diseases that once killed millions no longer pose a
serious problem, at least not in developed countries.
1
2 | Chapter 1 Matter, Energy, and Measurement
Photo by Bob Riha, Jr. Used courtesy of Childrens Hospital

Medical practice over time.
(a) A woman being bled by a leech
on her left forearm; a bottle of
Courtesy of the National Library of Medicine

leeches is on the table. From a
1639 woodcut. (b) Modern surgery
in a well-equipped operating room.
Los Angeles.
(a) (b)
How has this medical progress come about? The answer is that diseases
could not be cured until they were understood, and this understanding has
emerged through greater knowledge of how the body functions. It is progress
in our understanding of the principles of biology, chemistry, and physics
that has led to these advances in medicine. Because so much of modern
medicine depends on chemistry, it is essential that students who intend to
enter the health professions have some understanding of basic chemistry.
This book has been written to help you achieve that goal. Even if you choose
a different profession, you will find that the chemistry you learn in this
course will greatly enrich your life. ▲
The universe consists of matter, energy, and empty space. Matter is any-
thing that has mass and takes up space. Chemistry is the science that deals
with matter: the structure and properties of matter and the transformations
from one form of matter to another. We will introduce energy in Section 1.8
and discuss further in Section 4.8.
It has long been known that matter can change, or be made to change,
from one form to another. In a chemical change, more commonly called a
chemical reaction, some substances are used up (disappear) and others
are formed to take their place. An example is the burning of a mixture of
hydrocarbons, usually called “bottled gas.” In this mixture of hydrocarbons,
the main component is propane. When this chemical change takes place,
propane and oxygen from the air are converted to carbon dioxide and water.
Figure 1.1 shows another chemical change.
Charles D. Winters
Charles D. Winters
Charles D. Winters
(a)(a)
(a) (b)(b)
(b) (c)(c)(c)
Figure 1.1 A chemical reaction. (a) Bromine, an orange-brown liquid, and
aluminum metal. (b) These two substances react so vigorously that the aluminum
becomes molten and glows white hot at the bottom of the beaker. The yellow
vapor consists of vaporized bromine and some of the product of the reaction, white
aluminum bromide. (c) Once the reaction is complete, the beaker is coated with
aluminum bromide and the products of its reaction with atmospheric moisture.
(Note: This reaction is dangerous! Under no circumstances should it be done except
under properly supervised conditions.)
1.2 The Scientific Method | 3
Matter also undergoes other kinds of changes, called physical

changes. These changes differ from chemical reactions in that the iden-
tities of the substances do not change. Most physical changes involve
changes of state—for example, the melting of solids and the boiling of
liquids. Water remains water whether it is in the liquid state or in
the form of ice or steam. The conversion from one state to another is a phys-
ical—not a chemical—change. Another important type of physical change
involves making or separating mixtures. Dissolving sugar in water is a
physical change.
When we talk about the chemical properties of a substance, we mean
the chemical reactions that it undergoes. Physical properties are all
properties that do not involve chemical reactions. For example, density,
color, melting point, and physical state (liquid, solid, gas) are all physical
properties.
1.2 The Scientific Method

Scientists learn by using a tool called the scientific method. The heart of
the scientific method is the testing of theories. Prior to1600, philosophers
often believed scientific statements just because they sounded right. For ex-
ample, the great philosopher Aristotle (384–322 bce) believed that if you
took the gold out of a mine it would grow back. He believed this idea be-
cause it fit with a more general picture that he had about the workings of
nature. In ancient times, most thinkers behaved in this way. If a statement
sounded right, they believed it without testing it.
About 1600 ce, the scientific method came into use. Let us look at an
Courtesy of the National Library of Medicine

example to see how the scientific method operates. The Greek physi-
cian Galen (200–130 bce) recognized that the blood on the left side of the
heart somehow gets to the right side. This is a fact. A fact is a statement
based on direct experience. It is a consistent and reproducible observation.
Having observed this fact, Galen then proposed a hypothesis to explain
it. A hypothesis is a statement that is proposed, without actual proof, to
explain the facts and their relationship. Because Galen could not actually
see how the blood got from the left side to the right side of the heart, he
came up with the hypothesis that tiny holes must be present in the muscu- Galen did not do experiments to
test his hypothesis.
lar wall that separates the two halves.
▲
Up to this point, a modern scientist and an ancient philosopher would

behave the same way. Each would offer a hypothesis to explain the facts.
From this point on, however, their methods would differ. To Galen, his
explanation sounded right and that was enough to make him believe
it, even though he couldn’t see any holes. His hypothesis was, in fact,
Lawrence Berkeley Nat’l Lab – Roy

believed by virtually all physicians for more than 1000 years. When we
Kaltschmidt, photographer
use the scientific method, however, we do not believe a hypothesis just
because it sounds right. We test it, using the most rigorous testing we
can imagine.
▲
William Harvey (1578–1657) tested Galen’s hypothesis by dissecting

human and animal hearts and blood vessels. He discovered that one-
way valves separate the upper chambers of the heart from the lower Using a PET scanner is an
example of how modern scientists
chambers. He also discovered that the heart is a pump that, by contract-
collect information to confirm a
ing and expanding, pushes the blood out. Harvey’s teacher, Fabricius diagnosis and test a hypothesis.
(1537–1619), had previously observed that one-way valves exist in the
veins, so that blood in the veins can travel only toward the heart and not
the other way.
Harvey put these facts together to come up with a new hypothesis: blood
Hypothesis A statement that is
is pumped by the heart and circulates throughout the body. This was a proposed, without actual proof,
better hypothesis than Galen’s because it fit the facts more closely. Even to explain a set of facts and their
so, it was still a hypothesis and, according to the scientific method, had to relationship
be tested further. One important test took place in 1661, four years after
Harvey died. Harvey had predicted that because there had to be a way for
the blood to get from the arteries to the veins, tiny blood vessels must con-
nect them. In 1661, the Italian anatomist Malpighi (1628–1694), using the
newly invented microscope, found these tiny vessels, which are now called
capillaries.
Malpighi’s discovery supported the blood circulation hypothesis by ful-
filling Harvey’s prediction. When a hypothesis passes enough tests, we have
Theory The formulation of an more confidence in it and call it a theory. A theory is the formulation of an
apparent relationship among certain apparent relationship among certain observed phenomena, which has been
observed phenomena, which has verified to some extent. In this sense, a theory is the same as a hypothesis
been verified. A theory explains many
interrelated facts and can be used
except that we have a stronger belief in it because more evidence supports
to make predictions about natural it. No matter how much confidence we have in a theory, however, if we dis-
phenomena. Examples are Newton’s cover new facts that conflict with it or if it does not pass newly devised
theory of gravitation and the kinetic tests, the theory must be altered or rejected. In the history of science, many
molecular theory of gases, which we firmly established theories have eventually been thrown out because they
will encounter in Section 6.6. This type
of theory is also subject to testing and
could not pass new tests. For example, during the late twentieth century,
will be discarded or modified if it is two scientists claimed to have discovered that nuclear fusion, which you
contradicted by new facts. will read about in Section 9.8, could be accomplished at room temperature,
a theory known as cold fusion. However, after scientists were subsequently
unable to replicate the expected results associated with the nuclear experi-
ment, the theory of cold fusion was rejected.
One of the most important ways to test a hypothesis is by a controlled
experiment. It is not enough to say that making a change causes an effect,
we must also see that the lack of that change does not produce the observed
effect. If, for example, a researcher proposes that adding a vitamin mixture
to the diet of children improves growth, the first question is whether chil-
dren in a control group who do not receive the vitamin mixture do not grow
as quickly. Comparison of an experiment with a control is essential to the
scientific method.
The scientific method is thus very simple. We don’t accept a hypothesis
or a theory just because it sounds right. We devise tests, and only if the hy-
pothesis or theory passes the tests do we accept it. The enormous progress
made since 1600 in chemistry, biology, and the other sciences is a testimony
to the value of the scientific method.
You may get the impression from the preceding discussion that science
progresses in one direction: facts first, hypothesis second, theory last. Real
life is not so simple, however. Hypotheses and theories call the attention of
scientists to discover new facts. An example of this scenario is the discovery
of the element germanium. In 1871, Mendeleev’s Periodic Table—a graphic
description of elements organized by properties—predicted the existence of a
new element whose properties would be similar to those of silicon. Mendeleev
called this element eka-silicon. In 1886, it was discovered in Germany (hence
the name), and its properties were truly similar to those predicted by theory.
On the other hand, many scientific discoveries result from serendipity,
or chance observation. An example of serendipity occurred in 1926, when
James Sumner of Cornell University left an enzyme preparation of jack
bean urease in a refrigerator over the weekend. Upon his return, he found
that his solution contained crystals that turned out to be a protein. This
chance discovery led to the hypothesis that all enzymes are proteins. Of
course, serendipity is not enough to move science forward. Scientists must
have the creativity and insight to recognize the significance of their obser-
vations. Sumner fought for more than 15 years for his hypothesis to gain
acceptance because people believed that only small molecules can form
crystals. Eventually his view won out, and he was awarded a Nobel Prize in
Chemistry in 1946.
1.3 Reporting Numbers in Science | 5
1.3 Reporting Numbers in Science

Scientists often have to deal with numbers that are very large or very
small. For example, an ordinary copper penny (dating from before 1982,
when pennies in the United States were still made completely of copper)
contains approximately
29,500,000,000,000,000,000,000 atoms of copper
and a single copper atom weighs
0.00000000000000000000000023 pound
which is equal to
Photos showing different orders
0.000000000000000000000104 gram of magnitude.
One can easily see how cumbersome it would be to report numbers in this
way. A method, called exponential notation, was devised many years ago
to handle large and small numbers, based on powers of 10. In exponential
notation, the number of copper atoms in a penny is written
SuperStock/iskodonnell
2.95 3 1022
and the weight of a single copper atom is written
2.3 3 10225 pound
1. Football field ~10 meters
which is equal to
1.04 3 10222 gram
The origin of this shorthand form can be seen in the following examples:
100 5 1 3 10 3 10 5 1 3 102
1000 5 1 3 10 3 10 3 10 5 1 3 103
Tom Martin
What we have just said in the form of an equation is “100 is a one with two
zeros after the one, and 1000 is a one with three zeros after the one.” We can
2. Football field (~100 meters)
also write
1/100 5 1/10 3 1/10 5 1 3 1022
1/1000 5 1/10 3 1/10 3 1/10 5 1 3 1023
where negative exponents denote numbers less than 1. The exponent in a
Dean Fox / SuperStock

very large or very small number lets us keep track of the number of zeros.
That number can become unwieldy with very large or very small quantities,
and it is easy to lose track of a zero. Exponential notation helps us deal with
this possible source of systematic error.
▲
When it comes to measurements, not all the numbers you can generate 3. Vicinity of stadium (~1000
in your calculator or computer are of equal importance. Only the number of meters).
digits that are known with certainty are significant. Suppose you measured
the weight of an object as 3.4 g on a balance that reads to the nearest 0.1 g.
You can report the weight as 3.4 g but not as 3.40 or 3.400 g because you do
not know the added zeros with certainty. This becomes even more important
when you use a calculator. For example, you might measure a cube with a
ruler and find that each side is 2.9 cm. If you are asked to calculate the vol-
ume, you multiply 2.9 cm 3 2.9 cm 3 2.9 cm. The calculator will then give
you an answer that is 24.389 cm3. A detailed account of using significant
figures is presented in Appendix II. The following How To box describes
the way to determine the number of significant figures in a number. You
will find boxes like this at places in the text where detailed explanations of
concepts are useful.
How To Determine the Number of Significant Figures in a Number

1. Nonzero digits are always significant.
For example, 233.1 m has four significant figures; 2.3 g has two
significant figures.
2. Zeros at the beginning of a number are never significant.
For example, 0.0055 L has two significant figures; 0.3456 g has four
3. Zeros between nonzero digits are always significant.
For example, 2.045 kcal has four significant figures; 8.0506 g has five
4. Zeros at the end of a number that contains a decimal point
are always significant.
For example, 3.00 L has three significant figures; 0.0450 mm has
three significant figures.
5. Zeros at the end of a number that contains no decimal point
may or may not be significant.
We cannot tell whether they are significant without knowing some-
thing about the number. This is the ambiguous case. If you know
that a certain small business made a profit of $36,000 last year, you
can be sure that the 3 and 6 are significant, but what about the rest?
The profit might have been $36,126 or $35,786.53, or maybe even
exactly $36,000. We just don’t know because it is customary to round
off such numbers. On the other hand, if the profit were reported as
$36,000.00, then all seven digits would be significant.
In science, to get around the ambiguous case, we use exponential
otation. Suppose a measurement comes out to be 2500 g. If we made
n
the measurement, then we know whether the two zeros are significant,
but we need to tell others. If these digits are not significant, we write
our number as 2.5 3 103. If one zero is significant, we write 2.50 3 103.
If both zeros are significant, we write 2.500 3 103. Because we now
have a decimal point, all the digits shown are significant. We are going
to use decimal points throughout this text to indicate the number of
significant figures. ■
Example 1.1 Exponential Notation and Significant Figures

Multiply:
(a) (4.73 3 105)(1.37 3 102) (b) (2.7 3 1024)(5.9 3 108)
Divide:
7.08 3 1028 5.8 3 1026 7.05 3 1023
(c) (d) (e)
300. 6.6 3 1028 4.51 3 105
Strategy and Solution

The way to do calculations of this sort is to use a button on scientific
calculators that automatically uses exponential notation. The button
is usually labeled “E.” (On some calculators, it is labeled “EE.” In some
cases, it is accessed by using the second function key.)
(a) Enter 4.73E5, press the multiplication key, enter 1.37E2, and press
the “5” key. The answer is 6.48 3 107. The calculator will display
1.4 Making Measurements | 7
this number as 6.48E7. This answer makes sense. We add exponents

when we multiply, and the sum of these two exponents is correct
(5 1 2 5 7). We also multiply the numbers, 4.73 3 1.37. This is
approximately 4 3 1.5 5 6, so 6.48 is also reasonable.
(b) Here we have to deal with a negative exponent, so we use the “1/2”
key. Enter 2.7E1/24, press the multiplication key, enter 5.9E8, and
press the “5” key. The calculator will display the answer as 1.593E5.
To have the correct number of significant figures, we should report our
answer as 1.6E5. This answer makes sense because 2.7 is a little less
than 3 and 5.9 is a little less than 6, so we predict a number slightly
less than 18; also, the algebraic sum of the exponents (24 1 8) is
equal to 4. This gives 16 3 104. In exponential notation, we normally
prefer to report numbers between 1 and 10, so we rewrite our answer
as 1.6 3 105. We made the first number 10 times smaller, so we in-
creased the exponent by 1 to reflect that change.
(c) Enter 7.08E1/28, press the division key, enter 300., and press the
“5” key. The answer is 2.36 3 10210. The calculator will display this
number as 2.36E210. We subtract exponents when we divide, and we
can also write 300. as 3.00 3 102.
(d) Enter 5.8E1/26, press the division key, enter 6.6E1/28, and
press the “5” key. The calculator will display the answer as
87.878787878788. We report this answer as 88 to get the right num-
ber of significant figures. This answer makes sense. When we divide
5.8 by 6.6, we get a number slightly less than 1. When we subtract
the exponents algebraically (26 2 [28]), we get 2. This means that
the answer is slightly less than 1 3 102, or slightly less than 100.
(e) Enter 7.05E1/23, press the division key, enter 4.51E5, and press the
“5” key. The calculator displays the answer as 1.5632E28, which, to
the correct number of significant figures, is 1.56 3 1028. The algebraic
subtraction of exponents is 2 3 2 5 5 2 8.
■■ Quick Check 1.1
Multiply:
(a) (6.49 3 107) (7.22 3 1023) (b) (3.4 3 1025) (8.2 3 10211)
Divide:
6.02 3 1023 3.14
(a) (b)
3.10 3 105 2.30 3 1025
1.4 Making Measurements

In our daily lives, we are constantly making measurements. We measure
ingredients for recipes, driving distances, gallons of gasoline, weights of
fruits and vegetables, and the timing of TV programs. Doctors and nurses
measure pulse rates, blood pressures, temperatures, and drug dosages.
Chemistry, like other sciences, is based on measurements.
A measurement consists of two parts: a number and a unit. A number
without a unit is usually meaningless. If you were told that a person’s
weight is 57, the information would be of very little use. Is it 57 pounds,
which would indicate that the person is very likely a child, or 57 kilograms,
which is the weight of an average person? Or is it perhaps some other unit?
Because so many units exist, a number by itself is not enough; the unit
must also be stated.
In the United States, most measurements are made with the English sys-
tem of units: pounds, miles, gallons, and so on. In most other parts of the world,
however, few people could tell you what a pound or an inch is. Most countries
use the metric system, a system that originated in France about 1800 and
that has since spread throughout the world. Even in the United States, metric
measurements are slowly being introduced (Figure 1.2). For example, many
soft drinks and most alcoholic beverages now come in metric sizes. Scientists
in the United States have been using metric units all along.
▲
Around 1960, international scientific organizations adopted another sys-
tem, called the International System of Units (abbreviated SI). The SI
is based on the metric system and uses some of the metric units. The main
difference is that the SI is more restrictive: It discourages the use of certain
metric units and favors others. Although the SI has advantages over the
older metric system, it also has significant disadvantages. For this reason,
U.S. chemists have been very slow to adopt it. At this time, approximately
40 years after its introduction, not many U.S. chemists use the entire SI,
although some of its preferred units are gaining ground.
Alyssa White/Cengage Learning
In this book, we will use the metric system (Table 1.1). Occasionally we
will mention the preferred SI unit.
A. Length
The key to the metric system (and the SI) is that there is one base unit for
The label on this bottle of water each kind of measurement and that other units are related to the base unit
shows the metric size (one liter) by powers of 10. As an example, let us look at measurements of length. In
and the equivalent in quarts. the English system, we have the inch, the foot, the yard, and the mile (not
to mention such older units as the league, furlong, ell, and rod). If you want
Metric system A system of units of to convert one unit to another unit, you must memorize or look up these
measurement in which the divisions to conversion factors:
subunits are made by a power of 10
5280 feet 5 1 mile
Table 1.1 Base Units in the
Metric System 1760 yards 5 1 mile
Length meter (m) 3 feet 5 1 yard
Volume liter (L)
Mass gram (g)
12 inches 5 1 foot
Time second (s)
Temperature kelvin (K) All this is unnecessary in the metric system (and the SI). In both systems
Amount of mole (mol) the base unit of length is the meter (m). To convert to larger or smaller
substance units, we do not use arbitrary numbers like 12, 3, and 1760, but only 10,
100, 1/100, 1/10, or other powers of 10. This means that to convert from one
metric or SI unit to another, we only have to move the decimal point. Fur-
thermore, the other units are named by putting prefixes in front of “meter,”
and these prefixes are the same throughout the metric system and the SI.
Figure 1.2 Road sign in

California showing metric
equivalents of mileage.
GIPhotoStock Z/Alamy
Table 1.2 The Most Common Metric Prefixes
Prefix Symbol Value

giga G 109 5 1,000,000,000 (one billion) Conversion factors are defined
numbers. We use them as though
mega M 106 5 1,000,000 (one million) they have an infinite number of
kilo k 103 5 1000 (one thousand) significant figures.
deci d 1021 5 0.1 (one-tenth)

centi c 1022 5 0.01 (one-hundredth)
milli m 1023 5 0.001 (one-thousandth)
micro m 1026 5 0.000001 (one-millionth)
nano n 1029 5 0.000000001 (one-billionth)
pico p 10212 5 0.000000000001 (one-trillionth)
Table 1.2 lists the most important of these prefixes. If we put some of these
prefixes in front of “meter,” we have
1 kilometer (km) 5 1000 meters (m)

1 centimeter (cm) 5 0.01 meter
1 nanometer (nm) 5 1029 meter
For people who have grown up using English units, it is helpful to have some
idea of the size of metric units. Table 1.3 shows some conversion factors.
Table 1.3 Some Conversion Factors Between the English and Metric Systems
Length Mass Volume

1 in. 5 2.54 cm 1 oz 5 28.35 g 1 qt 5 0.946 L
1 m 5 39.37 in. 1 lb 5 453.6 g 1 gal 5 3.785 L
1 mile 5 1.609 km 1 kg 5 2.205 lb 1 L 5 33.81 fl oz
1 g 5 15.43 grains 1 fl oz 5 29.57 mL
1 L 5 1.057 qt
Some of these conversions are difficult enough that you will probably
not remember them and must, therefore, look them up when you need
them. Some are easier. For example, a meter is about the same as a yard. A
kilogram is a little over two pounds. There are almost four liters in a gallon.
These conversions may be important to you someday. For example, if you
rent a car in Europe, the price of gas listed on the sign at the gas station will
be in Euros per liter. When you realize that you are spending two dollars
per liter and you know that there are almost four liters to a gallon, you will
realize why so many people take the bus or a train instead.
B. Volume
Jonnie Miles/Getty Images
Volume is space. The volume of a liquid, solid, or gas is the space occupied by
that substance. The base unit of volume in the metric system is the liter (L).
This unit is a little larger than a quart (Table 1.3). The only other common
metric unit for volume is the milliliter (mL), which is equal to 1023 L.
▲
Hypodermic syringe. Note that

1 mL 5 0.001 L (or 1 3 1023 L) the volumes are indicated in
milliliters.
1000 mL (or 1 3 103 mL) 5 1 L
One milliliter is exactly equal to one cubic centimeter (cc or cm3):
1 mL 5 1 cc
Thus, there are 1000 (1 3 103) cc in 1 L.
C. Mass
Mass is the quantity of matter in an object. The base unit of mass in the
metric system is the gram (g). As always in the metric system, larger and
smaller units are indicated by prefixes. The ones in common use are
1 kilogram (kg) 5 1000 g

1 milligram (mg) 5 0.001 g
The gram is a small unit; there are 453.6 g in one pound (Table 1.3).
We use a device called a balance to measure mass. Figure 1.3 shows two
types of laboratory balances.
There is a fundamental difference between mass and weight. Mass is
independent of location. The mass of a stone, for example, is the same
whether we measure it at sea level, on top of a mountain, or in the depths
of a mine. In contrast, weight is not independent of location. Weight
is the force a mass experiences under the pull of gravity. This point was
dramatically demonstrated when the astronauts walked on the surface
of the Moon. The Moon, being a smaller body than the Earth, exerts a
weaker gravitational pull. Consequently, even though the astronauts
wore space suits and equipment that would be heavy on Earth, they felt
lighter on the Moon and could execute great leaps and bounces during
their walks.
Although mass and weight are different concepts, they are re-
lated to each other by the force of gravity. We frequently use the words
interchangeably because we weigh objects by comparing their masses to
standard reference masses (weights) on a balance, and the gravitational
pull is the same on the unknown object and on the standard masses. Be-
cause the force of gravity is essentially constant, mass is always directly
proportional to weight.
Figure 1.3 Two laboratory

balances for measuring mass.
Courtesy of Mettler Toledo, Inc.
Courtesy of Ohaus Corporation
CHEMICAL CONNECTIONS 1A Drug Dosage and Body Mass
In many cases, drug dosages are prescribed on the ba-

sis of body mass. For example, the recommended dos-
age of a drug may be 3 mg of drug for each kilogram of
body weight. In this case, a 50 kg (110 lb) person would
receive 150 mg and an 82 kg (180 lb) person would get
246 mg. This adjustment is especially important for
children, because a dose suitable for an adult will gen-
erally be too much for a child, who has much less body
mass. For this reason, manufacturers package and
sell smaller doses of certain drugs, such as aspirin, for
children.
Drug dosage may also vary with age. Occasionally,
when an elderly patient has an impaired kidney or
Charles D. Winters
liver function, the clearance of a drug from the body
is delayed, and the drug may stay in the body lon-
ger than is normal. This persistence can cause dizzi-
ness, vertigo, and migraine-like headaches, resulting
This package of Advil has a chart
in falls and broken bones. Such delayed clearance showing the proper doses for children
must be monitored and the drug dosage adjusted of a given weight.
accordingly. ■
Test your knowledge with Problems 54 and 55.
D. Time
Time is the one quantity for which the units are the same in all systems:
English, metric, and SI. The base unit is the second (s):
60 s 5 1 min
60 min 5 1 h
E. Temperature
Most people in the United States are familiar with the Fahrenheit scale of
temperature. The metric system uses the centigrade, or Celsius, scale. In
this scale, the boiling point of water is set at 100°C and the freezing point
at 0°C. We can convert from one scale to the other by using the following
formulas:
9
°F 5 °C 1 32
5
5
°C 5 (°F 2 32)
9
The 32 in these equations is a defined number and is, therefore, treated
as if it had an infinite number of zeros following the decimal point. (See
Appendix II.)
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CHAPTER VI
PUBLIC AND PRIVATE AFFAIRS
The news and literary center was between Front and Second
streets. Here the two newspapers were published. John Scull, the
owner of the Pittsburgh Gazette, lived at the northwest corner of
Market and Front streets; and on Front Street, immediately in the
rear of his dwelling, stood the small one-story building where the
newspaper was printed. In this house the post office had been
located until 1794, when Scull was succeeded as postmaster by
George Adams, who removed the post office to the log house on
Front Street near Ferry. At the northerly end of the block, at the
corner of Second Street, was the brick house of Dr. Peter Mowry,
who had the largest medical practice in the town. Directly across
Market Street from Dr. Mowry, Judge Hugh Henry Brackenridge had
erected for the Tree of Liberty, a one-story office, and behind this a
174
building where the paper was printed.
Judge Brackenridge’s dwelling adjoined the office of the Tree of
175
Liberty on the south. It was a large and commodious blue frame
building which had been, until recently, surrounded by a paling
fence. The larger part was now given over to trade. It was the best
known house in the town. In it General Lee had made his
headquarters while in Pittsburgh during the memorable days of
176
November, 1794. In front of this building, Brackenridge, according
to his own story, braved the indignation of Lee’s troops, by parading
before them dressed in his “large cocked hat, buff underdress, and
177
coat of military blue.” On the north side of Second Street, one
door west of Chancery Lane, stood William Turnbull’s large two-story
stone structure, occupied during the Whisky Insurrection by William
178
Semple as a store. Here also resided at that time Colonel Presley
179
Neville. General Daniel Morgan lived with his son-in-law during
the stay of the army in Pittsburgh. From this house General Morgan
and Colonel Neville rushed hatless to save Brackenridge from the
fury of the soldiers, who Brackenridge charged were planning his
180
assassination. In 1804, the building was occupied by the “Office
of Discount and Deposit,” as the branch of the Bank of Pennsylvania
was called. At the corner of Chancery Lane adjoining the Turnbull
house, was the home of Steele Semple, the famous advocate and
wit, and connoisseur of the polite and fashionable literature of the
181
day.
In the center of the block in which Brackenridge lived, was the
book store and bindery of Zadok Cramer, at the “Sign of the Franklin
Head.” “Its ancient appearance,” wrote one of its habitués, “is
agreeably associated in the memory of many amongst us with our
happiest moments, when the careless, airy hours of youth were
182
passing thoughtlessly and cheerfully away.” Men just as
substantial, but of less note, also had establishments in this square.
At the southerly corner of Front Street was the large store of Abner
183
and Jeffe Barker who sold bar iron and castings, and kept a
184
“general assortment of merchandise and boulting cloths.” All the
merchants were selling “boulting cloths,” which were cloths used by
millers for sifting flour. Adjoining Abner and Jeffe Barker’s store on
the north was the establishment of Jeremiah Barker who had for sale
185
a “handsome and general assortment of the freshest goods,” and
186
“a few boxes of glass eight by ten.” In addition to being a
merchant, Jeremiah Barker was justice of the peace, and in 1801
187
burgess. The store of Abner and Jeffe Barker, and the store of
Jeremiah Barker, were both on the site formerly occupied by Andrew
Watson’s tavern.
On the north side of Front Street, two doors east of Abner and
Jeffe Barker’s store, was an old two-story log building owned by
Andrew Watson. It had been formerly occupied as a store by John
188
and Samuel Calhoun, and when Allegheny County was formed,
was rented by the county for the use of the courts, and called the
“Court House.” In this house justice was dispensed for many years.
In December, 1788, the first court of quarter sessions for Allegheny
County was held there, George Wallace being president judge, and
John Scott, John Wilkins, and John Johnson associates. They were
all laymen, the constitution in force not requiring judges to be learned
in the law. The first court of common pleas was held in the building
on March 14, 1789.
The judges of the Supreme Court, or at least two of them, were
required to go on the circuit annually, visiting every county during the
intervals between the regular sessions of the Supreme Court, and to
hold courts of nisi prius and Oyer and Terminer for the trial of capital
189
cases. In Pittsburgh the sessions were held in Andrew Watson’s
house. Here Chief Justice McKean and Justice George Bryan held
the first court of Oyer and Terminer for Allegheny County. Judge
Henry M. Brackenridge related that he had been informed that, at
this session, they sat in scarlet robes. He stated further that when
going to and returning from court the judges were carefully attired in
black, with cocked hats, and were preceded by the Sheriff of the
County bearing a white wand. Leading the procession was a
190
drummer beating a drum.
The first court house was memorable for another reason. It was
in the court room that the townspeople assembled on that eventful
evening of the thirty-first day of July, during the stormiest days of the
191
Whisky Insurrection. The mail from Pittsburgh to Philadelphia had
been robbed by the Insurgents and among the letters taken were
several, written by prominent citizens of Pittsburgh, which indicated a
hostile spirit toward the insurrection. The sentiments expressed were
considered as reflecting the opinion of the town. The rage of the
Insurgents was now directed against Pittsburgh. In their wrath they
characterized it as another Sodom, and declared that they would
come and destroy it with fire, and leave nothing but smoking ruins to
mark the spot where it had stood. With this end in view they
commenced gathering in force at Braddocksfield. News of the
sinister purpose spread to the town. Alarm grew into terror, and a
meeting was hastily called to consider measures of protection. The
meeting was already in progress, when a committee sent by the
Insurgents arrived and announced that the town would be spared if
certain obnoxious persons, including the writers of the letters found
in the mail, were banished from the town. They reported that the task
of saving the town would be easier of accomplishment if the
inhabitants marched out in a body to meet the Insurgents, and by
fraternizing with them show that they were not hostile to the
Insurgent cause. The meeting deliberated far into the night, and at
two o’clock the next morning arrived at a humiliating conclusion.
They agreed to banish the men asked for, and to join the Insurgents
at Braddocksfield, “as brethren to carry into effect with them any
measure that may seem to them advisable for the common cause.”
Even then the panic did not subside. The people refused to go to
bed; women wept; valuables were hidden, and lights flickered in the
houses all night long.
At the northwest corner of Market and Second streets, in the
three-story double brick building owned by Colonel O’Hara, was the
store of Scott & Trotter, where they sold “merchandise of a superior
quality suitable to every station, which they are determined to sell on
very low terms for cash, peltry, furs, and approved country
192
produce.” Next door to Scott & Trotter was Dr. George Stevenson.
Like Dr. Richardson, Stevenson conducted an apothecary shop and
193
sold “drugs, medicines, surgical instruments, etc.” He was a
former Revolutionary officer, and had been third lieutenant in the
First Pennsylvania Regiment. In 1778, he resigned to study
medicine, and re-entered the service in 1779 as surgeon’s mate with
the rank of ensign. In 1798, he was major in the Tenth United States
194
Regiment. Stevenson was chief burgess in 1801.
At the southwest corner of Market and Third streets was the “hat
195
sales shop” of Thomas and Samuel Magee. Here they kept for
sale the beaver, castor, and roram hats, which they manufactured at
the corner of Front Street and Chancery Lane. On the opposite side
of Market Street from Scott & Trotter was William Herd’s dry goods
196
and grocery store. Also on this side of Market Street, at the
northeast corner of that street and Third Street, was another
197
physician, Dr. Hugh Scott. Then came the store of William
Gazzam, and adjoining was that of William Barrett. Farther on,
198
Fulton & Baird sold “soal and upper leather,” and James Riddle
199
had a boot and shoe-making establishment and sold “Halifax soal
200
leather, also boot legs, half and whole soals, and boot webbing.”
Another establishment was that of William Porter who had a cut and
201
forged nail manufactory.
Adjoining Porter on the north was the well-known tavern of Mrs.
Mary Murphy, commonly known as “Molly” Murphy, the widow of
Patrick Murphy, at the “Sign of General Butler.” Beginning on April 1,
1800, and for several years afterward, the tavern was conducted by
202
Richard Hancock. Next door to the “Sign of General Butler,” and
extending to Fourth Street at the “Sign of the Negro,” Joseph
McClurg sold dry goods, hardware, china, and glassware, and
203
conducted a tobacco manufactory. He also advertised as having
for sale “a large assortment of window and hollow glass of a superior
204
quality, from A. Gallatin, Esq’s., glass works at New Geneva.”
The “Sign of General Butler” was named for General Richard
Butler who in his day was the most noted character in Pittsburgh. He
had been Indian trader and Indian agent. In the Revolution he was
second in command to General Daniel Morgan at Saratoga, and
second in command to General Anthony Wayne at Stony Point. He
205
was a justice of the Court of Common Pleas of Allegheny County
and was the first lieutenant of the county, the officer who at that time
206
was commander of the militia. He was a member of the General
207
Assembly, and met a glorious death during St. Clair’s unfortunate
expedition against the Indians on the Miami River, on November 4,
208
1791. His name has been commemorated in that of Butler
209
County. His home was in the log house situated on the east side
of Marbury, now Third Street, one door south of Penn Street, now
210
Penn Avenue, where his widow continued to reside.
The “Sign of General Butler,” like the home of Brackenridge,
became famous during the Whisky Insurrection. President
Washington had appointed a commission to meet the Insurgents,
and procure their submission. It consisted of Senator James Ross,
Attorney General William Bradford, also a Pennsylvanian, and
Jasper Yeates, a justice of the Supreme Court of this State. The
commissioners on the part of Pennsylvania were Chief Justice
McKean and General William Irvine. The commission had arranged
to meet representatives of those in rebellion, on Wednesday, August
20, 1794. Two days before that date, the commissioners took up
their lodgings at the “Sign of General Butler.” When it became known
that they were at the tavern, a mob gathered before it on Market
Street, and made their sentiments apparent by raising a liberty pole,
the emblem everywhere in the disturbed districts of disaffection
toward the national government. A streamer was fastened to the
pole on which were inscribed the watchwords of the Insurgents:
“Liberty and no Excise.

Death to Cowards and Traitors.”
Judge Hugh Henry Brackenridge has stated that it was with difficulty
that he and others who were influential with the rioters prevailed on
them to forego their intention of placing on the pole the flag which
had been prepared, bearing six stripes, emblematical of the six
counties, five in Pennsylvania, and one in Virginia, which were
threatening to secede from the United States and set up a
government of their own. That the conferences which followed were
fruitless is well known. Only one man in attendance gained in
reputation. Albert Gallatin was on the committee sent by the
Insurgents. His ability and his firm stand in favor of law and order
won for him everywhere, and particularly in Allegheny and
Washington counties, the lasting regard of the citizens. Two months
later a member of Congress was to be elected in the district
composed of these counties, and Insurgents and non-insurgents
flocked to Gallatin’s support, and to the surprise of Brackenridge and
General John Woods, the other candidates, he was elected.
During the occupancy of the “Sign of General Butler” by Richard
Hancock, James Hilliard had a farrier shop and livery stable, in the
211
stable connected with the tavern. The public controversy in which
Hilliard engaged his wife, is a striking illustration of the mischievous
result of the husband’s absolute control of his wife’s separate estate
under the existing laws. Hilliard was married to Elizabeth Bausman,
a daughter of Jacob Bausman, who was possessed of property in
her own right which she had inherited from her father. Hilliard
212
published a notice advising the public that his wife had
“absconded from his bed and board,” and declaring that he would
not be responsible for debts contracted by her. To this charge Mrs.
213
Hilliard replied in a sharp letter. She denied her husband’s
accusation, and stated that she had gone with her children, at his
request, on a visit to Jacob Haymaker. She charged Hilliard with
having, during her absence, disposed of the household effects,
including her wearing apparel, to John Smur, a tavern keeper in the
town, and that everything had been taken away after nightfall; that
the articles were part of her separate estate; that now she had “no
bed nor board to go to.” She asked that no credit be extended to
Hilliard on the strength of her estate, and declared that thereafter
she would decline to pay his debts, but would use her estate for her
own benefit. “In the future,” she concluded, “it shall not be expended
in paying his tavern bills.”
A unique reputation attached to the houses in this block which,
while descriptive, was at the same time significant of the political
power of the occupants and their associates. Although the houses
were built separately, and were of different types, they were
collectively called by the not-over-euphonious name of “Clapboard
Row.” As the name indicated, they were constructed of clapboards.
So well known was “Clapboard Row” that the merchants who had
their establishments there were fond of advertising the fact.
Practically all the occupants were politicians, and without exception
belonged to the Republican party. Also the “Sign of General Butler”
was the headquarters of that party. By their opponents, these
leaders were termed the “Clapboard Row Junto,” “junto” being an
older word for “ring.” General Fowler, after he separated from the
Republican party, designated them as the “Clapboardonian
214
Democracy.” The Pittsburgh Gazette charged that the editor of
215
the Tree of Liberty was controlled by “Clapboard Row.” Some
were officeholders, others desired to be such, and in State and
national affairs they were supreme.
The members of the “Clapboard Row Junto” were men of dual
capacity. Their energies were devoted to their private affairs and to
politics with equal intensity. In politics the smallest details received
careful attention. Many of the methods employed by modern
Pittsburgh politicians were inherited from “Clapboard Row.” One of
the schemes for increasing the party vote, which originated with
“Clapboard Row,” was to encourage and assist the aliens who
settled in Pittsburgh to become naturalized. This was done through
the medium of a committee composed of Thomas Baird, James
216
Riddle, and Joseph McClurg.
Dr. Scott was high in the favor of the Republican leaders, and on
the death of George Adams on April 1, 1801, was appointed
postmaster, and established the post office in his store, continuing
the practice of medicine and the sale of drugs as before. William
Gazzam was an aggressive Irishman, who had been in the country
only a few years, but by dint of perseverance had pressed well
forward in politics, perhaps to the detriment of his business, as he
failed early in his career. He was brigade inspector of the Allegheny
County militia, and justice of the peace. He aroused the ire of
General Fowler, when with other “Clapboard Row” politicians he
refused to support Fowler for Congress.
The controversy was amusing. In the communications which
Fowler published in the Pittsburgh Gazette about his wrongs, he
designated Gazzam as a “little man—in the most emphatic sense.”
He declared that under “the cloak of Republicanism and religion,”
217
Gazzam was “artfully aiming at offices.” The allusion to Gazzam’s
“religion” referred to the gentleman’s well known activity in the affairs
of the Presbyterian Church, which he afterward left, owing, it was
alleged, to the fact that the minister, the Rev. Robert Steele, gave out
“two lines of a stanza to be sung, instead of the time-honored
218
one.” Fowler enlarged on Gazzam’s reputed yearning for office.
He enumerated the offices which Gazzam had held, and the others
that he desired. He claimed that Gazzam was an applicant for the
post office on the demise of George Adams; that he hoped to be
county commissioner; that he was scheming to become a member of
219
the General Assembly. To this abuse Gazzam replied with equal
venom. He said General Fowler had been drunk on the last occasion
that he had asked his support for Congress, and that he had abused
220
him in a very ungentlemanly manner.
Thomas Baird was a member of the firm of Fulton and Baird, and
was a candidate for burgess in 1803, the year that Colonel Neville
221
was elected. Joseph McClurg was a candidate for supervisor in
222
1803, but was defeated by A. McNickle. Affiliated with these men
were Samuel Ewalt, Nathaniel Irish, and Adamson Tannehill, the last
two being former Revolutionary officers. Nathaniel Irish was county
223 224
commissioner, and inspector of flour for the Western country.
Adamson Tannehill had formerly conducted a tavern on Water
225
Street, and had been president of the Pittsburgh Fire
226
Company. In October, 1800, while a justice of the peace, he was
tried and convicted of extortion, before Justices Jasper Yeates and
Thomas Smith of the Supreme Court while on circuit in Pittsburgh,
that court then having original jurisdiction of this offense, under the
constitution of 1790. Tannehill received a reprimand and was fined
fifty dollars. The conviction was thought to disqualify him from further
exercising the office of justice of the peace. Being a leading
Republican, and the offense, which consisted in charging on two
probates two shillings more than the law allowed, having been
committed five years before, Governor McKean, in January, 1801,
remitted the fine and reappointed Tannehill to the office which he had
227
formerly held. Dr. Andrew Richardson belonged to the “Clapboard
Row” faction until his desertion of the Republican party. Joseph
Davis, who had a grocery store on the other side of Market Street
from “Clapboard Row,” was another member of the clique, as was
228
Tarleton Bates, the prothonotary of the county, who had
succeeded John C. Gilkison in office.
“Clapboard Row,” was not allowed to win its victories
unopposed. The opposition was both able and active. Judge
Alexander Addison, Senator James Ross, and General John Woods
were the leaders of the Federalists. Colonel O’Hara, General Neville,
Colonel Neville, Major Craig, Major Ebenezer Denny, Dr. Stevenson,
and most of the former Revolutionary officers were also Federalists.
Other Federalists were William Christy, Dr. Mowry, Abner Barker,
Jeremiah Barker, and Alexander McLaughlin. They made a gallant
fight for their principles, but their voice was usually drowned in the
mighty chorus of Republicanism that had swept the country from its
former conservative moorings. In borough politics only were they
successful.
The views of the rival political parties were echoed with startling
frankness in the columns of the Tree of Liberty and the Pittsburgh
Gazette. On October 11, 1800, the Tree of Liberty announced the
election of the Republican candidate for inspector of elections in the
borough, and added jubilantly: “The people are no longer to be led
up like tame asses to vote against their inclination for the characters
that Ross, Woods, and Addison recommend. They now act for
themselves.” After the presidential election of 1800, it exulted further:
“It is laughable to hear some of the hot-blooded Federalists moaning
and groaning at the result of the last election. They know not what
cause to attribute it to. They curse the Tree and all its leaves, they
229
denounce ‘Clapboard Row’ with the yards and its size sticks.”
The Pittsburgh Gazette was equally outspoken, its ire being
particularly directed against Judge Hugh Henry Brackenridge. In an
article signed “A Citizen of Washington,” it gave what purported to be
an account of a drunken escapade of the Judge through Washington
and Allegheny Counties, which, if published to-day, would lead to a
230
personal encounter. On another occasion Scull paid his
compliments to Brackenridge in the following sarcastic terms: “You
who get two or three thousand dollars a year for setting up a
slanderous press, and for two or three journeys through the State to
sit as a mute on the bench, and wear the new cockade, in your
drunken frolics through the country, can afford to buy a press and
hire types, and pay under-devils to set types and fetch and carry
tales. I cannot afford such things. I have no salary, post, or
231
pension.”
A week later Scull attacked Brackenridge with even more
virulence: “Mr. Brackenridge cannot expect to live long. He has
already outlived all hope of fame. I doubt whether he feels that there
is a God above him. I doubt whether he does not think that he is his
own divinity while he lives, and that when he dies his dust will mingle
with that of the beasts that perish. He has labored with industry and
success to acquire the contempt and abhorrence of all whom it was
232
possible for him to esteem.”
REFERENCES
Chapter VI
174
Tree of Liberty, August 23, 1800.
175
176
H. H. Brackenridge. Incidents of the Insurrection in the
Western Parts of Pennsylvania, Philadelphia, 1795, vol.
ii., pp. 73–74.
177
ii., p. 72.
178
Pittsburgh Gazette, November 16, 1793.
179
Pittsburgh Gazette, June 28, 1794.
180
ii. p. 61.
181
Daniel Agnew. Address Delivered before the Allegheny
County Bar Association, December 1, 1888, p. 14.
182
Loomis’s Magazine Almanac for 1835, Pittsburgh, pp. 37–
40.
183
Pittsburgh Gazette, January 30, 1801.
184
Pittsburgh Gazette, October 10, 1800.
185
Pittsburgh Gazette, July 10, 1801.
186
Pittsburgh Gazette, September 25, 1801.
187
Pittsburgh Gazette, May 22, 1801.
188
189
William H. Loyd. The Early Courts of Pennsylvania, Boston,
1910, pp. 94–95, 124–125.
190
H. M. Brackenridge. The Literary Examiner and Western
Monthly Review, Pittsburgh, Pa., 1839, pp. 27–29.
191
John Wilkins. “The Western Insurrection.” In Contributions
to American History, Philadelphia, 1858, pp. 183–184;
H. M. Brackenridge. History of the Western Insurrection
in Western Pennsylvania, Pittsburgh, 1859, pp. 93–94.
192
Pittsburgh Gazette, December 5, 1800.
193
Pittsburgh Gazette, August 16, 1800.
194
195
Pittsburgh Gazette, June 30, 1798.
196
Tree of Liberty, June 18, 1803.
197
Pittsburgh Gazette, March 30, 1799.
198
Tree of Liberty, September 13, 1800.
199
Tree of Liberty, April 18, 1801.
200
201
202
Pittsburgh Gazette, April 5, 1800.
203
Pittsburgh Gazette, June 1, 1799; Tree of Liberty, August 30,
1800.
204
Tree of Liberty, February 28, 1801.
205
Colonial Records, Harrisburg, 1853, vol. xv., p. 604.
206
Pittsburgh Gazette, March 20, 1790.
207
Colonial Records, Harrisburg, 1853, vol. xvi., p. 537
208
Major Ebenezer Denny. Military Journal, Philadelphia,
1859, pp. 16–18.
209
William H. Egle. History of the Commonwealth of
Pennsylvania, Philadelphia, 1883, p. 454.
210
William G. Johnston. Life and Reminiscences, Pittsburgh,
MCMI, p. 33.
211
Tree of Liberty, January 10, 1801.
212
Tree of Liberty, December 13, 1800.
213
Pittsburgh Gazette, December 19, 1800; Tree of Liberty,
December 27, 1800.
214
Pittsburgh Gazette, August 14, 1801.
215
216
Tree of Liberty, June 25, 1803.
217
218
Centennial Volume of the First Presbyterian Church of
Pittsburgh, Pa., 1784–1884, Pittsburgh, 1884, p. 34.
219
220
221
Tree of Liberty, May 21, 1803.
222
Tree of Liberty, May 21, 1803.
223
Tree of Liberty, October 18, 1800.
224
225
226
227
Pittsburgh Gazette, January 30, 1801; Tree of Liberty,
February 7, 1801.
228
229
Tree of Liberty, October 25, 1800.
230
Pittsburgh Gazette, December 5, 1800.
231
Pittsburgh Gazette, February 6, 1801.
232
Pittsburgh Gazette, February 13, 1801.
CHAPTER VII
A DUEL AND OTHER MATTERS
On July 24, 1805, a third Richmond appeared in the Pittsburgh

newspaper field in the person of Ephraim Pentland. He established a
weekly newspaper called The Commonwealth, which was published
in a building situated in the West Diamond, opposite the southwest
corner of the new court house. The newspaper resulted from the
dissension in the Republican party in Pennsylvania.
Governor McKean’s second term was drawing to a close. For
two years prior to 1805, he had disagreed with the Republican
General Assembly because of its extreme radicalism. It had enacted
several revolutionary bills which he vetoed. The members appeared
to have an especial aversion to lawyers, and a bill was passed to
substitute, in civil cases, referees for juries, and prohibiting the
employment of counsel. This bill was also vetoed. The House
assumed that the Supreme Court was arrogating to itself powers
which it did not possess, and on February 28, 1803, scarcely a
month after the impeachment and removal from the bench of Judge
233
Addison, the first step was taken in the attempt to impeach three
of the judges of the Supreme Court for alleged arbitrary conduct in
committing to prison for contempt, the plaintiff in a suit pending in the
234
court. Brackenridge was absent from the bench when the
offender was imprisoned, and although accused of being largely
responsible for the impeachment of Judge Addison, was now loyal to
his colleagues, and sent a letter to the House in which he declared
his full concurrence in the course taken by the other judges, and
asked to share their fate. The House replied by addressing the
governor, and asking for Brackenridge’s removal. McKean refused to
comply with the request. On January 28, 1805, the impeachment trial
came to an end; a majority of the Senators pronounced the judges
guilty, but as the majority was short of two-thirds, the result was an
acquittal. The anger of the radical Republicans was boundless. A
division took place in the party, which caused intense feeling
throughout the State. McKean’s supporters took the name of
“Constitutionalists,” while the opposition called themselves “Friends
of the People.” The charm of French phrases was still strong.
The “Friends of the People” now put forward Simon Snyder as a
candidate for governor in opposition to McKean. The abuse that was
heaped on their former idol was appalling; threats of civil war were in
the air. McKean was charged with being a demagogue who
pandered to the worst elements in the Republican party, while being
by education and sentiment an aristocrat. He was also accused of
having gone over to the Federalists. The Tree of Liberty continued a
staunch supporter of McKean. Its former violence had given way to
an advocacy of “moderation.”
The Commonwealth was established in the interest of the faction
opposed to McKean, and its attacks on him and his supporter, the
Tree of Liberty, were brutal. Israel came in for the most violent
abuse. Pentland accused Israel of being ignorant. “Let a beardless
boy instruct you, old goat!” was one of his coarse thrusts. In the
same article he designated Israel as “the man with the long beard,
but no brains,” and concluded crudely, “Let a goslin’ instruct you, old
235
goose!”
The campaign teemed with personalities. The Federalists looked
on in amusement, but finally came to the support of McKean, and he
was elected. Pentland’s chagrin knew no bounds, and after the
election was over, he continued to attack the Tree of Liberty, the
management of which, by this time had changed. He vented his spite
on the supposed owners. He charged that, although the newspaper
was published in the name of Walter Forward, Tarleton Bates and
236
Henry Baldwin, the two most prominent politicians in Pittsburgh,
were the real proprietors, and that Bates was the editor. Baldwin,
who was not quite twenty-six years of age, later in life became a
member of Congress and a justice of the Supreme Court of the
United States. Forward was a young man of nineteen, a law student
in Baldwin’s office, and subsequently attained high political
distinction. He was several times a member of Congress, was
Secretary of the Treasury under President Tyler, chargé-d’-affaires to
Denmark, under President Taylor, and president judge of the District
Court of Allegheny County.
Bates was the oldest and best known of the three men. His
tragic end has caused a halo of romance to be cast about his striking
personality. He was a native of Virginia, where he was born on May
22, 1775. He was of Quaker origin, his father having lost his
membership in the Society of Friends because of his services as a
volunteer at the siege of Yorktown. The family seat was Belmont in
Goochland County. Tarleton Bates came to Pittsburgh when
eighteen years of age. During the early years of his residence he
was employed by the national government in the Quarter Master’s
Department under Major Isaac Craig, the Deputy Quarter Master and
Military Storekeeper at Pittsburgh, with whom for a time he made his
home. When the Spaniards surrendered their rights to the country on
the lower Mississippi in 1798, and the Mississippi Territory was
organized with Natchez as the capital, Bates determined to leave
Pittsburgh and settle in the southern town, but did not carry his
237
design into execution. Upon the appointment of John C. Gilkison
to the office of prothonotary, he became a clerk under him.
He had a fair education, was studiously inclined, and was
possessed of considerable culture, including a knowledge of the
French language. He owned the best copy of Lavater in Pittsburgh.
238
His letters to members of his family indicate that he was
generous, warm-hearted, and tender. The family fortunes were low.
His brother Frederick, just starting out in life, felt the need of money
and made his wants known to Tarleton. Although in the habit of
speaking of himself as living in “exiled poverty,” he responded
without hesitation: “Nothing within my ability shall be wanting to
smooth the entrance of the rugged path of life”; and he offered to
help Frederick to the extent of thirty dollars a month. He led an
upright life and ever attempted to deserve the good opinion of his
mother and “avoid the imprudencies of youth.” Frederick charged
him with being engaged to be married. His answer was an admission
that he was in love, and a frank intimation that thus far success had
not crowned his efforts. That he was fond of the society of ladies
appears from a letter in which he tells of the many charming ladies in
Pittsburgh. His acrostic on the name of Emily Morgan Neville, the
daughter of Colonel Presley Neville, lends color to the imputation
that at one time he was in love with that fascinating young woman.
His complete obsession with politics was probably responsible for his
remaining unmarried.
He was warmly attached to his party. In a letter written while the
Republican party—which he was in the habit of calling the
Democratic party—was still in its infancy in Pittsburgh, he said: “I
believe I am almost the only Pittsburgher who is not ashamed to call
himself a Democrat, and I am sure the appellation will never discredit
me.” He related humorously that on one occasion he attended a
Fourth of July celebration, and among the speakers was Colonel
Presley Neville, who, “abhors the Democrats as so many imps of
hell.” He was proud and told his family that he acknowledged no
superior, and “admitted no knave, however bloated with wealth, to be
an equal.” He was one of several famous brothers. His younger
brothers, Frederick, James, and Edward, after his death, emigrated
to the Missouri Territory where Frederick was the first secretary of
the Territory, and the second governor of the State. James afterward
settled in Arkansas and became a delegate to Congress from that
Territory. Edward became the friend of Henry Clay and in 1860 was a
candidate for President before the convention which nominated
Abraham Lincoln; he became Attorney-General in Lincoln’s Cabinet.
On Christmas Day, 1805, the article appeared in The
Commonwealth, which was the direct cause of the death of Tarleton
Bates in a duel. In the course of the incendiary diatribe, Pentland
declared that Bates and Baldwin were “two of the most abandoned
political miscreants that ever disgraced a State.” He demanded
savagely: “To what party do they belong?” and answered the
question himself. “To no party, to all parties. They have been Whigs
and Tories, High or Low Republicans, Democrats or Anti-Democrats,
Jacobins or Anti-Jacobins, Constitutionalists or Republicans,
according to existing circumstances.”
Pentland’s punishment was to be publicly cowhided by Bates on
Market Street on January 2, 1806. He is said to have fled
precipitately when attacked. Pentland gave a darkly colored account
of the occurrence: “On Thursday evening last, a considerable time
after dark, the editor of this paper was waylaid, and attacked in a
most outrageous manner, by Tarleton Bates, the prothonotary of this
county, and co-proprietor and editor of the Tree of Liberty. Bates was
in company with some persons who were no doubt to act as aids,
should their assistance be wanted, but owing to the mistiness of the
evening, and their quick disappearance, all of them could not be
recognized. Baldwin, Bates’s colleague in infamy, and the brave and
redoubtable Steele Semple, who never feels afraid but when he is in
danger, were in the gang,—both limbs of the law, students of
239
morality!”
Dueling had been forbidden in Pennsylvania since 1794, under
penalty of fine and imprisonment, and loss of citizenship for seven
240
years. An unconverted public sentiment, however, still approved
of the code of honor, and Pentland, who had at first threatened legal
proceedings against Bates, challenged him instead. The challenge
was carried by Thomas Stewart, a young Irishman who was a
merchant in the town. Bates declined to accept, on the ground that
Pentland’s conduct since his chastisement, had rendered him
unworthy of such notice. Pentland then posted Bates as a coward,
upon which on January 7, 1806, Bates published a letter in the Tree
of Liberty giving his reason for refusing the challenge, in which he
reflected on Stewart. Stewart demanded a retraction, which was
refused, whereupon he challenged Bates. This challenge was
accepted.
Bates immediately wrote his will. It was expressive of deep
feeling. There was every indication of a premonition of his
forthcoming end. He had always led a simple life, and in death he
desired to avoid display. In that moment he recalled the discussions
in the French Legislative Councils during the Directory, on the

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Chapter 1 Matter, Energy, and How To Draw Lewis Structures 77

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