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Table of Contents vii
Classifying Matter 30
The Periodic Table 32
Molecular Models 73
Representing Molecules 74
Radicals 80
Expanded Valence 80
Features
CHEMISTRY AND YOUR HEALTH Omega-3 Fatty Acids 112
SCIENCE IN ACTION: How Do We Know the Structures of Molecules? 118
Alcohol 130
Ether 130
Aldehyde 132
Ketone 133
Carboxylic Acid 133
Ester 135
A Summary of Functional Groups Containing Oxygen Atoms 136
Features
CHEMISTRY AND YOUR HEALTH How Does Your Body Metabolize
Alcohol? 134
CHEMISTRY IN YOUR LIFE Chemical Signaling in the Brain 139
SCIENCE IN ACTION: Chemical Synthesis of Antibiotics 148
Features
SCIENCE IN ACTION: Measuring the Sizes of Polymers 204
CHEMISTRY AND YOUR HEALTH Insulin and Diabetes 221
Features
CHEMISTRY AND YOUR HEALTH What Is “Freebase” Cocaine? 331
SCIENCE IN ACTION: Don’t Try This at Home: Discovering the Cause
of Stomach Ulcers 350
Features
SCIENCE IN ACTION: How Did Scientists Crack the Genetic Code? 406
CHEMISTRY AND YOUR HEALTH Human Insulin for Diabetes Therapy 412
How Do We Know that the Drugs We Take Are Safe and Effective? 472
The Stages of Drug Development and Approval 474
Features
SCIENCE IN ACTION: Studying Cells with Microscopes 457
CHEMISTRY AND YOUR HEALTH How Do Bacteria Keep Us
Healthy? 468
CHEMISTRY IN YOUR LIFE Why Can a Popular Painkiller Make You
Sick? 476
Glossary 563
Credits 573
Index 577
Preface
Why are many bacteria now resistant to antibiotic drugs that were effective in
the past? We pose this question in the opening pages of Chemistry: The Molecules
of Life. Providing an answer, which is the main focus of Chapter 1, requires an
understanding of pharmaceuticals, biological molecules, and bacterial cells. This
interdisciplinary case study serves as an introduction to our innovative approach
to teaching chemistry in the 21st century. Instead of viewing chemistry as an
isolated discipline, we emphasize its intersection with biology and medicine. By
focusing on “the molecules of life,” we demonstrate how chemistry is vital for
understanding human health. Chemistry: The Molecules of Life introduces non-
science majors to the fundamental chemical principles of biological molecules
and everyday life.
We have written this textbook for students who have a variety of academic and
career interests, not all of which necessarily align with the sciences or health pro-
fessions. We believe that all undergraduate students—not just science majors—
need to be educated about scientific knowledge and reasoning in order to make
informed decisions about their personal well-being and important societal issues.
Have you ever thought about how antibiotic medications work, or why it is im-
portant to take the entire dose that the doctor prescribed? Many of us also take
a vitamin supplement, often in the form of a daily multivitamin. Do you know
what roles these vitamins play in our body, or why the recommended daily dose
for some vitamins is much lower than for others? Does the federal government
regulate vitamin supplements with the same scrutiny that it applies to pharma-
ceuticals? Throughout this book, we examine relevant topics such as these and
many more.
Scientific knowledge is constantly advancing. Almost daily, we hear or read
stories in the media about a new scientific discovery, a new interpretation of what
foods or activities are good or bad for us, or the societal impact of a new medical
breakthrough. Given this rapid progress, we cannot learn science as a collection
of facts to be memorized. After a short time, our knowledge will quickly become
outdated. Instead, we need to understand how scientists investigate the natural
world—the methods they use, the evidence they generate, and the conclusions
they make based on that evidence. Throughout this textbook, we describe exam-
ples of scientific discovery. By analyzing these case studies, students will develop
the critical thinking skills necessary to thoughtfully evaluate scientific informa-
tion that is presented in the news media or obtained from other sources.
Approach
In Chemistry: The Molecules of Life, we use the chemistry of life to introduce,
explain, and apply foundational chemical principles. Each chapter begins with a
framing question to stimulate students’ interest and motivate them to explore the
chapter content that is necessary to answer the question. Many of these questions
are pertinent to students’ health, whereas others address foundational scientific
topics. The scientific content in each chapter is introduced on a “need-to-know”
basis that is related to the framing question. By the end of the chapter, students
will be able to answer the question using the chemical concepts they have learned.
xix
xx Preface
In addition to the core content, each chapter contains features that illustrate
important themes. Chemistry and Your Health demonstrates the relevance of the
chapter material by applying chemical concepts to students’ health. Examples
include omega-3 fatty acids, alcohol metabolism, and the potential hazards of
indoor tanning beds. Science in Action develops students’ understanding of scien-
tific investigation—in other words, how do we know what we know? Some of these
features focus on experimental techniques, such as using a mass spectrometer to
measure the mass of atoms, or the application of X-ray diffraction to determine
the structure of a molecule. Other examples describe an important historical ex-
periment, such as Antoine Lavoisier’s investigation regarding the role of atmo-
spheric oxygen in chemical reactions. Chemistry in Your Life, which is included in
selected chapters, uses chemical principles to explain students’ life experiences.
One such feature describes why chili peppers taste “hot,” whereas another ex-
plains why hydrogen peroxide bubbles when you put it on a cut.
Overview of Chapters
Chapter 1 uses the example of antibiotic-resistant bacteria as an interdisciplinary
overview of the molecules of life. This chapter also includes Textbook Previews
that highlight the chapters in which scientific topics will be examined in greater
depth.
The next four chapters of the textbook illustrate how atoms form the building
blocks of molecules. Chapter 2 examines the chemical elements and the structure
of atoms, including examples of elements that are beneficial or harmful to human
health. Chapter 3 explains how and why atoms form chemical bonds. Chapter 4
investigates the unique chemistry of carbon and why life is “carbon based.” Chap-
ter 5 explores the remarkable diversity of molecular structures that can be made
using only a handful of different atoms.
The textbook contains two chapters that describe the formation of molecules.
Chapter 6 shows how chemical reactions produce changes in matter and energy,
along with how these changes can be described in quantitative terms. Chapter 7
uses the example of sugars to illustrate the construction of very large molecules
from multiple copies of smaller components.
The following four chapters describe the chemistry of water and solutions.
Chapter 8 explains the unusual properties of water as deriving from interactions
among H 2O molecules. Chapter 9 examines the behavior of molecules and ions in
solution, with a focus on various types of vitamins. Chapter 10 provides a quan-
titative description of concentration, with applications to human health. Chapter
11 describes the chemistry of acids and bases, including the pH scale for measur-
ing acidity.
The final four chapters of the textbook explore the molecular basis of life.
Chapter 12 examines DNA from the perspective of the scientists who contributed
to the discovery of its molecular structure. Chapter 13 explains how information
stored within DNA is converted into various proteins, which perform most of
the essential biological functions of cells. Chapter 14 uses the example of lactose
intolerance to introduce the chemistry of enzymes and how they function as bi-
ological catalysts by accelerating chemical reactions. Chapter 15 returns to the
theme of Chapter 1, antibiotics, by investigating of how these drugs work against
various types of bacteria, with a special focus on the resurgent global problem of
antibiotic-resistant tuberculosis.
SUPPORT PACKAGE
Oxford University Press has created a comprehensive set of ancillary resources to
accompany Chemistry: The Molecules of Life. These resources are designed to help
students master the concepts introduced in the text and to assist instructors in
making chemistry accessible to those who are not science majors.
For Students
• Laboratory Manual: Written by the authors in conjunction with Bill
Gunderson, Assistant Professor of Chemistry at Hendrix College, this labo-
ratory manual includes more than 20 laboratory exercises that relate directly
to topics explained in the text. Each laboratory exploration provides an over-
view of the experiment, a detailed description of the procedures, and data
sheets that students use to record their observations and answer questions.
For Instructors
• Sapling Learning Online Homework System: Sapling Learning’s
online homework system includes more than 400 homework questions
designed to test students’ understanding of key concepts from the text. It
xxii Preface
Acknowledgments
Creating a textbook is a truly collaborative endeavor. We would like to thank the
wonderful team at Oxford University Press USA for their encouragement, advice,
and patience during the gestation of this project. First, we are grateful to Jason
Noe, senior editor, for serving as our guide from the initial prospectus to the
completion of the book. This project could not have reached the finish line with-
out his unwavering support. We also benefitted immensely from the insightful
comments provided by our development editors, Anne Kemper, Naomi Fried-
man, and Maegan Sherlock. Andrew Heaton, associate editor, reviewed our
text as it progressed through several drafts and then helped to prepare our final
manuscript. Production editor Micheline Frederick, production team leader The-
resa Stockton, and production manager Lisa Grzan worked together on a tight
deadline to turn the manuscript into a finished book. Wesley Morrison provided
eagle-eyes scrutiny of the pages during the proofreading stage. We are grateful
to the design team led by Michele Laseau, art director, for the beautiful textbook
design and page layout and Dragonfly Media Group’s team of Craig Durant, Cait-
lin Duckwall, and Rob Duckwall, for the imaginative artwork they created. We
would also like to thank Patrick Lynch, editorial director; John Challice, vice
president and publisher; Frank Mortimer, director of marketing; David Jurman,
marketing manager; Clare Castro, marketing manager; Ileana Paules-Brodet,
marketing assistant; Meghan Daris, market development associate; and Bill Mar-
ting, national sales manager.
Other individuals also made important contributions to the project. Robert
Weiss provided insightful editorial comments on many chapters. Anna Powers,
Tania Lupoli, and Jennifer Sniegowski supplied ideas for end-of-chapter questions.
Jennifer Lee invested many hours creating the art manuscript. Veronica Murphy
gave valuable assistance by checking calculations, appendices, and page proofs.
Our faculty colleagues at New York University, Bobby Arora, Daniela Buccella,
and John Halpin, provided expert advice about specific chemistry topics.
We wish to express our deep appreciation to the many friends and colleagues
who endured our fixation on this textbook for more years than we like to admit.
We are grateful to George and the Chicken for their weekly welcome at our local
diner. Finally, we thank Diana and Martha for supporting us throughout the
entire journey.
Preface xxiii
Manuscript Reviewers
Throughout the development of this textbook, we have benefited from the
insightful comments by many faculty members who provided expert reviews of
the chapters. They not only informed us when a topic was not expressed clearly
but also provided valuable suggestions for how to communicate it more effec-
tively. The names of these individuals and their affiliations are listed below. We
are enormously grateful to them for their guidance and advice.
“You see,” the ship owner began, as soon as he was assured of the
attention of his audience, “I have had my eye on these whaleback
steamers from the start. Three years ago, you know, nobody but
Captain Alexander MacDougall, the inventor, knew anything about
them.
“We are altogether too conservative here in the East,” continued
Adoniram warmly. “It takes the Westerners to get hold of new things,
and practically test them. These whalebacks are a Western idea and
were first used and tested on the Great Lakes.
“You don’t seem to realize, Caleb, that the boat was never built
which could sail as easily as those whalebacks. In the heaviest gales
they only roll slightly, as a log would at sea. The waves can beat
against the curved steel sides of the craft as much as they like, or
wash clean over her; but the boat is not affected by them in the
least.”
“It’s the most wonderful thing I ever heard of,” Brandon declared.
“They are wonderful boats, as you will declare, yourself, when you
see Number Three, tomorrow,” Adoniram returned. “My whaleback is
265 feet long, 38 feet beam, and 24 feet deep. She is warranted to
carry 3,000 tons of grain on a sixteen and one half foot draft. You
see, for her size, she carries an enormous cargo, for between the
collision bulkhead forward, and the bulkhead in front of the engine
room aft, the whole inside of the craft is open for lading.
“But my scheme—the reason I bought this vessel, in fact—is this,”
went on Mr. Pepper.
He hesitated a moment, and looked just a little doubtfully at Caleb.
“I presume this is what you will call a ‘crazy idea,’ Caleb,” he said.
“Several months ago my attention was drawn to the fact that great
numbers of these derelicts now afloat in the Atlantic, north of the
equator, are richly laden merchant vessels on whose cargoes and
hulls a large salvage might be demanded by any vessel towing them
into port.
“Now and then, you know, it happens that somebody does recover a
derelict with a valuable cargo. In these times, when the crews of
American ships, and even many of the officers, are ignorant and
untrustworthy fellows, lacking altogether the honor arm
perseverance which were characteristics of sailors forty years ago (I
don’t say that all are so, but many) under these circumstances, I say,
many a vessel which might be worked safely into port, is abandoned
in mid ocean by the frightened crew.
“With a vessel like Number Three one could recover and tow into
port many of these hulks, and net a large salvage from the owners.
Vessels which would not be worth saving themselves, might still
contain articles which it would pay to transfer to the hold of the
whaleback, before they were sunk; for it was my intention to have
Number Three destroy all the wrecks which are not worth saving.
“I have even sounded the Washington officials in the matter of aiding
me in the work of destroying these derelicts; but I find that the
Hydrographic Office is trying to get an appropriation from Congress
to build a vessel of about 800 tons burden, especially for the work of
blowing up these wrecks. Until that matter is decided, of course I can
get no bonus on what I do.
“Nevertheless,” Mr. Pepper continued, “I believe that there is money
enough in it to amply reward me for my outlay. Why, look at that New
England whaler which found the British ship Resolute fast in the ice
of Melville Bay in the summer of ’55.
“She was one of three vessels sent out by the British government to
find Sir John Franklin. She was ‘nipped’ by the ice in the winter of ’51
and was abandoned. The whaler brought her to New London, and
Congress bought her for $200,000 salvage and sent her to England.
Of course, I shouldn’t expect to get many such prizes as that,” and
the little man laughed, “but I do expect to make a handsome profit on
the venture.”
“Take, for instance, the case of the Silver Swan. I’ll make you a
proposition, Brandon, and you see if it isn’t a fair one. Caleb shall
judge himself. I’ll send the whaleback out after the brig at my own
expense. If we are successful and find the derelict and tow her to
port, I will take the cargo (I know it to be a valuable one) for my pains
—of course, not including the diamonds, which are your own
personal property, my boy. The brig herself is Caleb’s, any way,
according to the terms of your father’s will. Now what do you say?”
“I say it’s a good offer!” exclaimed Caleb, slapping his thigh heartily.
“You’re a man and a gentleman, Adoniram. And far from thinking this
scheme of yours crazy, I think well of it—mighty well.”
“That’s because it ‘hits you where you live,’ as the saying is,”
returned Mr. Pepper, smiling slily.
“Oh, I don’t know anything about whalebacks,” began Caleb.
“But you will,” the merchant declared, interrupting him. “I haven’t got
through with my proposition yet.”
“Fire ahead, old man,” said Caleb puffing steadily on his pipe.
“Well, then, first I want you for the captain of the steamer, Caleb.”
“Yes, so I supposed,” remarked the mate of the Silver Swan
imperturbably. “What else?”
“I want Brandon for second mate.”
“Me?” exclaimed Don. “Why, I never was aboard a steamship in my
life.”
“Oh, that doesn’t make any difference, Don,” returned Caleb
sarcastically. “It would be just like him (if he wanted to) to send the
vessel out with every blessed one of the crew landlubbers. It don’t
make a particle o’ difference.”
“Now, Caleb,” said the merchant deprecatingly.
“No, Adoniram, we can’t do it. The boy knows nothing at all about a
steamship, and I know but little more.”
“You’ve been mate on a steamer, Caleb.”
“On a dredger, you mean,” returned the old sailor, in disgust.
“There’s no reason why you can’t do it—both of you,” the ship owner
declared. “If I’m satisfied, you ought to be. I’ve already engaged
Lawrence Coffin for mate.”
“Coffin!” ejaculated Caleb, his face lighting up, as he forgot to pull on
his pipe in his interest. “Got him, eh? Well, that puts a different
complexion on the matter. I could sail the Great Eastern with
Lawrence Coffin for mate.”
“I thought so,” said Mr. Pepper, laughing gleefully. “Then I’ve got a
man by the name of Bolin for third. He’s a good man, and knows his
business, too.”
“That would make Don’s duties pretty light,” said Caleb reflectively.
“Of course. I shall put in rather a larger crew than a whaleback
usually carries—fourteen at least,” Mr. Pepper added; “to handle the
cargoes I shall expect the steamer to recover.”
“Well, well,” said Caleb, rising; “let’s sleep on it. It’s never best to
decide on anything too quickly.”
“If you’ll take up with my offer,” concluded the merchant, rising, too,
“the craft can be made ready, and you can get away this day week.”
“Let’s think it over,” repeated the old sailor, bound not to be hurried
into the business; but Don went to bed so excited by the prospect
that it was hours before he was able to sleep.
“Did a fellow ever have a better chance for fun and adventure?” was
his last thought as he finally sank into a fitful slumber.
CHAPTER XXII
INTO BAD COMPANY
“Here we are, mister,” said the ex-clerk; “see, there’s the sign—New
England Hotel. Did you expect to find your runaway nephew here?”
“No-o,” replied old Arad Tarr, eying the place with a good deal of
disfavor.
“See here,” said Weeks slowly, “I’ve been trying to remember
whereabouts I’ve heard that name ‘Brandon’ before. It’s not a
common name, you know.”
“No, ’taint common. D’ye thing ye’ve seen Brandon since he’s been
here in New York? He’s only been here two days, I reckon,” said old
Arad eagerly.
“Perhaps.”
“Where was he?” queried the old man. “I’m his lawful guardeen, an’
I’m a-goin’ ter hev him back, now I tell ye!”
“Let’s see; his name is Brandon Tarr, isn’t it?”
“That’s it; that’s it,” Arad declared.
“And he came from Chopmist, Rhode Island?”
“Sartin. You must have seen him, mister.”
“I guess I have,” said Weeks reflectively. “He was the son of a
Captain Horace Tarr, lost at sea on the Silver Swan not long ago,
eh?”
“The very feller!” cried Arad, with manifest delight.
“Then I guess I can help you find him,” declared Weeks cheerfully.
“Let’s go inside and I’ll tell you how I happened to run across him. It’s
not a very nice looking place, this isn’t; but they know me here and it
won’t be safe for them to treat any of my friends crooked.”
The old man, who had forgotten all about bunco men and their ilk in
his anxiety to recover his nephew, followed him into the bar room.
The place was but poorly patronized at this hour of the day, and with
a nod to Brady, who, his face adorned with a most beautiful black
eye, was behind the bar, Weeks led the way to an empty table in the
further corner.
“What’ll you an’ your friend hev ter drink?” inquired Mr. Brady, with
an atrocious grin.
“Oh, a bottle of sarsaparilla,” responded Weeks carelessly, and when
the bull necked barkeeper had brought it, the ex-clerk paid for the
refreshment himself.
Old Arad had looked rather scared at the appearance of the bottle.
His mind at once reverted to the stories he had read in the local
paper at home (which paper he had borrowed from a neighbor, by
the way) of countrymen being decoyed into dens in New York and
treated to drugged liquor.
But as Weeks allowed the bottle to stand on the table between them
untouched throughout their conference, the old man felt easier in his
mind.
“Ye say ye’ve seen Brandon?” inquired Arad, when Jack Brady had
returned to his position behind the bar, and there was nobody within
earshot.
“Yes. I’ll tell you how it was. You see, Mr. Tarr—that’s your name,
isn’t it?—I have a position in a shipping merchant’s office as clerk.
The office is—er—closed today, so I am out. This office is that of
Adoniram Pepper & Co. Ever hear of them?”
Old Arad shook his head negatively.
“Pepper was a great friend of this Brandon’s father, so I understand.”
“Mebbe,” snarled the farmer. “Cap’n Tarr’s friends warn’t my friends.”
“No? Well, your nephew steered straight for Pepper’s office, and I
believe that he’s staying at the old man’s house now—he and a man
by the name of Caleb Wetherbee.”
“Caleb Wetherbee? Gracious Peter!” ejaculated the old man. “Hez
he found him so soon.”
Mr. Weeks nodded briefly.
“This Wetherbee was mate of the Silver Swan.”
“That’s the man,” muttered Arad hopelessly.
“I take it you didn’t want your nephew and this Wetherbee to meet?”
suggested Weeks shrewdly.
“No—o——well, I dunno. I—I’m erfraid ’twon’t be so easy to git
Brandon back ter the farm ef he’s found this mate.”
“Perhaps we can fix it up,” said Weeks cheerfully.
“D’ye think so?”
“Let’s see; are you his legal guardian?”
“Yes, I be,” declared Arad savagely; “on’y the papers ain’t made
aout.”
“I don’t really see, then, how you can bring it about until you are
appointed,” said Mr. Weeks slowly.
“I jest kin!” asserted Arad, with confidence. “I gotter warrant here for
him.”
“Whew!” The astute Weeks looked at the old sinner admiringly. “Well,
well! you are a smart one. What’s the charge?”
“Robbing me,” responded the old man. “The day he run away he
took ’most fifty dollars outer a—a beury droor. Dretful bad boy is that
Brandon.”
“Yes, I should think so. Well, with that warrant I should think you had
him pretty straight.”
“D’ye think I kin find him all right?” asked Arad anxiously.