Fundamentals of general organic and biological chemistry 8th global edtion by mcmurry 1

Periodic Table of the Elements

Main groups

Main groups

1A
Period

1

1
2
3

8A

1
H

18
2A

1.00794

2

3

4

6

7A

13

14

15

16

17

5

6

7

8

9

4.00260
10

C

N

O

F

Ne

Be

B

9.01218
12

10.81
13

Na

Mg

K

Ca

Rb

Sr

85.4678
55

87.62
56

Cs

Ba

Fr
(223)

3B
3

4B
4

5B

6B

7B

5

6

7

8B
8

Ra

10

2B

11

12

12.011 14.0067 15.9994 18.9984 20.1797
16
17
18
14
15

Al

Si

P

S

Cl

Ar

26.98154 28.0855 30.9738 32.066 35.4527 39.948
31
32
33
34
35
36

21

22

23

24

25

26

27

28

29

30

Ti

V

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

As

Se

Br

Kr

58.69
46

63.546
47

65.39
48

69.72
49

72.61
50

74.9216
51

78.96
52

79.904
53

83.80
54

Pd

Ag

Cd

In

Sn

Sb

Te

I

Xe

Y

47.88
40

50.9415 51.996 54.9380 55.847 58.9332
42
43
44
41
45

Zr

*La

Hf

Mo

Tc

95.94
74

(98)
75

W

Re

Nb

88.9059 91.224 92.9064
72
57
73

Ac

226.0254 227.0278

Ta

Ru

Rh

101.07 102.9055 106.42 107.8682 112.41
76
77
78
80
79

Os

Ir

190.2
108

192.22
109

Pt

Au

Hg

Tl

Rf

Db

Sg

Bh

Hs

Mt

Ds

Rg

Cn

(262)

(266)

(264)

(269)

(268)

(271)

(272)

(285)

Nonmetals

114.82 118.710 121.757 127.60 126.9045 131.29
81
82
85
86
84
83

Pb

195.08 196.9665 200.59 204.383
110
112
113
111

(261)

Actinides

Metalloids

9

1B

2

He

Sc

Lanthanides

Metals

6A

Li

132.9054 137.33 138.9055 178.49 180.9479 183.85 186.207
87
104
105
106
107
89
88

7

5A

Transition metal groups

39.0983 40.078 44.9559
37
38
39

5

4A

6.941
11

22.98977 24.305
19
20

4

3A

(284)

Po

At

Rn

207.2 208.9804

114
115

Bi

(209)
116

(210)
117

(222)
118

(289)

(292)

(293)

(294)

(288)

58

59

60

61

62

63

64

65

66

67

68

69

70

71

Ce

Pr

Nd

Pm

Sm

Eu

Gd

Tb

Dy

Ho

Er

Tm

Yb

Lu

140.12 140.9077 144.24
90
91
92

Th

Pa

U

(145)
93

Np

232.0381 231.0399 238.0289 237.048

150.36 151.965 157.25 158.9254 162.50 164.9304 167.26 168.9342 173.04 174.967
103
94
95
96
97
98
99
100
101
102

Pu

Am

Cm

Bk

Cf

Es

Fm

Md

No

Lr

(244)

(243)

(247)

(247)

(251)

(252)

(257)

(258)

(259)

(262)

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Fundamentals of General, Organic, and Biological

Chemistry


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Fundamentals of General, Organic, and Biological

Chemistry
Eighth Edition in SI Units
John McMurry
Cornell University

David S. Ballantine
Northern Illinois University

Carl A. Hoeger
University of California, San Diego

Virginia E. Peterson
University of Missouri, Columbia

with contributions by

Sara Madsen
and SI conversions by

Christel Meert
Hogeschool Gent

Andrew Pearson
Griffith University

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A catalogue record for this book is available from the British Library
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ISBN 10: 1-292-12346-X
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Typeset by Lumina Datamatics, Inc.
Printed and bound in Malaysia

About the Authors
John McMurry, educated at Harvard and Columbia, has taught approximately
17,000 students in general and organic chemistry over a 30-year period. A professor of chemistry at Cornell University since 1980, Dr. McMurry previously spent
13 years on the faculty at the University of California at Santa Cruz. He has received numerous awards, including the Alfred P. Sloan Fellowship (1969–1971),
the National Institute of Health Career Development Award (1975–1980), the Alexander von Humboldt Senior Scientist Award (1986–1987), and the Max Planck
Research Award (1991).

David S. Ballantine received his B.S. in Chemistry in 1977 from the College of
William and Mary in Williamsburg, VA, and his Ph.D. in Chemistry in 1983 from
the University of Maryland at College Park. After several years as a researcher at
the Naval Research Labs in Washington, DC, he joined the faculty in the Department of Chemistry and Biochemistry of Northern Illinois University, where he
has been a professor since 1989. He was awarded the Excellence in Undergraduate Teaching Award in 1998. Since then, he has served as the coordinator for the
Introductory and General Chemistry programs, with responsibilities for supervision of supervising
the laboratory teaching assistants. He served as the departmental director of undergraduate studies
from 2008 to 2014 and is currently the associate dean for undergraduate affairs in the College of
Liberal Arts and Sciences. He continues to teach in the Department of Chemistry and Biochemistry.

Carl A. Hoeger received his B.S. in Chemistry from San Diego State University
and his Ph.D. in Organic Chemistry from the University of Wisconsin–Madison
in 1983. After a postdoctoral stint at the University of California–Riverside,
he joined the Peptide Biology Laboratory at the Salk Institute in 1985, where he
supervised the NIH Peptide Facility while doing basic research in the development
of peptide agonists and antagonists. During this time, he also taught general,
organic, and biochemistry at San Diego City College, Palomar College, and Miramar College. He joined the teaching faculty at University of California–San Diego (UCSD) in
1998. Dr. Hoeger has been teaching chemistry to undergraduates for 30 years, where he continues
to explore the use of technology in the classroom; his current project involves the use of video
podcasts as adjuncts to live lectures, along with the use of tablets to deliver real-time lectures
with slide annotations. In 2004, he won the Barbara and Paul Saltman Distinguished Teaching
Award from UCSD. He is deeply involved with both the general and organic chemistry programs
at UCSD and has shared partial responsibility for the training and guidance of teaching assistants

and new instructors in the Chemistry and Biochemistry department.

7


8

About the Authors

Virginia E. Peterson received her B.S. in Chemistry in 1967 from the University of
Washington in Seattle and her Ph.D. in Biochemistry in 1980 from the University
of Maryland at College Park. Between her undergraduate and graduate years, she
worked in lipid, diabetes, and heart disease research at Stanford University. Following her Ph.D., she took a position in the Biochemistry Department at the University of Missouri in Columbia and is now professor emerita. When she retired in
2011, she had been the director of undergraduate advising for the department for 8
years and had taught both senior capstone classes and biochemistry classes for nonscience majors.
Although retired, Dr. Peterson continues to advise undergraduates and teach classes. Awards
include both the college-level and the university-wide Excellence in Teaching Award and, in 2006,
the University’s Outstanding Advisor Award and the State of Missouri Outstanding University
Advisor Award. Dr. Peterson believes in public service and in 2003 received the Silver Beaver
Award for service from the Boy Scouts of America. In retirement, she continues her public service
activities by participating in a first-year medical student mentoring program and her more than
25-year commitment to the Boy Scouts of America as an active adult volunteer.

Sara K. Madsen received her B.S. in Chemistry at Central Washington University
in Ellensburg, Washington, in 1988 and her Ph.D in Inorganic Chemistry at the
University of Wyoming in 1998. She has been teaching since 2001. The beginning
of her teaching career started with a one-semester survey course and moved from
there to courses in general, organic, and biochemistry, general chemistry, organic
and inorganic chemistry for undergraduates, and inorganic chemistry for graduate
students. She loves helping students develop the connections between ideas and

concepts and, above all, exposing their realization about how chemistry is involved in their program of study or professional path.


Brief Contents
Features 16
Preface

18

1

Matter and Measurements 34

2

Atoms and the Periodic Table 76

3

Ionic Compounds 106

17

Carboxylic Acids and Their
Derivatives 556

18

Amino Acids and Proteins 588

19

Enzymes and Vitamins 624

4

Molecular Compounds 134

20

5

Carbohydrates 660

Classification and Balancing of Chemical
Reactions 170

21

The Generation of Biochemical
Energy 692

Chemical Reactions: Mole and Mass
Relationships 196

22

Carbohydrate Metabolism 724

23

Lipids 748

24

Lipid Metabolism 774

25

Protein and Amino Acid Metabolism 796

26

Nucleic Acids and Protein Synthesis 814

27

Genomics 840

28

Chemical Messengers: Hormones,
Neurotransmitters, and Drugs 858

29

Body Fluids 882

6
7

8
9
10
11

Chemical Reactions: Energy, Rates,
and Equilibrium 218
Gases, Liquids, and Solids 250
Solutions 288
Acids And Bases

324

Nuclear Chemistry 362

12

Introduction to Organic Chemistry:
Alkanes 390

13

Alkenes, Alkynes, and Aromatic
Compounds 436

14

Some Compounds with Oxygen, Sulfur,
or a Halogen 474

15

Aldehydes and Ketones 508

16

Amines 536

Appendices 905
Answers to Selected Problems 911
Glossary 949
Credits 957
Index

959

9


Contents
2.8
2.9

Features 16
Preface 18

1
1.1

1.2

1.3

1.4
1.5
1.6

1.7
1.8
1.9
1.10
1.11

1.12

2
2.1
2.2
2.3
2.4
2.5

2.6
2.7

10

Matter and
Measurements

34

3

Chemistry: The
Central Science 35
HANDS-ON CHEMISTRY
1.1 37
States of Matter 38
Classification of
Matter 39
CHEMISTRY IN ACTION:
Aspirin—A Case
Study 41
Chemical Elements and Symbols 41
Chemical Reactions: Examples of Chemical
Change 44
Physical Quantities: Units and Scientific Notation 45
CHEMISTRY IN ACTION: Mercury and Mercury
Poisoning 46
Measuring Mass, Length, and Volume 49
HANDS-ON CHEMISTRY 1.2 51
Measurement and Significant Figures 52
Rounding Off Numbers 55
Problem Solving: Unit Conversions and Estimating
Answers 57
Temperature, Heat, and Energy 61
CHEMISTRY IN ACTION: Temperature-Sensitive
Materials 63
Density and Specific Gravity 65
CHEMISTRY IN ACTION: A Measurement Example:

Obesity and Body Fat 67

3.10

Atoms and the Periodic Table

4.4

76
Atomic Theory and the Structure of Atoms 77
CHEMISTRY IN ACTION: Are Atoms Real? 78
Elements and Atomic Number 79
Isotopes and Atomic Mass 80
HANDS-ON CHEMISTRY 2.1 83
The Periodic Table 83
Some Characteristics of Different Groups 86
CHEMISTRY IN ACTION: Essential Elements and Group
Chemistry 88
Electronic Structure of Atoms 89
HANDS-ON CHEMISTRY 2.2 92
Electron Configurations 92

3.1
3.2
3.3
3.4
3.5
3.6
3.7
3.8

3.9

3.11

4
4.1
4.2
4.3

4.5
4.6
4.7

4.8
4.9
4.10

Electron Configurations and the Periodic Table 96
Electron-Dot Symbols 99
CHEMISTRY IN ACTION: Atoms and Light 100

Ionic Compounds

106
Ions 107
Ions and the Octet Rule 108
Ions of Some Common Elements 110
Periodic Properties and Ion Formation 112
Naming Monoatomic Ions 114
CHEMISTRY IN ACTION: Salt 115

Polyatomic Ions 116
CHEMISTRY IN ACTION: Biologically Important Ions 117
Ionic Bonds 118
Formulas of Ionic Compounds 119
HANDS-ON CHEMISTRY 3.1 122
Naming Ionic Compounds 122
HANDS-ON CHEMISTRY 3.2 124
Some Properties of Ionic Compounds 125
CHEMISTRY IN ACTION: Ionic Liquids 125
H+ and OH- Ions: An Introduction to Acids
and Bases 126
CHEMISTRY IN ACTION: Osteoporosis 127

Molecular
Compounds

134
Covalent Bonds 135
Covalent Bonds
and the Periodic
Table 137
Multiple Covalent
Bonds 140
Coordinate Covalent
Bonds 142
Characteristics
of Molecular
Compounds 143
Molecular Formulas and Lewis Structures 144
Drawing Lewis Structures 145

CHEMISTRY IN ACTION: CO and NO: Pollutants or
Miracle Molecules? 150
The Shapes of Molecules 150
CHEMISTRY IN ACTION: VERY Big Molecules 155
Polar Covalent Bonds and Electronegativity 156
Polar Molecules 158
HANDS-ON CHEMISTRY 4.1 160


Contents

4.11

5
5.1
5.2

5.3

5.4
5.5
5.6
5.7

6
6.1
6.2
6.3
6.4
6.5

Naming Binary Molecular Compounds 161
CHEMISTRY IN ACTION: Damascenone by Any Other
Name Would Smell as Sweet 162

Classification and
Balancing of
Chemical
Reactions 170
Chemical
Equations 171
Balancing Chemical
Equations 172
HANDS-ON
CHEMISTRY 5.1 175
Precipitation
Reactions and Solubility Guidelines 175
CHEMISTRY IN ACTION: Kidney Stones: A Problem
in Solubility 176
Acids, Bases, and Neutralization Reactions 177
HANDS-ON CHEMISTRY 5.2 178
Redox Reactions 179
CHEMISTRY IN ACTION: Batteries 184
Recognizing Redox Reactions 184
Net Ionic Equations 187

Chemical Reactions: Mole and Mass
Relationships 196
The Mole and Avogadro’s Number 197
Gram–Mole Conversions 201

Mole Relationships and Chemical Equations 203
Mass Relationships and Chemical Equations 204
Limiting Reagent and Percent Yield 207
HANDS-ON CHEMISTRY 6.1 211
CHEMISTRY IN ACTION: Anemia—A Limiting Reagent

Problem? 211

7
7.1
7.2
7.3

7.5
7.6

8
8.1
8.2
8.3
8.4

8.5

8.6

8.7
8.8
8.9
8.10

8.11
8.12
8.13
8.14

9
9.1
9.2

Chemical Reactions: Energy, Rates, and
Equilibrium 218
Energy and Chemical Bonds 219
Heat Changes during Chemical Reactions 219
Exothermic and Endothermic Reactions 221
CHEMISTRY IN ACTION: Energy from Food 225
HANDS-ON CHEMISTRY 7.1 226

7.4

7.7
7.8
7.9

Why Do Chemical Reactions Occur? Free
Energy 226
How Do Chemical Reactions Occur? Reaction
Rates 229
Effects of Temperature, Concentration, and Catalysts
on Reaction Rates 231

9.3
9.4
9.5
9.6
9.7
9.8

11

Reversible Reactions and Chemical Equilibrium 234
Equilibrium Equations and Equilibrium Constants 235
Le Châtelier’s Principle: The Effect of Changing
Conditions on Equilibria 239
CHEMISTRY IN ACTION: Regulation of Body
Temperature 242

Gases, Liquids, and Solids

250
States of Matter and Their Changes 251
Intermolecular Forces 252
Gases and the Kinetic–Molecular Theory 257
Pressure 257
CHEMISTRY IN ACTION: Greenhouse Gases and Global
Warming 260
Boyle’s Law: The Relation between Volume and
Pressure 261
CHEMISTRY IN ACTION: Blood Pressure 263
Charles’s Law: The Relation between Volume and
Temperature 264

HANDS-ON CHEMISTRY 8.1 265
Gay-Lussac’s Law: The Relation between Pressure
and Temperature 265
The Combined Gas Law 267
Avogadro’s Law: The Relation between Volume and
Molar Amount 268
The Ideal Gas Law 270
Partial Pressure and Dalton’s Law 272
Liquids 273
Solids 275
Changes of State Calculations 277
CHEMISTRY IN ACTION: CO2 as an Environmentally
Friendly Solvent 280

Solutions

288
Mixtures and
Solutions 289
The Solution
Process 290
CHEMISTRY IN ACTION:
Solid Hydrates—Salt
+ Water 292
Solubility 292
The Effect of Temperature on Solubility 293
The Effect of Pressure
on Solubility: Henry’s Law 295
Units of Concentration 297
CHEMISTRY IN ACTION: Breathing and Oxygen Transport 298

Dilution 304
Ions in Solution: Electrolytes 306
CHEMISTRY IN ACTION: Electrolytes, Fluid Replacement,
and Sports Drinks 308


12
9.9
9.10
9.11

Contents

Properties of Solutions 309
HANDS-ON CHEMISTRY 9.1 312
Osmosis and Osmotic Pressure 313
HANDS-ON CHEMISTRY 9.2 316
Dialysis 316
CHEMISTRY IN ACTION: Timed-Release Drug Delivery
Systems 317

10 Acids and Bases 324
10.1

Acids and Bases:
Definitions 325
10.2 Acid and Base Strength 329
CHEMISTRY IN ACTION: GERD—
Too Much Acid or Not
Enough? 333

10.3 Acid Dissociation
Constants 334
10.4 Water as Both an Acid and a
Base 335
10.5 Measuring Acidity in Aqueous Solution: The pH Scale 337
10.6 Working with pH 340
CHEMISTRY IN ACTION: Acid Rain 342
10.7 Acid and Base Equivalents 344
10.8 Some Common Acid-Base Reactions 345
HANDS-ON CHEMISTRY 10.1 347
10.9 Acidity and Basicity of Salt Solutions 347
10.10 Buffer Solutions 348
10.11 Titration 352
CHEMISTRY IN ACTION: Buffers in the Body: Acidosis
and Alkalosis 355

11 Nuclear Chemistry 362
11.1
11.2
11.3
11.4
11.5

11.6
11.7
11.8
11.9

Nuclear Reactions 363
The Discovery and Nature of Radioactivity 364

Stable and Unstable Isotopes 365
Nuclear Decay 366
Radioactive Half-Life 370
CHEMISTRY IN ACTION: Medical Uses
of Radioactivity 372
Ionizing Radiation 375
Detecting and Measuring Radiation 377
CHEMISTRY IN ACTION: Irradiated Food 379
Artificial Transmutation 380
CHEMISTRY IN ACTION: Body Imaging 381
Nuclear Fission and Nuclear Fusion 382
HANDS-ON CHEMISTRY 11.1 385

12 Introduction to Organic Chemistry:
Alkanes

390
12.1 The Nature of Organic Molecules 391
12.2 Families of Organic Molecules: Functional
Groups 393
HANDS-ON CHEMISTRY 12.1 399
12.3 The Structure of Organic Molecules: Alkanes
and Their Isomers 399
12.4 Drawing Organic Structures 402
12.5 The Shapes of Organic Molecules 407
12.6 Naming Alkanes 410
CHEMISTRY IN ACTION: How Important Can a Methyl
Group Really Be? 417
12.7 Properties of Alkanes 418
12.8 Reactions of Alkanes 419

MASTERING REACTIONS: Organic Chemistry and the
Curved Arrow Formalism 420
12.9 Cycloalkanes 424
12.10 Drawing and Naming Cycloalkanes 426
CHEMISTRY IN ACTION: Surprising Uses of
Petroleum 428

13 Alkenes, Alkynes,
and Aromatic
Compounds 436
13.1

Alkenes and
Alkynes 437
13.2 Naming Alkenes and
Alkynes 438
13.3 The Structure of
Alkenes: Cis–Trans
Isomerism 441
HANDS-ON CHEMISTRY
13.1 444
13.4 Properties of Alkenes and Alkynes 445
13.5 Types of Organic Reactions 445
CHEMISTRY IN ACTION: The Chemistry of Vision
and Color 448
13.6 Addition Reactions of Alkenes 449
MASTERING REACTIONS: How Addition Reactions
Occur 456
13.7 Alkene Polymers 458
13.8 Aromatic Compounds and the Structure

of Benzene 460
13.9 Naming Aromatic Compounds 462
13.10 Reactions of Aromatic Compounds 464
CHEMISTRY IN ACTION: Enediyne Antibiotics: A Newly
Emerging Class of Antitumor Agents 466


Contents

14 Some Compounds
with Oxygen,
Sulfur, or a
Halogen 474
14.1

Alcohols, Phenols,
and Ethers 475
14.2 Naming Alcohols 476
14.3 Properties of
Alcohols 480
14.4 Reactions of
Alcohols 481
MASTERING REACTIONS: How Eliminations Occur 483
14.5 Phenols 488
14.6 Acidity of Alcohols and Phenols 490
14.7 Ethers 490
CHEMISTRY IN ACTION: Inhaled Anesthetics 492
14.8 Thiols and Disulfides 493
14.9 Halogen-Containing Compounds 494
14.10 Stereochemistry and Chirality 496

HANDS-ON CHEMISTRY 14.1 498
CHEMISTRY IN ACTION: Fetal Alcohol Syndrome:

Ethanol as a Toxin 501

15 Aldehydes and Ketones 508
15.1
15.2

15.3
15.4
15.5
15.6
15.7

The Carbonyl Group 509
Naming Simple Aldehydes and Ketones 511
CHEMISTRY IN ACTION: Chemical Warfare among
the Insects 512
Properties of Aldehydes and Ketones 513
Some Common Aldehydes and Ketones 514
Oxidation of Aldehydes 515
Reduction of Aldehydes and Ketones 517
Addition of Alcohols: Hemiacetals and Acetals 519
HANDS-ON CHEMISTRY 15.1 526
MASTERING REACTIONS: Carbonyl Additions 527

HANDS-ON CHEMISTRY 17.1 565

17.2

17.3
17.4
17.5
17.6

16.1
16.2
16.3
16.4
16.5
16.6
16.7

Classifying Amines 537
Naming and Drawing Amines 538
Properties of Amines 540
HANDS-ON CHEMISTRY 16.1 542
Heterocyclic Nitrogen Compounds 543
Basicity of Amines 544
Amine Salts 547
Amines in Plants: Alkaloids 549
CHEMISTRY IN ACTION: Calming a Stormy Mind:
Amines as Anti-Anxiety Medications 551

17 Carboxylic Acids and Their Derivatives 556
17.1

Carboxylic Acids and Their Derivatives: Properties
and Names 557

Acidity of Carboxylic Acids 566
CHEMISTRY IN ACTION: Medicinally Important
Carboxylic Acids and Derivatives 568
Reactions of Carboxylic Acids: Ester and Amide
Formation 570
Hydrolysis of Esters and Amides 573
Polyamides and Polyesters 576
Phosphoric Acid Derivatives 577
CHEMISTRY IN ACTION: Medications, Body Fluids,
and the “Solubility Switch” 580

18 Amino Acids and Proteins 588
18.1
18.2
18.3
18.4

18.5

An Introduction to Biochemistry 589
Proteins and Their Functions: An Overview 589
Amino Acids 591
Acid-Base Properties of Amino Acids 595
CHEMISTRY IN ACTION: Protein Analysis by
Electrophoresis 596
Peptides 597
HANDS-ON CHEMISTRY 18.1 599
CHEMISTRY IN ACTION: Proteins in the Diet 600

Protein Structure: An Overview and Primary Protein
Structure 11°2 600
CHEMISTRY IN ACTION: What Is Sickle-Cell Anemia? 602
18.7 Secondary Protein Structure 12°2 603
18.8 Tertiary Protein Structure 13°2 607
18.9 Quaternary Protein Structure 14°2 612
18.10 Chemical Properties of Proteins 614
HANDS-ON CHEMISTRY 18.2 616
18.6

CHEMISTRY IN ACTION: Imperfect Collagen—

An Unfortunate Event 617

19 Enzymes and
Vitamins
19.1

CHEMISTRY IN ACTION: When Is Toxicity Beneficial? 529

16 Amines 536

13

19.2

19.3

19.4
19.5

19.6
19.7
19.8

624

Catalysis by
Enzymes 625
HANDS-ON CHEMISTRY
19.1 626
Enzyme
Cofactors 627
HANDS-ON CHEMISTRY
19.2 629
Enzyme
Classification 629
MASTERING REACTIONS: How to Read Biochemical
Reactions 629
How Enzymes Work 633
Factors Affecting Enzyme Activity 636
Enzyme Regulation: Inhibition 639
Enzyme Regulation: Allosteric Control and Feedback
Inhibition 642
Enzyme Regulation: Covalent Modification and
Genetic Control 644


14

Contents

CHEMISTRY IN ACTION: Enzyme Inhibitors as Drugs 646

19.9

Vitamins, Antioxidants, and Minerals 647
CHEMISTRY IN ACTION: Vitamins, Minerals, and Food
Labels 651
CHEMISTRY IN ACTION: Enzymes in Medical

Diagnosis 653

20 Carbohydrates 660
20.1
20.2

20.3

20.4

20.5
20.6
20.7

22 Carbohydrate Metabolism 724
22.1
22.2
22.3
22.4
22.5

An Introduction to
Carbohydrates 661
Handedness of
Carbohydrates
and Fischer
Projections 663
Structure of
Glucose and Other
Monosaccharides 667
HANDS-ON CHEMISTRY
20.1 669
Some Important Monosaccharides 671
CHEMISTRY IN ACTION: Cell-Surface Carbohydrates and
Blood Type 674
Reactions of Monosaccharides 674
Common Disaccharides 677
Some Important Polysaccharides Based
on Glucose 680
CHEMISTRY IN ACTION: Bacterial Cell Walls: Rigid
Defense Systems 682

22.6
22.7

HANDS-ON CHEMISTRY 20.2 684

23.4
23.5
23.6
23.7

Digestion of Carbohydrates 725
Glucose Metabolism: An Overview 725
Glycolysis 726
Entry of Other Sugars into Glycolysis 730
CHEMISTRY IN ACTION: Tooth Decay 731
The Fate of Pyruvate 732
HANDS-ON CHEMISTRY 22.1 734
Energy Output in Complete Glucose Catabolism 734
Regulation of Glucose Metabolism and Metabolism
during Stress 735
HANDS-ON CHEMISTRY 22.2 737
CHEMISTRY IN ACTION: The Biochemistry of

22.8
22.9

Running 738
Glycogen Metabolism: Glycogenesis and
Glycogenolysis 739
Gluconeogenesis: Glucose Synthesis from
Noncarbohydrates 740
CHEMISTRY IN ACTION: Diagnosis and Monitoring
of Diabetes 742

23 Lipids 748
23.1
23.2
23.3

Structure and Classification of Lipids 749
Fatty Acids and Their Esters 751
Properties of Fats and Oils 754
CHEMISTRY IN ACTION: Lipids in the Diet 755
HANDS-ON CHEMISTRY 23.1 755

21 The Generation of Biochemical Energy 692

Chemical Reactions of Triacylglycerols 756
Phospholipids and Glycolipids 758
Sterols 763
Cell Membranes: Structure and Transport 765
CHEMISTRY IN ACTION: Eicosanoids: Prostaglandins
and Leukotrienes 769

21.1

HANDS-ON CHEMISTRY 23.2 770

CHEMISTRY IN ACTION: Carbohydrates and Fiber

in the Diet 685

Energy, Life, and Biochemical Reactions 693
CHEMISTRY IN ACTION: Plants and Photosynthesis 696

21.2
21.3
21.4

21.5

Cells and Their Structure 697
An Overview of Metabolism and Energy
Production 698
Strategies of Metabolism: ATP and Energy
Transfer 701
CHEMISTRY IN ACTION: Harmful Oxygen Species and
Antioxidant Vitamins 703
Strategies of Metabolism: Metabolic Pathways
and Coupled Reactions 703
CHEMISTRY IN ACTION: Basal Metabolism 705
HANDS-ON CHEMISTRY 21.1 706

21.6
21.7
21.8

Strategies of Metabolism: Oxidized and Reduced
Coenzymes 706
The Citric Acid Cycle 709
The Electron-Transport Chain and ATP
Production 713
CHEMISTRY IN ACTION: Metabolic Poisons 717

24 Lipid
Metabolism
24.1
24.2
24.3

24.4
24.5
24.6

774

Digestion of
Triacylglycerols 775
Lipoproteins for Lipid
Transport 777
Triacylglycerol
Metabolism: An
Overview 778
Storage and
Mobilization of
Triacylglycerols 780
Oxidation of Fatty Acids 782
Ketone Bodies and Ketoacidosis 785
CHEMISTRY IN ACTION: The Liver—Clearinghouse
for Metabolism 787


Contents

24.7

Biosynthesis of Fatty Acids 788
CHEMISTRY IN ACTION: Fat Storage, Lipids, and
Atherosclerosis 790

27.4
27.5

15

Recombinant DNA 849
Genomics: Using What We Know 851
CHEMISTRY IN ACTION: DNA Fingerprinting 854

HANDS-ON CHEMISTRY 24.1 791

28 Chemical Messengers: Hormones,

25 Protein and
Amino Acid
Metabolism
25.1

25.2
25.3
25.4

25.5
25.6

Neurotransmitters, and Drugs
796

Digestion of
Proteins 797

HANDS-ON CHEMISTRY
25.1 798
Amino Acid
Metabolism:
An Overview 799
Amino Acid
Catabolism:
The Amino Group 800
The Urea Cycle 802
CHEMISTRY IN ACTION: Gout: When Biochemistry Goes
Awry 804
Amino Acid Catabolism: The Carbon Atoms 805
Biosynthesis of Nonessential Amino Acids 806
CHEMISTRY IN ACTION: The Importance of Essential
Amino Acids and Effects of Deficiencies 808

26 Nucleic Acids and Protein Synthesis 814
26.1
26.2
26.3
26.4
26.5
26.6
26.7
26.8
26.9

DNA, Chromosomes, and Genes 815
Composition of Nucleic Acids 815
The Structure of Nucleic Acid Chains 820

Base Pairing in DNA: The Watson–Crick Model 821
Nucleic Acids and Heredity 824
Replication of DNA 824
Structure and Function of RNA 827
Transcription: RNA Synthesis 828
The Genetic Code 830
HANDS-ON CHEMISTRY 26.1 831
CHEMISTRY IN ACTION: Influenza: Variations

28.1
28.2
28.3
28.4

28.5
28.6
28.7

Messenger Molecules 859
Hormones and the Endocrine System 860
How Hormones Work: Epinephrine and Fight-orFlight 863
Amino Acid Derivatives, Polypeptides, and Steroid
Hormones 865
CHEMISTRY IN ACTION: Homeostasis 868
Neurotransmitters 869
How Neurotransmitters Work: Acetylcholine,
Its Agonists and Antagonists 871
Histamines, Antihistamines, and Important
Neurotransmitters 873
HANDS-ON CHEMISTRY 28.1 877

29 Body Fluids 882
29.1
29.2

29.3

29.4
29.5
29.6
29.7
29.8

Body Water and Its
Solutes 883
Fluid Balance 885
HANDS-ON CHEMISTRY
29.1 886
Blood 887
CHEMISTRY IN ACTION:
The Blood–Brain
Barrier 889
Plasma Proteins,
White Blood Cells,
and Immunity 890
Blood Clotting 893
Red Blood Cells and Blood Gases 894
The Kidney and Urine Formation 897
Urine Composition and Function 898
CHEMISTRY IN ACTION: What’s in Your Blood Test? 899

on a Theme 832
26.10 Translation: tRNA and Protein Synthesis 833

APPENDICES 905

27 Genomics 840

ANSWERS TO SELECTED PROBLEMS 911

27.1
27.2
27.3

GLOSSARY 949

Mapping the Human Genome 841
DNA and Chromosomes 843
Mutations and Polymorphisms 845
HANDS-ON CHEMISTRY 27.1 846

CREDITS 957

CHEMISTRY IN ACTION: The Polymerase Chain

Reaction 848

858

INDEX 959

Features
CHEMiStry in ACtion
Aspirin—A Case Study 41
Mercury and Mercury Poisoning 46
Temperature-Sensitive Materials 63
A Measurement Example: Obesity and Body Fat 67
Are Atoms Real? 78
Essential Elements and Group Chemistry 88
Atoms and Light 100
Salt 115
Biologically Important Ions 117
Ionic Liquids 125
Osteoporosis 127
CO and NO: Pollutants or Miracle Molecules? 150
VERY Big Molecules 155
Damascenone by Any Other Name Would Smell as Sweet 162
Kidney Stones: A Problems in Solubility 176
Batteries 184
Anemia—A Limiting Reagent Problem? 211
Energy from Food 225
Regulation of Body Temperature 242
Greenhouse Gases and Global Warming 260
Blood Pressure 263
CO2 as an Environmentally Friendly Solvent 280
Solid Hydrates—Salt + Water 292
Breathing and Oxygen Transport 298
Electrolytes, Fluid Replacement, and Sports Drinks 308
Timed-Release Drug Delivery Systems 317

GERD—Too Much Acid or Not Enough? 333
Acid Rain 342
Buffers in the Body: Acidosis and Alkalosis 355
Medical Uses of Radioactivity 372
Irradiated Food 379
Body Imaging 381
How Important Can a Methyl Group Really Be? 417
Surprising Uses of Petroleum 428
The Chemistry of Vision and Color 448
Enediyne Antibiotics: A Newly Emerging Class
of Antitumor Agents 466
Inhaled Anesthetics 492
Fetal Alcohol Syndrome: Ethanol as a Toxin 501
Chemical Warfare among the Insects 512
When is Toxicity Beneficial? 529
Calming a Stormy Mind: Amines as Anti-Anxiety
Medications 551
Medicinally Important Carboxylic Acids and Derivatives 568
Medications, Body Fluids, and the “Solubility Switch” 580
Protein Analysis by Electrophoresis 596
Proteins in the Diet 600
What Is Sickle-Cell Anemia? 602
Imperfect Collagen—An Unfortunate Event 617
Enzyme Inhibitors as Drugs 646
Vitamins, Minerals, and Food Labels 651
Enzymes in Medical Diagnosis 653
Cell-Surface Carbohydrates and Blood Type 674
Bacterial Cell Walls: Rigid Defense Systems 682

16

Carbohydrates and Fiber in the Diet 685
Plants and Photosynthesis 696
Harmful Oxygen Species and Antioxidant Vitamins 703
Basal Metabolism 705
Metabolic Poisons 717
Tooth Decay 731
The Biochemistry of Running 738
Diagnosis and Monitoring of Diabetes 742
Lipids in the Diet 755
Eicosanoids: Prostaglandins and Leukotrienes 769
The Liver—Clearinghouse for Metabolism 787
Fat Storage, Lipids, and Atherosclerosis 790
Gout: When Biochemistry Goes Awry 804
The Importance of Essential Amino Acids and Effects
of Deficiencies 808
Influenza: Variations on a Theme 832
The Polymerase Chain Reaction 848
DNA Fingerprinting 854
Homeostasis 868
The Blood–Brain Barrier 889
What’s in Your Blood Test? 899

MAStEring rEACtionS
Organic Chemistry and the Curved Arrow Formalism
How Addition Reactions Occur 456
How Eliminations Occur 483
Carbonyl Additions 527
How to Read Biochemical Reactions 629

420

HAnDS-on CHEMiStry
1.1 Chemical and Physical Changes 37
1.2 Mass and Density 51
2.1 Isotopes 83
2.2 Atomic Structure 92
3.1 Formulas for Ionic Compounds 122
3.2 Names of Ionic Compounds 124
4.1 Molecular Shape and Polarity 160
5.1 Chemical Equations and Units 175
5.2 Evidence of Chemical Reactions 178
6.1 Limiting Reagents 211
7.1 Energy from Food 226
8.1 Charles’s Law 265
9.1 Boiling Point Elevation 312
9.2 Osmosis 316
10.1 Acid-Base Reactions 347
11.1 Nuclear Power Plans 385
12.1 How Organic Chemistry Impacts Your Daily Life: Its
Presence in Everyday Products 399
13.1 Modeling Double Bonds, Restricted Rotation, and Cis–Trans
Isomerism 444
14.1 Modeling Molecules: Chirality, Superimposable, and
Non-Superimposable Molecules 498


Features
15.1 Modeling Cyclic Hemiacetals and Hemiketals: Common
Sugars 526

16.1 The Amine Functional Group in Common Medications 542
17.1 The Carboxyl Functional Group in Common
Medications 565
18.1 Models of Amino Acids 599
18.2 Methods of Denaturing Proteins 616
19.1 Enzymes in Food 626
19.2 Coenzymes in Vitamin Pills 629
20.1 Fisher and Haworth Projections 669
20.2 Carbohydrates in Food Labels 684

21.1 Estimating Caloric Need 706
22.1 Fermentation 734
22.2 Exercise Effect on Metabolism 737
23.1 Classic Fat Test 755
23.2 Model Cell Membrane 770
24.1 Heart Attack Symptoms 791
25.1 Determining Your Daily Protein Intake 798
26.1 DNA and RNA Models 831
27.1 Genetics of Common Hereditary Diseases 846
28.1 Tracking Hormone Effects on Daily Activities 877
29.1 Sports Drinks and Energy Bars 886

17


Preface
This textbook and its related digital resources provide students in the allied health sciences with a needed background in chemistry and biochemistry while offering a general context for chemical concepts to ensure that students in other disciplines gain an
appreciation of the importance of chemistry in everyday life.
To teach chemistry all the way from “What is an atom?” to “How do we get energy
from glucose?” is a challenge. Throughout our general chemistry and organic chemistry

coverage, the focus is on concepts fundamental to the chemistry of living things and
everyday life. In our biochemistry coverage, we strive to meet the further challenge of
providing a context for the application of those concepts in biological systems. Our goal
is to provide enough detail for thorough understanding while avoiding so much detail
that students are overwhelmed. Many practical and relevant examples are included to
illustrate the concepts and enhance student learning.
The material covered is ample for a two-term introduction to general, organic, and
biological chemistry. While the general and early organic chapters contain concepts
that are fundamental to understanding the material in biochemistry, the later chapters
can be covered individually and in an order that can be adjusted to meet the needs of the
students and the duration of the course.
The writing style is clear and concise and punctuated with practical and familiar
examples from students’ personal experience. Art work, diagrams, and molecular models are used extensively to provide graphical illustration of concepts to enhance student
understanding. Since the true test of knowledge is the ability to apply that knowledge
appropriately, we include numerous worked examples that incorporate consistent
problem-solving strategies.
Regardless of their career paths, all students will be citizens in an increasingly technological society. When they recognize the principles of chemistry at work not just in
their careers but in their daily lives, they are prepared to make informed decisions on
scientific issues based on a firm understanding of the underlying concepts.

New to This Edition
The major themes of this revision are active learning, an increased focus on clinical
examples, updates based on current teaching and research findings, and digital innovations designed to engage and personalize the experience for students, all of which are
accomplished in a variety of ways:
• NEW! Chapter opening photos and vignettes with an increased clinical focus have
been added to provide a theme for each chapter and to strengthen connections between the concepts and applications in Chemistry in Action features in the chapter.
• NEW! Chapters now have a more focused roadmap that begins with specific
learning objectives and ends with a summary study guide that addresses these initial goals and offers students targeted problems designed to help them assess their
ability to understand those topics.
• NEW! Hands-On Chemistry boxes offer students an opportunity to solidify their

understanding of chemistry through elementary experiments that can be safely
done in their living spaces with household items. Many students strongly benefit
from kinesthetic activities, and regardless of whether this is their “preferred” style,
the evidence suggests that variety in exposure to concepts is by itself tremendously
valuable.
• NEW! Interactive Worked Examples have been developed and are identified in
the text with special icons.
• NEW! In-chapter questions have been added to the Chemistry in Action and
Mastering Reactions features to reinforce the connection between the chapter
content and practical applications.

18


Preface

• NEW! Concept Maps have been added to most chapters, and others have been
modified to draw connections between general, organic, and biological chemistry.
• Updated Concept Links offer visual reminders for students that indicate when
new material builds on concepts from previous chapters or foreshadow
related material that will be explained in more detail in future chapters.
• Updated questions in the end-of-chapter section build on Concept Links and
require students to recall information learned in previous chapters.
• Chemistry in Action features (many with a clinical focus) extend the discussion of
major chapter topics in new ways, providing students with enhanced perspective on
core concepts relevant to their future careers.
• All Learning Objectives tied to EOC problem sets: Chapter summaries include
a list of EOC problems that correspond to the learning objectives for a greater connection between problems and concepts.
• NEW! Group Problems at the end of every chapter are ideally used in class to get
students to carefully think about higher level problems, such as how concepts fit

together, or to put the concepts they have learned to use in a clinical application.
• Chapters 1 and 2 have been restructured: Chapter 1 focuses on building math
skills, while Chapter 2 focuses on matter, atomic structure, and the periodic table.
• An expanded discussion of stereochemistry and chirality has been moved to
Chapter 14 to allow instructors and students more time to get used to this challenging topic before coming across it again in biochemistry. The concept of symmetry
has also been introduced in this section.
• Chapter 16 is now the chapter on amines, allowing the discussion of organic
bases and acids (Chapter 17) to flow together, whereas in the seventh edition, they
were separated by the ketone and aldehyde chapter, which is now Chapter 15.
• Chapter 20 is now the chapter on carbohydrates, preceding the discussion of
energy generation (now Chapter 21) and carbohydrate metabolism.
• Chapter 25 is now the chapter on protein metabolism, completing the discussions
of metabolism before addressing DNA (Chapter 26) and Genomics (Chapter 27).
• The Use of SI Units: All the units in this edition have been converted to SI units,
except where a non-SI unit is commonly used in scientific, technical, and commercial literature in most regions.

Organization
General Chemistry: Chapters 1–11 The introduction to elements, atoms, the periodic
table, and the quantitative nature of chemistry (Chapters 1 and 2) is followed by chapters
that individually highlight the nature of ionic and molecular compounds (Chapters 3 and 4).
The next three chapters discuss chemical reactions and their stoichiometry, energies,
rates, and equilibria (Chapters 5, 6, and 7). Topics relevant to the chemistry of life follow: Gases, Liquids, and Solids (Chapter 8); Solutions (Chapter 9); and Acids and Bases
(Chapter 10). Nuclear Chemistry (Chapter 11) closes the general chemistry sequence.
Organic Chemistry: Chapters 12–17 These chapters concisely focus on what students
must know in order to understand biochemistry. The introduction to hydrocarbons (Chapters
12 and 13) includes the basics of nomenclature. Discussion of functional groups with single
bonds to oxygen, sulfur, or a halogen (Chapter 14) is followed by introducing aldehydes
and ketones (Chapter 15), where a double bond between carbon and oxygen plays a key
role in their chemistry. A short chapter on organic bases, the amines, which are so important
to the chemistry of living things and drugs (Chapter 16) follows. Finally, the chemistry of

carboxylic acids and their derivatives (esters and amides) is covered (Chapter 17), with a
focus on similarities among the derivatives. Attention to the mechanisms by which organic
reactions occur and the vernacular used to describe them has been retained in this edition.
Stereochemistry, which is key to the understanding of how biological molecules function as
they do, has been moved to Chapter 14 in this edition, allowing students more exposure to
this complicated topic before reaching the biological chemistry section of this text.
Biological Chemistry: Chapters 18–29 Rather than proceeding through the complexities of protein, carbohydrate, lipid, and nucleic acid structure before getting to the roles

19


20

Preface

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

Chapter-by-Chapter Changes
Coverage of general Chemistry
The major revisions in this section involve reorganization or revision of content to
strengthen the connections between concepts and to provide a more focused coverage

of specific concepts. Concept Maps, included in all general chemistry chapters, reinforce the relationship between topics.
Specific changes to chapters are provided below:
Chapter 1

• Content related to elements and the periodic table was moved to Chapter 2.
• Information on shape-memory alloys was added to the Chemistry in Action
“Temperature Sensitive Materials” and the clinical information in the Chemistry
in Action “Aspirin” and “A Measurement Example: Obesity and Body Fat” was
updated.
Chapter 2

• Content from Chapter 1 on matter and the periodic table was moved to Chapter 2 to
provide a more comprehensive and concentrated focus in the chapter.
• Information on the periodic table has been updated to reflect recent discoveries.
• A new Chemistry in Action, “Essential Elements and Group Chemistry,” has been
added. One Chemistry in Action was eliminated and “Are Atoms Real?” and “Atoms and Light” were revised to strengthen the connections between chapter content
and clinical applications.
Chapter 3

• Sections have been reorganized to provide a more logical progression from ions
and ion formation to the naming of ions and ionic compounds and finishing with
the properties of ionic compounds. Coverage on the octet rule was also expanded
and moved to earlier in the chapter.
• The Chemistry in Action “Salt” was streamlined to enhance clarity and relevancy
to the student, and clinical information added.
Chapter 4

• Additional tables and text have been added, including a new Worked Example on
coordinate covalent bonds, and some figures have been modified to enhance
student learning of molecular models and molecular shape.

• Both the Chemistry in Action “VERY Big Molecules” and “Damascenone by Any
Other Name Would Smell as Sweet” were updated with new clinical applications
and photos.


Preface
Chapter 5

• Content from Section 5.3 from the seventh edition (Classes of Chemical Reactions)
has been distributed to the individual sections dealing with the types of reactions:
5.3 (Precipitation Reactions), 5.4 (Neutralization Reactions), and 5.5 (Redox
Reactions).
• Both Chemistry in Action were streamlined, and the Chemistry in Action “Batteries” was updated with relevant, new clinical applications.
Chapter 6

• The limiting reactant and percent yield discussion was expanded and clarified with
new, specific examples to enhance student understanding.
• One Chemistry in Action was eliminated, and others were revised to strengthen the
connections between chapter content and practical applications.
Chapter 7

• The quantitative aspects of spontaneity, entropy, enthalpy discussions (including
the Worked Example) were revised to enhance clarity, and the Worked Example on
drawing energy diagrams was simplified.
• One Chemistry in Action was eliminated, and the Chemistry in Action “Regulation
of Body Temperature” was updated with new, practical applications.
Chapter 8

• The qualitative discussions on enthalpy and entropy in Section 8.1 were significantly streamlined.
• Section 8.13 from the seventh edition (Water: A Unique Liquid) has been deleted,

and the content has been distributed to other sections to provide relevant examples
for key concepts.
• The title to the last section (Section 8.14) was changed to “Change of State
Calculations” to more clearly identify the focus for this section and to distinguish
the content from the more general discussion on the changes of state of matter in
Section 8.1.
• The Chemistry in Action “CO2 as an Environmentally Friendly Solvent” was
updated with new, cutting-edge information on supercritical fluids as they relate to
allied health.
Chapter 9

• Section 9.3 (Solid Hydrates) was modified and converted into a new Chemistry in
Action, “Solid Hydrates—Salt + Water.”
• Section 9.10 from the seventh edition (Electrolytes in Body Fluids) has been modified in the eighth edition and combined with Section 9.9 (Ions in Solution: Electrolytes). References to gram-equivalents have been removed.
• The Chemistry in Action “Time-Release Drug Delivery Systems” was updated with
new, clinical content.
Chapter 10

• Sections 10.1 (Acids and Bases in Aqueous Solution) and 10.3 (The BronstedLowry Definition of Acids and Bases) have been combined to highlight the
relationship between the various definitions of acids and bases.
• The information in Section 10.2 (Some Common Acids and Bases) has been
condensed into Table 10.1.
• Section 10.7 (Measuring Acidity in Aqueous Solution: pH) and Section 10.9
(Laboratory Determinations of Acidity) have been combined to strengthen the
connection between these concepts.
• Section 10.12 (Some Common Acid-Base Reactions) has been moved forward in
the chapter, and Sections 10.10 (Buffer Solutions), 10.14 (Acidity and Basicity of

21

22

Preface

Salt Solutions), and 10.13 (Titrations) have been rearranged to improve the logical
progression of these concepts.
• The Chemistry in Action “Acid Rain” was updated with new statistics, maps, and
bar graphs.
Chapter 11

• Section 11.6 (Radioactive Decay Series) was abbreviated and combined with
Section 11.5 (Radioactive Half-Life). A new, additional Worked Example on
half-lives was added as metadata indicated students struggled with this concept.
• Sections 11.8 (Detecting Radiation) and 11.9 (Measuring Radiation) were
condensed and combined.

Coverage of organic Chemistry
Since organic and biological chemistry are so tightly allied with one another, a major emphasis has been placed on the introduction of biologically significant molecules throughout
the organic chapters in this edition. Emphasis on making the fundamental reactions that organic molecules undergo much clearer to the reader, with particular attention on those reactions encountered again in biochemical transformations has been retained in the Mastering
Reactions feature boxes. This boxed feature discusses in relative depth the “how” behind a
number of organic reactions. Mastering Reactions has been designed so that they may be
integrated into an instructor’s lecture or simply left out with no detriment to the material in
the text itself, to accommodate those that do not wish to discuss the mechanisms of organic
reactions. More emphasis on the use and evaluation of line-angle structure for organic molecules has been added, as this is incredibly important when discussing biomolecules. New
to this edition is the inclusion of a more detailed examination of stereochemistry and chirality; its new placement at the end of Chapter 14 will allow students more time to grasp these
concepts, but will also allow instructors who do not wish to discuss it to easily omit them.
New and updated application features (Chemistry in Action) have been included in almost
all the organic chapters, stressing the clinical aspects of the different classes of organic
molecules and reflecting current understanding and research into the topics covered. Additionally, each chapter includes a new supplementary feature known as Integrated Worked

Examples, which will provide students with tutor-like walkthroughs of topics and reactions
they need to be familiar with before heading into the biological chemistry sections of this
text.
Other specific changes to chapters are provided below:
Chapter 12

• Several figures were revised and/or simplified for clarity and to enhance understanding. Art was added to help students synthesize complex topics where visuals
were previously lacking.
• Table 12.1 has been reworked to highlight the atoms responsible for each functional group.
• Table 12.2 (Common Abbreviations in Organic Chemistry) has been added.
• A three-step mechanism (initiation, propagation, and termination) was added to the
halogenation section along with a new Worked Example on drawing halogenated
isomers; this Worked Example will be useful throughout the organic chapters in
learning to draw isomers of other organic molecules.
• A new Chemistry in Action discussing biological methylation, “How Important
Can a Methyl Group Really Be?,” has been added, and the Chemistry in Action
“Surprising Uses of Petroleum” was updated with new clinical information.
• There is an expanded functional group concept map that will aid in classifying
functional groups; this will be included at the end of each of the organic chapters,
with coloring added as each functional group family is discussed.


Preface
Chapter 13

• Expanded use and discussion of line structures has been added throughout.
• A new Chemistry in Action discussing biologically active alkynes, “Enediyne
Antibiotics: A Newly Emerging Class of Antitumor Agents,” has been added.
Chapter 14

• Table 14.1 (Common Alcohols and Their Uses) has been added, replacing and expanding on what was previously Section 14.3, making it easier for students to digest.
• A new and expanded discussion of stereochemistry and chirality has been added
(Section 14.10), moving the introduction of these topics from Chapter 18 to a more
appropriate location in the text.
• Two new Worked Examples, one on drawing alcohols, have been added.
• A new Chemistry in Action discussing the harm ethanol has on fetuses, “Fetal Alcohol Syndrome: Ethanol as a Toxin,” has been added.
Chapter 15

• Chapter 15, known previously as the amine chapter, now covers aldehydes and
ketones.
• The section on common aldehydes and ketones has been shortened by the inclusion
of Table15.2 (Common Aldehydes and Ketones and Their Uses) making it easier
for students to read.
• The Addition of Alcohols to Aldehydes and Ketones section was revised to clarify
the distinction between hemiketals and hemiacetals.
• Worked Examples and problems have been modified to include the early introduction of carbohydrates.
• A new Chemistry in Action discussing anticancer drugs, “When Is Toxicity Beneficial?,” has been added.
Chapter 16

• This is now the amine chapter, which was Chapter 15 in the seventh edition.
• The section on alkaloids has been simplified by the inclusion of Table16.2 (Some
Alkaloids and Their Properties) making it easier for students to digest the material.
• A new Worked Example on ammonium ions as acids has been included.
• A new Chemistry in Action discussing antidepressants, “Calming a Stormy Mind:
Amines as Anti-Anxiety Medications,” has been added.
Chapter 17

• The concept of pKa is discussed in Section 17.2; in addition, Table 17.2 now contains pKa values for the acids listed.
• Section 17.3 in the seventh edition has been expanded and converted into a new
Chemistry in Action, “Medicinally Important Carboxylic Acids and Derivatives.”

• The Worked Example on acid anhydrides has been removed and their coverage is
limited in this edition.
• The Chemistry in Action “Medications, Body Fluids, and the ‘Solubility Switch’”
that was in Chapter 15 in the seventh edition has been updated and moved to the
end of this chapter.

Coverage of Biological Chemistry
Biological chemistry, or biochemistry as professionals refer to the subject, is the chemistry of organisms and particularly chemistry at the cellular level—both inside and outside the cell. The foundations of biological chemistry are found in inorganic and organic
chemistry, the first two major topics of this textbook. Biological chemistry integrates

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24

Preface

inorganic and organic chemistry in the study of biological molecules, many of which are
large organic molecules with specific cellular roles. As you will see in the following chapters, biological molecules undergo the same reactions studied in the organic chemistry
part of this book, and the fundamentals of inorganic chemistry are also important in cells.
Chapter 18

• The chapter was reorganized for a smoother flow that is more pedagogically sound.
We now present an overview of proteins first, then discuss amino acids, peptides
and peptide bonds, followed by protein structure and chemical properties. The one
letter code for each amino acid was added to Table 18.3.
• The chirality discussion is limited to amino acids (the rest of this discussion moved
to Chapter 14).
• Diagrams of the specific examples of the forces involved in tertiary protein structure were added.
Chapter 19

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•
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•
•

Two new tables and a revised discussion enhance the “Enzyme Cofactors” section.
The enzyme classification section has a new table describing each classification.
The vitamins, minerals, and antioxidants section was streamlined for clarity.
A Mastering Reactions on how to read biochemical reactions has been added.
The Chemistry in Action “Enzymes in Medical Diagnosis” was updated to reflect
current blood chemistry tests used in diagnosis of a heart attack.

Chapter 20

• This is now the carbohydrates chapter.
• Two new tables, one on important monosaccharides and another on disaccharides,
make this content easy for students to digest. Both polysaccharides sections were
streamlined and combined into one section.
Chapter 21

• This is now the generation of biological energy chapter.
• The first two sections were streamlined by reducing much of the review material
from Chapter 7 (a Concept to Review link was added in place of lengthy narrative,
directing students back to where they can review the material if necessary) and
combined into one section.
• The citric acid cycle is now explained equation by equation with the description of
each step directly above the equation for better student understanding.
• The section on reactive oxygen species has been converted into a new Chemistry in

Action, “Reactive Oxygen Species and Antioxidant Vitamins.”
• The discussion of “uncouplers” has been integrated into a new Chemistry in
Action, “Metabolic Poisons.”
Chapter 22

• The discussion of the steps in glycolysis was improved by explicitly splitting the
descriptions of the reactions into individual steps.
• Most of the discussion of glucose metabolism in diabetes has been moved to a revised and now comprehensive Chemistry in Action “Diagnosis and Monitoring of
Diabetes.”
Chapter 23

• The Phospholipids and Glycolipids section was reorganized to ensure a smoother,
more logical presentation of concepts.
• The Chemistry in Action “Lipids in the Diet” was updated to include some information from the deleted Chemistry in Action “Butter and Its Substitutes” as well as
updated dietary and obesity statistics.