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To the Student
Welcome to the fascinating world of organic chemistry. You are about to embark on an exciting
journey. This book has been written with students like you in mind—those who are encounter-
ing the subject for the first time. The book’s central goal is to make this journey through organic
chemistry both stimulating and enjoyable by helping you understand central principles and asking
you to apply them as you progress through the pages. You will be reminded about these principles
at frequent intervals in references back to sections you have already mastered.
You should start by familiarizing yourself with the book. Inside the front and back covers is
information you may want to refer to often during the course. The list of Some Important Things
to Remember and the Reaction Summary at each chapter’s end provide helpful checklists of the
concepts you should understand after studying the chapter. The Glossary at the end of the book can
also be a useful study aid. The molecular models and electrostatic potential maps that you will find
throughout the book are provided to give you an appreciation of what molecules look like in three
dimensions and to show how charge is distributed within a molecule. Think of the margin notes
as the author’s opportunity to inject personal reminders of ideas and facts that are important to
remember. Be sure to read them.
Work all the problems within each chapter. These are drill problems that you will find at the end of
each section that allow you to check whether you have mastered the skills and concepts the particular
section is teaching before you go on to the next section. Some of these problems are solved for you in
the text. Short answers to some of the others—those marked with a diamond—are provided at the end of
the book. Do not overlook the “Problem-Solving Strategies” that are also sprinkled throughout the text;
they provide practical suggestions on the best way to approach important types of problems.
In addition to the within-chapter problems, work as many end-of-chapter problems as you can. The
more problems you work, the more comfortable you will be with the subject matter and the better
prepared you will be for the material in subsequent chapters. Do not let any problem frustrate you. If
you cannot figure out the answer in a reasonable amount of time, turn to the Study Guide and Solutions
Manual to learn how you should have approached the problem. Later on, go back and try to work the
problem on your own again. Be sure to visit www.MasteringChemistry.com, where you can explore
study tools, including Exercise Sets, an Interactive Molecular Gallery, and Biographical Sketches of
historically important chemists, and where you can access content on many important topics.
The most important advice to remember (and follow) in studying organic chemistry is DO NOT
FALL BEHIND! The individual steps to learning organic chemistry are quite simple; each by itself is
relatively easy to master. But they are numerous, and the subject can quickly become overwhelming if
you do not keep up.
Before many of the theories and mechanisms were figured out, organic chemistry was a discipline
that could be mastered only through memorization. Fortunately, that is no longer true. You will find
many unifying ideas that allow you to use what you have learned in one situation to predict what will
happen in other situations. So, as you read the book and study your notes, always make sure that you
understand why each chemical event or behavior happens. For example, when the reasons behind reac-
tivity are understood, most reactions can be predicted. Approaching the course with the misconception
that to succeed you must memorize hundreds of unrelated reactions could be your downfall. There is
simply too much material to memorize. Understanding and reasoning, not memorization, provide the
necessary foundation on which to lay subsequent learning. Nevertheless, from time to time some memo-
rization will be required: some fundamental rules will have to be memorized, and you will need to learn
the common names of a number of organic compounds. But that should not be a problem; after all, your
friends have common names that you have been able to learn and remember.
Students who study organic chemistry to gain entrance into professional schools sometimes w onder
why these schools pay so much attention to this topic. The importance of organic chemistry is not
in the subject matter alone. Mastering organic chemistry requires a thorough understanding of certain
fundamental principles and the ability to use those fundamentals to analyze, classify, and predict. Many
professions make similar demands.
Good luck in your study. I hope you will enjoy studying organic chemistry and learn to appreciate
the logic of this fascinating discipline. If you have any comments about the book or any suggestions
for improving it, I would love to hear from you. Remember, positive comments are the most fun, but
negative comments are the most useful.
Paula Yurkanis Bruice
pybruice@chem.ucsb.edu
Common Functional Groups
Alkane RCH3 Aniline NH2
Benzene
Alkene C C C CH2 Phenol OH
internal terminal
O N
Pyridine
Alkyne RC CR RC CH Carboxylic acid C
internal terminal R OH
O O
O
Nitrile RC N C P
Acyl chloride C R O O−
R Cl O−
Ether R O R Acyl phosphate
O O
O
Acid anhydride C C O O O
Epoxide R O R
R R C P P
O R O O O−
O− O−
Thiol RCH2 SH Ester C Acyl pyrophosphate
R OR
Sulfide R S R O
O O
Thioester C
R SR C P Ad
Disulfide R S S R R O O
O O−
Acyl adenylate
R Amide C (Ad = adenosyl)
+ R NH2 NHR NR2
Sulfonium ion R S R
O
Aldehyde C
R H
O
Ketone C
R R
primary secondary tertiary
R R
Alkyl halide R CH2 X R CH X R C X
X = F, Cl, Br, or I R
R R
Alcohol R CH2 OH R CH OH R C OH
R
R R
Amine R NH2 R NH R N
R
Approximate pKa Values
+ OH O
protonated carbonyl groups C a-carbon (aldehyde) C

R OH RCH H
+ H
protonated alcohols ROH <0 ~20
H O
a-carbon (ketone) C
+
protonated water HOH RCH R
H
H
O
O
carboxylic acids C
R OH ~5 a-carbon (ester) C ~25
RCH OR
+
protonated aniline ArNH3 H
+
protonated amines RNH3
amines RNH2 ~40
~10
phenol ArOH
alkanes RCH3 ~60
alcohols ROH
~15
water H2O
Common Symbols and Abbreviations
[a] specific rotation Ea energy of activation pH measure of the acidity of

a observed rotation Et ethyl a solution (= − log [H+])
Ad adenosyl Et2O diethyl ether pI isoelectric point
ATP adenosine triphosphate FAD flavin adenine dinucleotide pKa measure of the strength
B0 applied magnetic field H2CrO4 chromic acid of an acid (= − log Ka)
Bu butyl HOCl hypochlorous acid PLP pyridoxal phosphate
D Debye; a measure of dipole IR infrared ppm parts per million
moment k rate constant (of the applied field)
d partial or chemical shift Ka acid dissociation constant R alkyl group; group derived
Δ heat Keq equilibrium constant from a hydrocarbon
ΔG‡ free energy of activation LiAlH4 lithium aluminum hydride R,S configuration about an
ΔG° Gibbs standard free energy change MS mass spectroscopy asymmetric center
ΔH° change in enthalpy m dipole moment THF tetrahydrofuran or tetrahydrofolate

NaBH4 sodium borohydride TMS tetramethylsilane, (CH3)4Si
ΔS° change in entropy
NAD+ nicotinamide adenine TPP thiamine pyrophosphate
DMF dimethylformamide dinucleotide UV/Vis ultraviolet/visible
DMSO dimethyl sulfoxide NaOCl sodium hypochlorite X halogen atom
E entgegen (opposite sides in nm nanometers Z zusammen (same side in
E,Z nomenclature) NMR nuclear magnetic resonance E,Z nomenclature)
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Essential
Organic Chemistry
THIRD EDITION
global EDITION

UNIVERSITY OF CALIFORNIA
S A N TA B A R B A R A
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© Pearson Education Limited 2016
The rights of Paula Yurkanis Bruice to be identified as the author of this work have been
asserted by her in accordance with the Copyright, Designs and Patents Act 1988.
Authorized adaptation from the United States edition, entitled Essential Organic Chemistry,
3rd edition, ISBN 978-0-321-93771-1, by Paula Yurkanis Bruice, published by Pearson
Education © 2016.
All rights reserved. No part of this publication may be reproduced, stored in a retrieval
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All trademarks used herein are the property of their respective owners.The use of any
trademark in this text does not vest in the author or publisher any trademark ownership
rights in such trademarks, nor does the use of such trademarks imply any affiliation with or
endorsement of this book by such owners.
ISBN 10: 1-292-08903-2

ISBN 13: 978-1-292-08903-4
British Library Cataloguing-in-Publication Data
A catalogue record for this book is available from the British Library.
10 9 8 7 6 5 4 3 2 1
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Typeset in Times LT Std 10.5/12 by Lumina Datamatics, Inc.
Printed and bound in Malaysia.

Brief Table of Contents
Preface 19 CHapTER 12 Reactions of Aldehydes and Ketones • More

Reactions of Carboxylic Acid Derivatives 459
About the Author 23
CHapTER 13 Reactions at the a-Carbon of Carbonyl
CHapTER 1 Remembering General Chemistry:
Compounds 489
Electronic Structure and Bonding 29
CHapTER 14 Radicals 513
CHapTER 2 Acids and Bases:
Central to Understanding Organic CHapTER 15 Synthetic Polymers 527
Chemistry 68
CHapTER 16 The Organic Chemistry of Carbohydrates 553
TUTORIal Acids and Bases 93
CHapTER 17 The Organic Chemistry of Amino Acids,
CHapTER 3 An Introduction to Organic Compounds 101 Peptides, and Proteins 577
CHapTER 4 Isomers:
The Arrangement of Atoms in Space 144 CHapTER 18 How Enzymes Catalyze Reactions • The
Organic Chemistry of the Vitamins
CHapTER 5 Alkenes 176
available on-line
TUTORIal An Exercise in Drawing Curved Arrows:

Pushing Electrons 202
CHapTER 19 The Organic Chemistry of the Metabolic
CHapTER 6 The Reactions of Alkenes and Alkynes 210 Pathways 609
CHapTER 7 Delocalized Electrons and Their Effect on CHapTER 20 The Organic Chemistry of Lipids 634
Stability, pKa, and the Products of a Reaction •
CHapTER 21 The Chemistry of the Nucleic Acids 650
Aromaticity and the Reactions
of Benzene 242
appENDICEs I Physical Properties of Organic Compounds
TUTORIal Drawing Resonance Contributors 283
available on-line
CHapTER 8 Substitution and Elimination Reactions of a p p E N D I C E s I I Spectroscopy Tables

Alkyl Halides 291 available on-line
CHapTER 9 Reactions of Alcohols, Ethers, Epoxides,

Amines, and Thiols 331 Answers to Selected Problems A-1
Glossary G-1
CHapTER 10 Determining the Structure of Organic
Compounds 367 Photo Credits P-1
Index I-1
CHapTER 11 Reactions of Carboxylic Acids and Carboxylic
Acid Derivatives 421
7
Contents
1 Remembering General Chemistry:

Electronic Structure and Bonding 29
N at u r a l O r g a n i c Co m p o u n d s V e r s u s Sy n t h e t i c
O r g a n i c Co m p o u n d s 30
1.1 The Structure of an Atom 31

1.2 How the Electrons in an Atom Are Distributed 32
1.3 Ionic and Covalent Bonds 34
1.4 How the Structure of a Compound Is Represented 40
PR O B LEM - S O LV I N G STRATEGY 4 2
1.5 Atomic Orbitals 45

1.6 How Atoms Form Covalent Bonds 46
1.7 How Single Bonds Are Formed in Organic Compounds 47
1.8 How a Double Bond Is Formed: The Bonds in Ethene 50
D i a m on d , G r a p h i t e , G r a p h e n e , a n d F u l l e r e n e s :
S u b s ta n c e s t h at Con ta i n O n ly C a r bon At o m s 52
1.9 How a Triple Bond Is Formed: The Bonds in Ethyne 52

1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion 54
1.11 The Bonds in Ammonia and in the Ammonium Ion 56
1.12 The Bonds in Water 57
W at e r — A Co m p o u n d C e n t r a l t o L i f e 58
1.13 The Bond in a Hydrogen Halide 58

1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 60
1.15 The Dipole Moments of Molecules 63

SOME IMPORTANT THINGS TO REMEMBER 64 ■ PROBLEMS 65
New chapter on Acid/

Base Chemistry reinforces
2 Acids and Bases:
Central to Understanding Organic Chemistry 68
fundamental concepts 2.1 An Introduction to Acids and Bases 68
and foundational skills 2.2 pKa and pH 70
needed for future topics A c i d R a i n 7 2
in organic chemistry.
2.3 Organic Acids and Bases 72
Po i s ono u s A m i n e s 73
for Organic Chemistry

2.4 How to Predict the Outcome of an Acid–Base Reaction 76
2.5 How to Determine the Position of Equilibrium 76
MasteringChemistry tutorials guide you
through topics in chemistry with self-
2.6 How the Structure of an Acid Affects Its pKa Value 77
paced tutorials that provide individualized 2.7 How Substituents Affect the Strength of an Acid 81
coaching. These assignable, in-depth PR O B LEM - S O LV I N G STRATEGY 8 2
tutorials are designed to coach you
with hints and feedback specific to
2.8 An Introduction to Delocalized Electrons 83
your individual needs. For additional F o s a m a x P r e v e n t s B on e s f r o m B e i n g N i bb l e d Aw ay 84
practice on Acids and Bases, go to 2.9 A Summary of the Factors that Determine Acid Strength 85
MasteringChemistry where the following
tutorials are available:
2.10 How pH Affects the Structure of an Organic Compound 86
• Acids and Bases: Base Strength and the PR O B LEM - S O LV I N G STRATEGY 8 7
Effect of pH on Structure As p i r i n M u st B e i n I t s Bas i c F o r m to B e
• Acids and Bases: Factors that Influence P h ys i o l o g i c a l ly A c t i v e 88
Acid Strength
• Acids and Bases: Predicting the Position
of Equilibrium
• Acids and Bases: Definitions
8
9
2.11 Buffer Solutions 89

B l oo d : A B u ff e r e d So l u t i on 8 9
TUTORIAL Acids and Bases 93
3 An Introduction to Organic Compounds 101 New Feature—Tutorials

help students develop
and practice important
3.1 How Alkyl Substituents Are Named 104 problem solving skills.
B a d - S m e l l i n g Co m p o u n d s 10 5
3.2 The Nomenclature of Alkanes 108

How I s t h e O c ta n e N u m b e r of G a s o l i n e D e t e r m i n e d ? 110
3.3 The Nomenclature of Cycloalkanes • Skeletal Structures 111

3.4 The Nomenclature of Alkyl Halides 114

3.5 The Classification of Alkyl Halides, Alcohols, and Amines 115

Nitrosamines and Cancer 11 5
3.6 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 116
3.7 Noncovalent Interactions 118
PR O B LEM - S O LV I N G STRATEGY 1 2 1
D r u g s B i n d to T h e i r R e c e p to r s 122
3.8 Factors that Affect the Solubility of Organic Compounds 122

Cell Membranes 125
3.9 Rotation Occurs About Carbon—Carbon Single Bonds 125

3.10 Some Cycloalkanes have Angle Strain 128
V on B a e y e r , B a r b i t u r i c A c i d , a n d B l u e J e a n s 129
3.11 Conformers of Cyclohexane 129

3.12 Conformers of Monosubstituted Cyclohexanes 132
S ta r c h a n d C e l l u l o s e — A x i a l a n d E q uat o r i a l 133
3.13 Conformers of Disubstituted Cyclohexanes 134

3.14 Fused Cyclohexane Rings 137

Cholesterol and Heart Disease 138
How H i g h C h o l e s t e r o l I s T r e at e d C l i n i c a l ly 138
4 Isomers: The Arrangement of Atoms in Space 144

4.1 Cis–Trans Isomers Result from Restricted Rotation 145
C i s – T r a n s In t e r c onv e r s i on i n V i s i on 1 4 8
4.2 Designating Geometric Isomers Using the E,Z System 148 New coverage of
PR O B LEM - S O LV I N G STRATEGY 1 5 1 stereoisomers now
precedes the coverage of
4.3 A Chiral Object Has a Nonsuperimposable Mirror Image 151 the reactions of alkenes.
4.4 An Asymmetric Center Is a Cause of Chirality in a Molecule 152
4.5 Isomers with One Asymmetric Center 153
4.6 How to Draw Enantiomers 154
4.7 Naming Enantiomers by the R,S System 154
4.8 Chiral Compounds Are Optically Active 158

4.9 How Specific Rotation Is Measured 160
4.10 Isomers with More than One Asymmetric Center 162
4.11 Stereoisomers of Cyclic Compounds 163
4.12 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 165
10
4.13 Receptors 168

T h e En a n t i o m e r s of T h a l i d o m i d e 17 0
4.14 How Enantiomers Can Be Separated 170

Chiral Drugs 17 1
5 Alkenes 176
P h e r o m on e s 17 7
5.1 The Nomenclature of Alkenes 177

5.2 How an Organic Compound Reacts Depends on its Functional Group 180
5.3 How Alkenes React • Curved Arrows Show the Flow of Electrons 181
A F e w W o r d s Abo u t C u r v e d A r r ow s 18 3
MasteringChemistry tutorials guide you
through the toughest topics in chemistry
5.4 Thermodynamics: How Much Product Is Formed? 185
with self-paced tutorials that provide 5.5 Increasing the Amount of Product Formed in a Reaction 187
individualized coaching. These assignable, 5.6 Using ΔH° Values to Determine the Relative Stabilities of Alkenes 188
in-depth tutorials are designed to coach PR O B LEM - S O LV I N G STRATEGY 1 8 9
you with hints and feedback specific
to your individual misconceptions. For T r a n s Fat s 19 2
additional practice on Drawing Curved 5.7 Kinetics: How Fast Is the Product Formed? 192
Arrows: Pushing Electrons, go to
MasteringChemistry where the following
5.8 The Rate of a Chemical Reaction 194
tutorials are available: 5.9 The Reaction Coordinate Diagram for the Reaction of 2-Butene with HBr 194
• An Exercise in Drawing Curved Arrows: 5.10 Catalysis 196
Pushing Electrons 5.11 Catalysis by Enzymes 197
• An Exercise in Drawing Curved Arrows: SOME IMPORTANT THINGS TO REMEMBER 199 ■ PROBLEMS 200
Predicting Electron Movement
• An Exercise in Drawing Curved Arrows:
Interpreting Electron Movement
TUTORIAL An Exercise in Drawing Curved Arrows:
Pushing Electrons 202
6 The Reactions of Alkenes and Alkynes 210

G r e e n C h e m i s t r y: A i m i n g fo r S u s ta i n a b i l i t y 2 11
6.1 The Addition of a Hydrogen Halide to an Alkene 211

6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively
Charged Carbon 212
6.3 Electrophilic Addition Reactions Are Regioselective 215
W h i c h A r e Mo r e H a r m f u l , N at u r a l P e s t i c i d e s o r Sy n t h e t i c
P e s t i c i d e s ? 2 17
6.4 A Carbocation will Rearrange if It Can Form a More Stable Carbocation 219
6.5 The Addition of Water to an Alkene 221
6.6 The Stereochemistry of Alkene Reactions 222
6.7 The Stereochemistry of Enzyme-Catalyzed Reactions 225

6.8 Enantiomers Can Be Distinguished by Biological Molecules 226
6.9 An Introduction to Alkynes 227
Sy n t h e t i c A l k y n e s A r e U s e d t o T r e at Pa r k i n s on ’ s D i s e a s e 228
W h y A r e D r u g s So E x p e n s i v e ? 229
6.10 The Nomenclature of Alkynes 229

Sy n t h e t i c A l k y n e s A r e U s e d fo r B i r t h Con t r o l 230
6.11 The Structure of Alkynes 231

6.12 The Physical Properties of Unsaturated Hydrocarbons 231
6.13 The Addition of a Hydrogen Halide to an Alkyne 232
6.14 The Addition of Water to an Alkyne 233
6.15 The Addition of Hydrogen to an Alkyne 235
SOME IMPORTANT THINGS TO REMEMBER 236 ■ SUMMARY OF REACTIONS 237
■ PROBLEMS 238
11
7 Delocalized Electrons and Their Effect on Stability, pKa,

and the Products of a Reaction •
Aromaticity and the Reactions of Benzene 242
7.1 Delocalized Electrons Explain Benzene’s Structure 243
Kekulé’s Dream 245
7.2 The Bonding in Benzene 245 for Organic Chemistry

7.3 Resonance Contributors and the Resonance Hybrid 246 MasteringChemistry tutorials guide you
7.4 How to Draw Resonance Contributors 247 through the toughest topics in chemistry
with self-paced tutorials that provide
E l e c t r on D e l o c a l i z at i on Aff e c t s t h e T h r e e - D i m e n s i on a l S h a p e of individualized coaching. These assignable,
P r o t e i n s 250 in-depth tutorials are designed to coach
7.5 The Predicted Stabilities of Resonance Contributors 250 you with hints and feedback specific
to your individual misconceptions. For
7.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound 252 additional practice on Drawing Resonance
7.7 Delocalized Electrons Increase Stability 253 Contributors, go to MasteringChemistry
PR O B LEM - S O LV I N G STRATEGY 2 5 5 where the following tutorials are available:
• Drawing Resonance Contributors I
• Drawing Resonance Contributors II
7.8 Delocalized Electrons Affect pKa Values 256
• Drawing Resonance Contributors of
Substituted Benzenes
7.9 Electronic Effects 259
7.10 Delocalized Electrons Can Affect the Product of a Reaction 262
7.11 Reactions of Dienes 263
7.12 The Diels–Alder Reaction Is a 1,4-Addition Reaction 266 New Feature—
7.13 Benzene Is an Aromatic Compound 268 Organizing What We
7.14 The Two Criteria for Aromaticity 269 Know About Organic
7.15 Applying the Criteria for Aromaticity 270 Chemistry lets students
see how families of
Buckyballs 271
organic compounds
7.16 How Benzene Reacts 272 react in similar ways.
7.17 The Mechanism for Electrophilic Aromatic Substitution Reactions 273
T h y r ox i n e 275
7.18 Organizing What We Know About the Reactions of Organic Compounds 276
■ PROBLEMS 278
TUTORIAL DRAWING RESONANCE CONTRIBUTORS 283
8 Substitution and Elimination Reactions of Alkyl Halides 291

DDT: A S y n t h e t i c O r g a no h a l i d e T h at K i l l s D i s e a s e - S p r e a d i n g In s e c t s 292
8.1 The Mechanism for an SN2 Reaction 293

8.2 Factors That Affect SN2 Reactions 297
W h y A r e L i v i n g O r g a n i s m s Co m p o s e d of C a r bon In s t e a d of S i l i c on ? 3 01
8.3 The Mechanism for an SN1 Reaction 301

8.4 Factors That Affect SN1 Reactions 304
8.5 Comparing SN2 and SN1 Reactions 305
N at u r a l ly O c c u r r i n g O r g a no h a l i d e s T h at D e f e n d a g a i n s t P r e dat o r s 307
8.6 Intermolecular versus Intramolecular Reactions 307

8.7 Elimination Reactions of Alkyl Halides 309

8.8 The Products of an Elimination Reaction 311
8.9 Relative Reactivities of Alkyl Halides Reactions 315
T h e N ob e l P r i z e 3 16
8.10 Does a Tertiary Alkyl Halide Undergo SN2/E2 Reactions or SN1/E1 Reactions? 316
8.11 Competition between Substitution and Elimination 317
12
8.12 Solvent Effects 320

So lvat i on Eff e c t s 320
8.13 Substitution Reactions in Synthesis 324

■ PROBLEMS 327
9 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols 331

9.1 The Nomenclature of Alcohols 331
G r a i n A l c o h o l a n d W oo d A l c o h o l 333
9.2 Activating an Alcohol for Nucleophilic Substitution by Protonation 334

9.3 Activating an OH Group for Nucleophilic Substitution in a Cell 336
T h e In a b i l i t y t o P e r fo r m a n S N 2 R e a c t i on C au s e s a S e v e r e
Clinical Disorder 338
9.4 Elimination Reactions of Alcohols: Dehydration 338

9.5 Oxidation of Alcohols 341
B l oo d A l c o h o l Con t e n t 343
T r e at i n g A l c o h o l i s m w i t h An ta b u s e 343
M e t h a no l Po i s on i n g 344
9.6 Nomenclature of Ethers 344

9.7 Nucleophilic Substitution Reactions of Ethers 345
An e s t h e t i c s 347
9.8 Nucleophilic Substitution Reactions of Epoxides 347

9.9 Using Carbocation Stability to Determine the Carcinogenicity of an Arene Oxide 351
Benzo[a]pyrene and Cancer 353
C h i m n e y Sw e e p s a n d C a n c e r 354
9.10 Amines Do Not Undergo Substitution or Elimination Reactions 354

Alkaloids 355
L e a d Co m p o u n d s fo r t h e D e v e l o p m e n t of D r u g s 356
9.11 Thiols, Sulfides, and Sulfonium Salts 356

M u s ta r d G a s — A C h e m i c a l W a r fa r e A g e n t 357
A l k y l at i n g A g e n t s a s C a n c e r D r u g s 358
9.12 Methylating Agents Used by Chemists versus Those Used by Cells 358
E r a d i c at i n g T e r m i t e s 359
S - A d e no s y l m e t h i on i n e : A N at u r a l An t i d e p r e s s a n t 360
9.13 Organizing What We Know about the Reactions of Organic Compounds 360
■ PROBLEMS 363
10 Determining the Structure of Organic Compounds 367

10.1 Mass Spectrometry 368
10.2 The Mass Spectrum • Fragmentation 369
10.3 Using The m/z Value of The Molecular Ion to Calculate the Molecular Formula 371
10.4 Isotopes in Mass Spectrometry 373

10.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas 374
10.6 Fragmentation Patterns 375
10.7 Gas Chromatography–Mass Spectrometry 376
M as s S p e c t r o m e t ry i n F o r e n s i c s 3 76
10.8 Spectroscopy and the Electromagnetic Spectrum 376

10.9 Infrared Spectroscopy 378
10.10 Characteristic Infrared Absorption Bands 379
10.11 The Intensity of Absorption Bands 379
10.12 The Position of Absorption Bands 380
10.13 The Position and Shape of an Absorption Band Is Affected by Electron Delocalization,
Electron Donation and Withdrawal, and Hydrogen Bonding 380
13
10.14 The Absence of Absorption Bands 385

10.15 How to Interpret an Infrared Spectrum 386
10.16 Ultraviolet and Visible Spectroscopy 387
U lt r av i o l e t L i g h t a n d S u n s c r e e n s 388
10.17 The Effect of Conjugation on max 389

10.18 The Visible Spectrum and Color 390
W h at M a k e s B l u e b e r r i e s B l u e a n d S t r a wb e r r i e s R e d ? 391
10.19 Some Uses of UV/VIS Spectroscopy 391

10.20 An Introduction to NMR Spectroscopy 392
N i ko l a T e s l a ( 18 5 6 – 19 4 3 ) 393
10.21 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies 394
10.22 The Number of Signals in an 1H NMR Spectrum 395
10.23 The Chemical Shift Tells How Far the Signal Is from the Reference Signal 396
10.24 The Relative Positions of 1H NMR Signals 397
10.25 The Characteristic Values of Chemical Shifts 397
10.26 The Integration of NMR Signals Reveals the Relative Number of Protons
Causing Each Signal 399
10.27 The Splitting of Signals Is Described by the N + 1 Rule 401
10.28 More Examples of 1H NMR Spectra 404
10.29 C NMR Spectroscopy

13
407
N MR U s e d i n M e d i c i n e i s C a l l e d M a g n e t i c R e s on a n c e I m a g i n g 4 11
11 Reactions of Carboxylic Acids and Carboxylic Acid

Derivatives 421
11.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives 423
N at u r e ’ s S l e e p i n g P i l l 425
11.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives 426
11.3 The Physical Properties of Carbonyl Compounds 427
11.4 How Carboxylic Acids and Carboxylic Acid Derivatives React 427
11.5 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 430
11.6 The Reactions of Acyl Chlorides 431
11.7 The Reactions of Esters 432
11.8 Acid-Catalyzed Ester Hydrolysis and Transesterification 434
11.9 Hydroxide-Ion-Promoted Ester Hydrolysis 437
A s p i r i n , N SAID s , a n d C OX - 2 In h i b i t o r s 438
11.10 Reactions of Carboxylic Acids 440

11.11 Reactions of Amides 441
Da l m at i a n s : Do N o t F oo l w i t h Mo t h e r N at u r e 442
11.12 Acid-Catalyzed Amide Hydrolysis and Alcoholysis 442

T h e D i s c ov e r y of P e n i c i l l i n 4 4 4
P e n i c i l l i n a n d D r u g R e s i s ta n c e 444
Penicillins in Clinical Use 445
A S e m i sy n t h e t i c P e n i c i l l i n 4 4 5
11.13 Nitriles 446

11.14 Acid Anhydrides 447
W h at D r u g - Enfo r c e m e n t Do g s A r e R e a l ly D e t e c t i n g 449
11.15 How Chemists Activate Carboxylic Acids 449

11.16 How Cells Activate Carboxylic Acids 450
N e r v e I m p u l s e s , Pa r a lys i s , a n d In s e c t i c i d e s 453

■ PROBLEMS 456
14
12 Reactions of Aldehydes and Ketones •

More Reactions of Carboxylic Acid Derivatives 459
12.1 The Nomenclature of Aldehydes and Ketones 460
B u ta n e d i on e : An Un p l e a s a n t Co m p o u n d 461
12.2 The Relative Reactivities of Carbonyl Compounds 462

12.3 How Aldehydes and Ketones React 463
12.4 Organometallic Compounds 463
12.5 The Reactions of Carbonyl Compounds with Grignard Reagents 465
Sy n t h e s i z i n g O r g a n i c Co m p o u n d s 467
S e m i sy n t h e t i c D r u g s 468
12.6 The Reactions of Aldehydes and Ketones with Cyanide Ion 469
12.7 The Reactions of Carbonyl Compounds with Hydride Ion 470
12.8 The Reactions of Aldehydes and Ketones with Amines 473
Serendipity in Drug Development 4 76
12.9 The Reactions of Aldehydes and Ketones with Alcohols 477

C a r bo h y d r at e s F o r m H e m i a c e ta l s a n d A c e ta l s 479
12.10 Nucleophilic Addition to ,-Unsaturated Aldehydes and Ketones 479

12.11 Nucleophilic Addition to ,-Unsaturated Carboxylic Acid Derivatives 481
En z y m e - C ata ly z e d C i s – T r a n s In t e r c onv e r s i on 4 8 1
12.12 Conjugate Addition Reactions in Biological Systems 482

Ca n c e r C h e m ot h e r a py 482

■ PROBLEMS 485
13 Reactions at the -Carbon of Carbonyl Compounds 489

13.1 The Acidity of an -Hydrogen 490
13.2 Keto–Enol Tautomers 492

13.3 Keto–Enol Interconversion 493
13.4 Alkylation of Enolate Ions 495
T h e Sy n t h e s i s of A s p i r i n 4 9 6
13.5 An Aldol Addition Forms -Hydroxyaldehydes or -Hydroxyketones 496

13.6 The Dehydration of Aldol Addition Products forms ,-Unsaturated
Aldehydes and Ketones 498
13.7 A Crossed Aldol Addition 499
B r e a s t C a n c e r a n d A r o m ata s e In h i b i t o r s 500
13.8 A Claisen Condensation Forms a -Keto Ester 500

13.9 CO2 Can Be Removed from a Carboxylic Acid with a Carbonyl Group at the 3-Position 503
13.10 Reactions at the -Carbon in Cells 504
13.11 Organizing What We Know about the Reactions of Organic Compounds 508
■ PROBLEMS 510
14 Radicals 513
14.1 Alkanes are Unreactive Compounds 513
N at u r a l G a s a n d P e t r o l e u m 5 14
F o s s i l F u e l s : A P r ob l e m at i c En e r g y So u r c e 5 14
14.2 The Chlorination and Bromination of Alkanes 515

W h y R a d i c a l s N o Lon g e r H av e t o B e C a l l e d F r e e R a d i c a l s 5 16
14.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the
Unpaired Electron 516
15
14.4 The Distribution of Products Depends on Radical Stability 517

14.5 The Stereochemistry of Radical Substitution Reactions 519

14.6 Formation of Explosive Peroxides 520
14.7 Radical Reactions Occur in Biological Systems 521
D e c a ff e i n at e d Coff e e a n d t h e C a n c e r S c a r e 522
F oo d P r e s e r vat i v e s 523
I s C h o c o l at e a H e a lt h F oo d ? 523
14.8 Radicals and Stratospheric Ozone 524

A r t i f i c i a l B l oo d 525

■ PROBLEMS 526
15 Synthetic Polymers 527

15.1 There Are Two Major Classes of Synthetic Polymers 528
15.2 Chain-Growth Polymers 529
T e f l on : An A c c i d e n ta l D i s c ov e r y 532
R e cyc l i n g Sy m bo l s 533
15.3 Stereochemistry of Polymerization • Ziegler–Natta Catalysts 538

15.4 Organic Compounds That Conduct Electricity 539
15.5 Polymerization of Dienes • Natural and Synthetic Rubber 540
15.6 Copolymers 542
N a no c on ta i n e r s 542
15.7 Step-Growth Polymers 543

15.8 Classes of Step-Growth Polymers 543
H e a lt h Con c e r n s : B i s p h e no l A a n d P h t h a l at e s 547
D e s i g n i n g a Po ly m e r 547
15.9 Recycling Polymers 549

15.10 Biodegradable Polymers 549
16 The Organic Chemistry of Carbohydrates 553

16.1 Classification of Carbohydrates 554
16.2 The d and l Notations 555
16.3 The Configurations of Aldoses 556
16.4 The Configurations of Ketoses 557
16.5 The Reactions of Monosaccharides in Basic Solutions 558
M e a s u r i n g t h e B l oo d G l u c o s e L e v e l s i n D i a b e t e s 559
16.6 Monosaccharides Form Cyclic Hemiacetals 560

V i ta m i n C 5 6 2
16.7 Glucose Is the Most Stable Aldohexose 563

16.8 Formation of Glycosides 564
16.9 Disaccharides 566
L a c t o s e In t o l e r a n c e 567
16.10 Polysaccharides 568

Why the Dentist Is Right 569
H e pa r i n — A N at u r a l An t i c o a g u l a n t 569
Con t r o l l i n g F l e a s 571
16.11 Carbohydrates on Cell Surfaces 571

16.12 Artificial Sweeteners 572
A c c e p ta b l e Da i ly In ta k e 5 74

■ PROBLEMS 575
16
17 The Organic Chemistry of Amino Acids, Peptides, and

Proteins 577
17.1 The Nomenclature of Amino Acids 578
P r o t e i n s a n d N u t r i t i on 5 8 1
17.2 The Configuration of Amino Acids 582

A m i no A c i d s a n d D i s e a s e 582
17.3 The Acid–Base Properties of Amino Acids 583

17.4 The Isoelectric Point 584
17.5 Separating Amino Acids 585
W at e r Sof t e n e r s : E x a m p l e s of C at i on - E x c h a n g e C h r o m at o g r a p h y 588
17.6 The Synthesis of Amino Acids 589

17.7 The Resolution of Racemic Mixtures of Amino Acids 590
17.8 Peptide Bonds and Disulfide Bonds 591
R u nn e r ’ s H i g h 592
Diabetes 594
H a i r : S t r a i g h t o r C u r ly ? 594
17.9 An Introduction to Protein Structure 595

P r i m a r y S t r u c t u r e a n d Ta x ono m i c R e l at i on s h i p 595
17.10 How to Determine the Primary Structure of a Polypeptide or a Protein 595

17.11 Secondary Structure 600

17.12 Tertiary Structure 602
D i s e a s e s C au s e d by a M i s fo l d e d P r o t e i n 6 0 3
17.13 Quaternary Structure 604

17.14 Protein Denaturation 605
18 How Enzymes Catalyze Reactions •

The Organic Chemistry of the Vitamins available on-line
18.1 Enzyme-Catalyzed Reactions 1

18.2 An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions 4
How Ta m i f l u W o r k s 5
18.3 An Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide

and Ester Hydrolysis 8
18.4 An Enzyme-Catalyzed Reaction That Is Reminiscent of the Base-Catalyzed
Enediol Rearrangement 10
18.5 An Enzyme-Catalyzed Reaction That Is Reminiscent of a Retro-Aldol Addition 12
18.6 Vitamins and Coenzymes 13
V i ta m i n B 1 15
18.7 Niacin: The Vitamin Needed for Many Redox Reactions 15

N i a c i n D e f i c i e n cy 16
18.8 Riboflavin: Another Vitamin Used in Redox Reactions 20

18.9 Vitamin B1: The Vitamin Needed for Acyl Group Transfer 23
C u r i n g a H a n g ov e r w i t h V i ta m i n B 1 26
18.10 Vitamin H: The Vitamin Needed for Carboxylation of an -Carbon 28

PR O B LEM - S O LV I N G STRATEGY 30
18.11 Vitamin B6: The Vitamin Needed for Amino Acid Transformations 30
A s s e s s i n g t h e Da m a g e Af t e r a H e a r t At ta c k 34
18.12 Vitamin B12: The Vitamin Needed for Certain Isomerizations 35

18.13 Folic Acid: The Vitamin Needed for One-Carbon Transfer 37
T h e F i r s t An t i b i o t i c s 38
Co m p e t i t i v e In h i b i t o r s 41
C a n c e r D r u g s a n d S i d e Eff e c t s 41
17
18.14 Vitamin K: The Vitamin Needed for Carboxylation of Glutamate 41

a N t i cOag u l a N t s 42
tO O m uc h B r O c cO l i 43
19 The organic Chemistry of the Metabolic Pathways 609

d i F F e r e N c e s i N m e ta B O l i s m 6 10
19.1 ATP Is Used for Phosphoryl Transfer Reactions 610

W h y d i d N at u r e c h O O s e p h O s p h at e s ? 6 11
19.2 The “High-Energy” Character of Phosphoanhydride Bonds 611

19.3 The Four Stages of Catabolism 612
19.4 The Catabolism of Fats 613
19.5 The Catabolism of Carbohydrates 616
p r O B l e m - s O lV i N g s t r at e g y 620
19.6 The Fate of Pyruvate 620

19.7 The Catabolism of Proteins 621
p h e N y l k e t O N u r i a ( p k u ) : a N i N B O r N e r r O r O F m e ta B O l i s m 623
19.8 The Citric Acid Cycle 623

19.9 Oxidative Phosphorylation 626
B a s a l m e ta B O l i c r at e 627
19.10 Anabolism 627

19.11 Gluconeogenesis 628
19.12 Regulating Metabolic Pathways 629
19.13 Amino Acid Biosynthesis 630
20 The organic Chemistry of lipids 634

20.1 Fatty Acids Are Long-Chain Carboxylic Acids 635
O m e g a Fat t y a c i d s 636
W a x e s a r e e s t e r s t h at h aV e h i g h m O l e c u l a r W e i g h t s 636
20.2 Fats and Oils Are Triglycerides 637

W h a l e s a N d e c h O l O c at i O N 638
20.3 Soaps and Detergents 638

20.4 Phosphoglycerides and Sphingolipids 640
sNake VeNOm 641
m u lt i p l e s c l e r O s i s a N d t h e m y e l i N s h e at h 642
20.5 Prostaglandins Regulate Physiological Responses 642

20.6 Terpenes Contain Carbon Atoms in Multiples of Five 642
20.7 How Terpenes are Biosynthesized 644
p r O B l e m - s O lV i N g s t r at e g y 645
20.8 How Nature Synthesizes Cholesterol 646

20.9 Synthetic Steroids 647
21 The Chemistry of the nucleic Acids 650

21.1 Nucleosides and Nucleotides 650
t h e s t r u c t u r e O F d N a : W at s O N , c r i c k , F r a N k l i N , a N d W i l k i N s 653
21.2 Nucleic Acids Are Composed of Nucleotide Subunits 653

21.3 The Secondary Structure of DNA—The Double Helix 654
21.4 Why DNA Does Not Have a 2-OH Group 656
18
21.5 The Biosynthesis of DNA Is Called Replication 657

21.6 DNA and Heredity 658
N at u r a l p r O d u c t s t h at m O d i F y d N a 658
21.7 The Biosynthesis of RNA Is Called Transcription 659

21.8 The RNAs Used for Protein Biosynthesis 660
21.9 The Biosynthesis of Proteins Is Called Translation 662
sickle cell aNemia 664
a N t i B i O t i c s t h at a c t By i N h i B i t i N g t r a N s l at i O N 664
21.10 Why DNA Contains Thymine Instead of Uracil 665

a N t i B i O t i c s a c t By a c O m m O N m e c h a N i s m 666
21.11 Antiviral Drugs 666

i N F l u e N z a pa N d e m i c s 667
21.12 How the Base Sequence of DNA Is Determined 667

21.13 Genetic Engineering 669
resistiNg herBicides 669
u s i N g g e N e t i c e N g i N e e r i N g t O t r e at t h e e B O l a V i r u s 670
Appendix I Physical Properties of Organic Compounds available on-line

Appendix II Spectroscopy Tables available on-line
Answers to Selected Problems A-1

Glossary G-1
Photo Credits P-1
Index I-1
Preface
In deciding what constitutes “essential” organic chemistry, I asked myself the following
question: What do students need to know if they are not planning to be synthetic organic
chemists? In other words, what do they need to know for their careers in medicine, den-
tistry, applied health professions, nutrition, or engineering?
Based on the answers to that question, I made content and organizational choices with
the following goals in mind:
■ Students should understand how and why organic compounds react the way they do.
■ Students should understand that the reactions they learn in the first part of the
course are the same as the reactions that occur in biological systems (that is, that
occur in cells).
■ Students should appreciate the fun and challenge of designing simple syntheses.
(This is also a good way to check if they truly understand reactivity.)
■ Students should understand how organic chemistry is integral to biology, to medi-
cine, and to their daily lives.
■ In order to achieve the above goals, students need to work as many problems as
possible.
To counter the impression that the study of organic chemistry consists primarily
of memorizing a diverse collection of molecules and reactions, this book is organized
around shared features and unifying concepts, emphasizing principles that can be applied
again and again. I want students to learn how to apply what they have learned to new
settings, reasoning their way to a solution rather than memorizing a multitude of facts.
A new feature, “Organizing What We Know about the Reactions of Organic
Compounds,” lets students see where they have been and where they are going as they
proceed through the course, encouraging them to keep in mind the fundamental reason
behind the reactions of all organic compounds: electrophiles react with nucleophiles.
When students see the first reaction of an organic compound (other than an acid–base
reaction), they are told that all organic compounds can be divided into families and all
members of a family react in the same way. To make things even easier, each family can
be put into one of four groups and all the families in a group react in similar ways.
The book then proceeds with each of the four groups (Group I: compounds with c arbon–
carbon double and triple bonds; Group II: benzene; Group III: compounds with an electro-
negative group attached to an sp3 carbon; and Group IV: carbonyl compounds). When the
chemistry of all the members of a particular group has been covered, students see a sum-
mary of the characteristic reactions of that group (see pages 276, 360, 508) that they can
compare with the summary of the characteristic reactions of the group(s) studied previously.
The margin notes throughout the book encapsulate key points that students should
remember. (For example, “when an acid is added to a reaction, it protonates the most basic
atom in the reactant”; “with bases of the same type, the weaker the base, the better it is as a
leaving group”; and stable bases are weak bases”.) To simplify mechanistic understanding,
common features are pointed out in margin notes (see pages 435, 443, 474, 478).
There are about 140 application boxes sprinkled throughout the book. These are
designed to show the students the relevance of organic chemistry to medicine (dissolving
sutures, mad cow disease, artificial blood, cholesterol and heart disease), to agriculture
(acid rain, resisting herbicides, pesticides: natural and synthetic), to nutrition (trans fats,
basal metabolic rate, lactose intolerance, omega fatty acids), and to our shared life on this
planet (fossil fuels, biodegradable polymers, whales and echolocation).
19
20 Preface
Success in organic chemistry requires students to work as many problems as possible.

Therefore, the book is structured to encourage problem solving. The answers (and expla-
nations, when needed) to all the problems are in the accompanying Study Guide and
Solutions Manual, which I authored to ensure consistency in language with the text.
New Tutorials following relevant chapters give students extra practice so that they
can better master important topics: Acids and Bases, Drawing Curved Arrows: Pushing
Electrons, and Drawing Resonance Contributors.
The problems within each chapter are primarily drill problems. They appear at the end of
each section, so they allow students to test themselves on the material they have just read to
see if they are ready to move on to the next section. Selected problems in each chapter are
accompanied by worked-out solutions to provide insight into problem-solving techniques.
Short answers are provided at the back of the book for problems marked with a diamond to
give students immediate feedback concerning their mastery of a skill or concept.
The many Problem-Solving Strategies in the book teach students how to approach
various kinds of problems. Each Problem-Solving Strategy is followed by an exercise to
give the student an opportunity to use the strategy just learned.
The end-of-chapter problems vary in difficulty. They begin with drill problems that inte-
grate material from the entire chapter, requiring students to think in terms of all the material
in the chapter rather than focusing on individual sections. The problems become more chal-
lenging as the student proceeds. The net result for the student is a progressive building of both
problem-solving ability and confidence. (I have chosen not to label problems as particularly
challenging so as not to intimidate the students before they try to solve the problem.)
Many of the end-of-chapter problems can also be found in MasteringChemistry.
Students can master concepts through traditional homework assignments in Mastering
that provide hints and answer-specific feedback. Students learn chemistry by practicing
chemistry.
Additionally, tutorials in MasteringChemistry, featuring specific wrong-answer feedback,
hints, and a wide variety of educationally effective content, guide your students through the
course. The hallmark Hints and Feedback offer scaffolded instruction similar to what stu-
dents would experience in an office hour, allowing them to learn from their mistakes without
being given the answer. Organic Chemistry Tutorials in MasteringChemistry pinpoint errors
by assessing the logic and accuracy of the student’s answers. Individual evaluators written
and linked to each problem by organic chemists look at the validity of the student’s entry and
generate error-specific feedback based on information received from a JChem database.
The book contains two new chapters: “Radicals” and “Synthetic Polymers.” There
is no longer a chapter on the “Organic Chemistry of Drugs.” Much of the material that
was in that chapter is now in application boxes, so students have the opportunity to learn
about that material who may have not had that opportunity if that last chapter were not
covered in their course.
Similarly, some of the information on the chemistry of living systems has been inte-
grated into earlier chapters. As examples, noncovalent interactions in biological systems has
been added to Chapter 3, the discussion of catalysis in Chapter 5 now includes a discussion
of enzymatic catalysis, and acetal formation by glucose has been added to Chapter 12.
The six chapters (Chapters 16–21) that focus primarily on the organic chemistry of
living systems have been rewritten to emphasize the connection between the organic
reactions that occur in the laboratory and those that occur in cells. Each organic reaction
that occurs in a cell is explicitly compared to the organic reaction with which the student
is already familiar. Chapter 18 can be found on the Instructor Resource Center.
The chapter on spectroscopy is modular, so it can be covered at any time during the
course—at the very beginning, at the very end, somewhere in between, or not covered at
all. When I wrote that chapter, I did not want students to be overwhelmed by a topic they
may never revisit in their lives, but I did want them to enjoy being able to interpret rela-
tively simple spectra. In addition to the spectroscopy problems in the text, there are over
forty new spectroscopy problems in the Study Guide and Solutions Manual with worked-
out answers. The answers come after the problems, so students have the opportunity to
try to solve them on their own first.
New modern design, streamlined narrative, and bulleted summaries at the end of
each chapter allow students to navigate through the content and study more efficiently
with the next.
Preface 21
ACKNOWLEDGMENTS
It gives me great pleasure to acknowledge the dedicated efforts of Jordan Fantini and
Malcolm Forbes, who checked every inch of the book for accuracy; David Yerzley, M.D.,
for his assistance with the section on MRI; Warren Hehre of Wavefunction, Inc., and
Alan Shusterman of Reed College for their advice on the electrostatic potential maps
that appear in the book; and Jeremy Davis, who created the art that appears on page 147.
I am also very grateful to my students, who pointed out sections that needed clarification,
worked the problems and suggested new ones, and searched for errors.
The following reviewers have played an enormously important role in the develop-
ment of this book.
Third Edition Reviewers Second Edition Reviewers

Marisa Blauvelt, Springfield College Deborah Booth, University of Southern Mississippi
Dana Chatellier, University of Delaware Paul Buonora, California State University–Long
Karen Hammond, Boise State University Beach
Bryan Schmidt, Minot State University Tom Chang, Utah State University
Wade McGregor, Arizona State University, Tempe Dana Chatellier, University of Delaware
William Wheeler, Ivey Tech Community College Amy Deveau, University of New England
Julia Kubanek, Georgia Institute of Technology J. Brent Friesen, Dominican University
Colleen Munro-Leighton, Truman State University Anne Gorden, Auburn University
Rick Mullins, Xavier University Christine Hermann, University of Radford
Erik Berda, University of New Hampshire Scott Lewis, James Madison University
Michael Justik, Pennsylvania State University, Erie Cynthia McGowan, Merrimack College
Hilkka Kenttamaa, Purdue University Keith Mead, Mississippi State University
Kristina Mack, Grand Valley State University Amy Pollock, Michigan State University
Jason Serin, Glendale Community College
Second Edition Accuracy Reviewer
Anthony St. John, Western Washington University
Malcolm Forbes, University of North Carolina
Third Edition Accuracy Reviewers
Jordan Fantini, Denison University
Malcolm D.E. Forbes, University of North Carolina
I am deeply grateful to my editor, Jeanne Zalesky, whose talents guided this book
and caused it to be as good as it could be, and to Coleen Morrison, whose gentle
prodding and attention to detail made the book actually happen. I also want to
thank the other talented and dedicated people at Pearson whose contributions made
this book a reality. And thank you to Lauren Layn, the creative brains behind the
technology that accompanies the book.
I particularly want to thank the many wonderful and talented students I have had
over the years, who taught me how to be a teacher. And I want to thank my chil-
dren, from whom I may have learned the most.
To make this textbook as user friendly as possible, I would appreciate any com-
ments that will help me achieve this goal in future editions. If you find sections that
could be clarified or expanded, or examples that could be added, please let me know.
Finally, this edition has been painstakingly combed for typographical errors. Any
that remain are my responsibility; if you find any, please send me a quick e-mail so
that they can be corrected in future printings of this edition.
University of California, Santa Barbara
pybruice@chem.ucsb.edu
22 Preface
Pearson wishes to thank and acknowledge the following reviewers for their work on the
Global Edition:
Dharam Vir Singh Jain, Department of Chemistry, Punjab University

Rajarshi Banerjee, PhD Scholar, Delhi
About the Author
Paula Bruice with Zeus, Bacchus, and Abigail
Paula Yurkanis Bruice was raised primarily in Massachusetts. After graduating from the
Girls’ Latin School in Boston, she earned an A.B. from Mount Holyoke College and a
Ph.D. in chemistry from the University of Virginia. She then received an NIH postdoc-
toral fellowship for study in the Department of Biochemistry at the University of Virginia
Medical School and held a postdoctoral appointment in the Department of Pharmacology
at the Yale School of Medicine.
Paula has been a member of the faculty at the University of California, Santa Barbara
since 1972, where she has received the Associated Students Teacher of the Year Award,
the Academic Senate Distinguished Teaching Award, two Mortar Board Professor of the
Year Awards, and the UCSB Alumni Association Teaching Award. Her research interests
center on the mechanism and catalysis of organic reactions, particularly those of biologi-
cal significance. Paula has a daughter and a son who are physicians and a son who is a
lawyer. Her main hobbies are reading suspense novels, any biographies, and enjoying her
pets (three dogs, two cats, and two parrots).
23
Essential Skills
New features and major revisions to this third edition focus on developing
students’ problem solving and analytical reasoning skills. Organized around
mechanistic similarities, Bruice encourages students to be mindful of the New Tutorials Skill Builders
fundamental reasoning behind the reactions of all organic compounds:
following select chapters deepen student
electrophiles react with nucleophiles. understanding of key topics while develop-
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include acid-base chemistry, building
molecular models, and drawing curved
arrows and are paired with assignable
MasteringChemistry® tutorials with wrong
answer-specific feedback and coaching.
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Numerous new interest boxes throughout each chapter connect chemistry to students’ lives and often provide
any needed additional explanation on the organic chemistry occurring. New applications include: Using Genetic
Engineering to Treat Ebola, Diseases Caused by a Misfolded Protein, The Inability to Perform an SN2 Reaction Causes
a Severe Clinical Disorder, and Electron Delocalization Affects the Three-Dimensional Shape of Proteins.
Student Tutorials
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Mastering
Chemistry®
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28
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Essential Organic Chemistry provides an integrated teaching and learning package of
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Another random document with
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haystacks. I enquired the meaning, and was told I was looking upon an
Indian village, and these were wigwams. I was delighted to behold a
veritable Indian lodge, and to see real Indians, instead of those half
civilized beings I had met at Niagara. They are a body of Chippeway
Indians who reside upon Warpole Island under the care of a Missionary of
the Methodist church. Their wigwams consisted of poles meeting at top,
around which, coarse matting, formed of reeds is fastened. From the apex of
these cones smoke was rising, telling of culinary operations going on
within. Around each lodge was a small patch of potatoes or corn. A small
church, with the missionary cottage and a few log cabins, were in the midst.
Groups of Indians were lounging upon the bank gazing at us, while others
unconcernedly pursued their usual occupations of fishing or hoeing. How
much more graceful were those wild sons of the forest, than the civilized
men I had observed upon the shores I had passed. Their mantles of cloth or
blanket stuff, trimmed with gay colors, were gracefully thrown around
them, and their ornamented leggins or moccasins glittered as they walked.
How dignified is the tread of an Indian! we remarked as we passed the
island, many in various occupations and attitudes, yet they never moved
awkwardly, nor sprang, nor jumped in a clumsy manner. The missionary
cottage was an object of great interest to us. I had often read of these self-
denying disciples of Jesus, but never before looked upon the scene of their
labors. Here in this lonely shore, away from all they love—their friends and
home—and almost shut out from the face of civilized man, they spend their
days in laboring to ameliorate the lot of these unhappy children of the
forest. In bringing them to the feet of their master, they are indeed
conferring a blessing upon them past all return. As a recompense for the
bright land their fathers have taken from the bereaved Indian, they are
leading them to another, brighter and more lasting. There is no change, nor
shadow of turning—there, no enemy can destroy their homes—there, the
tears are wiped from their eyes, and all their sorrows soothed. Noble
missionary, who can appreciate thy sacrifice? None but those who have
come from a civilized land, where thou hast passed thy early days, and who
now sees thee among the endless forests with no associates save those
wretched savages, can understand the greatness of thy disinterestedness.
During the short summer, a residence may be tolerable, but when the rivers
and lakes are choaked up by ice, the short glimpse he has obtained of his
fellow man, while whirled past in a steamboat, will be denied him. The roar
of the winter wind will shake his cottage, and the wolf will scare him from
his slumbers. But what are earthly joys or sorrows to a child of Christ? His
meat and drink is to do the will of him that sent him, and in return for the
comforts and pleasures of civilized life, he receives a peace ‘the world
cannot give’—a joy, David in all the glory of his kingly life sighed for,
when he prayed ‘Give me the joy of thy salvation.’ A small settlement is
formed at the mouth of Black river, called Port Huron, which is to be the
termination of another canal across the state.
Here we found another vessel waiting for wind. It was the brig Rocky
Mountain, bound to Green Bay, being attached to our other side we passed
‘doubly armed.’ Near the point where the river leaves lake Huron stands
fort Gratiot, an United States military station whose white walls and
buildings, over which the American flag was waving, looked out brightly
from among the dark forest of the Michigan shore. A line of blue coats were
going through their morning drill; and a few cannons looked out fiercely
upon us. A small white Gothic church, and a cottage stood near; the whole
making a pretty cabinet picture. The river now narrowed to a quarter of a
mile, upon each side a point—the American side crowned by a light-house,
and the Canadian by a cluster of Indian cabins. A bark canoe, paddled by
five Indians, pushed off the shore and came after us with the greatest
rapidity, their long black hair flying wildly behind them. Our two vessels
retarded our motion a little, so that the Indians overtook us, and kept at our
side for some distance. They used their paddles with astonishing quickness,
and we were surprised to see them in their ‘light canoe,’ keep pace with our
large steamboat. It was however for a short distance only—they were soon
fatigued with such great exertion, and turned towards the point, and sprang
out, or rather stepped out with the greatest dignity, drew the canoe to the
shore, and then squatted down upon the bank evidently enjoying their race.
I use the above inelegant word, as being very expressive of their posture.
The Indian never sits down as we do—with his feet close beside each other,
and his body erect, he sinks slowly down—his blanket is then thrown over
his head and around his feet, so that nothing is seen except his dark glaring
eyes. Through the narrow pass before mentioned, between the two points,
the waters of Huron run with a swift current. Here we were furnished with
another evidence of the rise of these waters.
An officer of the army and his wife were our fellow voyagers, very
intelligent and agreeable persons. They had been stationed at fort Gratiot a
few years since, and had frequently roved over the beach around the light-
house in search of the pretty silecious pebbles, agate, camelian, and
calcedony, which are often found upon these shores. To their surprise, they
now found their favorite point, ‘curtailed of its fair proportions’ by a rise of
nearly five feet of water. Our steamboat and its two ‘tenders,’ passed
between the points out of St. Clair river, and we found ourselves at once in
a large and shoreless lake, with nothing in front, between us and the bright
blue sky, which touched the green waters in the far horizon beyond. The
transition is so sudden from the narrow opening, to the boundless lake as to
produce a grand and exciting effect. Once out upon the calm waters of
Huron, our two guests were loosened from their tackles, and spreading their
huge wings, they passed one to each shore, and we soon left them far
behind. About an hour after, the bell of our steamboat startled the still lake
with its clamors, denoting the approach of some vessel. We looked out in
time to see the noble steamboat Great Western rush past us as if upon the
wings of a whirlwind. She was on her way from Chicago to Buffalo. Her
bell answered ours, and the deck was crowded with passengers. One of
these standing alone by himself, and taking his hat off attracted our notice
and we discovered in him an old acquaintance from New York. These
meetings in a distant land are very interesting, carrying our feelings at once
to the home we had left. This steamboat is one of the largest upon the lakes,
is finished in a style of great elegance, and is said to be as long as the
English steamship of the same name.
This whole day since ten o’clock—we have been passing through Huron
under a cloudless sky. The lake is two hundred and fifty-five miles long,
and its waters are of a deeper tint than those we have passed, owing to its
great depth, as we are sailing over nine hundred feet of water, while in some
places it is said to be unfathomable. The color is a dark olive almost black,
and it is only when the sun shines through the waves that we can perceive
they are green. The cause of the various colors of water has produced many
a hypothesis. Sir Humphry Davy tells us the primitive color of water is like
the sky, a delicate azure.[13] He says ‘the finest water is that which falls
from the atmosphere—this we can rarely obtain in its pure state, as all
artificial contact gives more or less of contamination; but, in snow melted
by the sunbeams that has fallen upon glaciers, themselves formed from
frozen snow, may be regarded as in its state of greatest purity. Congelation
expels both salt and air from water whether existing below, or formed in the
atmosphere; and in the high and uninhabited region of glaciers, there can
scarcely be any substances to contaminate. Removed from animal and
vegetable life, they are even above the mineral kingdom.’ Water from
melted snow, then considered as the purest, Sir Humphrey goes on to
describe its color. ‘When a mass is seen through, it is a bright blue, and
according to its greater or less depth of substance, it has more or less of this
color.’ ‘In general when examining lakes and masses of water in high
mountains, their color is the same bright azure. Capt. Parry states that water
in the Polar ice has the like beautiful tint.’ The brown, green, and other
colors of rivers he imputes to substances over which they flow, as peat
bogs, vegetable and mineral substances. He allows the sea cannot be
colored from any thing upon the bottom, but imputes the tint to the infusion
of iodine, and brome which he has detected in sea water, the result of
decayed marine vegetables. Of this primitive water are our lakes formed,
originating as they do in regions of snow and ice. Lake Superior, from
whence they flow, is a vast basin of trap rock, of volcanic origin.[14] It is
the most magnificent body of water in the world, five hundred miles long,
and nine hundred deep, and perfectly pellucid. Into this pure, and originally,
azure primitive water, there flow forty rivers, upon the south side alone,
according to Mr. McKenney of the Indian department, who counted this
number from St. Mary’s to the river St. Louis. These rivers he tells us are
all amber colored. Why then may not these yellow rivers flowing into blue
water, produce green. You see I like to hazard a hypothesis as well as
others. I hope you will not call this absurd. Col. McKenney himself,
imputes the green color to reflection of the ‘rays of light passing through
the foliage of the shores, conveying their own green hue unto the surface of
the water from which they are reflected.’ This might be the case in small
rivers or lakes, but it cannot thus tint such a vast extent of water. A writer in
the American Journal of Science, is of opinion the color of water is
reflected from the sky, and is blue, dull, black, or golden, as the sky may be
—and that ‘green is produced in water, by the yellow light of the sun mixed
with the cerulean blue through which it shines.’ On the contrary the Count
Xavier de Maistre,[15] does not impute the color of water to any infused
substance, nor to reflection from above, but reflection from the surface
below, ‘as the blue color of the sky is owing to reflection from the earth
beneath.’ ‘Limpid waters, when they have sufficient depth,’ says the Count,
reflect like air, a blue color from below,—and this arises from a mixture of
air, which water always contains to a greater or lesser amount. This blue
color, being the primitive hue of water is sometimes clouded or lost by
earthy infusion, or reflections from a colored sky. The green tinge which he
sometimes observed in water, he tells us, is occasioned by reflection from a
white surface below. This he proves by his experiment of a sheet of tin
painted white let down beneath the water—and his description of the water
in the beautiful limestone grotto, on the shore of the Mediteranian at Capri.
The green tint observed in the ocean is only seen when it is so shallow, as to
reflect the sun’s rays from the earth beneath it.
As the States surrounding these lakes are more or less underlaid by
limestone, we may suppose the bottoms of the waters are in some places
paved with it; and from this, or the shores under the water and around it,
may be reflected, according to the Count’s theory, the light which gives the
water a green appearance. But I will not trouble you with any more
speculations; they come with an ill grace from me who only pretend to
describe all that passes before my eyes.
In the afternoon we were off Saginaw bay, an indentation in the coast of
Michigan running seventy or eighty miles deep and forty wide, making the
lake here very broad; in one spot we were out of sight of the land. A river of
the same name flows into the bay, upon which, about twenty-three miles
from its mouth, is a small town. A canal is proposed from this bay, across
the state to lake Michigan, at Grand or Washtenog river. How shall I convey
to you an idea of the loveliness which sat upon earth, air, and water this
afternoon! Certainly that sunset upon lake Huron is the most beautiful I
have ever beheld. The vast and fathomless lake, bounded by the heavens
alone, presented an immense circle, ‘calm as a molten looking-glass,’—to
quote from my favorite Job—surrounded by a band of fleecy clouds,
making a frame work of chased silver. Slowly and gracefully sank the orb,
the white clouds gently dispersing at his approach, and leaving their
monarch a free and glorious path. As he drew near that chrystal floor, all
brilliancy faded from the face of the lake, save one bright pathway from the
sun to us—like the bridge of Giamschid leading from earth to heaven. The
sun which I had always been accustomed to see above, was now below me,
near the water, on the water, under the water! A veil of purple is thrown
over it, and now the sun sleeps on lake Huron. The gold and rose which
painted the western sky have gone. Darkness has stolen over the world
below, and we turn our eyes above. What a high and noble dome of
loveliest blue! Upon one side there hangs a crescent of the purest pearly
white, while at its side steals forth one silver star, soon followed, as, saith
Ezekiel, by ‘all the bright lights of heaven,’ until night’s star-embroidered
drapery is canopied around us. What bosom is insensible to this gorgeous
firmament? Who hath not felt the ‘sweet influence of the Pleiades’ while
gazing at this starry roof above? I wish I could make you a piece of poetry
upon this subject, but as there is enough already composed upon the stars, I
will send you a bit of Byron and tell you—
Blue roll the waters—blue the sky
Spreads like an ocean hung on high,
Bespangled with those isles of light,
So wildly spiritually bright,
Whoever gazed upon them shining,
And turned to earth without repining.
Do you remember that little hymn our old nurse used to teach us in our
childhood:
Twinkle, twinkle, pretty star

Can’t you tell us what you are,
Up above the world so high
Like a diamond in the sky.
Yes, from childhood to manhood, we wish to penetrate into the mysteries of

those golden regions, and ever ask them to tell us ‘what you are.’ We see
them gem the night with their lustrous beauty; we watch them as they pace
their azure courts, and lose ourselves in high imaginings, too vast for us,
while earth still keeps our souls its prisoner. How much deeper must be the
interest with which the astrologer of old followed them in their ‘golden
tracks.’ In them he read his destiny, and thought to see the scenes of earth
reflected in their light. How must he have gazed upon them, as their rays
paled or brightened, while reading in them ‘the fate of man and empires.’
Man’s efforts to penetrate the mysteries of these glorious creations have not
been all in vain. The Almighty architect, from time to time, graciously
bestows upon him, knowledge of ‘parts of his ways.’ How much more has
been vouchsafed to us than to the early nations. Looking back through the
vista of the past, we shall see great men appear, as ‘stars to rule the night’ of
our darkness and tell us of creation’s mysteries. Solomon, Ptolemy,
Gallileo, Copernicus, Tycho Brahe, Paschal, Newton, Herschel, with a host
of satellites, have been graciously shown the book of knowledge, to light
man’s pathway through the earth, and enlarge his ideas of the magnificence
and the benevolence of his Creator. ‘In the beginning,’ it did not enter into
God’s purpose to tell mankind more of the starry host, than that they were
‘lights to rule the night,’ and for ‘signs and for seasons;’ now see what
amazing things have been shown to us. We know they are worlds like our
own, filled with mountains and seas; having night and day, summer and
winter. We see their fields, now white with snow, now dark with returning
vegetation. How our hearts bound with hopes of future knowledge; and
imagine the time will come, when we can gaze upon their landscapes, and
‘listen to the hum of their mighty population.’[16] We have seen nature in all
its power and grandeur, while tossed on Erie’s waves, or listening to the
thunder of Niagara; but here she is at rest in all her quiet loveliness; and
would her worshippers behold her in her fairest mood, let them come and
gaze at evening on lake Huron.
July 4th.—The sun and I arose at the same time. When I left my state-
room, as if waiting to greet me, it arose majestically from the bosom of the
water, flooding the lake with light. No land was descried upon the east, but
we were near the Michigan shore off Thunder bay. The Shanewaging
islands which stretch across it were distinctly visible, and presented various
beauties of shape and tint. All trace of man has now disappeared, for the
northern part of Michigan has never been settled owing to the intense cold
of the winters. We have passed a long line of coast without any inhabitant
(except a forlorn woodman’s hut in one spot) stretching for two hundred
and fifty miles, covered with boundless forests, in whose green recesses
there are paths ‘which no fowl knoweth, and which the vultures eye hath
not seen.’ Here is the home of the bear, the elk, and the moose-deer—and
upon the aspen, oak, and maple trees, sport the blue bird, the robin, and
yellow hammer, undisturbed by the foot of man. We have now past the
bounds of civilization, and our vessel is the only spot of life in this vast
region of forest and water.
From the entrance of Lake Huron to Mackinac, there were but two
places where man was visible. At the mouth of the Zappa river soon after
entering the lake, there is a cabin where a woodman resides in the summer
season to supply the steamboats; and at Presque Isle where we stopped in
the afternoon there is another cluster of cabins, and woodpiles. Our Captain
did not stop at this latter place, as he did not like their wood, it being chiefly
swamp ash. The shore is low, covered with trees, having below, a beach of
yellow sand, until just before coming in sight of Michilimackinac when the
land becomes a little elevated. Ten miles this side of the last mentioned
place, we passed Boisblanc, a large wooded island, taking its name of
‘white wood’ from the silver barked birch tree. This island belongs to
government, and its only inhabitants, save a few straggling Ottowas are the
family of the light-house keeper whose pretty tenement, and stately light-
house, appear upon a projecting point. There is also a farm upon the island
given by government to the Missionaries of Michilimackinac, who
sometimes maintain a farmer upon it. O Mackinaw, thou lonely island, how
shall I describe thy various beauties! certainly for situation, history, and
native loveliness, it is the most interesting island in our States. We approach
it through an avenue of islands, Drummond and Manitoulin, dimly seen on
our east, and Boisblanc, and Round, in our western side. Stretching across
our path, far away in front of us, is Mackinaw, painted against the clear blue
sky. The island of Michilimackinac, or Mackinaw, or Mackinac as it is
commonly spelt and pronounced, is a high and bold bluff of limestone
about three hundred feet above the water, covered with verdure. Its name
signifies in the Indian tongue great turtle, as it is something of the figure of
this animal. At the foot of the bluff are strewed the buildings of the town.
Among the most conspicuous of these are, the agency house and gardens,
residence of Mr. Schoolcraft, Indian Agent—and the church and mission
house. Along the beach were several Indian wigwams, while numerous
pretty bark canoes were going and coming, as this is the Indian stopping
place. A very beautiful, and conspicuous object was the United States fort,
presenting at a distance the appearance of a long white line of buildings
inserted, into the top of the island high above the town. As we approached,
its picturesque block-houses and the pretty balconied residences of the
officers, came out to view, having the banner of the ‘stripes and stars’
waving over them. While gazing at this fair picture, suddenly a brilliant
flame, and volumes of white smoke arose above the fort, while a booming
sound told us they were firing their mid-day salute in honor of the day. This
added much to the beauty and grandeur of the scene. As our boat was to
remain there for some hours, we disembarked and ascended to the fort to
visit our friends the commanding officer and his family. We found them
sitting upon their balcony, looking down upon the newly arrived steamboat.
After the first greetings and mutual enquiries were over, we were shown all
it was thought would interest us.
The view from our friend’s balcony was beautiful in the extreme. The
bay in front, the lovely islands around covered with a luxurious vegetation
—the town spread out at our feet—the Indian lodges, and the canoes
skimming the bright waters, each called forth our expressions of
admiration. Passing into the interior of the fort, and through the fine parade
ground and a large gateway, we found ourselves upon the summit of the
island. Our path lay through copses of white birch, maple, and various other
trees, and over green sward covered with strawberries and a variety of wild
flowers. Our friends kindly gathered for me a variety of these, among which
was a fine scarlet lilium superbum, blue bells, and kinni kanic, or Indian
tobacco, and a pretty plant called Indian strawberry. Suddenly the silver
tones of woman’s voice, sounded near, and in a fairy dell we came upon a
tent, surrounded by a party of ladies and gentlemen, busily engaged
preparing for a fete in honor of the day. Among them was the daughter of
our host, and some of the celebrated family of S——t. We were presented
to the party, and were quite chagrined our limited time would not permit us
to accept their invitation to remain and partake of their festivities. The grace
and beauty of Mrs. S——t made great impression upon us. To me she was
peculiarly interesting from the fact of her being descended from the native
lords of the forest; for you know I have always taken the greatest interest in
the fate of our Indian tribes. From the accent, the deep brunette of her
smooth skin, and her dark hair and eyes, I should have taken her for a
Spanish lady. From the tent we wound our way up to a high peak of the
island. When near the summit, we left a grove, and saw before us one of the
most picturesque and singular objects imaginable. It was a high arched rock
of white limestone, stretching across a chasm before us, making a pretty
natural bridge, through which we gazed far down into the waves of Huron,
at least two hundred feet below. The surprise, the beauty and novelty of this
striking object, brought forth expressions of admiration from us. The white
arch was adorned with tufts of wild flowers, and shrubbery. Ascending the
arch, we gazed down upon the white beach below, whose pebbles could be
here distinctly seen under the limpid water although many feet deep—and
out upon the fair waters, and the pretty islands, which
“——Like rich and various gems inlay

The unadorned bosom of the deep.”
We were obliged to be satisfied with a hasty view of this charming

scene, as our time was limited; and we turned reluctantly towards our boat,
without visiting the ruins of fort Holmes, upon the high summit of the
island. While passing through the town we observed several antique houses
which had been erected by the French, who first settled this place in sixteen
hundred and seventy three.
These are frail delapidated buildings, covered with roofs of bark. Upon
the beach a party of Indians had just landed, and we stood while they took
down their blanket sail, and hauled their birch bark canoe about twenty feet
long, upon the shore. These are the Menominies or wild rice eaters, the
ugliest Indians I had ever seen—also Winebagoes, with dark skin, low
foreheads and shaggy hair, and having no pretentions to dress. I saw a chief
however afterwards who was gaily bedizened with tinsel, beads, and paint,
having one side of his face a light pea green, and the other cheek scarlet.
We watched them erect their lodges which was done very soon—a few
poles were placed in a circle, one end of each stood in the earth, while the
others met at the top—coarse matting was folded around these, leaving an
opening for a door, over which a blanket was hung. Some matting being
spread upon the floor inside, the children and moveables were placed
inside, and the canoe drawn up near it. We visited some of the shops and
laid up a store of Indian articles, which are made by these poor people and
sold here. Among them were small baskets called Mococks, made of birch
bark embroidered with porcupine quills, stained different colors—this was
filled with maple sugar. It is pleasant to meet friends so far from home, but I
think the pleasure is almost counterbalanced by the pain of parting. This we
felt keenly, when the planks had withdrawn, and our friends had been
forced to leave us, as we gazed after them winding their way up to the fort,
the shores, and waters around seemed more desolate, more lonely than
before.
Just before the steamboat started we had an opportunity of judging of the
boasted transparency of this water, its depth having prevented this on our
voyage. I looked down into it from the boat, where it was twenty feet deep,
and could scarcely believe there was anything but air between us and those
shining pebbles below. We had also an opportunity of hearing some Indian
music. Upon the shore sat a group of unearthly beings, one of whom struck
several taps upon a sort of drum, accompanied by the others, in what
sounded like a wolf recitative—at the end of this all united in a yell which
dyed away over the lake, much in the style of a howling blast accompanied
by the shrieks of a drowning traveller. Our fishing party left us here to go
up the Sault St. Mary, into lake Superior, spending their summer days
among the picturesque scenery of that magnificent lake. We bade adieu with
much regret to this pretty island, whose green terraces, fort and picturesque
town, Indian lodges, and light canoes, made a beautiful scene—but the most
interesting point in the view, was that white handkerchief waving farewell
from the fortress balcony.
This island is 615 miles from Buffalo; 319 from Detroit. There are water
marks upon the rocks 200 feet above the lake, proving the water had once
stood so high. The scenery here has been prettily described by an author of
talent, Mrs. Jameson; but, as much pleased as I was with her book, I must
regret she came here under such circumstances. It is with reluctance I
censure one so gifted, but it is with a view of warning you, and my young
friends to whom I know you will show my letters, against errors to which
the very witchery of her genius would blind you. However passionate a
desire you may entertain for the picturesque, I hope you may never leave
the protection of your friends and wander in search of it alone. May your
curiosity to see great men never lead you to invade the retreat of a world
hating bachelor; and may you never stray in wild forests, through storms
and tempests, with no companion save a rude Indian, or a ‘bronzed,
brawney, unshaven, back-woodsman,’ ‘very much like a bear upon his hind
legs,’ and you ‘a poor, lonely, shivering woman.’ I quote her words. You
had better be a ‘tarry at home traveller,’ or write ‘voyages around my own
room.’ If you do thus, you must expect the ladies where you visit will look
‘formal and alarmed,’ as she tells us the ladies of Toronto looked upon her.
But now I have done scolding and will pursue my journey. Upon a green
slope of the Michigan shore, a pile of ruins were pointed out as the site of
old fort Mackinac, which was taken by Pontiac with a stratagem and
afterwards every one within were massacred. How must those unfortunates
have felt, upon this desolate shore, hundreds of miles away from their
country, and at the mercy of savages. A band of Chippewa’s or Ojibwa’s
were just passing in canoes thirty feet in length. This tribe stands higher in
rank than the others, and their language, like the French, is the polite tongue
among the Indian tribes. They have a ruler whose office has been hereditary
for ages. He is called Mudjikiwis, and they pride themselves much upon his
and their own rank and lineage. There is an anecdote, related by
Schoolcraft, of one of this tribe, which, if you have never seen, will amuse
you. Chi Waishki, alias the Buffalo, was presented by the commissioners of
the treaty of Fond du Lac, with a medal as a badge of distinction. ‘What
need have I of this?’ he said haughtily. ‘It is known whence I am
descended!’ These canoes are the prettiest and lightest things imaginable.
They are formed of the bark of the birch tree, sewn together with a thread
made from fine roots of cedar split. The bark is soaked to make it more
pliable. Sometimes they are very gaily painted and ornamented. The
paddles are of light wood. Our Captain placed before us at dinner a very
fine lake trout, which he had purchased at Mackinaw. It was two feet long,
and very delicious. Fine salmon are also taken in these lakes. We were now
upon the great lake Michigan, which stretches from here three hundred and
twenty miles, to the Illinois shore, and is nine hundred feet deep. Our
course lay near the Michigan shore, which presented high bluffs and points
of limestone, with banks of pebbles, and high jagged hills, or dunes of sand.
These pebbles and sand are said to be thrown up by the north-western
winds, but I should rather imagine them left up by the floods which have
swept over the land. Upon our right were Fox and Beaver isles, beyond
which, Green bay runs into Wisconsin, one hundred and three miles. This
northern shore of Michigan is uninhabited, and covered with dense forests.
The ledges and masses of white limestone upon some of these islands
looked like fortresses or other buildings.
July 5th.—Sunday upon the lake. When I left my cabin, I found the
morning was misty, and the sun looking like the yolk of an egg, was
bobbing up and down upon the water. It had just peeped above the waves,
which, dashing about, sometimes obscured it from our view. We were lying
at one of the Manitou islands, taking in wood. This is a pretty crescent
shape islet, covered with trees. In the centre we were told is a lake which is
unfathomable, and supposed to be connected with lake Michigan. It is filled
with the large trout, salmon and white fish of the lakes. There is a
woodman’s hut, and several large piles of wood upon the shore. ‘Oh that the
woodman would spare those trees.’ Soon the pretty island will be denuded
and forlorn. It is a sacred island—the Indians imagining it to be the
residence of their Manitou, never dare to land there, as they believe such an
intrusion would be followed by the anger of their Deity. One Indian, who
despised such superstition ventured upon the shore, and was never heard of
since. The forests and lake in the interior, they imagine is the abode of the
blessed after death, whose hours will there pass in hunting and fishing. The
Manitoulin islands in lake Huron, are also sacred; but they are much larger
than these, one of them being fifty-five miles in length. I secured a handful
of pebbles from the shore, which, like those of other lakes, are agate,
chalcedony and other sileceous minerals. Upon the shores of lake Superior
these are found very fine, mixed with trachte, lava, and other volcanic
rocks, and with masses of native copper. I had brought with me a package
of well selected tracks, which I opened this morning, and laid a few upon
the table of the ladies saloon. Soon after, a pretty little girl knocked at my
state-room door, saying her mother wished to know if I had any more tracts,
as she should like to read one. I asked her where were those I laid upon the
table? those, she replied, some ladies were reading. I gave her several. The
chambermaid next appeared begging for some; and then the cabin boy came
with the same request. While I was selecting one which I thought might suit
him, I observed a brawny dusky figure, with his shirt sleeves rolled up, and
his person begrimed with soot and smoke, gazing earnestly towards us.
‘That’s Tom, one of the fire-men,’ said the cabin boy with a snigger; ‘he
heard you had books to lend and wants one dreadfully.’ I beckoned to him,
and he came forward with alacrity, while behind him I discerned several
other ‘grim visaged’ beings peeping out from their compartment towards
us. I gave him a package to distribute among his fellows; and during the day
had the pleasure of observing the greater part of the crew and passengers
busily engaged with my books. During our long voyage, those who had
books had read them out, and those who had none, were getting very weary,
so that they eagerly received any thing in the shape of reading. But some of
them, I trust, read them for the sake of the benefit they hoped to receive
from their contents. It was a source of great satisfaction to behold so many
persons engaged in themes of high import to their soul’s best interest. These
seeds were sown with a prayer for their success; and who can tell what
immortal plants may spring up in some of their hearts, growing to a tree of
life, and bearing fruit to flourish in the garden of paradise. Let me urge you
never to travel without these, or other useful books to distribute on your
way—like the girl in the fairy tale of our youth, shedding gems and
treasures in your path. There is no library in this boat as upon our Hudson
and Eastern steamboats, and we were often amused with the alacrity with
which our books were snatched up when we laid them down for a strole, or
to look at some object upon the shores. When we returned we were always
sure to receive them again, and felt no vexation, as we knew they meant no
impoliteness, and would be willing to lend us their own in return. My
companion had never been used to such socialisms in his country, and was
quite amused at this free and easy sort of thing. Our books were some of
them French, and upon one occasion we found them in the hands of a
simple hearted son of the forest, to whom books were so rare a treasure he
could not resist examining them. He returned it with a smile, and said,
shaking his head, ‘how you can make any sense out of that I can’t see, for I
cannot read a word of it.’
We lost sight of the Michigan shore at ten o’clock, and stretched across
the lake towards the Wisconsin coast, which we first saw at four o’clock P.
M., thus being nearly all day out of the sight of land. This may give you an
idea of the vastness of these lakes. Wisconsin, or Ouisconsin, or Wiskonsan,
here presents a high bank, called ‘red banks,’ from the color of the soil,
covered with forests, and showing no trace of man, except at the mouth of
the river Sheboygan, two hundred and twenty miles from Mackinaw, where
is a small settlement called by the name of the river.
Fifty miles from Sheboygan we stopped at the town of Milwaukie,
towards which the tide of emigration has been rapidly flowing. As the bay
is crossed by a bar, our large boat could not enter, and a small steamboat
took from us much of our merchandise and most of our emigrants. We did
not go on shore, but contented ourselves with seeing the town from the
boat. It looked neat, with some comfortable dwellings, several shops, hotel,
court house, &c. It stands upon the Milwaukie river. Its population is 1,000.
Several rail-roads and canals are in contemplation from this place across the
territory, as rail-roads to Winnebago lake; from Belmont to Dubuque; from
Belmont to Dodgeville in the mine district; a canal from Milwaukie to the
Black river, and another through the Fox and Wisconsin to the Mississippi.
Wisconsin will be soon covered with a dense population, as it is now a
favorite point for emigration. The soil is very rich, from one to ten feet
deep, the surface undulating prairie and woodland, consisting of 100,000
square miles of fertile land. The grassy plains make fine pasture lands, and
the lakes and rivers produce abundance of fish, and give great
manufacturing power. Lakes Superior and Michigan, and the river
Mississippi surround three sides, thus enabling them to send their produce
to market. Flour, rye, corn, barley, white-fish, and many other articles have
been exported this year. Their lead mines are very rich, and their valuable
forests of pine trees will be another source of wealth. These growing to the
height of one hundred and eighty or two hundred feet, crown the heights of
the northern region of the country, which is mountainous, containing
several waterfalls, one of which is two hundred and fifty feet in height. The
scenery is very picturesque. Madison, the capital, is a pretty, thriving town,
surrounded by four transparent lakes, upon the shore of one of which it is
situated; it sometimes goes by the poetical appellation of ‘city of the four
lakes.’ When the roads and canals are formed, Wisconsin will soon become
a thoroughfare to the Mississippi and the vast regions beyond; and those
who have ‘the world before them,’ cannot make a better choice than this.
Here we left our Buffalo hunters. Racine is a town twenty-two miles below
Milwaukie. The houses looked new, and were arranged in rows upon the
high green bank. The court-house was quite showy, having a portico in
front, with pillars reaching to the roof, which was painted red, surmounted
by a tin cupola. It stands at the mouth of Root river. We were now again in
sight of Michigan, as the lake grows narrower towards the end. We have
passed completely around this state, it being in the shape of a triangle. It is
destined to be a great and flourishing State, surrounded as it is by the lakes,
crossed by rivers, canals, and railroads, and covered by a rich soil. It is two
hundred and eighty miles long by one hundred and eighty, and covers
40,000 square miles. It has only been admitted into the Union as a State in
1837, and now possesses a population of 211,705. The country is level,
except a table land in the center from which the rivers flow into lakes St.
Clair, Huron, and Michigan. The remainder is covered with grassy prairie
land, with transparent lakes, and tracts of woodland. Here grows the
valuable maple from which they obtain their sugar; the white birch, whose
bark is used for making canoes, roofing houses, or even when split fine, in
writing letters by the early settlers; the oak, the beech, the hickory,
sassafras, and various other valuable trees. Its energetic inhabitants are
busily engaged laying out canals and rail-roads to intersect it in every
direction, as means of conveying their produce to its market. One hundred
and thirty-one miles of rail-road has been contracted for, but only forty-four
miles finished, from Detroit to Ann Arbor. Over this 41,896 barrels of flour
were conveyed this year to Detroit. Three years since the inhabitants of this
state sent to Ohio for their flour, and now they export 125,000 barrels of
flour this year. Education is not neglected; the legislature have appropriated
1,200,000 acres of land as a school fund, which, as the land is rapidly
rising, will be of great value. The celebrated Schoolcraft tells us, it was
deemed so inaccessible from swamps, that in 1818, it was not thought fit for
the soldiers bounty lands. This was, however, soon discovered to be a
mistake. He further informs us, the soil is an argillaceous soil, mellowed
with sands and pebbles, underlaid with schistose and calcareous rocks,
clothed with an open growth of oaks and hickories, the ridges covered with
walnut, ash, beech, and maple, while the valleys are first rate corn land,
diversified with limpid lakes, grassy prairies and pebbly bottomed brooks.
July 6th.—When approaching Chicago, the ‘haven where we would be,’

I did not so much watch for the appearance of that famed town, as look
back with regret at the beautiful lake I was leaving, for I was well assured ‘I
ne’er should look upon its like again.’ Two days and two nights I had been
sailing over it, never tired of gazing at its varied shores, or beauteous
waters. Those who have never beheld these masses of pellucid, brilliant,
green waters, can never imagine the extraordinary loveliness of the scene.
They cover a surface of 150,000 square miles, and contain nearly half the
fresh water upon the surface of the globe. That the water is fresh, is of great
importance to those who dwell upon their shores, as it can be of more use
for household purposes, and machinery. The valley in which the lakes
repose, is said to have been hewed out by the deluge, leaving the deep
chasms in which the waters lie; this is called the valley of the St. Lawrence,
and very properly; but I must object to this immense chain of lakes, four
and five hundred miles long, and nine hundred deep, being called the ‘river
St. Lawrence,’ as some fashionable tourists have of late. The St. Lawrence
river is an outlet, but is no more entitled to this designation, than is Niagara
or St. Clair river. These lakes all lie in a valley which interposes between
the primitive and secondary formations. The northern shores are granite
rocks, sterile, and scarcely inhabited; while the southern is rich alluvion,
covering sandstone and limestone.
The bustle of arrival aroused me from these reflections, and we were
soon seated in the parlor of the Lake Hotel, in the famous state of Illinois,
and town of Chicago. The rapid growth of this place you have heard of: in
1833 it could only count three frame dwellings and two hundred and fifty
inhabitants; and now enumerates six churches, one hundred shops, several
hotels, dwelling houses, and ware-houses, and between six and seven
thousand inhabitants. Chicago, or Tshicawgo, as the inhabitants and Indians
call it, is divided by a river of the same name into two parts, between which
is a free ferry and a bridge. The shops are upon one side, and the dwellings
upon the other. These last are in the style of country residences, enclosed
with white palings, surrounded by piazzas and gardens; some of brick, but
many of wood and neatly painted. Every thing looks quite new, as indeed it
might; for where now the town stands, was, as late as 1833, a fort, before
which was encamped seven thousand Indians. Fort Dearborn was erected
for the purpose of protecting the frontier. It was attacked in 1812 by the
Indian tribes, and their allies, and those who escaped massacre, sought
protection in fort Wayne. Another fort was built in 1818, but is now
deserted and let out for tenements. There are houses of worship here for
several denominations; among them the Presbyterian church is most
conspicuous. It is of brick and neatly finished. Part of the money required
for its erection, was acquired by the ladies in a Fair. The Lake House is a
very good hotel, situated among the dwelling houses. It is built of brick,
painted white, which, with its green blinds, gives it a pleasant appearance;
every thing within was comfortable and good of its kind. According to our
usual practice, we ascended to the cupola of the hotel, where is a lovely
view of the cottages and gardens at our feet, the broad prairies beyond, and
the bright waters of Michigan behind us. This town is beautifully situated
upon the borders of the lake, through which it holds constant
communication with Buffalo and the east. The other route I mentioned,
from Detroit continues over the rail-road at that city, and by cross roads to
St. Joseph’s upon the lake, from which place steamboats are continually
plying to Chicago. It is a shorter road, and gives the traveller a view of the
interior of Michigan. The Illinois and Michigan canal commences here,
which is to be carried to Peru on the Illinois river, a distance of one hundred
miles, thus opening a communication with the Mississippi and the Gulf of
Mexico. It is six feet deep and sixty feet wide, and is nearly finished. The
climate here is variable. In the summer the wind will one day blow over the
surface of the prairies, and the weather will become very hot; but the next
day, perhaps, it will come from the lake and cool it again. In consequence of
the vicinity of the lake there is not much snow, and it is not very cold.
We spent here one day only, but were able to see every thing in and
about the town, and in conversation with those friends residing here,
obtained every information. We intended making a longer stay, but learned
that the regular line of stages left town that evening, which obliged us to go
on or to stay longer than our time would admit. Before reaching here, it was
our intention to go to Michigan City, which is in Indiana, upon the shores of
the lake, and from thence cross Indiana to Madison, upon the Ohio, through
a fine succession of rail and Macadamized roads. Our friends here,
however, seemed to think it so monstrous a thing to return without
beholding the celebrated Mississippi, when within a few hundred miles
only, that we determined to alter our course and go down the Illinois river.
At nine o’clock at night we entered a commodious stage drawn by four
good horses, which was to take us to Peoria, upon the Illinois, one hundred
and fifty-seven miles distant, for which we were to pay twenty-two dollars,
eleven each, bed and board included. Beside us were two other passengers.
Crossing the bridge, we took up the mail at the post office, and then drove
through a long range of cheerfully lighted shops until we found ourselves
out of town. Here the road crossed the wet prairie, as it is called, which, in
some seasons, when the lake is high, is overflown. Through this wet land
we went splash, splash, nearly half the night. A rail-road is proposed here,
which will render travelling more pleasant. Hour after hour passed away,
my companions all dozing while I sought sleep in vain. The vast plain over
which we were moving, seen through the dusk of a cloudy night, seemed a
fitting place for dark deeds—a fine Hounslow heath, or Indian lurking
place. But there are no bandits here, and the Indians were all over the
Mississippi, and I was bidding such idle fears avaunt, when suddenly a low
plaintive wail sounded over the waste, startling my companions from their
slumbers. ‘What was that unearthly cry?’ I asked. ‘Only a prairie wolf
madam.’ ‘Dear me!’ exclaimed the other passenger, a youth. ‘I hope there
are not many of them, for sometimes wolves attack horses.’ ‘Not in these
prairies, sir,’ replied the other passenger, ‘they are rather shy, and afraid of
us.’ ‘I am glad, at least, to see a light,’ returned the youth, ‘there must be a
house yonder.’ ‘Yes, a bower in the rushes, nothing else,’ replied the other
man. ‘If you follow that light it will lead you a pretty chase through the
marshes; it is a jack-o’lantern.’ The hour, seen by the light of the coach
lamp, proved to be twelve, and each settled in his corner for another doze.
A sudden halt of the stage awakened us. The coachman took down a lamp
and began to search for something on the ground. ‘Halo, driver, what have
you lost?’ asked the youth. ‘Only my road sir,’ he replied. ‘Lost your road!’
exclaimed the youth in dismay; ‘Lost in these lonely moors among
wolverines and jack-o’lanterns! Here’s a pretty fix!’ ‘Driver you ought to
keep the skin off your eyes in such a dark night, I guess,’ said the other
passenger. I only wondered he could ever keep his road, as there was no
house or tree to mark his course even in the day, and one might easily pass
over the worn pathway in these grassy plains. The driver soon resumed his
seat, having discovered his path; and gave us the agreeable intelligence, he
had gone three miles out of his way. A few hours after this, a huge body
suddenly appeared before the window—it turned out to be a tree, a sign we
were approaching a river. Soon after we found ourselves before the door of
a small house, upon the banks of a narrow but deep and placid stream
fringed with trees. This was the Des Plaines, a river which rises so near lake
Michigan, that in times of its overflow, boats have passed from one to
another. This interlocking of waters which flow different ways, Darby
considers ‘an astonishing hydrographical anomaly.’ All the waters we had
passed, have fallen into the Atlantic, while those we were now following
find their way into the gulf of Mexico. The Des Plaines is called a branch of
the Illinois, which joins with the Kankakee, and afterwards the Fox, and the
united streams take the name of the Illinois. Many modern writers consider
this as the Illinois, and drop the name of Des Plaines, which I should judge
a proper arrangement. We awakened the drowsy owner of the house,
procured some refreshment, and with fresh horses resumed our journey.
July 7th.—I fell asleep, and when I was awakened at dawn this morning,
by my companion, that I might not lose the scene, I started with surprise
and delight. I was in the midst of a prairie! A world of grass and flowers
stretched around me, rising and falling in gentle undulations, as if an
enchanter had struck the ocean swell, and it was at rest forever. Acres of
wild flowers of every hue glowed around me, and the sun arising from the
earth where it touched the horizon, was ‘kissing with golden face the
meadows green.’ What a new and wonderous world of beauty! What a
magnificent sight! Those glorious ranks of flowers! Oh that you could have

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Essential Organic Chemistry Paula

Organic Chemistry 7th Edition Paula Yurkanis Bruice

Student s Solutions Manual for Organic Chemistry 7th

Study Guide and Student s Solutions Manual for Organic

Organic Chemistry John Mcmurry

Organic chemistry William Henry Brown

Organic Chemistry David R. Klein

Intermediate organic chemistry Third Edition

Get ready for organic chemistry Karty

Alkane RCH3 Aniline NH2

primary secondary tertiary

protonated carbonyl groups C a-carbon (aldehyde) C

Common Symbols and Abbreviations

[a] specific rotation Ea energy of activation pH measure of the acidity of

ΔH° change in enthalpy m dipole moment THF tetrahydrofuran or tetrahydrofolate

Paula Yurkanis Bruice

Pearson Education Limited

and Associated Companies throughout the world

Visit us on the World Wide Web at: www.pearsonglobaleditions.com

© Pearson Education Limited 2016

ISBN 10: 1-292-08903-2

British Library Cataloguing-in-Publication Data

Typeset in Times LT Std 10.5/12 by Lumina Datamatics, Inc.

Printed and bound in Malaysia.

Preface 19 CHapTER 12 Reactions of Aldehydes and Ketones • More

TUTORIal An Exercise in Drawing Curved Arrows:

CHapTER 8 Substitution and Elimination Reactions of a p p E N D I C E s I I Spectroscopy Tables

CHapTER 9 Reactions of Alcohols, Ethers, Epoxides,

1 Remembering General Chemistry:

1.1 The Structure of an Atom 31

1.5 Atomic Orbitals 45

1.9 How a Triple Bond Is Formed: The Bonds in Ethyne 52

1.13 The Bond in a Hydrogen Halide 58

1.15 The Dipole Moments of Molecules 63

New chapter on Acid/

for Organic Chemistry

2.11 Buffer Solutions 89

SOME IMPORTANT THINGS TO REMEMBER 90 ■ PROBLEMS 91

TUTORIAL Acids and Bases 93

3 An Introduction to Organic Compounds 101 New Feature—Tutorials

3.2 The Nomenclature of Alkanes 108

3.3 The Nomenclature of Cycloalkanes • Skeletal Structures 111

3.4 The Nomenclature of Alkyl Halides 114

3.5 The Classification of Alkyl Halides, Alcohols, and Amines 115

3.8 Factors that Affect the Solubility of Organic Compounds 122

3.9 Rotation Occurs About Carbon—Carbon Single Bonds 125

3.11 Conformers of Cyclohexane 129

3.13 Conformers of Disubstituted Cyclohexanes 134

3.14 Fused Cyclohexane Rings 137

SOME IMPORTANT THINGS TO REMEMBER 139 ■ PROBLEMS 139

4 Isomers: The Arrangement of Atoms in Space 144

4.8 Chiral Compounds Are Optically Active 158

4.13 Receptors 168

4.14 How Enantiomers Can Be Separated 170

SOME IMPORTANT THINGS TO REMEMBER 171 ■ PROBLEMS 172

5.1 The Nomenclature of Alkenes 177

6 The Reactions of Alkenes and Alkynes 210

6.1 The Addition of a Hydrogen Halide to an Alkene 211

6.7 The Stereochemistry of Enzyme-Catalyzed Reactions 225

6.10 The Nomenclature of Alkynes 229

6.11 The Structure of Alkynes 231

7 Delocalized Electrons and Their Effect on Stability, pKa,

7.2 The Bonding in Benzene 245 for Organic Chemistry