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eleventh edition
 General, Organic,
and Biochemistry
ELEVENTH EDITION

Katherine J. Denniston
Towson University

Danaè R. Quirk
Minnesota State University, Mankato

Joseph J. Topping
Towson University

Robert L. Caret
University System of Maryland

ISTUDY
 GENERAL, ORGANIC, AND BIOCHEMISTRY

Published by McGraw Hill LLC, 1325 Avenue of the Americas, New York, NY 10019. Copyright ©2023 by
McGraw Hill LLC. All rights reserved. Printed in the United States of America. No part of this publication may
be reproduced or distributed in any form or by any means, or stored in a database or retrieval system, without
the prior written consent of McGraw Hill LLC, including, but not limited to, in any network or other electronic
storage or transmission, or broadcast for distance learning.

Some ancillaries, including electronic and print components, may not be available to customers outside the
United States.

This book is printed on acid-free paper.

1 2 3 4 5 6 7 8 9 LWI 27 26 25 24 23 22

ISBN 978-1-265-13846-2
MHID 1-265-13846-X

Cover Image: Dominic Cram/Moment/Getty Images

All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.

The Internet addresses listed in the text were accurate at the time of publication. The inclusion of a website does
not indicate an endorsement by the authors or McGraw Hill LLC, and McGraw Hill LLC does not guarantee the
accuracy of the information presented at these sites.

mheducation.com/highered

ISTUDY
 Brief Contents

GENERAL CHEMISTRY
1 Chemistry: Methods and Measurement. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
2 The Structure of the Atom and the Periodic Table. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44
3 Structure and Properties of Ionic and Covalent Compounds. . . . . . . . . . . . . . . . . . . . . . . . . . . 85
4 Calculations and the Chemical Equation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127
5 States of Matter: Gases, Liquids, and Solids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164
6 Solutions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 192
7 Energy, Rate, and Equilibrium. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 226
8 Acids and Bases and Oxidation-Reduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
9 The Nucleus, Radioactivity, and Nuclear Medicine. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299

ORGANIC CHEMISTRY
10 An Introduction to Organic Chemistry: The Saturated Hydrocarbons . . . . . . . . . . . . . . . . . . 330
11 The Unsaturated Hydrocarbons: Alkenes, Alkynes, and Aromatics . . . . . . . . . . . . . . . . . . . . . 369
12 Alcohols, Phenols, Thiols, and Ethers. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 412
13 Aldehydes and Ketones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 448
14 Carboxylic Acids and Carboxylic Acid Derivatives. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 478
15 Amines and Amides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 518

BIOCHEMISTRY
16 Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 556
17 Lipids and Their Functions in Biochemical Systems. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 592
18 Protein Structure and Function . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 627
19 Enzymes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 657
20 Introduction to Molecular Genetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 691
21 Carbohydrate Metabolism. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 733
22 Aerobic Respiration and Energy Production . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 767
23 Fatty Acid Metabolism. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 798

ISTUDY
 Contents

Perspectives xii Chapter Map 37

Preface xiv Summary 38
Questions and Problems 39
Multiple Concept Problems 42

GENERAL CHEMISTRY 2 The Structure of the Atom and

the Periodic Table 44
1 Chemistry: Methods and
Measurement 1 2.1 Composition of the Atom 45
Electrons, Protons, and
1.1 Strategies for Success in Neutrons 45
Antony Spencer/Vetta/Getty
Chemistry 2 Isotopes 47 Images
The Science of Learning Chemistry 2 2.2 Development of Atomic Theory 49
Learning General Chemistry 2 1joe/Getty Images Dalton’s Theory 49
1.2 The Discovery Process 4 Evidence for Subatomic Particles: Electrons, Protons,
Chemistry 4 and Neutrons 49
The Scientific Method 5 Chemistry at the Crime Scene: Microbial Forensics 50
Models in Chemistry 6 Evidence for the Nucleus 51
A Human Perspective: The Scientific Method 7 2.3 Light, Atomic Structure, and the Bohr Atom 52
1.3 The Classification of Matter 8 Electromagnetic Radiation 52
States of Matter 8 Photons 53
Composition of Matter 8 The Bohr Atom 53
Physical Properties and Physical Change 10 Green Chemistry: Practical Applications of Electromagnetic
Chemical Properties and Chemical Change 11 Radiation 55
Intensive and Extensive Properties 12 Modern Atomic Theory 56
1.4 The Units of Measurement 12 A Human Perspective: Atomic Spectra and the
Mass 13 Fourth of July 57
Length 14 2.4 The Periodic Law and the Periodic Table 58
Volume 14 Numbering Groups in the Periodic Table 58
Time 15 Periods 60
1.5 The Numbers of Measurement 15 Metals and Nonmetals 60
Significant Figures 15 A Medical Perspective: Copper Deficiency and Wilson’s
Recognition of Significant Figures 16 Disease 61
Scientific Notation 17 Information Contained in the Periodic Table 61
Accuracy and Precision 18 2.5 Electron Arrangement and the Periodic Table 62
Exact (Counted) and Inexact Numbers 19 The Quantum Mechanical Atom 62
Rounding Numbers 19 Principal Energy Levels, Sublevels, and Orbitals 63
Significant Figures in Calculation of Results 20 Electron Configurations 64
1.6 Unit Conversion 22 Guidelines for Writing Electron Configurations
Conversion of Units within the Same System 23 of Atoms 65
Factor-Label Method 23 Electron Configurations and the Periodic Table 69
Conversion of Units Between Systems 25 Shorthand Electron Configurations 69
A Medical Perspective: Curiosity and the Science 2.6 Valence Electrons and the Octet Rule 70
That Leads to Discovery 27 Valence Electrons 70
1.7 Additional Experimental Quantities 29 The Octet Rule 70
Temperature 29 Ions 71
Energy 30 Ion Formation and the Octet Rule 72
Concentration 31 A Medical Perspective: Dietary Calcium 75
Density and Specific Gravity 31 2.7 Trends in the Periodic Table 76
A Human Perspective: Food Calories 32 Atomic Size 76
A Medical Perspective: Assessing Obesity: Ion Size 77
The Body Mass Index 35 Ionization Energy 77
A Human Perspective: Quick and Useful Analysis 36 Electron Affinity 78

ISTUDY
 Contents v

Chapter Map 79 4.4 Balancing Chemical Equations 140

Summary 80 4.5 Precipitation Reactions 143
Questions and Problems 81
4.6 Net Ionic Equations 144
Multiple Concept Problems 84
Writing Net Ionic Equations 144
3 Structure and Properties of Ionic 4.7 Acid-Base Reactions 146
and Covalent Compounds 85 4.8 Oxidation-Reduction Reactions 146
3.1 Chemical Bonding 86 4.9 Calculations Using the Chemical Equation 146
Lewis Symbols 86 General Principles 146
Principal Types of Chemical Bonds: Using Conversion Factors 147
Ionic and Covalent 87 Source: James Gathany/CDC A Human Perspective: The Chemistry of Automobile Air Bags 151
Polar Covalent Bonding A Medical Perspective: Carbon Monoxide Poisoning: A Case of
and Electronegativity 90 Combining Ratios 154
3.2 Naming Compounds and Writing Formulas of Compounds 93 Theoretical and Percent Yield 155
Ionic Compounds 93 A Medical Perspective: Pharmaceutical Chemistry: The Practical
Covalent Compounds 98 Significance of Percent Yield 156
A Medical Perspective: Unwanted Crystal Formation 99 Chapter Map 158
3.3 Properties of Ionic and Covalent Compounds 101 Summary 159
Physical State 101 Questions and Problems 160
Melting and Boiling Points 101 Multiple Concept Problems 163
Structure of Compounds in the Solid State 101 5 States of Matter: Gases,
A Medical Perspective: Rebuilding Our Teeth 102
Liquids, and Solids 164
Solutions of Ionic and Covalent Compounds 102
3.4 Drawing Lewis Structures of Molecules and Polyatomic Ions 102 5.1 The Gaseous State 165
Lewis Structures of Molecules 102 Ideal Gas Concept 165
A Medical Perspective: Blood Pressure and the Sodium Ion/ Measurement of Properties
of Gases 166 Javier Larrea/Pixtal/age
Potassium Ion Ratio 105
Lewis Structures of Polyatomic Ions 105 Kinetic Molecular Theory of Gases 166 fotostock
Lewis Structure, Stability, Multiple Bonds, and Bond Energies 109 A Human Perspective: The Demise of the Hindenburg 167
Isomers 110 Properties of Gases and the Kinetic Molecular Theory 167
Lewis Structures and Resonance 110 Boyle’s Law 168
Lewis Structures and Exceptions to the Octet Rule 112 Charles’s Law 169
Lewis Structures and Molecular Geometry; VSEPR Theory 113 Combined Gas Law 171
Periodic Molecular Geometry Relationships 116 Avogadro’s Law 173
Lewis Structures and Polarity 118 Molar Volume of a Gas 174
Gas Densities 174
3.5 Properties Based on Molecular Geometry and Intermolecular
The Ideal Gas Law 175
Forces 120
Dalton’s Law of Partial Pressures 177
Solubility 120
Green Chemistry: The Greenhouse Effect and Global Climate
Boiling Points of Liquids and Melting Points of Solids 120
Change 178
Chapter Map 122 Ideal Gases Versus Real Gases 178
Summary 123
5.2 The Liquid State 179
Questions and Problems 124
Compressibility 179
Multiple Concept Problems 126
Viscosity 179
4 Calculations and the Chemical Surface Tension 180
Equation 127 Vapor Pressure of a Liquid 180
Boiling Point and Vapor Pressure 181
4.1 The Mole Concept and Atoms 128 van der Waals Forces 181
The Mole and Avogadro’s Number 128 Hydrogen Bonding 182
Calculating Atoms, Moles, and Mass 130 Chemistry at the Crime Scene: Explosives at the Airport 183
4.2 The Chemical Formula, Formula 5.3 The Solid State 184
Mass, and Molar Mass 134 Properties of Solids 184
The Chemical Formula 134 Wilawan Khasawong/Alamy Types of Crystalline Solids 185
Stock Photo
Formula Mass and Molar Mass 134 Sublimation of Solids 185
4.3 The Chemical Equation and the Information It Conveys 136 A Human Perspective: Gemstones 186
A Recipe for Chemical Change 136 Chapter Map 187
Features of a Chemical Equation 137 Summary 188
The Experimental Basis of a Chemical Equation 137 Questions and Problems 188
Strategies for Writing Chemical Equations 138 Multiple Concept Problems 191

ISTUDY
 vi Contents

6 Solutions 192 7.4 Equilibrium 245

Physical Equilibrium 245
6.1 Properties of Solutions 193 Chemical Equilibrium 246
General Properties of Liquid The Generalized Equilibrium Constant Expression for a
Solutions 193 Chemical Reaction 247
True Solutions, Colloidal Dispersions, Writing Equilibrium Constant Expressions 247
and Suspensions 194 Juice Images/Alamy Stock
Interpreting Equilibrium Constants 248
Photo
Degree of Solubility 195 Calculating Equilibrium Constants 250
Solubility and Equilibrium 196 Using Equilibrium Constants 251
Solubility of Gases: Henry’s Law 196 LeChatelier’s Principle 252
A Human Perspective: Scuba Diving: Nitrogen and the Bends 197 A Human Perspective: An Extraordinary Molecule 255
Henry’s Law and Respiration 197
Chapter Map 256
A Medical Perspective: Blood Gases and Respiration 198
Summary 256
6.2 Concentration Based on Mass 198 Questions and Problems 257
Mass/Volume Percent 198 Multiple Concept Problems 260
Mass/Mass Percent 200
Parts per Thousand (ppt) and Parts per Million (ppm) 201 8 Acids and Bases and
6.3 Concentration Based on Moles 202 Oxidation-Reduction 262
Molarity 202
8.1 Acids and Bases 263
Dilution 204
Acid and Base Theories 263
6.4 Concentration-Dependent Solution Properties 206 Amphiprotic Nature of Water 265
Vapor Pressure Lowering 207 Conjugate Acid-Base Pairs 265
Freezing Point Depression and Boiling Point Elevation 207 Acid and Base Strength 266
Calculating Freezing Points and Boiling Points of Aqueous Self-Ionization of Water and Kw 269 Don Farrall/Getty Images
Solutions 208
Osmosis, Osmotic Pressure, and Osmolarity 211 8.2 pH: A Measurement Scale for Acids and Bases 270
A Medical Perspective: Oral Rehydration Therapy 214 A Definition of pH 270
Measuring pH 271
6.5 Aqueous Solutions 214 Calculating pH 271
Water as a Solvent 214 A Medical Perspective: Drug Delivery 275
Kitchen Chemistry: Solubility, Surfactants, and the The Importance of pH and pH Control 275
Dishwasher 216
Concentration of Electrolytes in Solution 216 8.3 Reactions between Acids and Bases 276
Biological Effects of Electrolytes in Solution 219 Neutralization 276
A Medical Perspective: Hemodialysis 220 Polyprotic Substances 278
Green Chemistry: Hydrangea, pH, and Soil Chemistry 279
Chapter Map 221
Summary 221 8.4 Acid-Base Buffers 280
Questions and Problems 222 The Buffer Process 280
Multiple Concept Problems 225 Addition of Base or Acid to a Buffer Solution 280
Determining Buffer Solution pH 281
The Henderson-Hasselbalch Equation 284
7 Energy, Rate, and Control of Blood pH 285
Equilibrium 226 Green Chemistry: Acid Rain 286
7.1 Thermodynamics 227 8.5 Oxidation-Reduction Processes 287
The Chemical Reaction and Oxidation and Reduction 287
Energy 227 Voltaic Cells 288
The First Law of Thermodynamics 228 JonathanC Photography/ A Human Perspective: Lithium-Ion Batteries 290
Green Chemistry: Twenty-First Shutterstock Electrolysis 291
Century Energy 230 Applications of Oxidation and Reduction 292
The Second Law of Thermodynamics 231 Chapter Map 294
Free Energy 233 Summary 295
A Medical Perspective: Hot and Cold Packs 234 Questions and Problems 296
7.2 Experimental Determination of Energy Change in Reactions 235 Multiple Concept Problems 298
7.3 Kinetics 238 9 The Nucleus, Radioactivity,
Chemical Kinetics 238 and Nuclear Medicine 299
Activation Energy and the Activated Complex 239
Factors That Affect Reaction Rate 240 9.1 Natural Radioactivity 300
Mathematical Representation of Reaction Rate 242 Alpha Particles 301
A Human Perspective: Too Fast or Too Slow? 243 Beta Particles and Positrons 301 Mark Kostich/Getty Images

ISTUDY
 Contents vii

Gamma Rays 302 10.3 Alkanes 337

Properties of Alpha, Beta, Positron, and Gamma Radiation 302 Structure 337
A Human Perspective: Origin of the Elements 303 Physical Properties 341
9.2 Writing a Balanced Nuclear Equation 303 Alkyl Groups 341
Alpha Decay 304 Nomenclature 343
Beta Decay 304 Kitchen Chemistry: Alkanes in Our Food 344
Positron Emission 304 Green Chemistry: Biofuels: A Renewable Resource 346
Gamma Production 304 Constitutional or Structural Isomers 349
Predicting Products of Nuclear Decay 305 10.4 Cycloalkanes 350
cis-trans Isomerism in Cycloalkanes 352
9.3 Properties of Radioisotopes 308
Nuclear Structure and Stability 308 10.5 Conformations of Alkanes and Cycloalkanes 354
Half-Life 308 Alkanes 354
Radiocarbon Dating 310 Green Chemistry: The Petroleum Industry and
A Human Perspective: An Extraordinary Woman in Science 311 Gasoline Production 355
Cycloalkanes 355
9.4 Nuclear Power 312
Energy Production 312 10.6 Reactions of Alkanes and Cycloalkanes 356
Nuclear Fission 312 Combustion 356
Nuclear Fusion 314 Halogenation 357
Breeder Reactors 314 A Medical Perspective: Polyhalogenated Hydrocarbons
Green Chemistry: Nuclear Waste Disposal 315 Used as Anesthetics 359

9.5 Medical Applications of Radioactivity 315 Chapter Map 360

Cancer Therapy Using Radiation 315 Summary of Reactions 361
Nuclear Medicine 316 Summary 361
Making Isotopes for Medical Applications 317 Questions and Problems 362
A Medical Perspective: Magnetic Resonance Imaging 319 Multiple Concept Problems 367

9.6 Biological Effects of Radiation 319 11 The Unsaturated Hydrocarbons:

Radiation Exposure and Safety 319 Alkenes, Alkynes, and
9.7 Measurement of Radiation 321 Aromatics 369
Photographic Imaging 321
11.1 Alkenes and Alkynes: Structure and
Computer Imaging 321
Physical Properties 370
The Geiger Counter 322
Film Badges 322 11.2 Alkenes and Alkynes:
Units of Radiation Measurement 322 Nomenclature 372
Green Chemistry: Radon and Indoor Air Pollution 323 11.3 Geometric Isomers: A Consequence
of Unsaturation 375 cooperr/Shutterstock
Chapter Map 325
Summary 326 A Medical Perspective: Killer Alkynes in Nature 376
Questions and Problems 327 11.4 Alkenes in Nature 381
Multiple Concept Problems 329 11.5 Reactions Involving Alkenes and Alkynes 383
Hydrogenation: Addition of H2 384
Halogenation: Addition of X2 387
Hydration: Addition of H2O 389
ORGANIC CHEMISTRY Hydrohalogenation: Addition of HX 392
Addition Polymers of Alkenes 394
10 An Introduction to Organic Green Chemistry: Plastic Recycling 395
Chemistry: The Saturated 11.6 Aromatic Hydrocarbons 396
Hydrocarbons 330 A Human Perspective: The Dragonfly and the Moon 397
Structure and Properties 398
10.1 Strategies for Success in Organic Nomenclature 398
Chemistry 331 Kitchen Chemistry: Pumpkin Pie Spice: An Autumn Tradition 401
Prepare for Class 331 Pixtal/AGE Fotostock Polynuclear Aromatic Hydrocarbons 401
Make the Most of Class Time 331 Reactions Involving Benzene 402
10.2 The Chemistry of Carbon 333 11.7 Heterocyclic Aromatic Compounds 403
Important Differences between Organic and Kitchen Chemistry: Amazing Chocolate 404
Inorganic Compounds 333 Chapter Map 405
A Human Perspective: The Father of Summary of Reactions 406
Organic Chemistry 334 Summary 407
Families of Organic Compounds 334 Questions and Problems 407
Green Chemistry: Frozen Methane: Treasure or Threat? 336 Multiple Concept Problems 411

ISTUDY
 viii Contents

12 Alcohols, Phenols, Thiols, and 14 Carboxylic Acids and Carboxylic

Ethers 412 Acid Derivatives 478

12.1 Alcohols: Structure and Physical 14.1 Carboxylic Acids 479

Properties 413 Structure and Physical Properties 479
12.2 Alcohols: Nomenclature 416 Nomenclature 481
IUPAC Names 416 Chemistry at the Crime Scene: Stockbyte/Getty Images
Common Names 417 Darren Greenwood/Design Carboxylic Acids and the Body Farm 485
Pics Some Important Carboxylic Acids 486
12.3 Medically Important Alcohols 419 Green Chemistry: Garbage Bags from Potato Peels? 487
Methanol 419 Reactions Involving Carboxylic Acids 490
Ethanol 419
Kitchen Chemistry: Sugar Alcohols and the Sweet Tooth 420 14.2 Esters 493
Propan-2-ol 421 Structure and Physical Properties 493
Ethane-1,2-diol 421 Nomenclature 493
Propane-1,2,3-triol 421 Reactions Involving Esters 495
A Human Perspective: The Chemistry of Flavor and Fragrance 497
12.4 Reactions Involving Alcohols 421 A Human Perspective: Detergents 501
Preparation of Alcohols 421
Dehydration of Alcohols 424 14.3 Acid Chlorides and Acid Anhydrides 503
Oxidation Reactions 425 Acid Chlorides 503
Acid Anhydrides 503
12.5 Oxidation and Reduction in Living Systems 428
14.4 Nature’s High-Energy Compounds: Phosphoesters
12.6 Phenols 429 and Thioesters 507
Kitchen Chemistry: Spicy Phenols 430 A Medical Perspective: Esters for Appetite Control 509
A Medical Perspective: Resveratrol: Fountain of Youth? 431
Chapter Map 510
12.7 Ethers 432 Summary of Reactions 510
12.8 Thiols 435 Summary 511
Kitchen Chemistry: The Magic of Garlic 438 Questions and Problems 512
Chapter Map 440 Multiple Concept Problems 516
Summary of Reactions 441
Summary 441 15 Amines and Amides 518
Questions and Problems 442 15.1 Amines 519
Multiple Concept Problems 446 Structure and Physical Properties 519
Nomenclature 523
13 Aldehydes and Ketones 448
Medically Important Amines 526
13.1 Structure and Physical Reactions Involving Amines 528 ximagination/123RF
Properties 449 Chemistry at the Crime Scene: Methamphetamine 530
A Human Perspective: Powerful Quaternary Ammonium Salts 532
Weak Attractions 450 15.2 Heterocyclic Amines 533
13.2 IUPAC Nomenclature and Andrea Booher/FEMA photo 15.3 Amides 535
Common Names 452 Structure and Physical Properties 535
Naming Aldehydes 452 Kitchen Chemistry: Browning Reactions and Flavor:
Naming Ketones 454 The Maillard Reaction 536
13.3 Important Aldehydes and Ketones 457 Nomenclature 536
Green Chemistry: Aldehydes, Stink Bugs, and Wine 457 Medically Important Amides 537
Reactions Involving Amides 539
13.4 Reactions Involving Aldehydes and Ketones 458
A Medical Perspective: Semisynthetic Penicillins 540
Preparation of Aldehydes and Ketones 458
Oxidation Reactions 460 15.4 A Preview of Amino Acids, Proteins, and Protein Synthesis 543
Reduction Reactions 462 15.5 Neurotransmitters 544
A Human Perspective: Alcohol Abuse and Antabuse 463 Catecholamines 544
Addition Reactions 465 Serotonin 544
Kitchen Chemistry: The Allure of Truffles 466 A Medical Perspective: Opiate Biosynthesis and the Mutant
Keto-Enol Tautomers 469 Poppy 545
Chapter Map 471 Histamine 546
Summary of Reactions 472 γ-Aminobutyric Acid and Glycine 547
Summary 472 Acetylcholine 547
Questions and Problems 473 Green Chemistry: Neonicotinoid Pesticides and Bumble Bees 548
Multiple Concept Problems 476 Nitric Oxide and Glutamate 549

ISTUDY
 Contents ix

Chapter Map 549 17.2 Fatty Acids 595

Summary of Reactions 550 Structure and Properties 595
Summary 550 Omega-3 Fatty Acids 598
Questions and Problems 551 Eicosanoids: Prostaglandins, Leukotrienes,
Multiple Concept Problems 555 and Thromboxanes 599
17.3 Glycerides 601
Neutral Glycerides 601
Chemical Reactions of Fatty Acids and Glycerides 603
BIOCHEMISTRY Phosphoglycerides 606
Chemistry at the Crime Scene: Adipocere and Mummies
of Soap 608
16 Carbohydrates 556
17.4 Nonglyceride Lipids 608
16.1 Strategies for Success in Sphingolipids 608
Biochemistry 557 Steroids 610
A Medical Perspective: Disorders of Sphingolipid
16.2 Types of Carbohydrates 559
Metabolism 612
16.3 Monosaccharides 560 A Medical Perspective: Steroids and the Treatment
A Medical Perspective: Chemistry Science Photo Library RF/ of Heart Disease 613
through the Looking Glass 561 Getty Images Waxes 615
16.4 Stereoisomers and Stereochemistry 562 17.5 Complex Lipids 615
Stereoisomers 562
17.6 The Structure of Biological Membranes 618
Rotation of Plane-Polarized Light 564
Fluid Mosaic Structure of Biological Membranes 618
The Relationship between Molecular Structure and
A Medical Perspective: Liposome Delivery Systems 621
Optical Activity 565
Fischer Projection Formulas 565 Chapter Map 623
Racemic Mixtures 566 Summary 623
Diastereomers 567 Questions and Problems 624
Meso Compounds 568 Multiple Concept Problems 626
The d- and l- System of Nomenclature 569
16.5 Biologically Important Monosaccharides 569 18 Protein Structure
Glucose 570 and Function 627
Fructose 574
Galactose 574 18.1 Biological Functions
Ribose and Deoxyribose, Five-Carbon Sugars 575 of Proteins 628
Reducing Sugars 575 18.2 Protein Building Blocks:
Kitchen Chemistry: The Chemistry of Caramels 576 The α-Amino Acids 629 Catmando/Shutterstock
16.6 Biologically Important Disaccharides 578 Structure of Amino Acids 629
Maltose 578 Stereoisomers of Amino Acids 629
Lactose 579 Classes of Amino Acids 629
A Medical Perspective: Human Milk Oligosaccharides 580 18.3 The Peptide Bond 632
Sucrose 580 A Human Perspective: Plant-Based Meats 635
16.7 Polysaccharides 581 18.4 The Primary Structure of Proteins 636
Starch 581
Glycogen 583 18.5 The Secondary Structure of Proteins 636
Cellulose 583 α-Helix 637
A Medical Perspective: Monosaccharide Derivatives and β-Pleated Sheet 638
Heteropolysaccharides of Medical Interest 584 18.6 The Tertiary Structure of Proteins 639
Chapter Map 586 A Medical Perspective: Collagen, Cosmetic Procedures, and
Summary 587 Clinical Applications 641
Questions and Problems 588 18.7 The Quaternary Structure of Proteins 642
Multiple Concept Problems 590
18.8 An Overview of Protein Structure and Function 642
18.9 Myoglobin and Hemoglobin 644
17 Lipids and Their Functions
Myoglobin and Oxygen Storage 644
in Biochemical Systems 592 Hemoglobin and Oxygen Transport 644
Oxygen Transport from Mother to Fetus 645
17.1 Biological Functions of Lipids 593
Sickle Cell Anemia 645
A Medical Perspective: Lifesaving
Lipids 594 Juan Gaertner/Shutterstock 18.10 Proteins in the Blood 646

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 x Contents

18.11 Denaturation of Proteins 647 20 Introduction to Molecular

Temperature 647 Genetics 691
pH 648
Organic Solvents 648 20.1 The Structure of the Nucleotide 692
Detergents 648 Chemical Composition of DNA
Heavy Metals 648 and RNA 693
Mechanical Stress 648 Nucleosides 693
Kitchen Chemistry: Egg Foams: Meringues and Nucleotide Structure 694 Science Photo Library/Image
Soufflés 649 Source
20.2 The Structure of DNA and RNA 695
A Medical Perspective: Medications from Venoms 650
DNA Structure: The Double Helix 695
18.12 Dietary Protein and Protein Digestion 650 Chromosomes 697
Chapter Map 652 RNA Structure 699
Summary 653 A Medical Perspective: Molecular Genetics and Detection
Questions and Problems 654 of Human Genetic Disorders 700
Multiple Concept Problems 656 20.3 DNA Replication 700
Bacterial DNA Replication 702
Eukaryotic DNA Replication 703
19 Enzymes 657
20.4 Information Flow in Biological Systems 705
19.1 Nomenclature and Classification 658 Classes of RNA Molecules 705
Classification of Enzymes 658 Transcription 705
Nomenclature of Enzymes 661 Post-transcriptional Processing of RNA 707
Kitchen Chemistry: Transglutaminase:
20.5 The Genetic Code 709
aka Meat Glue 663 Krishna.Wu/Flickr Open/
Moment Open/Getty Images 20.6 Protein Synthesis 710
19.2 The Effect of Enzymes on the
The Role of Transfer RNA 712
Activation Energy of a Reaction 664
The Process of Translation 712
19.3 The Effect of Substrate Concentration on
20.7 Mutation, Ultraviolet Light, and DNA Repair 715
Enzyme-Catalyzed Reactions 665
The Nature of Mutations 715
19.4 The Enzyme-Substrate Complex 666 The Results of Mutations 715
19.5 Specificity of the Enzyme-Substrate Mutagens and Carcinogens 716
Complex 667 Ultraviolet Light Damage and DNA Repair 716
A Medical Perspective: Epigenomics 717
19.6 The Transition State and Product Formation 668 Consequences of Defects in DNA Repair 718
A Medical Perspective: HIV Protease Inhibitors and
Pharmaceutical Drug Design 670 20.8 Recombinant DNA 718
Tools Used in the Study of DNA 718
19.7 Cofactors and Coenzymes 671 Genetic Engineering 719
19.8 Environmental Effects 674 20.9 Polymerase Chain Reaction 722
Effect of pH 674
Effect of Temperature 674 20.10 The Human Genome Project 722
A Medical Perspective: α1-Antitrypsin and Familial Genetic Strategies for Genome Analysis 722
Emphysema 675 Chemistry at the Crime Scene: DNA Fingerprinting 723
DNA Sequencing 724
19.9 Regulation of Enzyme Activity 676 A Medical Perspective: CRISPR Technology and the
Allosteric Enzymes 676 Future of Genetics 725
Feedback Inhibition 677
Proenzymes 678 Chapter Map 727
Protein Modification 678 Summary 728
Questions and Problems 729
19.10 Inhibition of Enzyme Activity 679 Multiple Concept Problems 731
Irreversible Inhibitors 679
Reversible, Competitive Inhibitors 679
Chemistry at the Crime Scene: Enzymes, 21 Carbohydrate Metabolism 733
Nerve Agents, and Poisoning 680
21.1 ATP: The Cellular Energy
19.11 Proteolytic Enzymes 682 Currency 734
19.12 Uses of Enzymes in Medicine 683 21.2 Overview of Catabolic
Chapter Map 685 Processes 737
Summary 686 Stage I: Hydrolysis of Dietary
Questions and Problems 687 Macromolecules into Small
Multiple Concept Problems 689 Subunits 738 Purestock/SuperStock

ISTUDY
 Contents xi

Stage II: Conversion of Monomers into a Form That Can Be 22.7 The Degradation of Amino Acids 783
Completely Oxidized 738 Removal of α-Amino Groups: Transamination 783
Stage III: The Complete Oxidation of Nutrients and the Removal of α-Amino Groups: Oxidative Deamination 786
Production of ATP 738 The Fate of Amino Acid Carbon Skeletons 786
21.3 Glycolysis 739 22.8 The Urea Cycle 786
An Overview 739 Reactions of the Urea Cycle 786
Biological Effects of Genetic Disorders of Glycolysis 742 A Medical Perspective: Pyruvate Carboxylase Deficiency 789
Reactions of Glycolysis 742 22.9 Overview of Anabolism: The Citric Acid Cycle as a Source of
Entry of Fructose into Glycolysis 746 Biosynthetic Intermediates 790
A Medical Perspective: High Fructose Corn Syrup 747
Regulation of Glycolysis 747 Chapter Map 793
Summary 794
21.4 Fermentations 748 Questions and Problems 795
Lactate Fermentation 748 Multiple Concept Problems 797
Alcohol Fermentation 749
A Human Perspective: Fermentations: The Good,
the Bad, and the Ugly 750 23 Fatty Acid Metabolism 798
21.5 The Pentose Phosphate Pathway 751 23.1 Lipid Metabolism in Animals 799
21.6 Gluconeogenesis: The Synthesis of Glucose 752 Digestion and Absorption of Dietary
Triglycerides 799
21.7 Glycogen Synthesis and Degradation 754 Lipid Storage 800
The Structure of Glycogen 754 A Medical Perspective: Obesity:
Glycogenolysis: Glycogen Degradation 754 Letterberry/Shutterstock
A Genetic Disorder? 802
Glycogenesis: Glycogen Synthesis 755
A Medical Perspective: Diagnosing Diabetes 758 23.2 Fatty Acid Degradation 803
Compatibility of Glycogenesis and Glycogenolysis 760 An Overview of Fatty Acid Degradation 803
A Human Perspective: Glycogen Storage Diseases 761 The Reactions of β-Oxidation 804
A Medical Perspective: Carnitine: The Fat Mover 807
Chapter Map 762
Summary 762 23.3 Ketone Bodies 809
Questions and Problems 763 Ketosis 810
Multiple Concept Problems 765 Ketogenesis 810
A Human Perspective: Losing Those Unwanted Pounds of
22 Aerobic Respiration and Energy Adipose Tissue 812
Production 767 23.4 Fatty Acid Synthesis 813
A Comparison of Fatty Acid Synthesis and Degradation 813
22.1 The Mitochondria 768
Structure and Function 768 23.5 The Regulation of Lipid Metabolism 814
Origin of the Mitochondria 769 A Medical Perspective: Diabetes Mellitus and Ketone Bodies 815
A Human Perspective: Exercise and King Lawrence/Blend Images
The Liver 816
Energy Metabolism 770 Adipose Tissue 816
Muscle Tissue 817
22.2 Conversion of Pyruvate to Acetyl CoA 771 The Brain 817
22.3 An Overview of Aerobic Respiration 773 23.6 The Effects of Insulin and Glucagon on Cellular
22.4 The Citric Acid Cycle (the Krebs Cycle) 774 Metabolism 817
Biological Effects of Disorders of the Citric Acid Cycle 774 Chapter Map 819
Reactions of the Citric Acid Cycle 775 Summary 820
22.5 Control of the Citric Acid Cycle 778 Questions and Problems 820
Multiple Concept Problems 822
22.6 Oxidative Phosphorylation 780
Electron Transport Systems and the Hydrogen Ion Gradient 780 Glossary G-1
ATP Synthase and the Production of ATP 781 Answers to Practice Problems AP-1
Summary of the Energy Yield 781 Answers to Odd-Numbered Questions and Problems AP-13
A Medical Perspective: Babies with Three Parents? 782 Index I-1

ISTUDY
 Perspectives

A Human Perspective
The Scientific Method 7 An Extraordinary Woman in Science 311
Food Calories 32 The Father of Organic Chemistry 334
Quick and Useful Analysis 36 The Dragonfly and the Moon 397
Atomic Spectra and the Fourth of July 57 Powerful Weak Attractions 450
The Chemistry of Automobile Air Bags 151 Alcohol Abuse and Antabuse 463
The Demise of the Hindenburg 167 The Chemistry of Flavor and Fragrance 497
Gemstones 186 Detergents 501
Scuba Diving: Nitrogen and the Bends 197 Plant-Based Meats 635
Too Fast or Too Slow? 243 Fermentations: The Good, the Bad, and the Ugly 750
An Extraordinary Molecule 255 Glycogen Storage Diseases 761
Lithium-Ion Batteries 290 Exercise and Energy Metabolism 770
Origin of the Elements 303 Losing Those Unwanted Pounds of Adipose Tissue 812

A Medical Perspective
Curiosity and the Science that Leads to Discovery 27 Chemistry through the Looking Glass 561
Assessing Obesity: The Body Mass Index 35 Human Milk Oligosaccharides 580
Copper Deficiency and Wilson’s Disease 61 Monosaccharide Derivatives and Heteropolysaccharides of Medical
Dietary Calcium 75 Interest 584
Unwanted Crystal Formation 99 Lifesaving Lipids 594
Rebuilding Our Teeth 102 Disorders of Sphingolipid Metabolism 612
Blood Pressure and the Sodium Ion/Potassium Ion Ratio 105 Steroids and the Treatment of Heart Disease 613
Carbon Monoxide Poisoning: A Case of Combining Ratios 154 Liposome Delivery Systems 621
Pharmaceutical Chemistry: The Practical Significance Collagen, Cosmetic Procedures, and Clinical Applications 641
of Percent Yield 156 Medication from Venoms 650
Blood Gases and Respiration 198 HIV Protease Inhibitors and Pharmaceutical Drug Design 670
Oral Rehydration Therapy 214 α1-Antitrypsin and Familial Emphysema 675
Hemodialysis 220 Molecular Genetics and Detection of Human Genetic Disorders 700
Hot and Cold Packs 234 Epigenomics 717
Drug Delivery 275 CRISPR Technology and the Future of Genetics 725
Magnetic Resonance Imaging 319 High Fructose Corn Syrup 747
Polyhalogenated Hydrocarbons Used as Anesthetics 359 Diagnosing Diabetes 758
Killer Alkynes in Nature 376 Babies with Three Parents? 782
Resveratrol: Fountain of Youth? 431 Pyruvate Carboxylase Deficiency 789
Esters for Appetite Control 509 Obesity: A Genetic Disorder? 802
Semisynthetic Penicillins 540 Carnitine: The Fat Mover 807
Opiate Biosynthesis and the Mutant Poppy 545 Diabetes Mellitus and Ketone Bodies 815

xii

ISTUDY
 Green Chemistry
Practical Applications of Electromagnetic Radiation 55 Frozen Methane: Treasure or Threat? 336
The Greenhouse Effect and Global Climate Change 178 Biofuels: A Renewable Resource 346
Twenty-First Century Energy 230 The Petroleum Industry and Gasoline Production 355
Hydrangea, pH, and Soil Chemistry 279 Plastic Recycling 395
Acid Rain 286 Aldehydes, Stink Bugs, and Wine 457
Nuclear Waste Disposal 315 Garbage Bags from Potato Peels? 487
Radon and Indoor Air Pollution 323 Neonicotinoid Pesticides and Bumble Bees 548

Kitchen Chemistry
Solubility, Surfactants, and the Dishwasher 216 The Magic of Garlic 438
Alkanes in Our Food 344 The Allure of Truffles 466
Pumpkin Pie Spice: An Autumn Tradition 401 Browning Reactions and Flavor: The Maillard Reaction 536
Amazing Chocolate 404 The Chemistry of Caramels 576
Sugar Alcohols and the Sweet Tooth 420 Egg Foams: Meringues and Soufflés 649
Spicy Phenols 430 Transglutaminase: aka Meat Glue 663

Chemistry at the Crime Scene

Microbial Forensics 50 Adipocere and Mummies of Soap 608
Explosives at the Airport 183 Enzymes, Nerve Agents, and Poisoning 680
Carboxylic Acids and the Body Farm 485 DNA Fingerprinting 723
Methamphetamine 530

ISTUDY
 Preface

To Our Students subject and real life. For these reasons, we have included perspec-
tives and essays that focus on medicine and the function of the
Student engagement in the study of chemistry has been our primary
human body, as well as the environment, forensic science, and even
aim since the first edition of this book. We wanted to show you that
culinary arts.
chemistry is much more than an onerous obstacle in the journey toward
We begin that engagement with the book cover. Students may
your career goals. Through the Perspectives boxes in each chapter, we
wonder why the cover of a chemistry book has a photo of a tree in a
have tried to show that chemistry is a fascinating discipline that has an
Peruvian rainforest. What does a scenic sunset over a river in Peru
enormous impact on all aspects of your life—whether chemistry in the
have to do with the study of chemistry or the practice of medicine?
kitchen, investigations at a crime scene, issues of environmental con-
Students will remember that a drug called hydroxychloroquine was
cern, medicine, or the chemical reactions that keep our bodies
considered as a treatment for Coronavirus 2019 (COVID-19). That
functioning.
drug is a synthetic version of quinine, the ancient treatment for ma-
While engagement in a subject is a good place to begin, effective
laria. The indigenous people of Peru extracted the bark of the cin-
study practices will ensure your success in learning the course con-
chona tree (Cinchona officinalis) to produce a powder they used to
tent. In the preface of previous editions, we included suggestions for
treat chills and fever. In 1633 the Jesuits introduced this herbal medi-
studying chemistry that included the five stages of the Study Cycle.
cine to Europe where it also was used against malaria. Quinine was
Because education research has shown that effective use of the Study
isolated from the bark in 1820 and the synthetic analogue hydroxy-
Cycle improves student performance in all subjects, we wanted to
chloroquine was approved for medical use in 1955. Although it was
share this information with you. In this edition, we have expanded our
not found to be effective against COVID-19, hydroxychloroquine is
attention to research-based learning strategies by including specific
used in the treatment of rheumatoid arthritis, lupus erythematosus,
sections of the text devoted to effective study skills. In Section 1.1 you
and post-Lyme arthritis. In fact, it is the first-line treatment for lupus
will learn about the Study Cycle, as well as some useful strategies that
erythematosus.
are specific to general chemistry. In Section 10.1, the beginning of the
The cover sets the theme for the book: chemistry is not an ab-
organic chemistry section of the course, you will be challenged to
stract study, but one that has an immediate impact on our lives. We
apply study strategies that are specific to that discipline. Similarly, in
try to spark student interest with an art program that uses relevant
Section 16.1, the beginning of the biochemistry section, you will be
photography, clear and focused figures, and perspectives and essays
introduced to practices and ideas that will help you master that
that bring life to abstract ideas. We reinforce key concepts by ex-
content.
plaining them in a clear and concise way and encouraging students
We have also introduced a new type of problem, multiple concept
to apply the concept to solve problems. We provide guidance through
problems. These challenge you to apply your knowledge of many as-
the inclusion of a large number of in-chapter examples that are
pects of the topic to answer thought-provoking questions that will help
solved in a stepwise fashion and that provide students the opportu-
you develop a much deeper understanding of the principles of chemis-
nity to test their understanding through the practice problems that
try. Research has shown that this type of deeper understanding is cru-
follow and the suggested end-of-chapter questions and problems
cial to success in all areas of your education. It is our hope that these
that apply the same concepts.
new elements of the text will provide you with the tools you need to
successfully meet the challenges of this course.
Foundations for Our Revisions
To the Instructor Over the past thirty years, we have been guided by the collective
The eleventh edition of General, Organic, and Biochemistry, like our wisdom of reviewers who are expert chemists and excellent teachers.
earlier editions, has been designed to help undergraduate majors in They represent experience in community colleges, liberal arts col-
health-related fields understand key concepts and appreciate signifi- leges, comprehensive institutions, and research universities. We have
cant connections among chemistry, health, and the treatment of dis- followed their recommendations, while remaining true to our over-
ease. We have tried to strike a balance between theoretical and riding goal of writing a readable, student-centered text. All of our
practical chemistry, while emphasizing material that is unique to editions have been designed to be amenable to a variety of teaching
health-related studies. We have written at a level intended for students styles. Each feature incorporated into this edition has been carefully
whose professional goals do not include a mastery of chemistry, but considered with regard to how it may be used to support student
for whom an understanding of the principles and practice of chemistry learning in both the traditional classroom and the flipped learning
is a necessity. environment.
Although our emphasis is the importance of chemistry to the In addition to the faculty reviewers, we have been able to incorpo-
health-related professions, we wanted this book to be appropriate for rate real student data points and input, derived from thousands of our
all students who need a one- or two-semester introduction to chem- LearnSmart users, to help guide our revision. LearnSmart Heat Maps
istry. Students learn best when they are engaged. One way to foster provided a quick visual snapshot of usage of portions of the text and
that engagement is to help them see clear relationships between the the relative difficulty students experienced in mastering the content.

xiv

ISTUDY
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