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This page intentionally left blank
 Introduction to
Organic Chemistry

F I F T H E d iti o n
This page intentionally left blank
 Introduction to
Organic Chemistry

F I F T H E d iti o n

W i l l i a m H . B r ow n T ho m a s P oo n
Beloit College Claremont McKenna College
Scripps College
Pitzer College

J o h n W i l ey & S o ns, I n c .
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10  9  8  7  6  5  4  3  2  1
 To Carolyn,
with whom life is a joy
Bill Brown

To Sophia,
sky, fish, fireworks
Thomas Poon
This page intentionally left blank
 A b o u t th e A u t h o r s

William H. Brown is Professor Emeritus at Beloit College, where he was twice

named Teacher of the Year. He is also the author of two other college textbooks: Organic
Chemistry 5/e, coauthored with Chris Foote, Brent Iverson, and Eric Anslyn, published in
2009, and General, Organic, and Biochemistry 9/e, coauthored with Fred Bettelheim, Mary
Campbell, and Shawn Farrell, published in 2010. He received his Ph.D. from Columbia
University under the ­direction of Gilbert Stork and did postdoctoral work at California
Institute of Technology and the University of Arizona. Twice he was Director of a Beloit
College World Affairs Center seminar at the University of Glasgow, Scotland. In 1999, he
retired from Beloit College to devote more time to writing and development of educational
materials. Although officially retired, he continues to teach Special Topics in Organic Syn-
thesis on a yearly basis.
Bill and his wife Carolyn enjoy hiking in the canyon country of the Southwest. In ad-
dition, they both enjoy quilting and quilts.

Thomas Poon is Professor of Chemistry in the W.M. Keck Science Department of

­Claremont McKenna, Pitzer, and Scripps Colleges, three of the five undergraduate institu-
tions that make up the Claremont Colleges in Claremont, California. He received his B.S.
degree from Fairfield University (CT) and his Ph.D. from the University of California, Los
Angeles under the direction of Christopher S. Foote. Poon was a Camille and Henry Drey-
fus Postdoctoral Fellow under Bradford P. Mundy at Colby College (ME) before joining the
faculty at Randolph-Macon College (VA) where he received the Thomas Branch Award for
Excellence in Teaching in 1999. He was a visiting scholar at Columbia University (NY) in
2002 (and again in 2004) where he worked on projects in both research and education with
his friend and mentor, Nicholas J. Turro. He has taught organic chemistry, forensic chem-
istry, upper-level courses in advanced laboratory techniques, and a first-year seminar class
titled Science of Identity. His favorite activity is working alongside undergraduates in the
laboratory on research problems involving the investigation of synthetic methodology in
zeolites, zeolite photochemistry, natural products isolation, and reactions of singlet oxygen.
When not in the lab, he likes to play guitar and sing chemistry songs to his daughter
Sophie.

vii
This page intentionally left blank
 C o n t e n ts O v e r v i e w

01 Covalent Bonding and

Shapes of Molecules 1 12 Aldehydes and Ketones 416

02 Acids and Bases 41

13 Carboxylic Acids 457

03 Alkanes and Cycloalkanes 63

14 Functional Derivatives of
Carboxylic Acids 488

04 Alkenes and Alkynes 108

15 Enolate Anions 526

05 Reactions of Alkenes and Alkynes 129

16 Organic Polymer Chemistry 564

06 Chirality: The Handedness

of Molecules 167 17 Carbohydrates 586

07 Haloalkanes 200
18 Amino Acids and Proteins 619

08 Alcohols, Ethers, and Thiols 239

19 Lipids 649

09 Benzene and Its Derivatives 282

20 Nucleic Acids (Online Chapter) 674

10 Amines 331
21 The Organic Chemistry
of Metabolism (Online Chapter) 700

11 Spectroscopy 361

ix
Con tents

01 Covalent Bonding and Summary of Key Questions 57

Shapes of Molecules 1 Quick Quiz 58
Key Reactions 59
1.1 How Do We Describe the Electronic Problems 59
Structure of Atoms? 2 Looking Ahead 62
1.2 What Is the Lewis Model of Bonding? 5 Group Learning Activities 62
1.3 How Do We Predict Bond Angles and the
Shapes of Molecules? 14
1.4 How Do We Predict If a Molecule Is
Polar or Nonpolar? 18

03
1.5 What Is Resonance? 19
Alkanes and Cycloalkanes 63
1.6 What Is the Orbital Overlap Model of
Covalent Bonding? 22
1.7 What Are Functional Groups? 28
3.1 What Are Alkanes? 64
Summary of Key Questions 32
3.2 What Is Constitutional Isomerism in
Quick Quiz 34 Alkanes? 66
Problems 35 3.3 How Do We Name Alkanes? 69
Looking Ahead 40 3.4 What Are Cycloalkanes? 73
Group Learning Activities 40 3.5 What Is the IUPAC System of
C H E MI C AL C O NN E C T I O NS Nomenclature? 75
1A Buckyball: A New Form of Carbon 17 3.6 What Are the Conformations of Alkanes and
Cycloalkanes? 76
3.7 What Is Cis–Trans Isomerism in
Cycloalkanes? 83
3.8 What Are the Physical Properties of Alkanes

02 Acids and Bases 41 and Cycloalkanes? 87

3.9 What Are the Characteristic Reactions of
Alkanes? 91
3.10 What Are the Sources of Alkanes? 91
2.1 What Are Arrhenius Acids and
Bases? 42 Summary of Key Questions 94

2.2 What Are Brønsted–Lowry Acids and Quick Quiz 96

Bases? 43 Key Reactions 97
2.3 How Do We Measure the Strength of an Problems 97
Acid or Base? 46 Looking Ahead 102
2.4 How Do We Determine the Group Learning Activities 104
Position of Equilibrium in an
Putting It Together 104
Acid–Base Reaction? 48
2.5 What Are the Relationships C H E MI C AL C O NN E C T I O NS
between Acidity and Molecular 3A The Poisonous Puffer Fish 84
Structure? 50 3B Octane Rating: What Those Numbers at the
2.6 What Are Lewis Acids and Bases? 54 Pump Mean 94

x
 co n te n t s xi

04 Alkenes and Alkynes 108 Looking Ahead 165

Group Learning Activities 166
C H E MI C AL C O NN E C T I O NS
4.1 What Are the Structures and Shapes 5A Catalytic Cracking and the Importance of
of Alkenes and Alkynes? 110 Alkenes 133
4.2 How Do We Name Alkenes and Alkynes? 112
4.3 What Are the Physical Properties
of Alkenes and Alkynes? 120

06
4.4 Why Are 1-Alkynes (Terminal Alkynes) Chirality: The Handedness
Weak Acids? 122 of Molecules 167
Summary of Key Questions 123
Quick Quiz 124
6.1 What Are Stereoisomers? 168
Problems 124
6.2 What Are Enantiomers? 169
Looking Ahead 128
6.3 How Do We Designate the Configuration
Group Learning Activities 128 of a Stereocenter? 173
C H E MI C AL C O NN E C T I O NS 6.4 What Is the 2n Rule? 176
4A Ethylene, a Plant Growth 6.5 How Do We Describe the Chirality of Cyclic
Regulator 109 Molecules with Two Stereocenters? 180
4B Cis–Trans Isomerism in Vision 111 6.6 How Do We Describe the Chirality
4C Why Plants Emit Isoprene 121 of Molecules with Three or More
Stereocenters? 182
6.7 What Are the Properties of
Stereoisomers? 183
6.8 How Is Chirality Detected in the

05
Laboratory? 184
Reactions of Alkenes and
Alkynes 129 6.9 What Is the Significance of Chirality
in the Biological World? 185
6.10 How Can Enantiomers Be Resolved? 186
5.1 What Are the Characteristic Reactions of
Summary of Key Questions 189
Alkenes? 130
Quick Quiz 190
5.2 What Is a Reaction Mechanism? 130
Problems 191
5.3 What Are the Mechanisms of
Electrophilic Additions to Alkenes? 136 Chemical Transformations 195
5.4 What Are Carbocation Looking Ahead 196
Rearrangements? 147 Group Learning Activities 196
5.5 What Is Hydroboration–Oxidation of Putting It Together 196
an Alkene? 150
C H E MI C AL C O NN E C T I O NS
5.6 How Can an Alkene Be Reduced to an
6A Chiral Drugs 187
Alkane? 153
5.7 How Can an Acetylide Anion Be
Used to Create a New Carbon–Carbon
Bond? 155
5.8 How Can Alkynes Be Reduced to Alkenes
and Alkanes? 157
Summary of Key Questions 158
Quick Quiz 159
07
7.1
Haloalkanes 200

How Are Haloalkanes Named? 201

Key Reactions 160 7.2 What Are the Characteristic Reactions
Problems 161 of Haloalkanes? 203
xii co n te n t s

7.3 What Are the Products of Nucleophilic C H E MI C AL C O NN E C T I O NS

Aliphatic Substitution Reactions? 206 8A Nitroglycerin: An Explosive and a Drug 243
7.4 What Are the SN2 and SN1 Mechanisms 8B Blood Alcohol Screening 260
for ­Nucleophilic Substitution? 208
8C Ethylene Oxide: A Chemical Sterilant 268
7.5 What Determines Whether SN1
or SN2 Predominates? 211
7.6 How Can SN1 and SN2 Be Predicted Based

09
on Experimental Conditions? 217 Benzene and
7.7 What Are the Products of Its Derivatives 282
b-Elimination? 219
7.8 What Are the E1 and E2 Mechanisms
9.1 What Is the Structure of Benzene? 283
for b-Elimination? 222
9.2 What Is Aromaticity? 286
7.9 When Do Nucleophilic Substitution
and b-Elimination Compete? 225 9.3 How Are Benzene Compounds Named, and
What Are Their Physical Properties? 289
Summary of Key Questions 229
9.4 What Is the Benzylic Position, and How Does
Quick Quiz 230
It Contribute to Benzene Reactivity? 292
Key Reactions 231
9.5 What Is Electrophilic Aromatic
Problems 231 Substitution? 295
Chemical Transformations 236 9.6 What Is the Mechanism of Electrophilic
Looking Ahead 237 Aromatic Substitution? 296
Group Learning Activities 238 9.7 How Do Existing Substituents on
Benzene Affect Electrophilic Aromatic
C H E MI C AL C O NN E C T I O NS
Substitution? 305
7A The Environmental Impact
9.8 What Are Phenols? 314
of Chlorofluorocarbons 204
Summary of Key Questions 321
7B The Effect of Chlorofluorocarbon
Legislation on Asthma Sufferers 228 Quick Quiz 322
Key Reactions 322
Problems 324
Chemical Transformations 329

08 8.1
Alcohols, Ethers,
and Thiols 239

What Are Alcohols? 240

Looking Ahead 330
Group Learning Activities 330
C H E MI C AL C O NN E C T I O NS
9A Carcinogenic Polynuclear Aromatics and
8.2 What Are the Characteristic Cancer 293
Reactions of Alcohols? 246
9B Capsaicin, for Those Who Like It Hot 318
8.3 What Are Ethers? 260
8.4 What Are Epoxides? 264
8.5 What Are Thiols? 268

10
8.6 What Are the Characteristic Reactions Amines 331
of Thiols? 271
Summary of Key Questions 272
Quick Quiz 274
10.1 What Are Amines? 333
Key Reactions 274
10.2 How Are Amines Named? 334
Problems 275
10.3 What Are the Characteristic Physical
Chemical Transformations 279 Properties of Amines? 337
Looking Ahead 280 10.4 What Are the Acid–Base Properties of
Group Learning Activities 281 Amines? 340
 co n te n t s xiii
10.5 What Are the Reactions of Amines with C H E MI C AL C O NN E C T I O NS
Acids? 344 11A Infrared Spectroscopy: A Window on Brain
10.6 How Are Arylamines Synthesized? 346 Activity 368
10.7 How Do Amines Act as Nucleophiles? 347 11B Magnetic Resonance Imaging 391
Summary of Key Questions 349
Quick Quiz 350

12
Key Reactions 350 Aldehydes and Ketones 416
Problems 351
Chemical Transformations 356
Looking Ahead 357 12.1 What Are Aldehydes and Ketones? 417
Group Learning Activities 357 12.2 How Are Aldehydes and Ketones
Putting It Together 357 Named? 417

C H E MI C AL C O NN E C T I O NS
12.3 What Are the Physical Properties of
Aldehydes and Ketones? 421
10A Morphine as a Clue in the Design and
Discovery of Drugs 332 12.4 What Is the Most Common Reaction Theme
of Aldehydes and Ketones? 422
10B The Poison Dart Frogs of South America:
Lethal Amines 338 12.5 What Are Grignard Reagents, and How
Do They React with Aldehydes and
Ketones? 423
12.6 What Are Hemiacetals and Acetals? 427

11
12.7 How Do Aldehydes and Ketones React
Spectroscopy 361 with Ammonia and Amines? 434
12.8 What Is Keto–Enol Tautomerism? 437
12.9 How Are Aldehydes and Ketones
11.1 What Is Electromagnetic Radiation? 362 Oxidized? 441
11.2 What Is Molecular Spectroscopy? 364 12.10 How Are Aldehydes and Ketones
11.3 What Is Infrared Spectroscopy? 364 Reduced? 443
11.4 How Do We Interpret Infrared Spectra? 367 Summary of Key Questions 445
11.5 What Is Nuclear Magnetic Resonance? 378 Quick Quiz 447
11.6 What Is Shielding? 380 Key Reactions 447
11.7 What Is an NMR Spectrum? 380 Problems 448
11.8 How Many Resonance Signals Chemical Transformations 454
Will a Compound Yield in Its NMR Spectroscopy 455
Spectrum? 382
Looking Ahead 456
11.9 What Is Signal Integration? 385
Group Learning Activities 456
11.10 What Is Chemical Shift? 386
C H E MI C AL C O NN E C T I O NS
11.11 What Is Signal Splitting? 388
12A A Green Synthesis of Adipic Acid 442
11.12 What Is 13C-NMR Spectroscopy, and
How Does It Differ from 1H-NMR
Spectroscopy? 391

13 Carboxylic Acids 457

11.13 How Do We Solve an NMR
Problem? 394
Summary of Key Questions 398
Quick Quiz 400 13.1 What Are Carboxylic Acids? 458
Problems 401 13.2 How Are Carboxylic Acids Named? 458
Looking Ahead 414 13.3 What Are the Physical Properties
Group Learning Activities 415 of Carboxylic Acids? 461
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MARGARET FULLER.
By Julia Ward Howe.

MARIA EDGEWORTH.
By Helen Zimmern.

London: W. H. Allen & Co., 13 Waterloo Place. S.W.

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1. Typos fixed; non-standard spelling and dialect
retained.
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