General, Organic, and
Biological Chemistry:
An Integrated Approach,
Second Edition

Kenneth W. Raymond

John Wiley & Sons, Inc.
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GENERAL, ORGANIC, AND
BIOLOGICAL CHEMISTRY

An Integrated Approach
SECOND

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EDITION


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GENERAL, ORGANIC, AND
BIOLOGICAL CHEMISTRY

An Integrated Approach
SECOND

Kenneth W. Raymond

Eastern Washington University

John Wiley & Sons, Inc.

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EDITION


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This volume contains selected illustrations from the following texts,
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• Boyer, Rodney, Concepts in Biochemistry, Second Edition,
â 2002.
ã Hein, Morris; Best, Leo R.; Pattison, Scott; Arena, Susan,
Introduction to General, Organic, and Biochemistry,
Eighth Edition, © 2005.
• Holum, John R., Fundamentals of General, Organic, and
Biological Chemistry, Sixth Edition, â 1998.
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â 2004.
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Fundamentals of Biochemistry: Life at the Molecular Level,
2nd Edition, © 2006.

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P R E F A C E

his second edition of General, Organic, and Biochemistry: an Integrated Approach
T
has been written for students preparing for careers in health-related fields such as
nursing, dental hygiene, nutrition, medical technology, and occupational therapy. The
text is also suitable for students majoring in other fields where it is important to have an
understanding of chemistry and its relationship to living things. Students need have no
previous background in chemistry, but should possess basic math skills. For those whose
math is a bit rusty, the text provides reviews of the important material. While designed for
use in one-semester or two-quarter General, Organic, and Biochemistry (GOB) courses,
instructors have found that it also works well for one-year courses, especially when combined with the supplement Chemistry Case Studies For Allied Health Students by Colleen
Kelley and Wendy Weeks.
In a GOB course it is essential to show how the subject matter relates to the students’
future careers. For this reason, this text makes extensive use of real-life examples from the
health sciences.

O R G A N I Z A T I O N
In most GOB texts, a group of chapters on general chemistry is followed by a series of
organic chemistry chapters, which is followed by chapters devoted to biochemistry. Years
of experience in teaching health science courses have shown the author that there is a
drawback to this approach: in many cases there is a long time interval between when a
topic is first presented and when it is used again—enough of a break that students’ familiarity with the subject matter has often lapsed.
In introducing GOB material, this text uses an integrated approach in which related general
chemistry, organic chemistry, and biochemistry topics are presented in adjacent chapters. This
approach helps students see the strong connections that exist between these three branches of
chemistry and allows instructors to discuss these interrelationships while the material is still
fresh in students’ minds. This integration involves the following sets of chapters:
• Chapter 3 (Compounds) and Chapter 4 (An Introduction to Organic
Compounds). An introduction to bonding and compounds is followed by a look

at the members of a few key organic families.
• Chapters 3 and 4 and Chapter 6 (Reactions). A study of inorganic and organic
compounds is followed (after a look at gases, liquids, and solids in Chapter 5) by an
introduction to their reactions.
• Chapter 7 (Solutions) and Chapter 8 (Lipids and Membranes). A discussion of
solubility is followed by a look at the importance of solubility in biochemistry.
Some reactions from Chapter 6 are reintroduced.
• Chapter 9 (Acids and Bases) and Chapter 10 (Carboxylic Acids, Phenols,
and Amines). Principles of acid/base chemistry from an inorganic perspective are
followed by a chapter on the organic and biochemical aspects of this topic.

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x

PREFACE

• Chapter 11 (Alcohols, Aldehydes, and Ketones) and Chapter 12 (Carbohydrates).
An introduction to the chemistry of alcohols, aldehydes and ketones is followed by
a presentation of related biochemical applications.
The many reviewers of this text have made helpful suggestions. The major changes to the
second edition are:

K E Y F E AT U R E S
OF THE SECOND
EDITION

• Newly introduced material: Molar mass (Chapter 2), step-by-step instructions for
drawing molecules and polyatomic ions (Chapter 4), ionic equations and net ionic

equations (Chapter 7), and naming esters and amides (Chapter 10).
• Revised material: Changed group naming from IA, IIA format to 1A, 2A format
(Chapter 2), added details on naming binary molecules and introduced a table of
prefixes used for naming them (Chapter 2), modified treatment of the combined gas
law and the ideal gas law (Chapter 5), and updated discussion of waxes, fatty acids,
phospholipids, and eicosanoids (Chapter 8).
• New Appendicies: Important families of organic compounds (Appendix B) and
Naming ions, ionic compounds, binary molecules, and organic compounds
(Appendix C).
• Addition of new chapter sections: Reaction types (Section 6.2), Maintaining the pH
of blood serum (Section 9.10), and Oxidation of phenols (Section 10.5).

P R O B L E M

S O LV I N G
Learning to do anything requires practice, and in chemistry this practice involves solving
problems. This text offers students ample opportunities to do so.

102

CHAPTER 4 | AN INTRODUCTION

■ FIGURE |

TO

ORGANIC COMPOUNDS

H H H H


4.3
H

(Continued)

C

C

C

CH3CH2CHCH3

C H

H H F

F

H

F

2-Fluorobutane

O
H
H

C

C

C
C
C

O H
C
C

O

O H

O C

C H
HC

H

HC

H

H

C
C
C

H

OH
C

O

O CCH3

O

OH
O

CH

O

• Sample Problems and Practice Problems.

Aspirin

In skeletal structures (Figure 4.3), covalent bonds are represented by lines, carbon atoms
are not shown, and hydrogen atoms are drawn only when attached to atoms other than carbon. To read a skeletal structure, you assume that a carbon atom appears where lines (bonds)
meet and at the end of each line. To simplify matters, nonbonding electrons (Section 3.5)
are sometimes omitted from skeletal and other structural formulas.
S AMPLE P ROBLEM

4.4


Drawing condensed and skeletal structures
Draw condensed and skeletal structures of diethyl ether, a compound once used as a
general anesthetic.
H H
ƒ

ƒ

ƒ

ƒ

H H
ƒ

ƒ

ƒ

ƒ

Each major topic is followed by a sample problem and
a related practice problem. The solution to each sample
problem is accompanied by a strategy to use when solving
the problem. The answers to practice problems are given
at the end of the chapter.

ã ơ C ơ C ơH
Hơ C ơ C ¬O
¶

H H

H H

Strategy

To write the condensed formula, begin by thinking of the molecule as a chain of five
atoms (C¬ C¬O¬ C¬C) and then add in the atoms attached to these five (CH3, etc.).
The skeletal structure of diethyl ether is drawn by leaving out all of the carbon and
hydrogen atoms, showing only the oxygen atom and the C¬C and C¬ O bonds.
Solution

O

CH3CH2OCH2CH3
Condensed structure

P RACTICE P ROBLEM

Skeletal structure

4.4

Research suggests that drinking green tea may help boost the immune system.
Ethylamine (below), produced when one of the compounds in green tea is broken down
in the liver, may be responsible for this immune response. Draw condensed and skeletal
structures for the molecule.
H H
ƒ


ƒ

ƒ

ƒ

H¬ C ¬ C ¬ N
¶ ¬H
ƒ

H H H

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PREFACE

END

CHAPTER PROBLEMS

OF

131

8 Define the term “functional group” and describe the features

that distinguish hydrocarbons, alcohols, carboxylic acids, and
esters from one another.
Functional groups are atoms, groups of atoms, or bonds that give a molecule a particular set of chemical properties. The functional groups represented in hydrocarbons are the carbon–carbon double bond (in alkenes), the carbon–carbon triple

bond (in alkynes), and alternating double and single bonds in a ring (in aromatic
compounds). Alcohols contain the hydroxyl (¬ OH) functional group attached to
an alkane-like carbon atom. Carboxylic acids contain the hydroxyl group attached
to a carbonyl (C“ O) group, and esters contain a C¬ O¬ C linkage, with one of the
carbon atoms belonging to a carbonyl group.

• End of Chapter Problems. A large number of
END

OF

CHAPTER

problems can be found and the end of each chapter, and
Appendix D provides answers for the odd-numbered ones.
Many of the end of chapter problems are paired and some,
marked with an asterisk, are more challenging than others.
Each chapter includes a set of Thinking It Through
problems that ask students to go a bit further with one or
more of the concepts presented in the chapter. Over two
hundred and fifty new problems have been added to the
second edition. Of these, more than half are multi-part
questions and many are challenging.

PROBLEMS

Answers to problems whose numbers are printed in color are given in Appendix D. More
challenging questions are marked with an asterisk. Problems within colored rules are paired.
ILW = Interactive Learning Ware solution is available at www.wiley.com/college/raymond.
|


4.1 S T R U C T U R A L F O R M U L A S

AND

FORMAL CHARGES
4.1 Draw the line-bond structure of each molecule.

CH3
a.

HC

C
C
H

ã
a. Hơ ả
S ơH

C

CH3CH2CHCH2CH3

HC

following molecules or ions?

following molecules or ions?

+

H H
ƒ

ƒ

ƒ

ƒ

a. D H¬ C ¬N¬H T

4.2 Draw the line-bond structure of each molecule.

CH3
ƒ

S

‘

•
≠O

CH

ƒ

ƒ


•l≠
≠C

2−

4.10 What is the formal charge on each atom in the

CH

a. CH3CCH2CH3

ãlơN
ãl
c. C
ả
ảơ C
ả

ã ơ C ơO
ã
b. O
ả
ả

CH2CH2NH2
b.

4.9 What is the formal charge on each atom in the


b. CH3CHCHCHCH2

CH3

ãlơO
ã ơC
ã4
ả
ả
ả
c. 3O

H H
O
ả


b. Hơ C ơH
4.11 Draw each polyatomic ion and assign formal charges.

4.3 What is the shape around the nitrogen and sulfur atoms

in the ions shown in Figure 4.2?
4.4 What is the shape around each of the carbon atoms in

Each atom, except for hydrogen, should have an octet
of valence electrons.
a. OHϪ
b. NH4ϩ
c. CNϪ

4.12 Draw each polyatomic ion and assign formal charges.

aspirin (Figure 4.3)?
4.5 Draw each molecule.
a. C2H6
b. C2H4

c. C2H2

4.6 Draw each molecule.
a. C3H8
b. C3H6

c. C3H4

4.7 Draw each diatomic element.
a. F2
b. O2
c. N2

* 4.8 Draw two different molecules that have the formula
C2H6O.

Each atom, except for hydrogen, should have an octet
of valence electrons.
a. PO43Ϫ
b. HPO42Ϫ
c. H2PO4Ϫ
4.13 Draw each of the following and assign formal charges.


Each atom should have an octet of valence electrons.
a. SO3
b. SO32Ϫ
4.14 Draw each molecule and assign formal charges. Each

atom should have an octet of valence electrons.
a. CO
b. SO2

SOLUTIONS

H E A LT H L i n k | CT and MRI Imaging

2.71 A nurse is assisting a patient who has just undergone

cancer treatment that involved exposure to gamma
radiation from cobalt-60. Should the nurse be
concerned that he will be exposed to gamma radiation
given off by the patient?
2.72 In late 2006, a former Russian spy was poisoned when a
small amount of polonium-210 was put in his food. He
died a few weeks later.
a. Polonium-210 emits alpha particles. Write a balanced
nuclear equation for this process.
b. This radioisotope has a half-life of 138 days. Of a
2 mg sample, how much would remain after 5
half-lives?
c. If alpha particles can be blocked by a sheet of paper
(Figure 2.13), why is polonium-210 so poisonous?


2.69 a. One of the two techniques described in this Health

Link is considered “invasive.” What do you suppose
is meant by this term?
b. To which technique does this term apply?
c. In some cases, the images produced by CT and MRI

are quite similar. If given a choice, which would you
rather have run?

ILW

INTERACTIVE

0 +
a. 20
12Mg ¡ ? + 1β
148
b. 152
67Ho ¡ 65Tb + ?
0
c. 31
14Si ¡ ? + −1β

TO

PRACTICE

2.2 a. atomic number = 8, mass number = 18; b. atomic number = 17,
mass number = 37

2.3

31
15P

and 28
15P

2.5 S
2.6 a. 3.7 × 1023 atoms; b. 4.8 × 10−12 mol
2.7 a. 2.53 g; b. 0.860 g
2.8

209
81Tl

2.9

192
77Ir

¡

2.10 132 days

192
76Os

+ 01β+


PROBLEMS

2.74 Identify the missing product in each nuclear equation.
ILW

2.1 a. protons and neutrons; b. protons and electrons; c. protons and neutrons

2.4 10.8 amu

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LEARNING

2.73 How many atoms are contained in:
a. 1.0 mol of calcium?
b. 7.88 × 10−6 mol of calcium?
c. 7.88 g of calcium?
d. 5.2 mg of calcium?

SOLUTIONS

59

term) of using radiation to treat cancer?

for arterial plaque. Why is the presence of plaque in
arteries a concern?
b. What role does the particle similar to HDL play in
the technique that is described?


ILW

PRACTICE PROBLEMS

2.70 What are the pros and cons (both long-term and short-

2.68 a. “Cholesterol Marker” describes using MRI to look

• Interactive Learning Ware Problems. The text’s
website ( features
Interactive Learning Ware (ILW), a step-by-step problem
solving tutorial program that guides students through
selected problems from the book. The ILW problems are
representative of those that students frequently find most
difficult and they reinforce students’ critical thinking and
problem solving skills. An ILW icon identifies each ILW
problem in the end-of-chapter question section.

TO

THINKING IT THROUGH

PROBLEMS

xi


xii

PREFACE


H E A LT H L I N K S
A N D B I O C H E M I S T R Y
CHAPTER 4 | AN INTRODUCTION

118

TO

L I N K S

To emphasize the importance of chemistry to the health sciences and to living
things, each chapter includes Health Links and Biochemistry Links. In the second
edition, eight new Health Links have been added: Body Mass Index (Chapter 1),
Dental Fillings (Chapter 3), Making Weight
(Chapter 5), Saliva (Chapter 7), Omega-3 fatty
acids (Chapter 8), Biofilms (Chapter 10), Drugs
in the environment (Chapter 11), and RNA
Interference (Chapter 14). In addition, six Health
Links from the first edition have been updated:
Body Temperature (Chapter 1), Dietary
Reference Intakes (formerly Recommended
Daily Allowances) (Chapter 2), CT and MRI
(formerly CT and PET) (Chapter 2),
Sunscreens (Chapter 4), Trans fats (Chapter 8),
and Proteins in Medicine (formerly Enzymes in
Medicine) (Chapter 13).

ORGANIC COMPOUNDS


Prion Diseases

The conformation, or shape, that a molecule takes can greatly influence its biological action. This point is well illus-

trated by a particular class of proteins, called prions, that have been identified as the cause of mad cow disease
(in cattle), scrapie (in sheep), chronic wasting disease (in deer and elk), and new variant Creutzfeldt-Jakob disease,
or vCJD (in humans).
Proteins are very large molecules formed from amino acid building blocks. Each protein has a favored conformation—
some with the protein chain twisted into
spirals and bends and some with the chain
zigzagged back and forth in a compact form.
Prions, short for proteinaceous infection particles, are a type of protein found in the
membranes of nerve cells. The prion diseases
mentioned above are caused 128
when theC H A P T E R 4 | A N I N T R O D U C T I O N T O O R G A N I C C O M P O U N D S
normal prion conformation (PrPc) is twisted
into an abnormal shape (PrPsc) (Figure 4.14).
When PrPsc comes into contact with PrPc,
the PrPc proteins change conformation and
become PrPsc. As PrPsc accumulates in affecNormal Prion Protein (PrPc)
Disease-Causing Prion (PrPsc)
ted animals or humans, sponge-like holes
form in the brain, causing dizziness, seizuOdor and Flavor
res, and death.
■ FIGURE | 4.14
Prion diseases can be transferred from one
he senses of smell and taste depend on specific receptors located in the nose and in the mouth, respectively. We detect an odor or
species to another. Cattle are known to get
Prions
flavor when a compound attaches to these receptors and triggers nerve responses. How the compound interacts with a given recepmad cow disease when fed parts of scrapie(a) The prion protein (PrPc) in its normal conformation. (b) The prion in its

tor been
determines the particular odor or flavor that it has. In 2004, the Nobel Prize in Physiology or Medicine was awarded to two
infected sheep, and vCJD in humans has
incorrectly folded (PrPsc) form.
researchers who study the biochemistry of the sense of smell.
linked to eating mad cow–infected beef.
Source: Fred E. Cohen, M.D., D. Phil and Cedric Govaerts, Ph.D., Department of
The odor and flavor of fruits is often due to a mixture of esters. The structure of a particular ester determines how it fits a given
Cellular & Molecular Pharmacology, University of California San Francisco (UCSF).
receptor, so esters containing a different number of carbon atoms are associated with different odors and flavors. For example, the
“pineapple” and “apricot” esters differ by three CH2 groups (Figure 4.24).
Constitutional isomers can also have different odors and flavors, as is the case for the “apple-like” and “banana” esters, each of
which has the molecular formula C7H14O2.

T

4.7

CYCLOALKANES

O
In some alkanes, called cycloalkanes, carbon atoms are joined into rings (Figure 4.15). Like
CH3CH2CH2C OCH2CH3
their noncyclic counterparts, cycloalkanes are nonpolar molecules that are attracted to one
Pineapple
another by London forces. To simplify matters, cycloalkanes are usually drawn using
skeletal structures, although side views can be useful when considering the orientation of
O
substituents attached to a ring.
When naming cycloalkanes, the ring is usually designated as the parent, which CH

is 3CH2CH2C OCH2CH2CH2CH2CH3
named by combining “cyclo” with the appropriate numbering prefix (Table 4.5) and
Apricot
“ane.” When only one alkyl group is attached to a cycloalkane parent, the carbon atom
O
that holds that group is carbon 1 (Figure 4.16a), but the number is not included in the
name. When a ring holds more than one alkyl group, the ring is numbered from the position and in the direction that gives the lowest numbers. Figure 4.16b shows how this CH3CH2CH2CH2C OCH2CH3
Apple-like

works for the three dimethylcyclopentane constitutional isomers.

The limited rotation of the carbon–carbon single bonds in cycloalkanes has an interesting
side effect in that it allows for the existence of stereoisomers, molecules that
• have the same molecular formula
• have the same atomic connections
• have different three-dimensional shapes
• are interchanged only by breaking bonds

Orange

O

CH3CH2CH2C

CH3C

O

OCH2CH2CHCH3


Peach

CH3

O

Banana

CH2C OCH2CH3

O
CH3CH2C

Honey

OCH2CHCH3
CH3

O

Rum

C OCH3

O
H

OCH2

Rose


CH3C OCH2

O

Geometric Isomers

O

CH3C OCH2CH2CH2CH2CH2CH2CH2CH3

C

H2N
OCH2CHCH3
CH3
Raspberry

■ FIGURE |

O N - L I N E
124

CHAPTER 4 | AN INTRODUCTION

P RACTICE P ROBLEM

TO

ORGANIC COMPOUNDS


Designate each of the carbon–carbon double bonds in bombykol, a moth pheromone,
as cis or trans.
H

H
C

C

H
C C

H

CH2CH2CH2CH2CH2CH2CH2CH2CH2OH
Bombykol

Sunscreens

I

CH3O

n addition to the visible light that is present in sunlight, a higher energy form of electromagnetic radiation called
ultraviolet (UV) is also found. It is this UV radiation that makes spending too much time in the sun hazardous to
your health.
UV radiation is divided into three categories (arranged in order of increasing energy) UV-A, UV-B, and
UV-C. Although all forms of UV radiation can be harmful, UV-C is the most damaging. We do not usually
worry about exposure to UV-C from sunlight, however, because most is screened out by atmospheric

ozone. The UV-A and UV-B in sunlight are not blocked by the atmosphere and it is exposure to UV-B that causes
sunburns. This form of radiation has also been identified as one of the causes of skin cancer. While UV-A was once
thought to be relatively harmless, there is now strong evidence that links wrinkles, other skin damage, and skin cancer to UV-A exposure.
To some extent, your skin can protect itself from UV radiation. When sunlight hits the skin, a particular type of
cells produce melanin, a black pigment that absorbs UV radiation. A suntan is the result of melanin production.
Sunscreens can also provide some degree of protection from the sun. These contain aromatic compounds that block
UV-A and UV-B light (Figure 4.22). Not all aromatic compounds are suitable for use as sunscreens—many do not
absorb UV, and many are toxic.
The SPF (sun protection factor)
H
O
listed on the label of a sunscreen
indicates how effective it is at
C
C
Octyl
blocking UV radiation. An SPF of
C
OCH2CHCH2CH2CH2CH3
methoxycinnamate
25 means that it takes 25 times
H
CH2CH3
longer to get sunburned with the
sunscreen applied than without.

O

Avobenzone


CH2SO3H

H

O

C

C

O

CH3
Ecamsule

H

For one topic in each chapter, a special icon is used to indicate that an on-line
ScienCentral article and video clip are available for viewing.
These articles and video clips are of interest because they show how the
chemistry being presented pertains to current events. Each set of end of chapter
problems includes some related to the video content. The video titles include:
Pork on the Run (Chapter 1), Cholesterol Marker (Chapter 2), Glowing Fish
(Chapter 3), Tanning & Health (Chapter 4), Breath Of Life (Chapter 5),
Hydrogen Cars (Chapter 6), Kidney Bones (Chapter 7), Teen Steroids (Chapter
8), Cystic Fibrosis Mucus (Chapter 9), Meth and the Brain (Chapter 10), Toxin
Eaters (Chapter 11), Sweet Spot (Chapter 12), Young Hearts (Chapter 13),
Cancer Screening (Chapter 14), Exercise Gene (Chapter 15).

CH3

CH2SO3H

■ FIGURE |

4.22

UV-B and UV-A absorbing
compounds in sunscreens

C(CH3)3

CH3O

H3C

Many esters have pleasing odors and flavors.

O

CCH2C

H3C

Grape
Esters

V I D E O S

4.11


CH3CH2CH2

4.24

Octyl methoxycinnamate is the
UV-B blocker most commonly
used in sunscreens. Avobenzone
and Ecamsule are UV-A blockers.
Ecamsule, which was recently
approved for use in the
United States, has been a
sunscreen ingredient in Canada
and Europe since 1993.

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PREFACE

O T H E R

T E X T

xiii

F E A T U R E S
Chapter Opening Vignettes Each chapter begins with a story that
focuses on the connection between chemistry and high-interest, everyday
topics that students can relate to.


Macular degeneration is a disease of the eye with symptoms that include
loss of color vision and distortion, blurring, or complete loss of central vision.
Peripheral vision is usually unaffected. People with this disease usually have

4

A

N

I N T R O D U C T I O N
T O
O R G A N I C
C O M P O U N D S

Objectives Each chapter begins with a
list of goals for the student to achieve.
These objectives identify key concepts
within each chapter. A summary of how
these objectives were met appears at the
end of each chapter.

trouble when it comes to reading or recognizing faces. There are a number of
factors

that

increase

the


risk

of

getting

macular

degeneration,

including

advanced age, a history of smoking, and diabetes.
Stargardt’s disease, an inherited form of macular degeneration that usually

Now that we have seen the basics of how atoms (Chapter 2) and compounds
(Chapter 3) are put together, it is time to set the stage for the organic and biochem-

appears before age 30, results from damage to the retina caused by a mal-

istry topics that we will encounter as we move through the text. This chapter will

function in the recycling of an organic molecule essential to the visual process.

begin with an introduction to a range of diverse topics, all of which relate to how bonding patterns, the distribution of electrons, and the shape of a molecule influence the
way that it interacts with others. In later sections of the chapter we will apply our
knowledge of these interactions to understand the properties of a number of different
families of organic compounds (contain carbon atoms). The shape that a molecule has
and its interactions with others are important in determining its biological effects.

Diseases ranging from Stargardt’s disease (mentioned on the facing page) to mad
cow disease (Health Link: Prion Diseases) are directly related to these properties.

Photo source:

92

Science VU/NIH/Visual Unlimited.

objectives
After completing this chapter, you should be able to:
1 Draw molecules and polyatomic ions using electron dot and line-bond structures.

Assign formal charges.
2 Describe how condensed structural formulas and skeletal structures differ from

electron dot and line-bond structures.
3 Define electronegativity and explain its relationship to polar covalent bonds. Give a

simple rule that can be used to predict whether or not a covalent bond is polar.
4 List the five basic shapes about an atom in a molecule and describe the rules used

to predict shape. Explain how shape plays a role in determining overall polarity.
5 Describe the noncovalent interactions that attract one compound to another.
6 Describe the four families of hydrocarbons.
7 Explain the difference between constitutional isomers, conformations, and the

stereoisomers known as geometric isomers. Give examples of two different families
of hydrocarbons that can exist as geometric isomers.
8 Define the term functional group and describe the features that distinguish


hydrocarbons, alcohols, carboxylic acids, and esters from one another.
93

Student Web Site Within each chapter you will find an icon
a indicating that there
is a ScienCentral
news video at the website with a news story related to
chapter content. The web site also features practice quizzes and Interactive Learningware problems.
Student Solutions Manual and Study Guide Written by Byron Howell, Tyler Junior
College and Adeliza Flores, of Las Positas College, this supplement contains worked
out solutions to the odd-numbered text problems; chapter summaries; sample problems, and practice problems.
Laboratory Manual Written by David Macaulay, Joseph Bauer, and Molly Bloomfield. This lab manual is written for the one or two-term chemistry lab course for students in the allied health sciences and related fields. These experiments are presented in
an integrated table of contents and contain chapter references from General, Organic,
and Biological Chemistry: An Integrated Approach, Second Edition.
Chemistry Case Studies For Allied Health Students Written by Colleen Kelley and
Wendy Weeks. This manual was designed to bring relevance and critical thinking skills
to the allied health chemistry course. Students are encouraged to become “diagnosticians” and apply their newly-acquired chemistry knowledge to solving real life health
and environmental cases. The case manual also encourages a holistic approach by asking students to synthesize information across topics.

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SUPPORT
PACKAGE FOR
STUDENTS


xiv

PREFACE


SUPPORT
PA C K A G E F O R
INSTRUCTORS

PowerPoint Lecture Slides Created by Colleen Kelley, Pima Community College,
these slides contain lecture outlines and key topics from each chapter of the text, along
with supporting artwork and figures from the text. The slides also contain assessment
questions and questions for in-class discussion.
WileyPlus Homework Management System WileyPlus is a powerful on-line tool that
provides a completely integrated suite of teaching and learning resources in one easyto-use web site. WileyPlus integrates Wiley’s world-renowned content with media,
including a multimedia version of the text, PowerPoint slides, on-line assessment,
and more.
Digital Image Archive The text web site includes downloadable files of text images in
JPEG format.
Test Bank Written by John Singer, Jackson Community College, the test bank
includes multiple choice, true/false, and short answer questions.
Computerized Test Bank The IBM and Macintosh compatible version of the entire
Test Bank has full editing features to help the instructor customize tests.
Instructor’s Manual Written by Colleen Kelley, Pima Community College, this
supplement provides Chapter Summaries and lecture outlines.
Instructor’s Solutions Manual Written by Adeliza Flores, of Las Positas College, this
supplement contains worked-out solutions to all of the end-of-chapter problems.

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A C K N O W L E D G M E N T S

I wish to thank my wife Susan and my son William for their encouragement, support, and

patience.
It is with great appreciation that I acknowledge the important contributions made by
Jennifer Yee, Catherine Donovan, Suzanne Ingrao, Janet Foxman, Lisa Gee, Hope Miller,
Thomas Kulesa, Gabriel Dillon, Amanda Wygal, and all of the others at Wiley who were
involved in helping to prepare this second edition.
Finally, I wish to acknowledge the important contributions made by the following
reviewers of this text:
Jeannie Collins
University of Southern Indiana

Shaun Schmidt
Washburn University

Lynette Rushton
South Puget Sound Community College

Myriam Cotton
Pacific Lutheran University

John Singer
Jackson Community College

Sean Schmidt
Washburn University

Stephen Dunham
Moravian College

Carnetta Skipworth
Bowling Green Community College


Sara Selfe
Edmonds Community College

Joseph Fassler
Santa Rosa Junior College

Steven Stefanides
Wenatchee Valley College

Anna Sequeira
Forsyth Tech Community College

Louis Giacinti
Milwaukee Area Technical College

Maria Vogt
Bloomfield College

Sonja Siewert
West Shore Community College

Christina Goode
California State University, Fullerton

William Wagener
West Liberty State College

Carnetta Skipworth
Western Kentucky University


Saifunnissa B. Hassam
Santa Rosa Junior College

Wendy Weeks
Pima Community College

Robert St. Amand
Union County College

Colleen Kelley
Pima Community College

Lynda Peebles
Texas Woman’s University

Richard Tarkka
University of Central Arkansas

Ira Krull
Northeastern University

Jennifer Powers
Kennesaw State University

Thottumkara Vinod
Western Illinois University

Paul Moggach
Georgian College


Parris Powers
Volunteer State Community College

Tracy Whitehead
Henderson State University

Michael Myers
California State University, Long Beach

Rita Rhodes
University of Tulsa

Todd Wimpfheimer
Salem State College

Lynette Rushton
South Puget Sound Community College

Lenore Rodicio
Miami-Dade College

xv

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A B O U T
T H E
A U T H O R

Ken Raymond received a B.S. in Chemistry from Central Washington

University in 1975 and a Ph.D. in Organic Chemistry from the University of
Washington in 1981. Since joining the faculty of Eastern Washington University
in 1982, his primary teaching responsibilities have been in the general, organic,
and biochemistry series for the health sciences and in the upper-division organic
chemistry lecture and laboratory series. In 1990 he received EWU’s annual
award for excellence in teaching. He has been chair of the Department of
Chemistry and Biochemistry since 2000. When not grading papers, he plays
mandolin and button accordion in a local folk band.

xvii

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B R I E F
C O N T E N T S

The asterisks are color
coded to indicate which
chapters are integrated.

CHAPTER 1


SCIENCE

CHAPTER 2

AT O M S

CHAPTER 3

C O M P O U N D S 60

CHAPTER 4

AN INTRODUCTION
C O M P O U N D S 92

CHAPTER 5

GASES, LIQUIDS,

*
*

CHAPTER 6

R E A C T I O N S 176

CHAPTER 7

SOLUTIONS, COLLOIDS,

S U S P E N S I O N S 212

*
*

CHAPTER 8

LIPIDS

CHAPTER 9

ACIDS, BASES,
E Q U I L I B R I U M 286

*

CHAPTER 10

CARBOXYLIC ACIDS, PHENOLS,
A M I N E S 320

*

CHAPTER 11

ALCOHOLS, ETHERS, ALDEHYDES,
A N D K E T O N E S 360

*


CHAPTER 12

C A R B O H Y D R AT E S 396

CHAPTER 13

PEPTIDES, PROTEINS,
E N Z Y M E S 432

CHAPTER 14

N U C L E I C A C I D S 468

CHAPTER 15

M E TA B O L I S M 504

*
*

AND

AND

AND

xviii

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MEASUREMENTS 1

E L E M E N T S 26

TO

AND

ORGANIC

S O L I D S 138

AND

M E M B R A N E S 252
AND

AND

AND


C O N T E N T S

CHAPTER

1.1

1


SCIENCE

The Scientific Method

AND

MEASUREMENTS

2

H EALTH Link Science and Medicine

4

1.2

Matter and Energy

1.3

Units of Measurement

1.4

Scientific Notation and Metric Prefixes

9

1.5


Measurements and Significant Figures

11

4
6

H EALTH Link Body Mass Index
1.6

13

Conversion Factors and the Factor Label Method

H EALTH Link Body Temperature
CHAPTER

2

2.1

Atoms

2.2

Elements

ATOMS

ELEMENTS


AND

29

Atomic Number and Mass Number

2.4

Periodic Table

2.5

The Mole

2.6

Radioactive Isotopes

2.7

Radioisotopes in Medicine

31

32

34

37

40
43

H EALTH Link CT and MRI Imaging
Fission and Fusion

3

49

50

COMPOUNDS

3.1

Ions

3.2

The Arrangement of Electrons

65

B IOCHEMISTRY Link Bioluminescence

70

3.3


60

62

The Octet Rule

71

B IOCHEMISTRY Link Ionophores and Biological Ion Transport
3.4

Ionic Compounds

3.5

Covalent Bonds

3.6

Molecules

73

74
77

78

H EALTH Link Dental Fillings
3.7


26

28

2.3

CHAPTER

15

16

H EALTH Link Dietary Reference Intakes (DRIs)

2.8

1

80

Formula Weight, Molecular Weight, and Molar Mass

B IOCHEMISTRY Link Ethylene, a Plant Hormone

84

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81

xix


xx

CONTENTS

4

CHAPTER

AN INTRODUCTION
COMPOUNDS
92

4.1

Structural Formulas and Formal Charges

4.2

Polar Covalent Bonds, Shape, and Polarity

4.3

Noncovalent Interactions

4.4

Alkanes


4.5

Constitutional Isomers

4.6

Conformations

94
103

108

110
115

117

H EALTH Link Prion Diseases

118

4.7

Cycloalkanes

4.8

Alkenes, Alkynes, and Aromatic Compounds


118

H EALTH Link Sunscreens
4.9

B IOCHEMISTRY Link Odor and Flavor
5

125

128

GASES, LIQUIDS,

5.1

States of Matter and Energy

5.2

Gases and Pressure
The Gas Laws

5.4

Partial Pressure

5.5


Liquids

AND

SOLIDS

140

146

H EALTH Link Blood Pressure
5.3

120

124

Alcohols, Carboxylic Acids, and Esters

CHAPTER

ORGANIC

TO

150

150
158


161

H EALTH Link Making Weight 164
H EALTH Link Breathing 166
5.6

Solids

CHAPTER

167

6

REACTIONS

6.1

Chemical Equations

6.2

Reaction Types

6.3

Oxidation and Reduction

176


178

182
183

H EALTH Link Antiseptics and Oxidation

187

6.4

Reactions Involving Water

6.5

Mole and Mass Relationships in Reactions

6.6

Calculating the Yield of a Reaction

6.7

Free Energy and Reaction Rate

H EALTH Link Carbonic Anhydrase
CHAPTER

7


189

198

201

SOLUTIONS, COLLOIDS,
SUSPENSIONS
212

7.1

Solutions

7.2

Reactions of Ions in Aqueous Solutions

Hard Water

191

195

214
220

7.3

Solubility of Gases in Water


7.4

Organic Compounds

221

222

H EALTH Link Hyperbaric Medicine

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222

216

AND

138


CONTENTS

7.5

Biochemical Compounds

224


H EALTH Link Prodrugs

227
228

7.6

Concentration

7.7

Dilution

7.8

Colloids and Suspensions

236

H EALTH Link Saliva
7.9

237

239

Diffusion and Osmosis

240


H EALTH Link Diffusion and the Kidneys
CHAPTER

8.1

8

LIPIDS

Fatty Acids

242

MEMBRANES

AND

252

254

H EALTH Link Omega-3 fatty acids
8.2

Waxes

8.3

Triglycerides


257

258
259

H EALTH Link Trans Fats 265
H EALTH Link Olestra 266
8.4

Phospholipids and Glycolipids

8.5

Steroids

8.6

Eicosanoids

270
272

H EALTH Link Anabolic Steroids
8.7

Membranes

CHAPTER

266


275

275

9

ACIDS, BASES,
EQUILIBRIUM

AND

9.1

Acids and Bases

9.2

Brønsted–Lowry Acids and Bases

9.3

Equilibrium

9.4

Le Châtelier’s Principle

286


288
289

290
293

B IOCHEMISTRY Link Diving Mammals, Oxygen, and Myoglobin
9.5

Ionization of Water

9.6

The pH Scale

295

296

297

Math Support–Logs and Antilogs 300
B IOCHEMISTRY Link Plants as pH Indicators

301

9.7

Acid and Base Strength


9.8

Neutralizing Acids and Bases

9.9

Effect of pH On Acid and Conjugate Base Concentrations

9.10 Buffers

301
303

9.11 Maintaining the pH of Blood Serum
CHAPTER

305

306

10

308

CARBOXYLIC ACIDS, PHENOLS,
AMINES
320

AND


10.1 Carboxylic Acids
10.2 Phenols

323

324

H EALTH Link A Chili Pepper Painkiller

325

10.3 Carboxylic Acids and Phenols As Weak Organic Acids
10.4 Other Reactions of Carboxylic Acids

329

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326

xxi


xxii

CONTENTS

10.5 Oxidation of Phenols
10.6 Amines


332

333

10.7 Amines As Weak Organic Bases
10.8 Amides

336

337

H EALTH Link Biofilms 339
B IOCHEMISTRY Link A Cure for Fleas
10.9 Stereoisomers

340

341

H EALTH Link Adrenaline and Related Compounds
CHAPTER

11

346

ALCOHOLS, ETHERS, ALDEHYDES,
KETONES
360


AND

11.1 Alcohols, Ethers, and Related Compounds
11.2 Preparation

363

367

11.3 Reactions

370

11.4 Aldehydes and Ketones
11.5 Oxidation of Aldehydes

373
374

H EALTH Link Aldehyde Dehydrogenase

376

11.6 Reduction of Aldehydes and Ketones

H EALTH Link Protective Enzymes

376

378


11.7 Reactions of Alcohols with Aldehydes and Ketones

H EALTH Link Drugs in the Environment
CHAPTER

12

382

C A R B O H Y D R AT E S

12.1 Monosaccharides

404

12.3 Monosaccharides in Their Cyclic Form
12.4 Oligosaccharides

417

418

H EALTH Link Blood Type
13

406

410


H EALTH Link Relative Sweetness 415
H EALTH Link Indigestible Oligosaccharides

CHAPTER

396

398

12.2 Reactions of Monosaccharides

12.5 Polysaccharides

422

PEPTIDES, PROTEINS,
ENZYMES
432

13.1 Amino Acids

379

AND

434

13.2 The Peptide Bond

437


13.3 Peptides, Proteins, and pH
13.4 Protein Structure

440

441

B IOCHEMISTRY Link Collagen and a-Keratin, Two Fibrous Proteins
B IOCHEMISTRY Link Hemoglobin, a Globular Protein 448
13.5 Denaturation
13.6 Enzymes

449

449

13.7 Control of Enzyme-Catalyzed Reactions

H EALTH Link Proteins in Medicine

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459

453

447



CONTENTS

14

CHAPTER

NUCLEIC ACIDS

468

14.1

Nucleic Acid Building Blocks

14.2

Nucleoside di-and Triphosphates, Cyclic Nucleotides

14.3

Polynucleotides

476

14.4

DNA Structure

477


14.5

Denaturation

14.6

Nucleic Acids and Information Flow

14.7

DNA Replication

14.8

RNA

14.9

Translation

470
475

480
481

482

484
487


H EALTH Link Viruses

489
14.10 Control of Gene Expression

489

H EALTH Link RNA Interference
14.11 Mutation

491

491

H EALTH Link Breast Cancer Genes
14.12 Recombinant DNA

492

492

B IOCHEMISTRY Link DNA Fingerprinting
CHAPTER

15

M E TA B O L I S M

494

504

15.1

Metabolic Pathways, Energy, and Coupled Reactions

15.2

Overview of Metabolism

507

B IOCHEMISTRY Link The Origin of Mitochondria

512

15.3

Digestion

512

15.4

Glycolysis

514

15.5


Gluconeogenesis

15.6

Glycogen Metabolism

15.7

Citric Acid Cycle

15.8

Electron Transport Chain and Oxidative Phosphorylation

H EALTH Link Brown Fat
15.9

Lipid Metabolism

519
521

522
524

527
528

15.10 Amino Acid Metabolism


Appendix A

506

Scientific Calculators

532

A-1

Appendix B

Important Families of Organic Compounds

Appendix C

Naming Ions, Ionic Compounds, Binary Molecules, and Organic
Compound A-8

Appendix D

Answers to Odd-Numbered Problems

Appendix E

Glossary

Index

A-5


A-23

A-51

I-1

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xxiii