Dennis Tonnn

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General, Organic, and Biochemistry
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Study Guide Table of Contents
General, Organic, and Biochemistry

Third Edition
Katherine J. Denniston
Towson University
Joseph J. Topping
Towson University
Robert L. Caret
San Jos State University
Boston Burr Ridge, IL Dubuque, IA Madison, WI New York San Francisco St. Louis
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GENERAL, ORGANIC, AND BIOCHEMISTRY

THIRD EDITION
Published by McGraw-Hill, an imprint of The McGraw-Hill Companies, Inc., 1221 Avenue of the
Americas, New York, NY 10020. Copyright 2001, 1997 by The McGraw-Hill Companies, Inc.
All rights reserved. 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
The McGraw-Hill Companies, Inc., 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 0 VNH/VNH 0 9 8 7 6 5 4 3 2 1 0
ISBN 0072317841
ISBN 0071180737 (ISE)
Vice president and editor-in-chief: Kevin T. Kane
Publisher: James M. Smith
Sponsoring editor: Kent A. Peterson
Developmental editor: Shirley R. Oberbroeckling
Editorial assistant: Jennifer L. Bensink
Senior marketing manager: Martin J. Lange
Senior marketing assistant: Tami Petsche
Senior project manager: Marilyn M. Sulzer
Production supervisor: Sandy Ludovissy
Design manager: Stuart D. Paterson
Cover/interior designer: Elise Lansdon
Cover image: FPG International
Senior photo research coordinator: Lori Hancock
Photo research: Feldman and Associates
Senior supplement coordinator: Brenda A. Ernzen
Compositor: GACIndianapolis
Typeface: 10/12 Palatino
Printer: Von Hoffman Press, Inc.
The credits section for this book begins on page 823 and is considered an extension of the copyright
page.
Library of Congress Cataloging-in-Publication Data
Denniston, K. J. (Katherine J.)
General, organic, and biochemistry / Katherine J. Denniston, Joseph J. Topping,
Robert L. Caret. 3rd ed.
p. ; cm.
Rev. ed. of : Principles & applications of organic & biological chemistry / Robert L.
Caret, Katherine J. Denniston, Joseph J. Topping. 2nd ed. 1997.
Includes index.
ISBN 0072317841
1. Chemistry, Organic. 2. Biochemistry. I. Topping, Joseph J. II. Caret, Robert L.,
1947 . III. Caret, Robert L., 1947 Principles & applications of organic & biological
chemistry. IV. Title.
[DNLM: 1. Chemistry. 2. Biochemistry. 3. Chemistry, Organic. QD 33 D411g 2001]
QD253 . C27 2001
547dc21
99088202
CIP
INTERNATIONAL EDITION ISBN 0071180737
Copyright 2001. Exclusive rights by The McGraw-Hill Companies, Inc., for manufacture
and export. This book cannot be re-exported from the country to which it is sold by McGraw-Hill.
The International Edition is not available in North America.
www.mhhe.com
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Brief Contents
Preface
xx
General Chemistry
1
2
Chemistry Methods and Measurement
The Composition and Structure

of the Atom 33
Elements, Atoms, Ions, and the Periodic

Table 57
Structure and Properties of Ionic and

Covalent Compounds 81
5
6
Calculations and the Chemical Equation 117
7
8
Reactions and Solutions
9
10
States of Matter: Gases, Liquids, and

Solids 149
175
Chemical and Physical Change: Energy, Rate,

and Equilibrium 205
Charge-Transfer Reactions: Acids and Bases
and Oxidation-Reduction 237
The Nucleus, Radioactivity, and Nuclear
Medicine 269
Organic Chemistry
11
An Introduction to Organic Chemistry: The

Saturated Hydrocarbons 295
12
The Unsaturated Hydrocarbons: Alkenes,

Alkynes, and Aromatics 323
13
14
15
Alcohols, Phenols, Thiols, and Ethers
16
Amines and Amides
Aldehydes and Ketones
355
383
Carboxylic Acids and Carboxylic Acid

Derivatives 407
439
Biochemistry
17
18
Carbohydrates
19
20
21
22
Protein Structure and Function
23
24
Fatty Acid Metabolism 665
467
Lipids and Their Functions in Biochemical

Systems 495
Enzymes
533
565
Carbohydrate Metabolism 599

Aerobic Respiration and Energy
Production 635
Introduction to Molecular Genetics
691
Appendixes 729
Glossary 769
Answers to Selected Problems 785
Credits 821
Index 823
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Contents
Preface
xx
Temperature 22
Energy 23
Concentration 24
Density and Specific Gravity 24
General Chemistry
1 Chemistry:
A HUMAN PERSPECTIVE:
Methods and
Measurement 1
Food Calories 25
A CLINICAL PERSPECTIVE:
CHEMISTRY CONNECTION:
Diagnosis Based on Waste 28
Chance Favors the Prepared

Mind 2
1.1
Summary 28
Key Terms 29
Questions and Problems 30
Critical Thinking Problems 31
The Discovery Process 3

Chemistry 3
Major Areas of
Chemistry 3
The Scientific Method 3
2 The Composition
and Structure of
the Atom 33
The Scientific Method 4
1.4
1.5
1.6
1.2
1.3
Models in Chemistry 5
Science and Technology 6
Data, Results, and Units 6
Measurement in Chemistry 7
English and Metric Units 7
Unit Conversion: English and Metric Systems
Conversion of Units within the Same System
Conversion of Units from One System to
Another 11
Error, Accuracy, Precision, and Uncertainty
Significant Figures and Scientific Notation
Significant Figures 14
Recognition of Significant Figures 15
Scientific Notation 16
Significant Figures in Calculation of Results
Rounding Off Numbers 19
Experimental Quantities 20
Mass 20
Length 21
Volume 21
Time 22
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Curiosity, Science,
and Medicine 34
2.1
9
9
13
14
2.2
2.3
17
2.4
Matter and Properties 34

Matter and Physical Properties 34
Matter and Chemical Properties 35
Intensive and Extensive Properties 36
Classification of Matter 37
Matter and Structure 39
Atomic Structure 39
Isotopes 41
Ions 44
Development of the Atomic Theory 44
Daltons Theory 44
Subatomic Particles: Electrons, Protons, and
Neutrons 45
The Nucleus 46
Light and Atomic Structure 47
The Bohr Atom 49
Modern Atomic Theory 50
viii
Contents
4 Structure and
Atomic Spectra and the Fourth of July 51
Properties of Ionic and

Covalent
Compounds 81
AN ENVIRONMENTAL PERSPECTIVE:
Electromagnetic Radiation and Its Effects on Our
Everyday Lives 52
Summary 54
Key Terms 54
Magnets and Migration 82

4.1
3 Elements,
Atoms, Ions,
and the Periodic
Table 57
4.2
4.3
Managing Mountains
of Information 58
3.1
The Periodic Law and the Periodic Table 58

Numbering Groups in the Periodic Table 60
Periods and Groups 61
Metals and Nonmetals 61
Atomic Number and Atomic Mass 61
Copper Deficiency and Wilsons Disease 62
3.2
3.3
Electron Arrangement and the Periodic Table 63

Valence Electrons 63
The Quantum Mechanical Atom 66
Energy Levels and Sublevels 66
Electron Configuration and the Aufbau
Principle 68
Abbreviated Electron Configurations 70
The Octet Rule 71
Ion Formation and the Octet Rule 71
Dietary Calcium 73
Trends in the Periodic Table
Atomic Size 74
Ion Size 74
Ionization Energy 74
Electron Affinity 76
Summary 77
Key Terms 77
3.4
How the Elements Came into Being 95
4.4
A MEDICAL PERSPECTIVE:
73
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Chemical Bonding 82
Lewis Symbols 83
Principal Types of Chemical
Bonds: Ionic and Covalent 83
Polar Covalent Bonding and Electronegativity 85
Naming Compounds and Writing Formulas of
Compounds 86
Ionic Compounds 87
Covalent Compounds 92
Properties of Ionic and Covalent
Compounds 94
Physical State 94
Melting and Boiling Points 94
Structure of Compounds in the Solid State 94
Solutions of Ionic and Covalent Compounds 95

Drawing Lewis Structures of Molecules and
Polyatomic Ions 95
Lewis Structures of Molecules 95
Blood Pressure and the Sodium Ion/Potassium Ion
Ratio 96
Lewis Structures of Polyatomic Ions 99
Lewis Structure, Stability, Multiple Bonds, and
Bond Energies 102
Lewis Structures and Resonance 103
Lewis Structures and Exceptions to the Octet
Rule 104
Lewis Structures and Molecular Geometry; VSEPR
Theory 106
Lewis Structures and Polarity 110
4.5 Properties Based on Molecular Geometry 112
Solubility 112
Boiling Points of Liquids and Melting Points of
Solids 113
Summary 114
Key Terms 115
ix
Contents
5 Calculations
6.1
and the
Chemical
Equation 117
Autoclaves and the Gas Laws 156
The Chemistry of
Automobile Air Bags 118
5.1
5.2
5.3
5.4
5.5
5.6
The Mole Concept and Atoms 119

The Mole and Avogadros Number 119
Calculating Atoms, Moles, and Mass 120
Compounds 123
The Chemical Formula 123
The Mole Concept Applied to Compounds 124
The Chemical Equation and the Information It
Conveys 126
A Recipe for Chemical Change 126
Features of a Chemical Equation 127
The Experimental Basis of a Chemical
Equation 127
Balancing Chemical Equations 128
The Extent of Chemical Reactions 132
Carbon Monoxide Poisoning: A Case of Combining
Ratios 133
5.7
The Gaseous State 151

Ideal Gas Concept 151
Measurement of Gases 151
Boyles Law 152
Charless Law 154
Calculations Using the Chemical Equation 133

General Principles 133
Use of Conversion Factors 134
The Limiting Reactant Problem 140
Theoretical and Percent Yield 141
Pharmaceutical Chemistry: The Practical
Significance of Percent Yield 144
Combined Gas Law 156

Avogadros Law 158
Molar Volume of a Gas 159
Gas Densities 159
The Ideal Gas Law 160
Daltons Law of Partial Pressures 162
Kinetic Molecular Theory of Gases 162
The Greenhouse Effect and Global Warming 163
6.2
Ideal Gases Versus Real Gases

The Liquid State 164
Compressibility 165
Viscosity 165
Surface Tension 165
164
Blood Gases and Respiration 166
Vapor Pressure of a Liquid 166
Van der Waals Forces 167
Hydrogen Bonding 167
6.3 The Solid State 169
Properties of Solids 169
Types of Crystalline Solids 169
Summary 170
Key Terms 171
Summary 144
Key Terms 145
7 Reactions and
Solutions 175
6 States of
Seeing a Thought 176
Matter: Gases,
Liquids, and
Solids 149
7.1
The Demise of the

Hindenburg 150
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Writing Chemical
Reactions 177
Combination Reactions 177
Decomposition
Reactions 177
Replacement Reactions 177
x
7.2
7.3
7.4
Contents
Types of Chemical Reactions 178

Precipitation Reactions 178
Reactions with Oxygen 180
AcidBase Reactions 180
Oxidation-Reduction Reactions 180
Properties of Solutions 181
General Properties of Liquid Solutions 181
Solutions and Colloids 182
Degree of Solubility 183
Solubility and Equilibrium 183
Solubility of Gases: Henrys Law 183
Concentration of Solutions: Percentage 184
Weight/Volume Percent 184
Enthalpy 208
Spontaneous and Nonspontaneous Reactions
Entropy 209
Free Energy 210
Triboluminescence: Sparks in the Dark
with Candy 211
8.2
8.3
Scuba Diving: Nitrogen and the Bends 185
7.5
7.6
7.7
7.8
Weight/Weight Percent 186

Concentration of Solutions: Moles and
Equivalents 187
Molarity 187
Dilution 188
Representation of Concentration of Ions in
Solution 190
Concentration-Dependent Solution
Properties 191
Vapor Pressure Lowering 191
Freezing Point Depression and Boiling Point
Elevation 192
Osmotic Pressure 193
Water as a Solvent 196
Electrolytes in Body Fluids 197
Hot and Cold Packs 218

Mathematical Representation of Reaction
Rate 221
8.4 Equilibrium 223
Rate and Reversibility of Reactions 223
Physical Equilibrium 223
Chemical Equilibrium 225
The Generalized Equilibrium-Constant Expression
for a Chemical Reaction 226
LeChateliers Principle 230
Summary 233
Key Terms 234
9 Charge-Transfer
An Extraordinary Molecule 198
Reactions: Acids
and Bases and
Oxidation
Reduction 237
Hemodialysis 200
Summary 200
Key Terms 202
Drug Delivery 238
9.1
8 Chemical and Physical

Change: Energy, Rate,
and Equilibrium 205
9.2
The Cost of Energy? More Than
You Imagine 206
Thermodynamics 206
The Chemical Reaction and
Energy 207
Exothermic and Endothermic Reactions 207
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Experimental Determination of Energy Change

in Reactions 212
Kinetics 215
The Chemical Reaction 216
Activation Energy and the Activated
Complex 216
Factors That Affect Reaction Rate 217
8.1
209
9.3
Acids and Bases 239

Arrhenius Theory of Acids and Bases 239
BrnstedLowry Theory of Acids and Bases 239
Conjugate Acids and Bases 240
Solutions of Acids and Bases 244
Strengths of Acids and Bases 244
The Dissociation of Water 243
The pH Scale 244
The Importance of pH and pH Control 249
Reactions between Acids and Bases 249
Neutralization 249
Acid Rain 252
xi
Contents
9.4
Polyprotic Substances 252

AcidBase Buffers 254
The Buffer Process 254
Addition of Base (OH) to a Buffer Solution 254
Addition of Acid (H3O) to a Buffer Solution 255
Preparation of a Buffer Solution 255
10.5
Nuclear Waste Disposal 281
10.6
Control of Blood pH 258

9.5
OxidationReduction Processes
Oxidation and Reduction 258
258
10.7
Magnetic Resonance Imaging 286

260
10.8
Electrochemical Reactions in the Statue of Liberty

and in Dental Fillings 261
Biological Processes
Voltaic Cells 262
262
10.9
Turning the Human Body into a Battery 264
Electrolysis 265
Summary 266
Key Terms 266
Radon and Indoor Air Pollution 291

Summary 291
Key Terms 291
Radioactivity, and
Nuclear Medicine 269
Organic Chemistry
An Extraordinary Woman in
Science 270
10.3
10.4
Natural Radioactivity 271

Alpha Particles 271
Beta Particles 272
Gamma Rays 272
Properties of Alpha, Beta, and Gamma
Radiation 272
Writing a Balanced Nuclear Equation 273
Alpha Decay 273
Beta Decay 274
Gamma Production 274
Predicting Products of Nuclear Decay 274
Properties of Radioisotopes 275
Nuclear Structure and Stability 275
Half-Life 276
Nuclear Power 277
Energy Production 277
Nuclear Fission 278
10.2
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Radiation Exposure and Safety 286

Detection and Measurement of Radiation
Nuclear Imaging 288
Computer Imaging 288
The Geiger Counter 289
Film Badges 289
Units of Radiation Measurement 289
The Curie 290
The Roentgen 290
The Rad 290
The Rem 290
10 The Nucleus,
10.1
Medical Applications of Radioactivity 282

Cancer Therapy Using Radiation 282
Nuclear Medicine 282
Making Isotopes for Medical Applications 284
Biological Effects of Radiation 285
Oxidizing Agents for Chemical Control of

Microbes 259
Applications of Oxidation and Reduction
Nuclear Fusion 278

Breeder Reactors 280
Radiocarbon Dating 280
11 An Introduction to
Organic Chemistry:
The Saturated
Hydrocarbons 295
The Origin of Organic
Compounds 296
11.1
11.2
The Chemistry of
Carbon 297
Important Differences between Organic and
Inorganic Compounds 298
Families of Organic Compounds 299
Alkanes 300
Structure and Physical Properties 300
Alkyl Groups 302
Nomenclature 304
288
xii
Contents
Constitutional Isomers
307
Oil-Eating Bacteria 309
11.3
11.4
11.5
Cycloalkanes 309
cis-trans Isomerism in Cycloalkanes 311
Conformations of Alkanes and
Cycloalkanes 313
Reactions of Alkanes and Cycloalkanes 314
Combustion 314
12.6 Heterocyclic Aromatic Compounds 347

Summary of Reactions 348
Summary 349
Key Terms 350
13 Alcohols,
Phenols, Thiols,
and Ethers 355
Polyhalogenated Hydrocarbons Used as
Anesthetics 315
Fetal Alcohol
Syndrome 356
Halogenation 315
Summary 317
Key Terms 317
13.1
13.2
13.3
13.4
13.5
12 The Unsaturated
Hydrocarbons:
Alkenes,
Alkynes, and
Aromatics 323
13.6
A Cautionary Tale: DDT and Biological
Magnification 324
12.1
12.2
12.3
12.4
Alkenes and Alkynes: Structure and Physical

Properties 325
Alkenes and Alkynes: Nomenclature 326
Geometric Isomers: A Consequence of
Unsaturation 329
Reactions Involving Alkenes 332
Hydrogenation: Addition of H2 to an Alkene 332
Halogenation: Addition of X2 to an Alkene 334
Hydration: Addition of H2O to an Alkene 336
Hydrohalogenation: Addition of HX to an
Alkene 337
Oxidation Reactions 339
Addition Polymers of Alkenes 339
Alcohol Consumption and the Breathalyzer

Test 371
Multistep Organic Synthesis 372
13.7 Phenols 373
13.8 Ethers 374
13.9 Thiols 376
Summary 379
Key Terms 379
14 Aldehydes and
Life without Polymers? 340

12.5
Ketones 383
Aromatic Hydrocarbons 342

Structure and Properties 342
Nomenclature 343
Genetic Complexity from
Simple Molecules 384
Aromatic Compounds and Carcinogenesis 346
Reactions Involving Benzene
Alcohols: Structure and Physical

Properties 357
Alcohols: Nomenclature 358
I.U.P.A.C. Names 358
Common Names 359
Medically Important Alcohols 360
Classification of Alcohols 361
Reactions Involving Alcohols 363
Preparation of Alcohols 363
Dehydration of Alcohols 366
Oxidation and Reduction in Living
Systems 370
346
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14.1
Structure and Physical

Properties 385
xiii
Contents
14.2
14.3
14.4
I.U.P.A.C. Nomenclature and Common

Names 386
Naming Aldehydes 386
Naming Ketones 389
Important Aldehydes and Ketones 390
Reactions Involving Aldehydes and
Ketones 391
Preparation of Aldehydes and Ketones 391
Summary 434
Key Terms 434
16 Amines and
Amides 439
The Nicotine Patch 440
Aldehydes in Medicine 392

16.1

Reduction Reactions 395
Addition Reactions 396
KetoEnol Tautomers 398
Aldol Condensation 399
Amines 441
Properties 441
Nomenclature 445
Medically Important Amines 447
The Chemistry of Vision 401
Reactions Involving Amines
448

Summary 403
Key Terms 404
Secondary Amines and Cancer 451

16.2
16.3
Quaternary Ammonium Salts 452

Heterocyclic Amines 452
Amides 454
15 Carboxylic Acids and
Amines and the Central Nervous System 455
Carboxylic Acid
Derivatives 407

Nomenclature 456
Reactions Involving Amides 456
Wake Up, Sleeping Gene 408

15.1
Medically Important Amides 457
Carboxylic Acids 409

Properties 409
Nomenclature 410
Some Important Carboxylic Acids 414
Reactions Involving Carboxylic Acids 415
A Preview of Amino Acids, Proteins, and Protein

Synthesis 460
Summary 462
Key Terms 462
16.4
Garbage Bags from Potato Peels 416

15.2
15.3
15.4
Esters 418
Nomenclature 419
Reactions Involving Esters 419
Acid Chlorides and Acid Anhydrides 424
Acid Chlorides 424
Acid Anhydrides 426
Natures High-Energy Compounds:
Phosphoesters and Thioesters 429
Carboxylic Acid Derivatives of Special Interest 430
Summary of Reactions
433
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Biochemistry
17 Carbohydrates
467
Chemistry Through
the Looking
Glass 468
Tooth Decay and Simple Sugars 470
xiv
17.1
17.2
17.3
Contents
Types of Carbohydrates 471

Monosaccharides 471
Nomenclature 471
Stereoisomers 472
Some Important Monosaccharides
Reducing Sugars 480
Disaccharides 481
Maltose 482
Lactose 482
Sucrose 483
Anabolic Steroids and Athletics 513
Steroids and the Treatment of Heart Disease 515
473
18.5
18.6
17.4
Waxes 516
Complex Lipids 516
The Structure of Biological Membranes 519
Fluid Mosaic Structure of Biological
Membranes 519
Membrane Transport 522
Blood Transfusions and the Blood Group Antigens

484
Polysaccharides
Starch 485
Glycogen 487
Cellulose 487
Energy Requirements for Transport

Summary 529
Key Terms 529
485
Antibiotics That Destroy Membrane Integrity 524

528
The Bacterial Cell Wall 488
Monosaccharide Derivatives and
Heteropolysaccharides of Medical Interest 490
Summary 492
Key Terms 492
19 Protein
Structure and
Function 533
Angiogenesis
Inhibitors: Proteins
that Inhibit Tumor
Growth 534
18 Lipids and Their

Functions in
Biochemical
Systems 495
19.1
19.2
19.3
18.2
18.3
18.4
Biological Functions of
Lipids 496
Fatty Acids 498
Structure and Properties 498
Chemical Reactions of Fatty Acids 501
Eicosanoids: Prostaglandins, Leukotrienes, and
Thromboxanes 503
Glycerides 505
Neutral Glycerides 505
Phosphoglycerides 507
Nonglyceride Lipids 509
Sphingolipids 509
Disorders of Sphingolipid Metabolism 510
512
Steroids
e-Text Main Menu
535
Life-Saving Lipids 496

18.1
Cellular Functions of Proteins

The -Amino Acids 535
The Peptide Bond 539
The Opium Poppy and Peptide Synthesis in the

Brain 542
19.4
19.5
19.6
The Primary Structure of Proteins 543

The Secondary Structure of Proteins 544
-Helix 544
-Pleated Sheet 546
The Tertiary Structure of Proteins 546
Collagen: A ProteinThat Makes Us Strong 548
19.7
19.8
19.9
The Quaternary Structure of Proteins 549

An Overview of Protein Structure and
Function 551
Myoglobin and Hemoglobin 552
Myoglobin and Oxygen Storage 552
Hemoglobin and Oxygen Transport 552
xv
Contents
20.11 Proteolytic Enzymes
Immunoglobulins: Proteins That Defend the
Body 554
Oxygen Transport from Mother to Fetus 556
Sickle Cell Anemia 557
19.10 Denaturation of Proteins 557
19.11 Dietary Protein and Protein Digestion 560
Summary 562
Key Terms 563
590
Enzymes, Isoenzymes, and Myocardial
Infarction 592
20.12 Uses of Enzymes in Medicine
Summary 595
Key Terms 596
594
21 Carbohydrate
Metabolism 599
20 Enzymes 565
The Man Who Got Tipsy from

Eating Pasta 600
Super Hot Enzymes

and the Origin of
Life 566
20.1
20.2
20.3
20.4
20.5
20.6
21.1
Nomenclature and
Classification 567
Nomenclature of Enzymes 567
Classification of Enzymes 568
The Effect of Enzymes on the Activation Energy
of a Reaction 571
The Effect of Substrate Concentration on
Enzyme-Catalyzed Reactions 572
The EnzymeSubstrate Complex 573
Specificity of the EnzymeSubstrate
Complex 574
The Transition State and Product
Formation 575
21.2
21.3
21.4
The AIDS Test 576
21.5
Cofactors and Coenzymes 579

Environmental Effects 581
Effect of pH 581
Effect of Temperature 583
20.9 Regulation of Enzyme Activity 584
Allosteric Enzymes 584
Feedback Inhibition 586
Zymogens 586
20.10 Inhibition of Enzyme Activity 587
Irreversible Inhibitors 587
Reversible, Competitive Inhibitors 587
20.7
20.8
Enzymes, Nerve Transmission, and Nerve
Agents 588
Reversible, Noncompetitive Inhibitors 590
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21.6
21.7
ATP: The Cellular Energy

Currency 601
Overview of Catabolic
Processes 604
Stage I: Hydrolysis of Dietary Macromolecules
into Small Subunits 604
Stage II: Conversion of Monomers into a Form
That Can Be Completely Oxidized 606
Stage III: The Complete Oxidation of Nutrients
and the Production of ATP 607
Glycolysis 608
An Overview 608
Reactions of Glycolysis 609
Regulation of Glycolysis 615
Fermentations 616
Lactate Fermentation 616
Alcohol Fermentation 617
The Pentose Phosphate Pathway 618
Gluconeogenesis: The Synthesis of Glucose
Glycogen Synthesis and Degradation 621
The Structure of Glycogen 621
Glycogenolysis: Glycogen Degradation 621
Glycogenesis: Glycogen Synthesis 624
Fermentations: The Good, the Bad, and the
Ugly 626
Compatibility of Glycogenesis and
Glycogenolysis 628
Glycogen Storage Diseases 630
Summary 631
Key Terms 631
619
xvi
Contents

23.1
22 Aerobic
23.2
Respiration
and Energy
Production 635
Losing Those Unwanted Pounds of Adipose
Tissue 672
22.1
23.3
The Mitochondria 637

Structure and Function 637
Origin of the Mitochondria 637
674
Diabetes Mellitus and Ketone Bodies 680

Fatty Acid Synthesis 682
A Comparison of Fatty Acid Synthesis and
Degradation 682
23.5 The Regulation of Lipid and Carbohydrate
Metabolism 684
The Liver 684
Adipose Tissue 685
Muscle Tissue 685
The Brain 686
23.6 The Effects of Insulin and Glucagon on Cellular
Metabolism 686
Summary 688
Key Terms 688
23.4
Exercise and Energy Metabolism 638
22.5
22.6
The Reactions of -Oxidation

Ketone Bodies 677
Ketosis 677
Ketogenesis 678
Mitochondria from
Mom 636
22.2
22.3
22.4
Lipid Metabolism in Animals 667

Digestion and Absorption of Dietary
Triglycerides 667
Lipid Storage 668
Fatty Acid Degradation 670
An Overview of Fatty Acid Degradation 670
Conversion of Pyruvate to Acetyl CoA 638

An Overview of Aerobic Respiration 641
The Citric Acid Cycle (The Krebs Cycle) 642
Reactions of the Citric Acid Cycle 642
Control of the Citric Acid Cycle 645
Oxidative Phosphorylation 646
Electron Transport Systems and the Hydrogen Ion
Gradient 646
ATP Synthase and the Production of ATP 647
Summary of the Energy Yield 648
Brown Fat: The Fat That Makes You Thin? 650
The Degradation of Amino Acids 652
Removal of -Amino Groups:
Transamination 652
Removal of -Amino Groups: Oxidative
Deamination 654
The Fate of Amino Acid Carbon Skeletons 654
22.8 The Urea Cycle 656
Reactions of the Urea Cycle 656
22.9 Overview of Anabolism: The Citric Acid Cycle as
a Source of Biosynthetic Intermediates 659
Summary 661
Key Terms 662
22.7
24 Introduction
to Molecular
Genetics 691
Molecular Genetics and
Detection of Human Genetic
Disease 692
24.1
24.2
23 Fatty Acid
Metabolism 665
Fooling the AIDS Virus with Look-Alike

Nucleotides 698
Obesity: A Genetic
Disorder? 666
24.3
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The Structure of the

Nucleotide 693
Chemical Composition of DNA and RNA
Nucleotide Structure 693
The Structure of DNA and RNA 696
DNA Structure: The Double Helix 696
RNA Structure 699

DNA Replication 700
693
xvii
Contents
24.4
24.5
24.6
24.7
Information Flow in Biological Systems 701

Classes of RNA Molecules 702
Transcription 703
Post-transcriptional Processing of RNA 705
The Genetic Code 707
Protein Synthesis 708
The Role of Transfer RNA 709
The Process of Translation 711
Mutation, Ultraviolet Light, and DNA
Repair 713
The Nature of Mutations 713
The Results of Mutations 713
Mutagens and Carcinogens 714
Ultraviolet Light Damage and DNA Repair 714
The Ames Test for Carcinogens 715
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Genetic Engineering 721

Polymerase Chain Reaction
24.9
716
723
1-Antitrypsin and Familial Emphysema 724
Summary 725
Key Terms 726
Appendixes
Glossary
Credits
Consequences of Defects in DNA Repair

Recombinant DNA 716
Tools Used in the Study of DNA 716
DNA Fingerprinting 720
729
769
Answers to Selected Problems
24.8
Index
785
821
823
Chemistry Connections and Perspectives
Chemistry Connection
A Human Perspective
Chance Favors the Prepared Mind
The Scientific Method
Curiosity, Science, and Medicine
34
Food Calories
25
Managing Mountains of Information
58
Atomic Spectra and the Fourth of July
51
Magnets and Migration
82
How the Elements Came into Being
95
The Chemistry of Automobile Air Bags
118
Scuba Diving: Nitrogen and the Bends
185
The Demise of the Hindenburg
150
An Extraordinary Molecule
198
Seeing a Thought
176
The Cost of Energy? More Than You Imagine
206

with Candy
211
Drug Delivery
238
Life without Polymers?
340
An Extraordinary Woman in Science
270
Aromatic Compounds and Carcinogenesis
346
The Origin of Organic Compounds
296
A Cautionary Tale: DDT and Biological

Magnification
Alcohol Consumption and the

Breathalyzer Test
371
324
The Chemistry of Vision
401
Fetal Alcohol Syndrome
356
Carboxylic Acid Derivatives of Special Interest
430
Genetic Complexity from Simple Molecules
384
Amines and the Central Nervous System
455
Wake Up, Sleeping Gene
408
Tooth Decay and Simple Sugars
470
The Nicotine Patch
440
Chemistry Through the Looking Glass
468
Blood Transfusions and the Blood Group

Antigens
484
Life-Saving Lipids
496
Anabolic Steroids and Athletics
513
Angiogenesis Inhibitors: Proteins that

Inhibit Tumor Growth
534
The Opium Poppy and Peptide Synthesis

in the Brain
542
Collagen: A Protein That Makes Us Strong
548
Super Hot Enzymes and the Origin of Life
566
The Man Who Got Tipsy from Eating Pasta
600
Fermentations: The Good, the Bad,

and the Ugly
626
Mitochondria from Mom
636
Glycogen Storage Diseases
630
Obesity: A Genetic Disorder?
666
Exercise and Energy Metabolism
638
Molecular Genetics and Detection

of Human Genetic Disease
Brown Fat: The Fat That Makes You Thin?
650
692
xviii
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Chemistry Connections and Perspectives
Losing Those Unwanted Pounds of

Adipose Tissue
672
DNA Fingerprinting
720
xix
Diabetes Mellitus and Ketone Bodies
680
Fooling the AIDS Virus with Look-Alike

Nucleotides
698
The Ames Test for Carcinogens
715
A Clinical Perspective
A Medical Perspective
28
Dietary Calcium
73
Copper Deficiency and Wilsons Disease
Blood Pressure and the Sodium Ion/

Potassium Ion Ratio
96
Pharmaceutical Chemistry:
The Practical Significance of Percent Yield
144
Carbon Monoxide Poisoning: A Case

of Combining Ratios
Turning the Human Body into a Battery
264
133
Autoclaves and the Gas Laws
156
Polyhalogenated Hydrocarbons
Used as Anesthetics
315
Blood Gases and Respiration
166
Secondary Amines and Cancer
451
Hemodialysis
200
Hot and Cold Packs
218
Monosaccharide Derivatives and

Heteropolysaccharides of Medical Interest
490
Control of Blood pH
258
Oxidizing Agents for Chemical Control

of Microbes
Immunoglobulins: Proteins That

Defend the Body
554
259
1-Antitrypsin and Familial Emphysema
724
Electrochemical Reactions on the

Statue of Liberty and in Dental Fillings
261
Magnetic Resonance Imaging
286
Multistep Organic Synthesis
372
Aldehydes in Medicine
392
Medically Important Amines
447
Electromagnetic Radiation and Its Effects

on Our Everyday Life
Medically Important Amides
457
The Greenhouse Effect and Global Warming
163
The Bacterial Cell Wall
488
Acid Rain
252
Disorders of Sphingolipid Metabolism
510
Nuclear Waste Disposal
281
Steroids and the Treatment of Heart Disease
515
Radon and Indoor Air Pollution
291
Antibiotics That Destroy Membrane Integrity
524
Oil-Eating Bacteria
309
The AIDS Test
576
Garbage Bags from Potato Peels
416
Enzymes, Nerve Transmission, and

Nerve Agents
588
Enzymes, Isoenzymes, and Myocardial

Infarction
592
Diagnosis Based on Waste
e-Text Main Menu
62
An Environmental Perspective
52
Preface
Ours is an age when an understanding of chemistry has become an increasingly important aspect of medicine. The
third edition of General, Organic, and Biochemistry has been
designed to help undergraduate health-related majors and
students of all majors understand key concepts and appreciate the significant connections between chemistry, health,
disease, and the treatment of disease. This text strikes a
balance between theoretical and practical chemistry, while
emphasizing material that is unique to health-related studies. It is written at a level intended for students whose professional goals do not include a mastery of chemistry, but
for whom an understanding of the principles of chemistry
and their practical ramifications is a necessity.
Key Changes to the Third Edition

In the preparation of the third edition, we have been
guided by the collective wisdom of reviewers who represent the diversity of higher education experiences, including two-year and four-year colleges and universities. Over
fifty different reviewers participated in the review process.
We also received very valuable comments from a focus
group of faculty who regularly teach this material.
New Organization
Recognizing that courses based on this textbook are organized in a variety of formats within both quarter and semester systems, we have reorganized the chapter sequence
into three sections: inorganic chemistry (Chapters 110),
organic chemistry (Chapters 1116), and biochemistry
(Chapters 1724). The new organization will allow tremendous latitude in usage. The course may be taught in a traditional sense, following the new chapter order, within
either the semester or quarter system. If you prefer the organization in the second edition, you may continue to
teach using the different teaching order without affecting
your students understanding of the material. Many users
of the second edition choose to integrate traditional organic
and biochemistry and we have constructed the chapters to
allow for alternate order of coverage. Frequent use of crossreferencing and reviewing of material discussed earlier in
the book support this needed flexibility.
Clear Presentation
Todays students have numerous demands on their time.
Many students are nontraditional students, working full
time, who have families. Students need to be able to identify important concepts quickly and easily. Each section of
the book was reviewed with the goal of becoming more
concise while retaining the intellectual rigor of a college
textbook. Some of the ways we have accomplished this
goal include:
New design facilitates access to information and
engages student interest.
Key terms are bolded and are immediately defined.
In-chapter examples provide stepwise guidance to
problem-solving strategies.
New tables were created allowing easier access to
information.
More headings allow students to find important
material faster.
Key Features of the Third Edition

Engaging Applications
We believe that there are a variety of factors in a text that
can promote student learning and facilitate teaching. It is
important to engage the interest of the student, especially
when the subject may appear difficult and does not seem
directly related to the students career goals. We have included a diverse array of applications to accomplish our
goals.
Perspectives: We have added eleven new Clinical,
Medical, and Human Perspectives throughout the
book. A list of Chemistry Connections and
Perspectives is provided on page xviii. These provide
new and updated applications of chemistry to engage
the students interest and help them understand
chemistry in the context of their daily lives.
Learning goal icons 1 : These icons help to alert
the student to the important concepts covered in the
text. An icon is placed next to the textual material that
supports the learning goal.
xx
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Supplementary
Materials
Supplements
This text has a complete support package for instructors

and students. Several print and media supplements have
been prepared to accompany the text and make learning as
meaningful and up-to-date as possible.
2.
For the Instructor:

1. Instructors Manual: The Instructors Manual
contains the printed test item file and solutions to the
even-numbered problems. Written by the authors, this
ancillary also contains suggestions for organizing
lectures, additional Perspectives, and a list of each
chapters key problems and concepts.
2. Transparencies: A set of 100 transparencies is
available to help the instructor coordinate the lecture
with key illustrations from the text.
3. Computerized Test Bank: This computerized
classroom management system/service includes a
database of test questions, reproducible student selfquizzes, and a grade-recording program. Disks are
available for IBM and Macintosh computers, and
require no programming experience.
4. Laboratory Resource Guide: This helpful prep guide
contains the hints that the authors have learned over
the years to ensure students success.
5. Book-Specific Website: A book-specific website is
available to students and instructors using this text.
The website will offer quizzes, key definitions, and
interesting links for the students. The instructor will
find a downloadable version of the Test Bank, the
transparencies in a PowerPoint Presentation, the
Instructors Manual, and Solutions Manual. Also
available for the instructor is PageOut, which allows
the instructor to create his or her own personal course
website. The address for the book-specific website is
http://www.mhhe.com/physsci/chemistry/
denniston.
3.
4.
5.
6.
7.
For the Students:

1. Student Study Guide/Solutions Manual: A separate
Student Study Guide/Solutions Manual is available.
It contains the answers and complete solutions for the
odd-numbered problems. It also offers students a
variety of exercises and keys for testing their

comprehension of basic, as well as difficult, concepts.
Laboratory Manual: Written by Charles H.
Henrickson, Larry C. Byrd, and Norman W. Hunter,
all of Western Kentucky University, Experiments in
General, Organic, and Biochemistry, carefully and safely
guides students through the process of scientific
inquiry. The manual features self-contained
experiments that can easily be reorganized to suit
individual course needs.
Is Your Math Ready for Chemistry? Developed by
Walter Gleason of Bridgewater State College, this
unique booklet provides a diagnostic test that
measures the students math ability. Part II of the
booklet provides helpful hints in the math skills
needed to successfully complete a chemistry course.
Problem Solving Guide to General Chemistry:
Written by Ronald DeLorenzo of Middle Georgia
College, this exceptional supplement provides the
student with over 2500 problems and questions. The
guide holds the students interest by integrating the
solution of chemistry problems with real-life
applications, analogies, and anecdotes.
Schaums Outline of General, Organic, and
Biological Chemistry: Written by George Odian and
Ira Blei, this supplement provides students with over
1400 solved problems with complete solutions. It also
teaches effective problem-solving techniques.
How to Study Science: Written by Fred Drewes of
Suffolk County Community College, this excellent
workbook offers students helpful suggestions for
meeting the considerable challenges of a science
course. It offers tips on how to take notes and how to
overcome science anxiety. The books unique design
helps to stir critical thinking skills, while facilitating
careful note taking on the part of the student.
Book-Specific Website: A book-specific website is
available to students and instructors using this text.
The website will offer quizzes, key definitions, and
interesting links for the students. The address for the
book-specific website is http://www.mhhe.com/
physsci/chemistry/denniston.
xxiii
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Acknowledgements
We are grateful to our families, whose patience and support made it possible for us to undertake this project. We
are grateful to our colleagues at McGraw-Hill, especially
Jim Smith, publisher, and Kent Peterson, sponsoring editor,
for their support of our book. We would like to thank
Shirley Oberbroeckling, developmental editor, for her
guidance during the reviewing and writing process. We
also would like to express our appreciation to Marilyn
Sulzer, project manager, for her skilled assistance throughout production.
A revision cannot move forward without the feedback
of professors teaching the course. The reviewers have our
gratitude and assurance that their comments received serious consideration.
The following professors provided reviews, participated in a focus group, or gave valuable advice for the
preparation of the third edition:
Hugh Akers, Lamar University
Catherine A. Anderson, San Antonio College
A. G. Andrewes, Saginaw Valley State University
Mark A. Benvenuto, University of Detroit-Mercy
Warren L. Bosch, Elgin Community College
James R. Braun, Clayton College and State University
Philip A. Brown, Barton College
Teresa L. Brown, Rochester Community College
Scott Carr, Trinity Christian College
Bernadette Corbett, Metropolitan Community College
Wayne B. Counts, Georgia Southwestern State University
Robert P. Dixon, Southern Illinois University
Wes Fritz, College of DuPage
Edwin J. Geels, Dordt College
Deepa Godambe, William Rainey Harper College
Judith M. Iriarte-Gross, Middle Tennessee State University
T. G. Jackson, University of South Alabama
Paul G. Johnson, Duquesne University
Warren Johnson, University of Wisconsin-Green Bay
James F. Kirby, Quinnipiac College
Roscoe E. Lancaster, Golden West College
Richard H. Langley, Stephen F. Austin State University
Julie E. Larson, Bemidji State University
K. W. Loach, Plattsburgh State University
Ralph Martinez, Humboldt State University
John Mazzella, William Paterson University
Lawrence McGahey, College of St. Scholastica

Cleon McKnight, Hinds Community College
Melvin Merken, Worcester State College
Robert Midden, Bowling Green State University
David Millsap, South Plains College
Ellen M. Mitchell, Bridgewater College
Jay Mueller, Green River Community College
Lynda P. Nelson, Westark College
Richard E. Parent, Housatonic Community Technical College
Chetna Patel, Aurora University
Jeffrey A. Rahn, Eastern Washington University
B. R. Ramachandran, Indiana State University
John W. Reasoner, Western Kentucky University
Rill Ann Reuter, Winona State University
Terry Salerno, Minnesota State University-Mankato
Karen Sanchez, Florida Community College at Jacksonville
Sarah Selfe, University of Washington
Kevin R. Siebenlist, Marquette University
Steven M. Socal, Southern Utah University
Gordon Sproul, University of South Carolina-Beaufort
Pratibha Varma-Nelson, Saint Xavier University
Robert T. Wang, Salem State University
Steven Weitstock, Indiana University
Catherine Woytowicz, Loyola University
Jesse Yeh, South Plains College
Edward P. Zovinka, St. Francis College
The following professors provided reviews and other
valuable advice for the previous editions:
Raymond D. Baechler, Russell Sage College
Satinder Bains, Arkansas State University-Beebe
Sister Marjorie Baird, O.P., West Virginia Northern
Community College
Ronald Bost, North Central Texas College
Fred Brohn, Oakland Community College
Sister Helen Burke, Chestnut Hill College
Sharmaine S. Cady, East Stroudsburg University
Robert C. Costello, University of South Carolina-Sumter
Marianne Crocker, Ozarks Technical Community College
Peter DiMaria, Delaware State University
Ronald Dunsdon, Iowa Central Community College
Donald R. Evers, Iowa Central Community College
Patrick Flash, Kent State University-Ashtabula
xxv
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The General, Organic, and Biochemistry Learning System

The General, Organic, and Biochemistry Learning System is easy to follow, and will allow the
student to excel in this course. The materials are presented in such a way that the student will
effectively learn and retain the important information.
Clear Approach to Solving Problems
Because problem solving is most efficiently
learned by a combination of studying examples
and practicing, problems with step-by-step
solutions are provided wherever appropriate.
Examples are followed by a question requiring
the student to integrate the newly learned
material.
275
10.3 Properties of Radioisotopes
Predicting the Products of Radioactive Decay
EXAMPLE
10.1
Determine the identity of the unknown product of the alpha decay of californium-245:
4
2He
245
96Cm
X
Solution
Step 1. The mass number of the californium isotope is 245. Therefore the
sum of the mass numbers of the products must also be 245, and X
must have a mass number of 241.
Step 2. Likewise, the charge on the left is 96, and the charge on the right
must also be 96. The sum of the unknown nuclear charge plus the
charge of the alpha particle (2) must equal 96.
Step 3. The unknown charge must be 94, because [94 (2) 96]. The unknown is
241
94X
Referring to the periodic table, we find that the element that has atomic number 94 is plutonium; therefore X 241
94Pu.
Complete each of the following nuclear equations:

a. 85
36Kr
b. X
Complete each of the following nuclear equations:

382
a.
b.
13 Alcohols, Phenols, Thiols, and Ethers
CH2OH
d. 2
13.56 We have seen that alcohols are capable of hydrogen bonding to each other. Hydrogen bonding is also possible between alcohol molecules and water molecules or between
alcohol molecules and ether molecules. Ether molecules do
not hydrogen bond to each other, however. Explain.
Thiols
13.57 Cystine is an amino acid formed from the oxidation of two
cysteine molecules to form a disulfide bond. The molecular
formula of cystine is C6H12O4N2S2. Draw the structural formula of cystine. (Hint: For the structure of cysteine, see Figure 19.11.)
13.58 Explain the way in which British Anti-Lewisite acts as an
antidote for mercury poisoning.
13.59 Give the I.U.P.A.C. name for each of the following thiols.
(Hint: Use the rules for alcohol nomenclature and the suffix
-thiol.)
a. CH3CH2CH2SH
b. CH3CHCH2CH3
A
SH
c.
CH2CH3
A
CH3CCH3
A
SH
d.
HSO
OSH
13.60 Give the I.U.P.A.C. name for each of the following thiols.
(Hint: Use the rules for alcohol nomenclature and the suffix
-thiol.)
a. CH2CHCH3
A A
SH SH
b.
OSH
c. CH3CHCH2CH2CH3
A
SH
d. CH3CH2CH2CH2CH2CH2CH2SH
Critical Thinking Problems

1. You are provided with two solvents: water (H2O) and hexane
(CH3CH2CH2CH2CH2CH3). You are also provided with two
biological molecules whose structures are shown here:
O
B
COH
A
HOCOOH
A
HOOCOH
A
HOCOOH
A
HOCOOH
A
CH2OH
239
92U
11
5B
Q u e s t i o n 10.3
X 10e
4
222
2He 86Rn
Q u e s t i o n 10.4
X 10e
7
3Li X
H
O
A
B
HOCOOOCOCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
O
B
O
B
A
H
Predict which biological molecule would be more soluble in

water and which would be more soluble in hexane. Defend
your prediction. Design a careful experiment to test your
hypothesis.
Consider the digestion of dietary molecules in the digestive tract. Which of the above two biological molecules
would be more easily digested under the conditions present
in the digestive tract?
2. Cholesterol is an alcohol and a steroid (Section 18.4). Diets
that contain large amounts of cholesterol have been linked to
heart disease and atherosclerosis, hardening of the arteries.
The narrowing of the artery, caused by plaque buildup, is
very apparent. Cholesterol is directly involved in this
buildup. Describe the various functional groups and principal structural features of the cholesterol molecule. Would
you use a polar or nonpolar solvent to dissolve cholesterol?
Explain your reasoning.
CH3
CH3
%
CH3
%
CH3
D
A
CH3
D
HO
Cholesterol
3. An unknown compound A is known to be an alcohol with
the molecular formula C4H10O. When dehydrated, compound A gave only one alkene product, C4H8, compound B.
Compound A could not be oxidized. What are the identities
of compound A and compound B?
4. Sulfides are the sulfur analogs of ethers, that is, ethers in
which oxygen has been substituted by a sulfur atom. They
are named in an analogous manner to the ethers with the
term sulfide replacing ether. For example, CH3SCH3 is dimethyl sulfide. Draw the sulfides that correspond to the following ethers and name them:
a. diethyl ether
c. dibutyl ether
b. methyl propyl ether
d. ethyl phenyl ether
5. Dimethyl sulfoxide (DMSO) has been used by many sports
enthusiasts as a linament for sore joints; it acts as an antiinflammatory agent and a mild analgesic (pain killer). However, it is no longer recommended for this purpose because it
carries toxic impurities into the blood. DMSO is a sulfoxide
it contains the SPO functional group. DMSO is prepared
from dimethyl sulfide by mild oxidation, and it has the
molecular formula C2H6SO. Draw the structure of DMSO.
A variety of questions and problems that

range in level of difficulty help students
measure their mastery of the chapter material.
The odd-numbered questions are answered in
the back of the text.
At the end of the chapter, the student will
find several problems that require thoughtprovoking answers dealing with daily life and
the health care sciences.
1328
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20
1 Chemistry: Methods and Measurement
1.6 Experimental Quantities

Thus far we have discussed the scientific method and its role in acquiring data and
converting the data to obtain the results of the experiment. We have seen that such
data must be reported in the proper units with the appropriate number of significant figures. The quantities that are most often determined include mass, length,
volume, time, temperature, and energy. Now lets look at each of these quantities
in more detail.
Learning Goal
Dynamic Visuals
Mass
Many of the equations and

reactions are color coded to help
the student understand the
chemical changes that occur in
complex reactions. The student can
easily recognize the chemical
groups being added or removed in
a reaction by the color coding.
Green background illustrates an
important equation or key reaction;
yellow background illustrates
energy in the general and
biochemistry sections and reveals
the parent chain of a compound in
the organic section; red and blue
lettering distinguish two or more
compounds that appear similar.
The art program has been
significantly updated with the use
of molecular art and drawings. The
students will gain a better
perspective and understanding of a
molecule with a Spartan computergenerated model.
Mass describes the quantity of matter in an object. The terms weight and mass, in
common usage, are often considered synonymous. They are not, in fact. Weight is
the force of gravity on an object:
Weight mass acceleration due to gravity
When gravity is constant, mass and weight are directly proportional. But gravity
is not constant; it varies as a function of the distance from the center of the earth.
Therefore weight cannot be used for scientific measurement because the weight of
an object may vary from one place on the earth to the next.
Mass, on the other hand, is independent of gravity; it is a result of a comparison of an unknown mass with a known mass called a standard mass. Balances are
instruments used to measure the mass of materials
The Chemical Reaction

Consider the exothermic reaction that we discussed in Section 8.1:
CH4(g) 2O2(g)
CO2(g) 2H2O(l) 211 kcal
For the reaction to proceed, CH and OO bonds must be broken, and C

O and HO bonds must be formed. Sufficient energy must be available to cause
the bonds to break if the reaction is to take place. This energy is provided by the
collision of molecules. If sufficient energy is available at the temperature of the reaction, one or more bonds will break, and the atoms will recombine in a lower en11.2 Alkanes
307
ergy arrangement, in this case as carbon dioxide and water. A collision producing
product molecules is termed an effective collision. Only effective collisions lead to
Now add the substituents. In this example a bromine atom is bonded to carbon-1,
chemical reaction.
and a methyl group is bonded to carbon-4:
Br
Activation Energy and the Activated Complex
A ALearning
A Goal
A A A
The minimum amount of energy required to produce a chemical reaction is called
OCOCOCOCOCOCO
5
A A A
A Athe activation energy for the reaction.
812
HOCOH
A
H
4 5 6
2 3
Finally, add the correct number of hydrogen atoms so that each carbon has four
covalent bonds:
Br H H H H H
A A A A A A
HOCOCOCOCOCOCOH
A A A
A A
H H H
H H
HOCOH
A
H
4 5 6
2 3
As a final check of your accuracy, use the I.U.P.A.C. system to name the compound
that you have just drawn, and compare the name with that in the original problem.
The molecular formula and condensed formula can be written from the struc
EXAMPLE
Calculating the pH of a Buffer Solution
9.10
Calculate the pH of a buffer solution similar to that described in Example 9.9

except that the acid concentration is doubled, while the salt concentration remains the same.
303
11.2 Alkanes
Solution
Acetic acid is the acid; [acid] 2.00 101 M (remember, the acid concentration is twice that of Example 9.9; 2 [1.00 101] 2.00 101 M
Sodium acetate is the salt; [salt] 1.00 101 M
The equilibrium is
HH
C$
C 109.5
i
H
H
i
C
@
H &
H
(a)
CH3COOH(aq) H2O(l)
(b)
H3O(aq) CH3COO(aq)
acid
salt
and the hydronium ion concentration,

H
HH
C$
HH
C$
C
C
@&
HH
C
@&
HH
(c)
(a)
Table 11.4
[H3O]
Figure 11.2
(a) Drawing and (b) ball-and-stick model

of ethane. All the carbon atoms have a
tetrahedral arrangement, and all bond
angles are approximately 109.5.
(c) Drawing and (d) ball-and-stick model
of a more complex alkane, butane.
(d)
H C
H
H
(b)
(c)
Substituting the values given in the problem

[H3O]
Figure 11.3
H
A
H ^CG
;
H
H
[2.00 101]1.75 105

[1.00 101]
[H3O ] 3.50 105

The tetrahedral carbon atom: (a) a tetrahedron; (b) the tetrahedral carbon drawn
with dashes and wedges; (c) the stick
drawing of the tetrahedral carbon atom;
(d) drawing of a ball-and-stick model of
methane.
(d)
[acid]Ka
[salt]
and because
pH log [H3O]
pH log 3.50 105
Names and Formulas of the First Five Continuous-Chain

Alkyl Groups
Alkyl Group Structure
Name
CH3
CH3CH2
CH3CH2CH2
CH3CH2CH2CH2
CH3CH2CH2CH2CH2
Methyl
Ethyl
Propyl
Butyl
Pentyl
4.456
The pH of the buffer solution is 4.456.
A comparison of the two solutions described in Examples 9 9 and 9 10 demon-
Carbon atoms are classified according to the number of other carbon atoms to
which they are attached. A primary carbon (1) is directly bonded to one other carbon. A secondary carbon (2) is bonded to two other carbon atoms; a tertiary carbon (3) is bonded to three other carbon atoms, and a quaternary carbon to four.
Alkyl groups are classified according to the number of carbons attached to the
carbon atom that joins the alkyl group to a molecule.
H
A
COC O
A
H
C
A
COCO
A
H
C
A
COCO
A
C
Primary
alkyl group
Secondary
alkyl group
Tertiary
alkyl group
119
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144
5 Calculations and the Chemical Equation
Pharmaceutical Chemistry: The Practical Significance of Percent Yield
In recent years the major pharmaceutical industries have in-
troduced a wide variety of new drugs targeted to cure or alleviate the symptoms of a host of diseases that afflict humanity.
The vast majority of these drugs are synthetic; they are
made in a laboratory or by an industrial process. These substances are complex molecules that are patiently designed and
constructed from relatively simple molecules in a series of
chemical reactions. A series of ten to twenty steps, or sequential reactions, is not unusual to put together a final product that
has the proper structure, geometry, and reactivity for efficacy
against a particular disease.
Although a great deal of research occurs to ensure that each
of these steps in the overall process is efficient (having a large
percent yield), the overall process is still very inefficient (low
percent yield). This inefficiency, and the research needed to
minimize it, at least in part determines the cost and availability
of both prescription and over-the-counter preparations.
Consider a hypothetical five-step sequential synthesis. If
each step has a percent yield of 80% our initial impression
might be that this synthesis is quite efficient. However, on
closer inspection we find quite the contrary to be true.
The overall yield of the five-step reaction is the product of
the decimal fraction of the percent yield of each of the sequential reactions. So, if the decimal fraction corresponding to 80%
is 0.80:
Health/Life Related Applications

There are four different Perspective boxes in the
text. Chemistry Connections provides an
introductory scenario for the chapter, Medical
Perspective and Clinical Perspective demonstrate
use of the chapter material in an allied health field,
Environmental Perspective demonstrates chapter
concepts in ecological problems, and Human
Perspective demonstrates how important chemistry
is in our day to day lives.
0.80 0.80 0.80 0.80 0.80 0.33

Converting the decimal fraction to percentage:
0.33 100% 33% yield
Many reactions are considerably less than 80% efficient, especially those that are used to prepare large molecules with complex arrangements of atoms. Imagine a more realistic scenario
in which one step is only 20% efficient (a 20% yield) and the
other four steps are 50%, 60%, 70%, and 80% efficient. Repeat-
0.20 0.50 0.60 0.70 0.80 0.0336

0.0336 100% 3.36% yield
a very inefficient process.
If we apply this logic to a fifteen- or twenty-step synthesis
we gain some appreciation of the difficulty of producing modern pharmaceutical products. Add to this the challenge of predicting the most appropriate molecular structure that will have
the desired biological effect and be relatively free of side effects.
All these considerations give new meaning to the term wonder
drug that has been attached to some of the more successful synthetic products.
We will study some of the elementary steps essential to the
synthesis of a wide range of pharmaceutical compounds in
later chapters, beginning with Chapter 11.
A more practical unit for defining a collection of

atoms is the mole:
Summary
156
5.1
ing the calculation with these numbers (after conversion to a

decimal fraction):
Converting the decimal fraction to a percentage:
6 States of Matter: Gases, Liquids, and Solids
1 mol of atoms 6.022 1023 atoms of an element
The Mole Concept and Atoms
This number is often referred to as Avogadros number.

The mole and the atomic mass unit are related. The
atomic mass of a given element corresponds to the average mass of a single atom in atomic mass units and the
mass of a mole of atoms in grams. One mole of atoms of
24
Autoclaves
and
the Gas Laws
1 amu 1.661 10 g
any element contains the same number, Avogadros
number, of atoms.
The periodic table provides atomic masses in atomic
acques Charles and Joseph Gay-Lussac were eighteenthmass units.
Atoms are exceedingly small, yet their masses have been

experimentally determined for each of the elements. The
unit of measurement for these determinations is the
atomic mass unit, abbreviated amu:
century chemists and physicists. They were also balloon enthusiasts. It is clear that their hobby and their scientific pursuits
were intertwined. Charless law is actually attributed to the
work of both men. The observation that the pressure and temperature of a gas are directly proportional
528
P T
follows directly from Charless law and Boyles law. The equality
PkT
is often termed Gay-Lussacs law. You can readily verify this proportionality by observing the fate of a balloon when it is heated
or cooled (try putting an inflated balloon in the refrigerator, remove it, and allow it to return to room temperature).
A very practical application of Gay-Lussacs law is the autoclave, a piece of equipment commonly found in hospital, clinical, and biological laboratories. It is designed and used to
sterilize laboratory materials such as glassware, surgical instruments, and so forth. It uses steam at high temperatures and
pressures and takes advantage of the exceptionally high heat
capacity (energy storage capability) of steam.
The autoclave kills microorganisms by using the heat energy in steam. However, steam has a temperature of 100C at
normal atmospheric pressure; this temperature is too low (insufficient energy) to kill all harmful bacteria. Gay-Lussacs law
predicts that, at a constant volume (the volume of the auto-
Q u e s t i o n 6.6
Chemical and Physical

Change: Energy, Rate,
and Equilibrium
A rapid, exothermic
chemical reaction
Learning Goals
1
Correlate the terms endothermic and

exothermic with heat flow between
a system and its surroundings.
State the meaning of the terms

enthalpy, entropy, and free energy
and know their implications.
Describe experiments that yield

thermochemical information and
calculate fuel values based on
experimental data.
Describe the concept of reaction

rate and the role of kinetics in
chemical and physical change.
Describe the importance of

activation energy and the activated
complex in determining reaction
rate.
Predict the way reactant structure,

concentration, temperature, and
catalysis affect the rate of a
chemical reaction.
Write rate equations for elementary

procedures.
Recognize and describe equilibrium

situations.
Write equilibrium-constant
expressions and use these
expressions to calculate equilibrium
constants.
10
Outline
The Cost of Energy? More Than You
Imagine
8.1 Thermodynamics
The Chemical Reaction and
Energy
Exothermic and Endothermic
Reactions
Enthalpy
Spontaneous and Nonspontaneous Reactions
Entropy
Free Energy
with Candy
8.2 Experimental Determination
of Energy Change in
Reactions
8.3 Kinetics
The Chemical Reaction
Activation Energy and the
Activated Complex
Factors That Affect Reaction
Rate
Hot and Cold Packs
Mathematical Representation
of Reaction Rate
8.4 Equilibrium
Rate and Reversibility of
Reactions
Physical Equilibrium
Chemical Equilibrium
The Generalized EquilibriumConstant Expression for a
Chemical Reaction
LeChateliers Principle
Summary
Key Terms
Questions and Problems
Critical Thinking Problems
Use LeChateliers principle to

predict changes in equilibrium
position.
205
Figure 6.4
Charless law predicts that the volume of air
in the balloon will increase when heated.
We assume that the volume of the balloon
is fixed; consequently, some air will be
pushed out. The air remaining in the balloon is less dense (same volume, less mass)
and the balloon will rise. When the heater
is turned off the air cools, the density
increases, and the balloon returns to earth.
clave), if the steam is heated further, both the pressure and temperature of the steam will increase. At the maximum safe operating pressure of the autoclave, temperatures may reach as
much as 150C; when maintained for a sufficient interval, this
temperature is sufficiently high to kill most microorganisms.
A sample of nitrogen gas has a volume of 3.00 L at 25C. What volume will it occupy at each of the following temperatures if the pressure and number of moles
are constant?
a. 546 K
b. 0.00C
c. 373 K
The behavior of a hot-air balloon is a commonplace consequence of Charless

law. The balloon rises because air expands when heated (Figure 6.4). The volume
of the balloon is fixed because the balloon is made of an inelastic material; as a result, when the air expands some of the air must be forced out. Hence the density of
the remaining air is less (less mass contained in the same volume), and the balloon
rises. Turning down the heat reverses the process, and the balloon descends.
Boyles law describes the inverse proportional relationship between volume
and pressure; Charless law shows the direct proportional relationship between
volume and temperature.
Combined Gas Law

Often, a sample of gas (a fixed number of moles of gas) undergoes change involving volume, pressure, and temperature simultaneously. It would be useful to have
one equation that describes such processes.
68
Clear Presentation
Each chapter begins with an outline that
introduces students to the topics to be
presented. This outline also provides the
instructor with a quick topic summary to
organize lecture material.
A list of learning goals, based on the major
concepts covered in the chapter, enables
students to preview the material and become
aware of the topics they are expected to master.
This icon is found within the chapters
wherever the associated learning goal is first
presented, allowing the student to focus
attention on the major concepts.
xxix
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Because k2 is a constant, we may equate them, resulting in

Vi
V
f
Ti
Tf
and use this expression to solve some practical problems.
Consider a gas occupying a volume of 10.0 L at 273 K. The ratio V/T is a constant, k2. Doubling the temperature, to 546 K, increases the volume to 20.0 L as
shown here:
Appendix A contains a review of the
mathematics used here.
10.0 L
Vf

273 K 546 K
Vf 20.0 L
Margin notes direct the student to a

reference in the book for further
material or review.
All bold-faced terms in the chapter
are listed at the end of each chapter and
defined in the Glossary at the end of the
text. The student can easily find
important terms when reading and
studying.
At the end of each chapter is a
summary designed to help students
more easily identify important concepts
and help them review for quizzes and
tests.
Tripling the temperature, to 819 K, increases the volume by a factor of 3:

10.0 L
Vf

273 K 819 K
Vf 30.0 L
These relationships are illustrated in Figure 6.3.
66
379
13.7
Summary
Phenols
Phenols are compounds in which the hydroxyl group is

attached to a benzene ring; they have the general formula ArOH. Many phenols are important as antiseptics and disinfectants.
13.1 Alcohols: Structure and Physical

Properties
Alcohols are characterized by the hydroxyl group (OH)
and have the general formula ROH. They are very polar, owing to the polar hydroxyl group, and are able to
form intermolecular hydrogen bonds. Because of hydrogen bonding between alcohol molecules, they have
higher boiling points than hydrocarbons of comparable
molecular weight. The smaller alcohols are very water
soluble.
13.8
13.9
13.2 Alcohols: Nomenclature

In the I.U.P.A.C. system, alcohols are named by determining the parent compound and replacing the -e ending
with -ol. The chain is numbered to give the hydroxyl
group the lowest possible number. Common names are
derived from the alkyl group corresponding to the parent compound.
Ethers
Ethers are characterized by the ROR functional

group. Ethers are generally nonreactive but are extremely
flammable. Diethyl ether was the first general anesthetic
used in medical practice. It has since been replaced by
penthrane and enthrane, which are less flammable.
Thiols
Thiols are characterized by the sulfhydryl group (SH).

The amino acid cysteine is a thiol that is extremely important for maintaining the correct shapes of proteins.
Coenzyme A is a thiol that serves as a carrier of acetyl
groups in biochemical reactions.
Key Terms
13.3 Medically Important Alcohols

Methanol is a toxic alcohol that is used as a solvent.
Ethanol is the alcohol consumed in beer, wine, and distilled liquors. Isopropanol is used as a disinfectant. Ethylene glycol (1,2-ethanediol) is used as antifreeze, and
glycerol (1,2,3-propanetriol) is used in cosmetics and
pharmaceuticals.
13.4 Classification of Alcohols

Alcohols may be classified as primary, secondary, or tertiary, depending on the number of alkyl groups attached
to the carbinol carbon, the carbon bearing the hydroxyl
group. A primary alcohol has a single alkyl group
bonded to the carbinol carbon. Secondary and tertiary alcohols have two and three alkyl groups, respectively.
13.5 Reactions Involving Alcohols

Alcohols can be prepared by the hydration of alkenes. Alcohols can undergo dehydration to yield alkenes. Primary
and secondary alcohols undergo oxidation reactions to
yield aldehydes and ketones, respectively. Tertiary alcohols do not undergo oxidation.
13.6 Oxidation and Reduction in Living

Systems
In organic and biological systems oxidation involves the
gain of oxygen or loss of hydrogen. Reduction involves
the loss of oxygen or gain of hydrogen. Nicotinamide
adenine dinucleotide, NAD, is a coenzyme involved in
many biological oxidation and reduction reactions.
alcohol (13.1)
carbinol carbon (13.4)
dehydration (13.5)
disulfide (13.9)
elimination reaction
(13.5)
ether (13.8)
fermentation (13.3)
hydration (13.5)
hydroxyl group (13.1)
oxidation (13.6)
phenol (13.7)
primary (1) alcohol
(13.4)
reduction (13.6)
secondary (2) alcohol
(13.4)
tertiary (3) alcohol (13.4)
thiol (13.9)
Zaitsevs rule (13.5)

Alcohols: Structure and Physical Properties
13.11 Arrange the following compounds in order of increasing
boiling point, beginning with the lowest:
a. CH3CH2CH2CH2CH3 b. CH3CHCH2CHCH3
A
A
OH
OH
c. CH3CHCH2CH2CH3 d. CH3CH2CH2OCH2CH3
A
OH
13.12 Why do alcohols have higher boiling points than alkanes?
Why are small alcohols readily soluble in water whereas
large alcohols are much less soluble?
13.13 Which member of each of the following pairs is more soluble in water?
or
CH3CH2CH2CH2OH
a. CH3CH2OH
or
CH3CH2CH2CH2OOH
b. CH3CH2CH2CH2CH3
c.
or
CH3CHCH3
OH
A
A
OH
1325
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General, Organic, and Biochemistry

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Textbook Table of Contents

Study Guide Table of Contents

General, Organic, and Biochemistry

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Textbook Table of Contents

Study Guide Table of Contents

GENERAL, ORGANIC, AND BIOCHEMISTRY

e-Text Main Menu

Textbook Table of Contents

Study Guide Table of Contents

Chemistry Methods and Measurement

The Composition and Structure

Elements, Atoms, Ions, and the Periodic

Structure and Properties of Ionic and

Calculations and the Chemical Equation 117

Reactions and Solutions

States of Matter: Gases, Liquids, and

Chemical and Physical Change: Energy, Rate,

An Introduction to Organic Chemistry: The

The Unsaturated Hydrocarbons: Alkenes,

Alcohols, Phenols, Thiols, and Ethers

Amines and Amides

Aldehydes and Ketones

Carboxylic Acids and Carboxylic Acid

Protein Structure and Function

Fatty Acid Metabolism 665

Lipids and Their Functions in Biochemical

Carbohydrate Metabolism 599

Introduction to Molecular Genetics

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Textbook Table of Contents

Study Guide Table of Contents

Diagnosis Based on Waste 28

Chance Favors the Prepared

The Discovery Process 3

The Scientific Method 4

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Matter and Properties 34

Textbook Table of Contents

Study Guide Table of Contents

Properties of Ionic and

Magnets and Migration 82

The Periodic Law and the Periodic Table 58

Electron Arrangement and the Periodic Table 63

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Solutions of Ionic and Covalent Compounds 95

Textbook Table of Contents

Study Guide Table of Contents

Autoclaves and the Gas Laws 156

The Mole Concept and Atoms 119

The Gaseous State 151

Calculations Using the Chemical Equation 133

Combined Gas Law 156

Ideal Gases Versus Real Gases

Seeing a Thought 176

The Demise of the

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