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General, Organic, and
Biological Chemistry
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General, Organic, and
Biological Chemistry
F I F T H E D I T I O N
H. STEPHEN STOKER
Weber State University
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
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General, Organic, and Biological Chemistry, Fifth © 2010 Brooks/Cole, Cengage Learning
Edition
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Brief Contents
Preface xiv
PART I GENERAL CHEMISTRY
Chapter 1 Basic Concepts About Matter 1
Chapter 2 Measurements in Chemistry 22
Chapter 3 Atomic Structure and the Periodic Table 51
Chapter 4 Chemical Bonding: The Ionic Bond Model 83
Chapter 5 Chemical Bonding: The Covalent Bond Model 108
Chapter 6 Chemical Calculations: Formula Masses, Moles, and Chemical
Equations 137
Chapter 7 Gases, Liquids and Solids 163
Chapter 8 Solutions 192
Chapter 9 Chemical Reactions 223
Chapter 10 Acids, Bases, and Salts 253
Chapter 11 Nuclear Chemistry 292
PART II ORGANIC CHEMISTRY
Chapter 12 Saturated Hydrocarbons 321
Chapter 13 Unsaturated Hydrocarbons 361
Chapter 14 Alcohols, Phenols, and Ethers 399
Chapter 15 Aldehydes and Ketones 442
Chapter 16 Carboxylic Acids, Esters, and Other Acid Derivatives 473
Chapter 17 Amines and Amides 514
PART III BIOLOGICAL CHEMISTRY
Chapter 18 Carbohydrates 555
Chapter 19 Lipids 608
Chapter 20 Proteins 655
Chapter 21 Enzymes and Vitamins 698
Chapter 22 Nucleic Acids 734
Chapter 23 Biochemical Energy Production 777
Chapter 24 Carbohydrate Metabolism 811
Chapter 25 Lipid Metabolism 842
Chapter 26 Protein Metabolism 875
Answers to Selected Exercises A-1
Photo Credits A-26
Index/Glossary A-27
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Contents
Preface xiv 3.2 Atomic Number and Mass Number 53
3.3 Isotopes and Atomic Masses 55
CHEMISTRY AT A GLANCE Atomic Structure 58
3.4 The Periodic Law and the Periodic Table 59
PART I GENERAL CHEMISTRY 3.5 Metals and Nonmetals 62
3.6 Electron Arrangements Within Atoms 63
Chapter 1 Basic Concepts About Matter 1 CHEMISTRY AT A GLANCE Shell–Subshell–Orbital
Interrelationships 67
1.1 Chemistry: The Study of Matter 1
3.7 Electron Confi gurations and Orbital Diagrams 67
1.2 Physical States of Matter 2
3.8 The Electronic Basis for the Periodic Law and the
1.3 Properties of Matter 2
Periodic Table 71
1.4 Changes in Matter 4
3.9 Classifi cation of the Elements 73
CHEMISTRY AT A GLANCE Use of the Terms Physical and
Chemical 5 CHEMISTRY AT A GLANCE Element Classifi cation Schemes
and the Periodic Table 75
1.5 Pure Substances and Mixtures 6
1.6 Elements and Compounds 7 CHEMICAL CONNECTIONS
CHEMISTRY AT A GLANCE Classes of Matter 8 Protium, Deuterium, and Tritium: The Three Isotopes of
1.7 Discovery and Abundance of the Elements 9 Hydrogen 55
1.8 Names and Chemical Symbols of the Elements 11 Metallic Elements and the Human Body 64
1.9 Atoms and Molecules 12 Iron: The Most Abundant Transition Element in the Human Body 74
1.10 Chemical Formulas 15
CHEMICAL CONNECTIONS Chapter 4 Chemical Bonding: The Ionic
“Good” Versus “Bad” Properties for a Chemical Substance 3 Bond Model 83
Elemental Composition of the Human Body 11 4.1 Chemical Bonds 83
4.2 Valence Electrons and Lewis Symbols 84
Chapter 2 Measurements in 4.3 The Octet Rule 86
Chemistry 22 4.4 The Ionic Bond Model 87
4.5 The Sign and Magnitude of Ionic Charge 89
2.1 Measurement Systems 22
4.6 Lewis Structures for Ionic Compounds 91
2.2 Metric System Units 23
4.7 Chemical Formulas for Ionic Compounds 92
2.3 Exact and Inexact Numbers 26
4.8 The Structure of Ionic Compounds 93
2.4 U ncertainty in Measurement and Signifi cant
4.9 R ecognizing and Naming Binary Ionic
Figures 26
Compounds 94
CHEMISTRY AT A GLANCE Signifi cant Figures 28
CHEMISTRY AT A GLANCE Ionic Bonds and Ionic
2.5 Signifi cant Figures and Mathematical
Compounds 95
Operations 28 4.10 Polyatomic Ions 98
2.6 Scientifi c Notation 32 4.11 C hemical Formulas and Names for Ionic Compounds
2.7 Conversion Factors 34 Containing Polyatomic Ions 100
2.8 Dimensional Analysis 36
CHEMISTRY AT A GLANCE Nomenclature of Ionic
CHEMISTRY AT A GLANCE Conversion Factors 38 Compounds 102
2.9 Density 39
CHEMICAL CONNECTIONS
2.10 Temperature Scales 41
2.11 Heat Energy and Specifi c Heat 43 Fresh Water, Seawater, Hard Water, and Soft Water: A Matter
of Ions 90
CHEMICAL CONNECTIONS
Tooth Enamel: A Combination of Monatomic and
Body Density and Percent Body Fat 40 Polyatomic Ions 100
Normal Human Body Temperature 44
Chapter 5 Chemical Bonding: The Covalent
Chapter 3 Atomic Structure and the Bond Model 108
Periodic Table 51
5.1 The Covalent Bond Model 108
3.1 Internal Structure of an Atom 51 5.2 Lewis Structures for Molecular Compounds 109
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5.3 Single, Double, and Triple Covalent Bonds 111 7.11 Vapor Pressure of Liquids 177
5.4 Valence Electrons and Number of Covalent Bonds 7.12 Boiling and Boiling Point 180
Formed 112 7.13 Intermolecular Forces in Liquids 181
5.5 Coordinate Covalent Bonds 113 CHEMISTRY AT A GLANCE Intermolecular Forces 185
5.6 Systematic Procedures for Drawing Lewis
CHEMICAL CONNECTIONS
Structures 114
The Importance of Gas Densities 167
5.7 Bonding in Compounds with Polyatomic Ions
Blood Pressure and the Sodium Ion/Potassium Ion Ratio 178
Present 117
Hydrogen Bonding and the Density of Water 184
5.8 Molecular Geometry 118
CHEMISTRY AT A GLANCE The Geometry
of Molecules 121
5.9 Electronegativity 121
5.10 Bond Polarity 124
5.11 Molecular Polarity 126
CHEMISTRY AT A GLANCE Covalent Bonds and Molecular
Compounds 127
5.12 Naming Binary Molecular Compounds 130
CHEMICAL CONNECTIONS
Nitric Oxide: A Molecule Whose Bonding Does Not Follow
“The Rules” 117
The Chemical Senses of Smell and Taste 122
Chapter 6 C hemical Calculations: Formula
Masses, Moles, and Chemical
Equations 137
6.1 Formula Masses 137
6.2 The Mole: A Counting Unit for Chemists 138
Chapter 8 Solutions 192
6.3 The Mass of a Mole 140
6.4 Chemical Formulas and the Mole Concept 142 8.1 Characteristics of Solutions 192
6.5 The Mole and Chemical Calculations 143 8.2 Solubility 193
6.6 Writing and Balancing Chemical Equations 146 8.3 Solution Formation 196
6.7 Chemical Equations and the Mole Concept 150 8.4 Solubility Rules 197
CHEMISTRY AT A GLANCE Relationships Involving the Mole 8.5 Solution Concentration Units 198
Concept 151 8.6 Dilution 205
6.8 Chemical Calculations Using Chemical CHEMISTRY AT A GLANCE Solutions 207
Equations 151 8.7 Colloidal Dispersions and Suspensions 208
8.8 Colligative Properties of Solutions 209
CHEMICAL CONNECTIONS
8.9 Osmosis and Osmotic Pressure 210
Carbon Monoxide Air Pollution: A Case of Combining Ratios 153
CHEMISTRY AT A GLANCE Summary of Colligative Property
Chemical Reactions on an Industrial Scale: Sulfuric Acid 156
Terminology 215
8.10 Dialysis 215
Chapter 7 Gases, Liquids, and Solids 163
CHEMICAL CONNECTIONS
7.1 The Kinetic Molecular Theory of Matter 163 Factors Affecting Gas Solubility 195
7.2 Kinetic Molecular Theory and Physical States 165 Solubility of Vitamins 199
7.3 Gas Law Variables 167 Controlled-Release Drugs: Regulating Concentration, Rate,
7.4 Boyle’s Law: A Pressure-Volume Relationship 168 and Location of Release 206
7.5 Charles’s Law: A Temperature-Volume The Artifi cial Kidney: A Hemodialysis Machine 216
Relationship 170
7.6 The Combined Gas Law 172
Chapter 9 Chemical Reactions 223
7.7 The Ideal Gas Law 172
7.8 Dalton’s Law of Partial Pressures 173 9.1 Types of Chemical Reactions 223
CHEMISTRY AT A GLANCE The Gas Laws 175 9.2 Redox and Nonredox Chemical Reactions 226
7.9 Changes of State 176 CHEMISTRY AT A GLANCE Types of Chemical
7.10 Evaporation of Liquids 177 Reactions 228
viii Contents
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9.3 Terminology Associated with Redox 11.3 Equations for Radioactive Decay 295
Processes 230 11.4 Rate of Radioactive Decay 297
9.4 Collision Theory and Chemical Reactions 233 CHEMISTRY AT A GLANCE Radioactive Decay 299
9.5 Exothermic and Endothermic Chemical 11.5 Transmutation and Bombardment Reactions 300
Reactions 234 11.6 Radioactive Decay Series 302
9.6 Factors That Infl uence Chemical Reaction 11.7 Chemical Effects of Radiation 302
Rates 235 11.8 Biochemical Effects of Radiation 305
9.7 Chemical Equilibrium 237 11.9 Detection of Radiation 306
CHEMISTRY AT A GLANCE Factors That Increase Reaction 11.10 Sources of Radiation Exposure 307
Rates 238 11.11 Nuclear Medicine 309
9.8 Equilibrium Constants 239 11.12 Nuclear Fission and Nuclear Fusion 312
9.9 Altering Equilibrium Conditions: Le Châtelier’s CHEMISTRY AT A GLANCE Characteristics of Nuclear
Principle 243 Reactions 315
11.13 Nuclear and Chemical Reactions Compared 316
CHEMICAL CONNECTIONS
Combustion Reactions, Carbon Dioxide, and Global CHEMICAL CONNECTIONS
Warming 227 Tobacco Radioactivity and the Uranium-238 Decay Series 303
“Undesirable” Oxidation–Reduction Processes: Metallic Preserving Food Through Food Irradiation 307
Corrosion 232 The Indoor Radon-222 Problem 309
Stratospheric Ozone: An Equilibrium Situation 240
Chapter 10 Acids, Bases, and Salts 253
10.1 Arrhenius Acid–Base Theory 253
PART II ORGANIC CHEMISTRY
10.2 Brønsted–Lowry Acid–Base Theory 254
10.3 Mono-, Di-, and Triprotic Acids 257
Chapter 12 Saturated Hydrocarbons 321
CHEMISTRY AT A GLANCE Acid–Base Defi nitions 258
10.4 Strengths of Acids and Bases 258 12.1 Organic and Inorganic Compounds 321
10.5 Ionization Constants for Acids and Bases 260 12.2 Bonding Characteristics of the Carbon Atom 322
10.6 Salts 261 12.3 Hydrocarbons and Hydrocarbon Derivatives 322
10.7 Acid–Base Neutralization Chemical Reactions 262 12.4 Alkanes: Acyclic Saturated Hydrocarbons 323
10.8 Self-Ionization of Water 263 12.5 Structural Formulas 324
10.9 The pH Concept 266 12.6 Alkane Isomerism 326
10.10 The pK Method for Expressing Acid Strength 269 12.7 Conformations of Alkanes 327
a
10.11 The pH of Aqueous Salt Solutions 270 12.8 IUPAC Nomenclature for Alkanes 329
CHEMISTRY AT A GLANCE Acids and Acidic 12.9 Line-Angle Structural Formulas for Alkanes 335
Solutions 271 CHEMISTRY AT A GLANCE Structural Representations for
10.12 Buffers 274 Alkane Molecules 338
10.13 The Henderson–Hasselbalch Equation 277 12.10 Classifi cation of Carbon Atoms 338
CHEMISTRY AT A GLANCE Buffer Systems 278 12.11 Branched-Chain Alkyl Groups 339
10.14 Electrolytes 278 12.12 Cycloalkanes 340
10.15 Equivalents and Milliequivalents of 12.13 IUPAC Nomenclature for Cycloalkanes 341
Electrolytes 280 12.14 Isomerism in Cycloalkanes 342
10.16 Acid–Base Titrations 282 12.15 Sources of Alkanes and Cycloalkanes 344
12.16 Physical Properties of Alkanes
CHEMICAL CONNECTIONS
and Cycloalkanes 346
Excessive Acidity Within the Stomach: Antacids and Acid
12.17 C hemical Properties of Alkanes
Inhibitors 265
and Cycloalkanes 347
Acid Rain: Excess Acidity 272
CHEMISTRY AT A GLANCE Properties of Alkanes
Blood Plasma pH and Hydrolysis 274
and Cycloalkanes 349
Buffering Action in Human Blood 279
12.18 Nomenclature and Properties of Halogenated
Electrolytes and Body Fluids 283
Alkanes 350
CHEMICAL CONNECTIONS
Chapter 11 Nuclear Chemistry 292
The Occurrence of Methane 325
11.1 Stable and Unstable Nuclides 292 The Physiological Effects of Alkanes 348
11.2 The Nature of Radioactive Emissions 293 Chlorofl uorocarbons and the Ozone Layer 351
Contents ix
