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Organic Chemistry SECOND EDITION
DAVID KLEIN
vi CONTENTS
PRACTICALLY SPEAKING An Introduction 6.3 Gibbs Free Energy 243

to Polymers 158 PRACTICALLY SPEAKING Explosives 244
4.6 Drawing Newman Projections 158 PRACTICALLY SPEAKING Do Living Organisms Violate
4.7 Conformational Analysis of Ethane the Second Law of Thermodynamics? 245
and Propane 160 6.4 Equilibria 246
4.8 Conformational Analysis of Butane 162 6.5 Kinetics 248
MEDICALLY SPEAKING Drugs and Their MEDICALLY SPEAKING Nitroglycerin: An Explosive
Conformations 166 with Medicinal Properties 251
4.9 Cycloalkanes 167 PRACTICALLY SPEAKING Beer-Making 252
MEDICALLY SPEAKING Cyclopropane as an Inhalation 6.6 Reading Energy Diagrams 253
Anesthetic 168
6.7 Nucleophiles and Electrophiles 256
4.10 Conformations of Cyclohexane 169
6.8 Mechanisms and Arrow Pushing 260
4.11 Drawing Chair Conformations 170
6.9 Combining the Patterns of Arrow Pushing 266
4.12 Monosubstituted Cyclohexane 172
6.10 Drawing Curved Arrows 268
4.13 Disubstituted Cyclohexane 175
6.11 Carbocation Rearrangements 271
4.14 cis-trans Stereoisomerism 180
6.12 Reversible and Irreversible Reaction Arrows 273
4.15 Polycyclic Systems 181
Review of Concepts & Vocabulary • SkillBuilder Review •
Review of Concepts & Vocabulary • SkillBuilder Review • Practice Problems • Integrated Problems •
Practice Problems • Integrated Problems • Challenge Problems Challenge Problems
5
Stereoisomerism 192
5.1 Overview of Isomerism 193
7
Substitution Reactions 287
5.2 Introduction to Stereoisomerism 196
PRACTICALLY SPEAKING The Sense of Smell 202 7.1 Introduction to Substitution Reactions 288
5.3 Designating Configuration Using the 7.2 Alkyl Halides 289
Cahn-Ingold-Prelog System 203 7.3 Possible Mechanisms for Substitution
MEDICALLY SPEAKING Chiral Drugs 208 Reactions 292
5.4 Optical Activity 209 7.4 The SN2 Mechanism 296
5.5 Stereoisomeric Relationships: Enantiomers PRACTICALLY SPEAKING SN2 Reactions in Biological
and Diastereomers 214 Systems—Methylation 302
5.6 Symmetry and Chirality 218 7.5 The SN1 Mechanism 303
5.7 Fischer Projections 223 7.6 Drawing the Complete Mechanism
5.8 Conformationally Mobile Systems 225 of an SN1 Reaction 309
5.9 Resolution of Enantiomers 226 7.7 Drawing the Complete Mechanism

of an SN2 Reaction 316
Practice Problems • Integrated Problems • Challenge Problems MEDICALLY SPEAKING Radiolabelled Compounds in
Diagnostic Medicine 319
7.8 Determining Which Mechanism
Predominates 320
6
Chemical Reactivity and Mechanisms 236
7.9 Selecting Reagents to Accomplish Functional Group
Transformation 327
MEDICALLY SPEAKING Pharmacology and Drug
Design 330
Review of Reactions • Review of Concepts & Vocabulary
6.1 Enthalpy 237 SkillBuilder Review • Practice Problems
6.2 Entropy 240 Integrated Problems • Challenge Problems
CONTENTS vii
8
PRACTICALLY SPEAKING Partially Hydrogenated
Fats and Oils 434
9.8 Halogenation and Halohydrin Formation 435
Alkenes: Structure and Preparation via 9.9 Anti Dihydroxylation 440
Elimination Reactions 341 9.10 Syn Dihydroxylation 443
9.11 Oxidative Cleavage 444
8.1 Introduction to Elimination Reactions 342
9.12 Predicting Products of an Addition Reaction 446
8.2 Alkenes in Nature and in Industry 342
9.13 Synthesis Strategies 448
PRACTICALLY SPEAKING Pheromones to Control
Insect Populations 343 Review of Reactions • Review of Concepts & Vocabulary
• SkillBuilder Review • Practice Problems
8.3 Nomenclature of Alkenes 345
Integrated Problems • Challenge Problems
8.4 Stereoisomerism in Alkenes 348
MEDICALLY SPEAKING Phototherapy Treatment for
10
Neonatal Jaundice 352
8.5 Alkene Stability 353
8.6 Possible Mechanisms for Elimination 356
Alkynes 464
8.7 The E2 Mechanism 358
8.8 Drawing the Products of an E2 Reaction 371 10.1 Introduction to Alkynes 465
8.9 The E1 Mechanism 372 MEDICALLY SPEAKING The Role of Molecular
8.10 Drawing the Complete Mechanism Rigidity 466
of an E1 Process 377 PRACTICALLY SPEAKING Conducting Organic
8.11 Drawing the Complete Mechanism of Polymers 467
an E2 Process 382 10.2 Nomenclature of Alkynes 467
8.12 Substitution vs. Elimination: Identifying 10.3 Acidity of Acetylene and Terminal Alkynes 470
the Reagent 383
10.4 Preparing Alkynes 473
8.13 Substitution vs. Elimination: Identifying
10.5 Reduction of Alkynes 474
the Mechanism(s) 387
10.6 Hydrohalogenation of Alkynes 478
8.14 Substitution vs. Elimination: Predicting
the Products 391 10.7 Hydration of Alkynes 481
Review of Synthetically Useful Elimination Reactions 10.8 Halogenation of Alkynes 487
Review of Concepts & Vocabulary • SkillBuilder Review • 10.9 Ozonolysis of Alkynes 487
Practice Problems • Integrated Problems • Challenge Problems
10.10 Alkylation of Terminal Alkynes 488
9
SkillBuilder Review • Practice Problems
Addition Reactions of Alkenes 404
11
9.1 Introduction to Addition Reactions 405
9.2 Addition vs. Elimination: A Thermodynamic
Perspective 406
9.3 Hydrohalogenation 407 Radical Reactions 500
PRACTICALLY SPEAKING Cationic Polymerization
and Polystyrene 415 11.1 Radicals 501
9.4 Acid-Catalyzed Hydration 416 11.2 Common Patterns in Radical Mechanisms 506
PRACTICALLY SPEAKING Industrial Production 11.3 Chlorination of Methane 510
of Ethanol 420 11.4 Thermodynamic Considerations for Halogenation
9.5 Oxymercuration-Demercuration 420 Reactions 513
9.6 Hydroboration-Oxidation 422 11.5 Selectivity of Halogenation 516
9.7 Catalytic Hydrogenation 428 11.6 Stereochemistry of Halogenation 519
viii CONTENTS
11.7 Allylic Bromination 522 13.5 Preparation of Diols 595

11.8 Atmospheric Chemistry and the Ozone Layer 524 PRACTICALLY SPEAKING Antifreeze 596
PRACTICALLY SPEAKING Fighting Fires with 13.6 Preparation of Alcohols via Grignard
Chemicals 526 Reagents 596
11.9 Autooxidation and Antioxidants 527 13.7 Protection of Alcohols 600
MEDICALLY SPEAKING Why is an Overdose of 13.8 Preparation of Phenols 602
Acetaminophen Fatal? 530 MEDICALLY SPEAKING Phenols as Antifungal
11.10 Radical Addition of HBr: Anti-Markovnikov Agents 603
Addition 531 13.9 Reactions of Alcohols: Substitution
11.11 Radical Polymerization 535 and Elimination 603
11.12 Radical Processes in the Petrochemical Industry 538 PRACTICALLY SPEAKING Drug Metabolism 607
11.13 Halogenation as a Synthetic Technique 538 13.10 Reactions of Alcohols: Oxidation 609
Review of Synthetically Useful Radical Reactions PRACTICALLY SPEAKING Breath Tests to Measure
Review of Concepts & Vocabulary • SkillBuilder Review • Blood Alcohol Level 610
13.11 Biological Redox Reactions 613
PRACTICALLY SPEAKING Biological Oxidation
of Methanol and Ethanol 614
12
13.12 Oxidation of Phenol 615
Synthesis 547 SkillBuilder Review • Practice Problems
12.1 One-Step Syntheses 548
12.2 Functional Group Transformations 549
12.3 Reactions that Change the Carbon Skeleton 554
MEDICALLY SPEAKING Vitamins 556
12.4 How to Approach a Synthesis Problem 557
MEDICALLY SPEAKING The Total Synthesis of
14
Ethers and Epoxides; Thiols and
Vitamin B12 559 Sulfides 633
12.5 Retrosynthetic Analysis 560
PRACTICALLY SPEAKING Retrosynthetic Analysis 568 14.1 Introduction to Ethers 634
12.6 Practical Tips for Increasing Proficiency 568 14.2 Nomenclature of Ethers 634
MEDICALLY SPEAKING Total Synthesis of Taxol 570 14.3 Structure and Properties of Ethers 637
Review of Concepts & Vocabulary • SkillBuilder Review • MEDICALLY SPEAKING Ethers as Inhalation
Practice Problems • Integrated Problems • Challenge Problems Anesthetics 638
14.4 Crown Ethers 639
MEDICALLY SPEAKING Polyether Antibiotics 641
13
14.5 Preparation of Ethers 641
14.6 Reactions of Ethers 644
14.7 Nomenclature of Epoxides 647
Alcohols and Phenols 576 MEDICALLY SPEAKING Epothilones as Novel
Anticancer Agents 648
13.1 Structure and Properties of Alcohols 577 14.8 Preparation of Epoxides 648
MEDICALLY SPEAKING Chain Length as a Factor MEDICALLY SPEAKING Active Metabolites
in Drug Design 582 and Drug Interactions 651
13.2 Acidity of Alcohols and Phenols 583 14.9 Enantioselective Epoxidation 652
13.3 Preparation of Alcohols via Substitution 14.10 Ring-Opening Reactions of Epoxides 654
or Addition 586
PRACTICALLY SPEAKING Ethylene Oxide as a Sterilizing
13.4 Preparation of Alcohols via Reduction 587 Agent for Sensitive Medical Equipment 657
CONTENTS ix
16
MEDICALLY SPEAKING Cigarette Smoke
and Carcinogenic Epoxides 662
14.11 Thiols and Sulfides 663
14.12 Synthesis Strategies Involving Nuclear Magnetic Resonance
Epoxides 667 Spectroscopy 731
• SkillBuilder Review • Practice Problems 16.1 Introduction to NMR Spectroscopy 732
Integrated Problems • Challenge Problems 16.2 Acquiring a 1H NMR Spectrum 734
16.3 Characteristics of a 1H NMR Spectrum 736
16.4 Number of Signals 736
15
16.5 Chemical Shift 743
16.6 Integration 749
16.7 Multiplicity 752
Infrared Spectroscopy 16.8 Drawing the Expected 1H NMR Spectrum of
and Mass Spectrometry 683 a Compound 760
16.9 Using 1H NMR Spectroscopy to Distinguish
15.1 Introduction to Spectroscopy 684 between Compounds 762
PRACTICALLY SPEAKING Microwave Ovens 686 MEDICALLY SPEAKING Detection of Impurities in
15.2 IR Spectroscopy 686 Heparin Sodium Using 1H NMR Spectroscopy 764
MEDICALLY SPEAKING IR Thermal Imaging for 16.10 Analyzing a 1H NMR Spectrum 764
Cancer Detection 687 16.11 Acquiring a 13C NMR Spectrum 767
15.3 Signal Characteristics: Wavenumber 689 16.12 Chemical Shifts in 13C NMR Spectroscopy 768
15.4 Signal Characteristics: Intensity 693 16.13 DEPT 13C NMR Spectroscopy 770
PRACTICALLY SPEAKING IR Spectroscopy for Testing MEDICALLY SPEAKING Magnetic Resonance Imaging
Blood Alcohol Levels 696 (MRI) 772
15.5 Signal Characteristics: Shape 696 Review of Concepts & Vocabulary • SkillBuilder Review •
15.6 Analyzing an IR Spectrum 700 Practice Problems • Integrated Problems • Challenge Problems
15.7 Using IR Spectroscopy to Distinguish between
Two Compounds 705
17
15.8 Introduction to Mass Spectrometry 707
PRACTICALLY SPEAKING Mass Spectrometry
for Detecting Explosives 708
15.9 Analyzing the (M) +•
Peak 709 Conjugated Pi Systems
15.10 Analyzing the (M+1)+• Peak 710 and Pericyclic Reactions 782
15.11 Analyzing the (M+2)+• Peak 712
17.1 Classes of Dienes 783
15.12 Analyzing the Fragments 714
17.2 Conjugated Dienes 784
15.13 High Resolution Mass Spectrometry 717
17.3 Molecular Orbital Theory 786
15.14 Gas Chromatography—Mass
Spectrometry 719 17.4 Electrophilic Addition 790
15.15 Mass Spectrometry of Large 17.5 Thermodynamic Control vs. Kinetic Control 793
Biomolecules 720 PRACTICALLY SPEAKING Natural and Synthetic
MEDICALLY SPEAKING Medical Applications of Rubbers 796
Mass Spectrometry 720 17.6 An Introduction to Pericyclic Reactions 797
15.16 Hydrogen Deficiency Index: Degrees of 17.7 Diels–Alder Reactions 798
Unsaturation 721
17.8 MO Description of Cycloadditions 804
17.9 Electrocyclic Reactions 806
17.10 Sigmatropic Rearrangements 812
MEDICALLY SPEAKING The Photoinduced
Biosynthesis of Vitamin D 814
x CONTENTS
17.11 UV-VIS Spectroscopy 814 MEDICALLY SPEAKING The Discovery of Prodrugs 884
PRACTICALLY SPEAKING Sunscreens 819 19.6 Friedel–Crafts Acylation 887
17.12 Color 820 19.7 Activating Groups 889
PRACTICALLY SPEAKING Bleach 820 19.8 Deactivating Groups 893
17.13 The Chemistry of Vision 821 19.9 Halogens: The Exception 895
Review of Reactions • Review of Concepts & Vocabulary 19.10 Determining the Directing Effects of
SkillBuilder Review • Practice Problems a Substituent 897
19.11 Multiple Substituents 900
19.13 Nucleophilic Aromatic Substitution 914
18
Aromatic Compounds 832
19.14 Elimination-Addition 916
19.15 Identifying the Mechanism of an Aromatic
Substitution Reaction 918
18.1 Introduction to Aromatic Compounds 833 Integrated Problems • Challenge Problems
PRACTICALLY SPEAKING What Is Coal? 834
18.2 Nomenclature of Benzene Derivatives 834
20
18.3 Structure of Benzene 838
18.4 Stability of Benzene 838
PRACTICALLY SPEAKING Molecular Cages 843
18.5 Aromatic Compounds Other than Benzene 845 Aldehydes and Ketones 931
MEDICALLY SPEAKING The Development of
Nonsedating Antihistamines 852 20.1 Introduction to Aldehydes and Ketones 932
18.6 Reactions at the Benzylic Position 854 20.2 Nomenclature 933
18.7 Reduction of the Aromatic Moiety 858 20.3 Preparing Aldehydes and Ketones:
A Review 936
18.8 Spectroscopy of Aromatic Compounds 861
20.4 Introduction to Nucleophilic Addition
PRACTICALLY SPEAKING Buckyballs and Reactions 937
Nanotubes 864
20.5 Oxygen Nucleophiles 939
SkillBuilder Review • Practice Problems MEDICALLY SPEAKING Acetals as Prodrugs 946
Integrated Problems • Challenge Problems 20.6 Nitrogen Nucleophiles 947
PRACTICALLY SPEAKING Beta-Carotene and
Vision 951
19
20.7 Hydrolysis of Acetals, Imines, and Enamines 956
MEDICALLY SPEAKING Prodrugs 958
20.8 Sulfur Nucleophiles 959
Aromatic Substitution Reactions 874 20.9 Hydrogen Nucleophiles 960
20.10 Carbon Nucleophiles 962
19.1 Introduction to Electrophilic Aromatic
Substitution 875 PRACTICALLY SPEAKING Cyanohydrin Derivatives
in Nature 964
19.2 Halogenation 876
20.11 Baeyer-Villiger Oxidation of Aldehydes
MEDICALLY SPEAKING Halogenation and Ketones 967
in Drug Design 879
19.3 Sulfonation 879
20.13 Spectroscopic Analysis of Aldehydes
PRACTICALLY SPEAKING What Are Those Colors and Ketones 972
in Fruity Pebbles? 881
19.4 Nitration 882 • SkillBuilder Review • Practice Problems
19.5 Friedel–Crafts Alkylation 883 Integrated Problems • Challenge Problems
CONTENTS xi
21
22.6 Conjugate Addition Reactions 1079
MEDICALLY SPEAKING Glutathione Conjugation
and Biological Michael Reactions 1082
Carboxylic Acids 22.7 Synthesis Strategies 1086
and Their Derivatives 984 Review of Reactions • Review of Concepts & Vocabulary
21.1 Introduction to Carboxylic Acids 985 Integrated Problems • Challenge Problems
21.2 Nomenclature of Carboxylic Acids 986
21.3 Structure and Properties of Carboxylic Acids 987
21.4 Preparation of Carboxylic Acids 991
23
21.5 Reactions of Carboxylic Acids 992
21.6 Introduction to Carboxylic Acid Derivatives 993
MEDICALLY SPEAKING Sedatives 995
21.7 Reactivity of Carboxylic Acid Derivatives 997
Amines 1102
21.8 Preparation and Reactions of Acid Chlorides 1005
23.1 Introduction to Amines 1103
21.9 Preparation and Reactions of Acid Anhydrides 1011
MEDICALLY SPEAKING Drug Metabolism Studies 1104
MEDICALLY SPEAKING How does Aspirin Work? 1013
23.2 Nomenclature of Amines 1105
21.10 Preparation of Esters 1013
23.3 Properties of Amines 1107
21.11 Reactions of Esters 1015
MEDICALLY SPEAKING Fortunate Side Effects 1109
PRACTICALLY SPEAKING How Soap Is Made 1016
MEDICALLY SPEAKING Amine Ionization and Drug
MEDICALLY SPEAKING Esters as Prodrugs 1018 Distribution 1114
21.12 Preparation and Reactions of Amides 1020 23.4 Preparation of Amines: A Review 1114
PRACTICALLY SPEAKING Polyamides and Polyesters 1021 23.5 Preparation of Amines via Substitution
MEDICALLY SPEAKING Beta-Lactam Antibiotics 1024 Reactions 1115
21.13 Preparation and Reactions of Nitriles 1025 23.6 Preparation of Amines via Reductive Amination 1119
21.14 Synthesis Strategies 1027 23.7 Synthesis Strategies 1121
21.15 Spectroscopy of Carboxylic Acids 23.8 Acylation of Amines 1124
and Their Derivatives 1033 23.9 The Hofmann Elimination 1125
Review of Reactions • Review of Concepts & Vocabulary 23.10 Reactions of Amines with Nitrous Acid 1128
23.11 Reactions of Aryldiazonium Ions 1131
23.12 Nitrogen Heterocycles 1135
MEDICALLY SPEAKING H2-Receptor Antagonists
and the Development of Cimetidine 1136
22
Alpha Carbon Chemistry:
23.13 Spectroscopy of Amines 1138
Enols and Enolates 1044
24
22.1 Introduction to Alpha Carbon Chemistry:
Enols and Enolates 1045
22.2 Alpha Halogenation of Enols and Enolates 1052
22.3 Aldol Reactions 1057 Carbohydrates 1151
PRACTICALLY SPEAKING Muscle Power 1060
PRACTICALLY SPEAKING Why Meat from Younger 24.1 Introduction to Carbohydrates 1152
Animals is Softer 1064 24.2 Classifying Monosaccharides 1152
22.4 Claisen Condensations 1068 24.3 Configuration of Aldoses 1155
22.5 Alkylation of the Alpha Position 1071 24.4 Configuration of Ketoses 1157
xii CONTENTS
24.5 Cyclic Structures of Monosaccharides 1158 26.4 Reactions of Triglycerides 1245

24.6 Reactions of Monosaccharides 1166 PRACTICALLY SPEAKING Soaps vs. Synthetic
24.7 Disaccharides 1173 Detergents 1250
MEDICALLY SPEAKING Lactose Intolerance 1176 26.5 Phospholipids 1254
PRACTICALLY SPEAKING Artificial Sweeteners 1177 MEDICALLY SPEAKING Selectivity of Antifungal

Agents 1257
24.8 Polysaccharides 1178
26.6 Steroids 1258
24.9 Amino Sugars 1179
MEDICALLY SPEAKING Cholesterol
24.10 N-Glycosides 1180 and Heart Disease 1261
MEDICALLY SPEAKING Aminoglycoside Antibiotics 1181 MEDICALLY SPEAKING Anabolic Steroids
MEDICALLY SPEAKING Erythromycin Biosynthesis 1185 and Competitive Sports 1264
Review of Reactions • Review of Concepts & Vocabulary 26.7 Prostaglandins 1265
SkillBuilder Review • Practice Problems MEDICALLY SPEAKING NSAIDs and COX-2
Integrated Problems • Challenge Problems Inhibitors 1267
26.8 Terpenes 1268
25
Review of Synthetically Useful Reactions •
Review of Concepts & Vocabulary •
SkillBuilder Review • Practice Problems •
Amino Acids, Peptides, and Proteins 1193
25.1 Introduction to Amino Acids, Peptides,
27
and Proteins 1194
25.2 Structure and Properties of Amino Acids 1195
PRACTICALLY SPEAKING Nutrition and Sources
of Amino Acids 1197 Synthetic Polymers 1279
PRACTICALLY SPEAKING Forensic Chemistry
and Fingerprint Detection 1202 27.1 Introduction to Synthetic Polymers 1280
25.3 Amino Acid Synthesis 1202 27.2 Nomenclature of Synthetic Polymers 1280
25.4 Structure of Peptides 1207 27.3 Copolymers 1282
MEDICALLY SPEAKING Polypeptide 27.4 Polymer Classification by Reaction Type 1284
Antibiotics 1213 27.5 Polymer Classification by Mode of Assembly 1292
25.5 Sequencing a Peptide 1214 27.6 Polymer Classification by Structure 1294
25.6 Peptide Synthesis 1216 27.7 Polymer Classification by Properties 1297
25.7 Protein Structure 1225 PRACTICALLY SPEAKING Safety Glass and Car
MEDICALLY SPEAKING Diseases Caused Windshields 1299
by Misfolded Proteins 1228 27.8 Polymer Recycling 1299
25.8 Protein Function 1229 Review of Reactions • Review of Concepts & Vocabulary
Review of Reactions • Review of Concepts & Vocabulary SkillBuilder Review • Practice Problems
SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems
Appendix A: Nomenclature of Polyfunctional
Compounds A-1
26
Glossary G–1
Credits Cr–1
Index I–1
Lipids 1239
26.1 Introduction to Lipids 1240
26.2 Waxes 1241
26.3 Triglycerides 1242
Preface
WHY I WROTE THIS BOOK
Students who perform poorly on organic chemistry exams often report having invested count-
less hours studying. Why do many students have difficulty preparing themselves for organic
chemistry exams? Certainly, there are several contributing factors, including inefficient study
habits, but perhaps the most dominant factor is a fundamental disconnect between what students
learn in the lecture hall and the tasks expected of them during an exam. To illustrate the discon-
nect, consider the following analogy.
Imagine that a prestigious university offers a course entitled “Bike-Riding 101.” Throughout
the course, physics and engineering professors explain many concepts and principles (for exam-
ple, how bicycles have been engineered to minimize air resistance). Students invest significant
time studying the information that was presented, and on the last day of the course, the final
exam consists of riding a bike for a distance of 100 feet. A few students may have innate talents
and can accomplish the task without falling. But most students will fall several times, slowly
making it to the finish line, bruised and hurt; and many students will not be able to ride for
even one second without falling. Why? Because there is a disconnect between what the students
learned and what they were expected to do for their exam.
Many years ago, I noticed that a similar disconnect exists in traditional organic chemistry
instruction. That is, learning organic chemistry is much like bicycle riding; just as the students in
the bike-riding analogy were expected to ride a bike after attending lectures, it is often expected
that organic chemistry students will independently develop the necessary skills for solving prob-
lems. While a few students have innate talents and are able to develop the necessary skills inde-
pendently, most students require guidance. This guidance was not consistently integrated within
existing textbooks, prompting me to write the first edition of my textbook, Organic Chemistry,
1e. The main goal of my text was to employ a skills-based approach to bridge the gap between
theory (concepts) and practice (problem-solving skills). The phenomenal success of the first
edition has been extremely gratifying because it provides strong evidence that my skills-based
approach is indeed effective at bridging the gap described above.
I firmly believe that the scientific discipline of organic chemistry is NOT merely a compila-
tion of principles, but rather, it is a disciplined method of thought and analysis. Students must
certainly understand the concepts and principles, but more importantly, students must learn
to think like organic chemists . . . that is, they must learn to become proficient at approaching
new situations methodically, based on a repertoire of skills. That is the true essence of organic
chemistry.
A SKILLS-BASED APPROACH
To address the disconnect in organic chemistry instruction, I have developed a skills-based
approach to instruction. The textbook includes all of the concepts typically covered in an organic
chemistry textbook, complete with conceptual checkpoints that promote mastery of the concepts,
but special emphasis is placed on skills development through SkillBuilders to support these
concepts. Each SkillBuilder contains 3 parts:
Learn the Skill: contains a solved problems that demonstrates a particular skill.
Practice the Skill: includes numerous problems (similar to the solved problem in Learn the
Skill) that give students valuable opportunities to practice and master the skill.
Apply the Skill: contains one or two more challenging problems in which the student must
apply the skill in a slightly different environment. These problems include conceptual, cumu-
lative, and applied problems that encourage students to think outside of the box. Sometimes
problems that foreshadow concepts introduced in later chapters are also included.
xiii
xiv PREFACE
At the end of each SkillBuilder, a Need More Practice? reference suggests end-of-chapter
problems that students can work to practice the skill.
This emphasis upon skills development will provide students with a greater opportunity
to develop proficiency in the key skills necessary to succeed in organic chemistry. Certainly,
not all necessary skills can be covered in a textbook. However, there are certain skills that are
fundamental to all other skills.
As an example, resonance structures are used repeatedly throughout the course, and stu-
dents must become masters of resonance structures early in the course. Therefore a significant
portion of Chapter 2 is devoted to pattern-recognition for drawing resonance structures. Rather
than just providing a list of rules and then a few follow-up problems, the skills-based approach
provides students with a series of skills, each of which must be mastered in sequence. Each skill
is reinforced with numerous practice problems. The sequence of skills is designed to foster and
develop proficiency in drawing resonance structures.
As another example of the skills-based approach, Chapter 7, Substitution Reactions, places
special emphasis on the skills necessary for drawing all of the mechanistic steps for SN2 and SN1
processes. Students are often confused when they see an SN1 process whose mechanism is com-
prised of four or five mechanistic steps (proton transfers, carbocation rearrangements, etc.). This
chapter contains a novel approach that trains students to identify the number of mechanistic
steps required in a substitution process. Students are provided with numerous examples and are
given ample opportunity to practice drawing mechanisms.
The skills-based approach to organic chemistry instruction is a unique approach. Certainly,
other textbooks contain tips for problem solving, but no other textbook consistently presents
skills development as the primary vehicle for instruction.
WHAT’S NEW IN THIS EDITION

Peer review played a very strong role in the development of the first edition of Organic Chemistry.
Specifically, the first edition manuscript was reviewed by nearly 500 professors and over 5,000
students. In preparing the second edition, peer review has played an equally prominent role.
We have received a tremendous amount of input from the market, including surveys, class tests,
diary reviews, and phone interviews. All of this input has been carefully culled and has been
instrumental in identifying the focus of the second edition.
Literature-based Challenge Problems

The first edition of my textbook, Organic Chemistry 1e, was written to address a gap between
theory (concepts) and practice (problem-solving skills). In Organic Chemistry 2e, I have endeav-
ored to bridge yet another gap between theory and practice. Specifically, students who have
studied organic chemistry for an entire year are often left profoundly disconnected from the
dynamic and exciting world of research in the field of organic chemistry. That is, students are
not exposed to actual research performed by practicing organic chemists around the world. To
bridge this gap and to address market feedback suggesting that the text would benefit from a
larger number of challenge problems, I’ve created literature-based Challenge Problems for this
edition. These problems will expose students to the fact that organic chemistry is an evolving,
active branch of science, central to addressing global challenges.
The literature-based Challenge Problems are more challenging than the problems presented
in the text’s SkillBuilders because they require the students to think “outside the box” and to pre-
dict or explain an unexpected observation. Over 225 new literature-based Challenge Problems
have been added in Organic Chemistry, 2e. All of these problems are based on the chemical litera-
ture and include references. The problems are all designed to be thought-provoking puzzles that
are challenging, but possible to solve with the principles and skills developed in the textbook.
The inclusion of literature-based problems will expose students to exciting real-world examples
of chemical research being conducted in real laboratories. Students will see that organic chem-
istry is a vibrant field of study, with endless possibilities for exploration and research that can
benefit the world in very concrete ways. Most chapters of Organic Chemistry, 2e will have 8-10
literature-based Challenge Problems. These problems are all coded for assigning and grading in
PREFACE xv
WileyPLUS. In addition, within the WileyPLUS course for Organic Chemistry, 2e, I’ve created
problem solving videos that provide key strategies for solving a subset of these problems.
Rewriting for Clarity

In response to market feedback a few sections in the textbook have been rewritten for clarity:
Chapter 7: Substitution Reactions/Section 7.5: The SN1 Mechanism
• The discussion of the rate-determining step has been revised to focus on the highest
energy transition state. A more detailed discussion of the thermodynamic principles
involved is now included.
Chapter 20: Aldehydes and Ketones/Section 20.7: Mechanism Strategies
• The section on hydrolysis, as well as the corresponding SkillBuilder, have been rewritten
for clarity.
Chapter 20: Aldehydes and Ketones/Section 20.10: Carbon Nucleophiles
• The discussion of the Wittig reaction mechanism has been revised to better reflect the
observations and insights discussed in the literature.
Applications and Chapter Openers

Much like the literature-based Challenge Problems underscore the relevance of organic chemis-
try to current research in the field, the Medically Speaking and Practically Speaking applications
demonstrate how the first principles of organic chemistry are relevant to practicing physicians
and have everyday commercial applications. We have received very positive feedback from the
market regarding these applications. In recognition of the fact that some applications generate
more interest than others, we’ve replaced approximately 10% of the applications, to make them
even more relevant and exciting. Since these applications are often foreshadowed in the Chapter
Openers, many Chapter Openers have been revised as well.
Reference Materials
An appendix containing rules for naming polyfunctional compounds as well as a reference table
of pKa values are now included.
In addition, all known errors, inaccuracies, or ambiguities have been corrected in the sec-
ond edition.
TEXT ORGANIZATION
The sequence of chapters and topics in Organic Chemistry, 2e do not differ markedly from that
of other organic chemistry textbooks. Indeed, the topics are presented in the traditional order,
based on functional groups (alkenes, alkynes, alcohols, ethers, aldehydes and ketones, carboxylic
acid derivatives, etc.). Despite this traditional order, a strong emphasis is placed on mechanisms,
with a focus on pattern recognition to illustrate the similarities between reactions that would
otherwise appear unrelated (for example, acetal formation and enamine formation, which are
mechanistically quite similar). No shortcuts were taken in any of the mechanisms, and all steps
are clearly illustrated, including all proton transfer steps.
Two chapters (6 and 12) are devoted almost entirely to skill development and are generally
not found in other textbooks. Chapter 6, Chemical Reactivity and Mechanisms, emphasizes skills
that are necessary for drawing mechanisms, while Chapter 12, Synthesis, prepares the students
for proposing syntheses. These two chapters are strategically positioned within the traditional
order described above and can be assigned to the students for independent study. That is, these
two chapters do not need to be covered during precious lecture hours, but can be, if so desired.
The traditional order allows instructors to adopt the skills-based approach without having
to change their lecture notes or methods. For this reason, the spectroscopy chapters (Chapters
15 and 16) were written to be stand-alone and portable, so that instructors can cover these chap-
ters in any order desired. In fact, five of the chapters (Chapters 2, 3, 7, 13, and 14) that precede
the spectroscopy chapters include end-of-chapter spectroscopy problems, for those students who
xvi PREFACE
covered spectroscopy earlier. Spectroscopy coverage also appears in subsequent functional group
chapters, specifically Chapter 18 (Aromatic Compounds), Chapter 20 (Aldehydes and Ketones),
Chapter 21 (Carboxylic Acids and Their Derivatives), Chapter 23 (Amines), Chapter 24
(Carbohydrates), and Chapter 25 (Amino Acids, Peptides, and Proteins).
THE WileyPLUS ADVANTAGE

WileyPLUS is a research-based online environment for effective teaching and learning.
WileyPLUS is packed with interactive study tools and resources, including the complete online
textbook.
New to WileyPLUS for Organic Chemistry, 2e

WileyPLUS for Organic Chemistry, 2e highlights David Klein’s innovative pedagogy and teach-
ing style:
•• NEW Solved Problem Videos by David Klein, extends the SkillBuilding pedagogy
by walking students through problem solving strategies for the new end of chapter
literature-based Challenge Problems.
•• NEW Guided Online (GO) Tutorials walk students step-by-step through solving the
problem using David Klein’s problem-solving pedagogy.
•• NEW Do you Remember? Practice Quizzes help students prepare for chapter course
materials by evaluating students’ foundational knowledge.
WileyPLUS for Organic Chemistry, 2e is now supported by an adaptive learning module called
ORION. Based on cognitive science, ORION provides students with a personal, adaptive learn-
ing experience so they can build proficiency in concepts and use their study time effectively.
WileyPLUS with ORION helps students learn by learning about them.
WileyPLUS with ORION is great as:
• An adaptive pre-lecture tool that assesses your students’ conceptual knowledge so they
come to class better prepared.
• A personalized study guide that helps students understand both strengths and areas
where they need to invest more time, especially in preparation for quizzes and exams.
Unique to ORION, students begin by taking a quick diagnostic for any chapter.
This will determine each student’s baseline proficiency on each topic in the chapter.
Students see their individual diagnostic report to help them decide what to do next
with the help of ORION’s recommendations.
BEGIN
For each topic, students can either Study, or Practice. Study directs the students
to the specific topic they choose in WileyPLUS, where they can read from the
e-textbook, or use the variety of relevant resources available there. Students can
also practice, using questions and feedback powered by ORION’s adaptive learn-
ing engine. Based on the results of their diagnostic and ongoing practice, ORION
will present students with questions appropriate for their current level of under-
PRACTICE standing, and will continuously adapt to each student, helping them build their
proficiency.
ORION includes a number of reports and ongoing recommendations for students

to help them maintain their proficiency over time for each topic. Students can
easily access ORION from multiple places within WileyPLUS. It does not require
any additional registration, and there will not be any additional charge for students
MAINTAIN using this adaptive learning system.
PREFACE xvii
Hallmark Features of WileyPLUS for Organic Chemistry, 2e

Breadth and Depth of Assessment: Four unique silos of assessment are available to
Instructors for creating online homework and quizzes.
wileyPlus assessment for organic chemistry
Reaction Explorer Meaningful practice of mechanisms and synthesis

problems (a database of over 100,000 questions)
I n C h a p t e r / EOC a s s e s s m e n t 100% of Review Problems and end of chapter

questions are coded for on line assessment
Pre-build concept mastery assignments ( from
C o n c e p t M a s t e ry database of over 12,500 questions)
Test Bank Rich Testbank consisting of over 3,000 questions
ADDITIONAL INSTRUCTOR RESOURCES

Testbank Authored by Kevin Minbiole, Villanova University and Vidyullata Waghulde, St.
Louis Community College, Meramec.
PowerPoint Lecture Slides with Answer Slides Authored by James Beil, Lorain County
Community College.
PowerPoint Art Slides Images selected by Christine Hermann, Radford University.
Personal Response System (“Clicker”) Questions Authored by Cynthia Lamberty, Cloud
County Community College, Geary County Campus, Neal Tonks, College of Charleston, Christine
Whitlock, Georgia Southern University.
STUDENT RESOURCES
Student Study Guide and Solutions Manual (ISBN 9781118700815) Authored by David
Klein. The second edition of the Student Study Guide and Solutions Manual to accompany
Organic Chemistry, 2e contains:
• More detailed explanations within the solutions for every problem.
• Concept Review Exercises Scan this code to view
• SkillBuilder Review Exercises a sample Chapter of
the Student Study/
• Reaction Review Exercises Solutions Manual for
Organic Chemistry, 2e
• A list of new reagents for each chapter, with a description of their function.
• A list of “Common Mistakes to Avoid” in every chapter.
Molecular Visions™ Model Kit To support the learning of organic chemistry concepts and
allow students the tactile experience of manipulating physical models, we offer a molecular
modeling kit from the Darling Company. The model kit can be bundled with the textbook or
purchased stand alone.
CUSTOMIZATION AND FLEXBILE

OPTIONS TO MEET YOUR NEEDS
All Access Packs
The All Access Pack for Organic Chemistry, 2e by David Klein gives today’s students everything
they need for their course anytime, anywhere, and on any device. The All Access Pack includes:
• WileyPLUS
• Wiley eText powered by VitalSource
• Student Solutions Manual in a binder-ready looseleaf format
xviii PREFACE
Wiley Custom Select

Wiley Custom Select allows you to create a textbook with precisely the content you want, in a
simple, three-step online process that brings your students a cost-efficient alternative to a tradi-
tional textbook. Select from an extensive collection of content at http://customselect.wiley.com,
upload your own materials as well, and select from multiple delivery formats—full color or black
and white print with a variety of binding options, or eBook. Preview the full text online, get an
instant price quote, and submit your order; we’ll take it from there.
WileyFlex
WileyFlex offers content in flexible and cost-saving options to students. Our goal is to deliver
our learning materials to our customers in the formats that work best for them, whether it’s tra-
ditional text, eTextbook, WileyPLUS, loose-leaf binder editions, or customized content through
Wiley Custom Select.
Contributors to Organic Chemistry, 2e

I owe special thanks to my contributors for their collaboration, hard work and creativity. Many
of the new, literature-based, challenge problems were written by Kevin Caran, James Madison
University; Danielle Jacobs, Rider University; William Maio, New Mexico State University, Las
Cruces; Kensaku Nakayama, California State University, Long Beach; and Justin Wyatt, College of
Charleston. Many of the new Medically Speaking and Practically Speaking applications throughout
the text were written by Susan Lever, University of Missouri, Columbia; Glenroy Martin, University
of Tampa; John Sorensen, University of Manitoba; and Ron Swisher, Oregon Institute of Technology.
ACKNOWLEDGEMENTS
The feedback received from both faculty and students supported the creation, development, and
execution of both the first and second editions of Organic Chemistry. I wish to extend sincere
thanks to my colleagues (and their students) who have graciously devoted their time to offer
valuable comments that helped shape this textbook.
second edition
Reviewers
Al abama Megan Bolitho, University of San Francisco Mapi Cuevas, Santa Fe College
Marco Bonizzoni, The University of Alabama Elaine Carter, Los Angeles City College Donovan Dixon, University of Central
Richard Rogers, University of South Carl Hoeger, University of California, Florida
Alabama San Diego Andrew Frazer, University of Central
Kevin Shaughnessy, The University of Ling Huang, Sacramento City College Florida
Alabama Marlon Jones, Long Beach City College Randy Goff, University of West Florida
Timothy Snowden, The University of Jens Kuhn, Santa Barbara City College Harpreet Malhotra, Florida State College,
Alabama Barbara Mayer, California State University, Kent Campus
Fresno Glenroy Martin, University of Tampa
A rizon a Hasan Palandoken, California Polytechnic Tchao Podona, Miami Dade College
Satinder Bains, Paradise Valley Community State University Bobby Roberson, Pensacola State College
College Teresa Speakman, Golden West College
Cindy Browder, Northern Arizona Linda Waldman, Cerritos College Georgia
University Vivian Mativo, Georgia Perimeter College
John Pollard, University of Arizona Color ado Michele Smith, Georgia Southwestern State
Kenneth Miller, Fort Lewis College University
California
Dianne A. Bennett, Sacramento City Florida Indiana
College Eric Ballard, University of Tampa Hal Pinnick, Purdue University Calumet
PREFACE xix
K ansas N e va da William Loffredo, East Stroudsburg

Cynthia Lamberty, Cloud County Pradip Bhowmik, University of Nevada, University
Community College Las Vegas Gloria Silva, Carnegie Mellon University
Marcus Thomsen, Franklin & Marshall
Kentuck y New Jersey College
Lili Ma, Northern Kentucky University Thomas Berke, Brookdale Community Eric Tillman, Bucknell University
Tanea Reed, Eastern Kentucky University College William Wuest, Temple University
Chad Snyder, Western Kentucky University Danielle Jacobs, Rider University
South Carolina
Louisiana Ne w York Rick Heldrich, College of Charleston
Kathleen Morgan, Xavier University of Michael Aldersley, Rensselaer Polytechnic
Louisiana Institute S o u t h D a k o ta
Sarah Weaver, Xavier University of Brahmadeo Dewprashad, Borough of Grigoriy Sereda, University of South Dakota
Louisiana Manhattan Community College
Eric Helms, SUNY Geneseo Tennessee
Maine Ruben Savizky, Cooper Union Phillip Cook, East Tennessee State University
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North Carolina Texas
Maryl and Deborah Pritchard, Forsyth Technical Frank Foss, University of Texas at Arlington
Jesse More, Loyola University Maryland Community College Scott Handy, Middle Tennessee State
Benjamin Norris, Frostburg State University University
Ohio Carl Lovely, University of Texas at Arlington
Massachuset ts James Beil, Lorain County Community Javier Macossay, The University of Texas-Pan
Rich Gurney, Simmons College College American
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Michigan College Claudia Taenzler, University of Texas, Dallas
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Community College Virginia
Missouri Joyce Easter, Virginia Wesleyan College
Eike Bauer, University of Missouri, St. Louis Okl a h o m a Christine Hermann, Radford University
Alexei Demchenko, University of Missouri, Steven Meier, University of Central
St. Louis Oklahoma C anada
Donna Friedman, St. Louis Community Ashley Causton, University of Calgary
College at Florissant Valley Oregon Michael Chong, University of Waterloo
Jack Lee Hayes, State Fair Community Gary Spessard, University of Oregon Isabelle Dionne, Dawson College
College Paul Harrison, McMaster University
Vidyullata Waghulde, St. Louis Community P e n n s y lva n i a Edward Lee-Ruff, York University
College, Meramec Rodrigo Andrade, Temple University R. Scott Murphy, University of Regina
Geneive Henry, Susquehanna University John Sorensen, University of Manitoba
Nebr ask a Michael Leonard, Washington & Jefferson Jackie Stewart, The University of British
James Fletcher, Creighton University College Columbia
Class Testers
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College James Mackay, Elizabethtown College Univeristy of Denver
Laurel Habgood, Rollins College Tom Russo, Florida State College, Kent
Shane Lamos, St. Michael’s College Campus
Focus Group Participants

Beverly Clement, Blinn College Randy Goff, University of West Andrew Morehead, East Carolina
Greg Crouch, Washington State Florida University
University Jonathan Gough, Long Island Joan Muyanyatta-Comar, Georgia State
Ishan Erden, San Francisco State University University
University Thomas Hughes, Siena College Christine Pruis, Arizona State University
Henry Forman, University of California, Willian Jenks, Iowa State University Laurie Starkey, California Polytechnic
Merced Paul Jones, Wake Forest University University at Pomona
Chammi Gamage-Miller, Blinn College Phillip Lukeman, St. John’s University Don Warner, Boise State University
xx PREFACE
Accuracy Checkers
Eric Ballard, University of Tampa Michael Leonard, Washington and John Sorenson, University of Manitoba
Kevin Caran, James Madison University Jefferson College
James Fletcher, Creighton University Kevin Minbiole, Villanova University
First Edition Reviewers: Class Test Participants, Focus

Group Participants, and Accuracy Checkers
Philip Albiniak, Ball State University Brad Chamberlain, Luther College Susan Ensel, Hood College
Thomas Albright, University of Houston Paul Chamberlain, George Fox University David Flanigan, Hillsborough Community
Michael Aldersley, Rensselaer Polytechnic Seveda Chamras, Glendale Community College
Institute College James T. Fletcher, Creighton University
David Anderson, University of Colorado, Tom Chang, Utah State University Francis Flores, California Polytechnic State
Colorado Springs Dana Chatellier, University of Delaware University, Pomona
Merritt Andrus, Brigham Young University Sarah Chavez, Washington University John Flygare, Stanford University
Laura Anna, Millersville University Emma Chow, Palm Beach Community Frantz Folmer-Andersen, SUNY New Paltz
Ivan Aprahamian, Dartmouth College College Raymond Fong, City College of San
Yiyan Bai, Houston Community College Jason Chruma, University of Virginia Francisco
Satinder Bains, Paradise Valley Community Phillip Chung, Montefiore Medical Center Mark Forman, Saint Joseph’s University
College Steven Chung, Bowling Green State Frank Foss, University of Texas at Arlington
C. Eric Ballard, University of Tampa University Annaliese Franz, University of California,
Edie Banner, Richmond University Nagash Clarke, Washtenaw Community Davis
James Beil, Lorain County Community College Andrew Frazer, University of Central Florida
College Adiel Coca, Southern Connecticut State Lee Friedman, University of Maryland,
Peter Bell, Tarleton State University University College Park
Dianne Bennet, Sacramento City College Jeremy Cody, Rochester Institute of Steve Gentemann, Southwestern Illinois
Thomas Berke, Brookdale Community Technology College
College Phillip Cook, East Tennessee State Tiffany Gierasch, University of Maryland,
Daniel Bernier, Riverside Community University Baltimore County
College Jeff Corkill, Eastern Washington University Scott Grayson, Tulane University
Narayan Bhat, University of Texas Pan Sergio Cortes, University of Texas at Dallas Thomas Green, University of Alaska,
American Philip J. Costanzo, California Polytechnic Fairbanks
Gautam Bhattacharyya, Clemson University State University, San Luis Obispo Kimberly Greve, Kalamazoo Valley
Silas Blackstock, University of Alabama Wyatt Cotton, Cincinnati State College Community College
Lea Blau, Yeshiva University Marilyn Cox, Louisiana Tech University Gordon Gribble, Dartmouth College
Megan Bolitho, University of San Francisco David Crich, University of Illinois at Ray A. Gross, Jr., Prince George’s
Matthias Brewer, The University of Vermont Chicago Community College
David Brook, San Jose State University Mapi Cuevas, Sante Fe Community College Nathaniel Grove, University of North
Cindy Browder, Northern Arizona Scott Davis, Mercer University, Macon Carolina, Wilmington
University Frank Day, North Shore Community Yi Guo, Montefiore Medical Center
Pradip Browmik, University of Nevada, Las College Sapna Gupta, Palm Beach State College
Vegas Peter de Lijser, California State University, Kevin Gwaltney, Kennesaw State University
Banita Brown, University of North Carolina Fullerton Asif Habib, University of Wisconsin,
Charlotte Roman Dembinski, Oakland University Waukesha
Kathleen Brunke, Christopher Newport Brahmadeo Dewprashad, Borough of Donovan Haines, Sam Houston State
University Manhattan Community College University
Timothy Brunker, Towson University Preeti Dhar, SUNY New Paltz Robert Hammer, Louisiana State University
Jared Butcher, Ohio University Bonnie Dixon, University of Maryland, Scott Handy, Middle Tennessee State
Arthur Cammers, University of Kentucky, College Park University
Lexington Theodore Dolter, Southwestern Illinois Christopher Hansen, Midwestern State
Kevin Cannon, Penn State University, College University
Abington Norma Dunlap, Middle Tennessee State Kenn Harding, Texas A&M University
Kevin Caran, James Madison University University Matthew Hart, Grand Valley State
Jeffrey Carney, Christopher Newport Joyce Easter, Virginia Wesleyan College University
University Jeffrey Elbert, University of Northern Iowa Jack Hayes, State Fair Community College
David Cartrette, South Dakota State J. Derek Elgin, Coastal Carolina University Eric Helms, SUNY Geneseo
University Derek Elgin, Coastal Carolina University Maged Henary, Georgia State University,
Steven Castle, Brigham Young University Cory Emal, Eastern Michigan University Langate
PREFACE xxi
Amanda Henry, Fresno City College Lili Ma, Northern Kentucky University John Picione, Daytona State College
Christine Hermann, Radford University Javier Macossay-Torres, University of Texas Chris Pigge, University of Iowa
Patricia Hill, Millersville University Pan American Harold Pinnick, Purdue University, Calumet
Ling Huang, Sacramento City College Kirk Manfredi, University of Northern Iowa Tchao Podona, Miami Dade College
John Hubbard, Marshall University Ned Martin, University of North Carolina, John Pollard, University of Arizona
Roxanne Hulet, Skagit Valley College Wilmington Owen Priest, Northwestern University,
Christopher Hyland, California State Vivian Mativo, Georgia Perimeter College, Evanston
University, Fullerton Clarkston Paul Primrose, Baylor University
Danielle Jacobs, Rider University Barbara Mayer, California State University, Christine Pruis, Arizona State University
Christopher S. Jeffrey, University of Nevada, Fresno Martin Pulver, Bronx Community College
Reno Dominic McGrath, University of Arizona Shanthi Rajaraman, Richard Stockton
Dell Jensen, Augustana College Steven Meier, University of Central College of New Jersey
Yu Lin Jiang, East Tennessee State University Oklahoma Sivappa Rasapalli, University of
Richard Johnson, University of New Dina Merrer, Barnard College Massachusetts, Dartmouth
Hampshire Stephen Milczanowski, Florida State College Cathrine Reck, Indiana University,
Marlon Jones, Long Beach City College Nancy Mills, Trinity University Bloomington
Reni Joseph, St. Louis Community College, Kevin Minbiole, James Madison University Ron Reese, Victoria College
Meramec Campus Thomas Minehan, California State Mike Rennekamp, Columbus State
Cynthia Judd, Palm Beach State College University, Northridge Community College
Eric Kantorowski, California Polytechnic James Miranda, California State University, Olga Rinco, Luther College
State University, San Luis Obispo Sacramento Melinda Ripper, Butler County Community
Andrew Karatjas, Southern Connecticut Shizue Mito, University of Texas at El Paso College
State University David Modarelli, University of Akron Harold Rogers, California State University,
Adam Keller, Columbus State Community Jesse More, Loyola College Fullerton
College Andrew Morehead, East Carolina University Mary Roslonowski, Brevard Community
Mushtaq Khan, Union County College Sarah Mounter, Columbia College of College
James Kiddle, Western Michigan University Missouri Robert D. Rossi, Gloucester County College
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Silvia Kolchens, Pima Community College Kensaku Nakayama, California State Gillian Rudd, Northwestern State University
Dalila Kovacs, Grand Valley State University University, Long Beach Thomas Russo, Florida State College—Kent
Jennifer Koviach-Côté, Bates College Thomas Nalli, Winona State University Campus
Paul J. Kropp, University of North Carolina, Richard Narske, Augustana College Lev Ryzhkov, Towson University
Chapel Hill Donna Nelson, University of Oklahoma Preet-Pal S. Saluja, Triton College
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Silvia Kölchens, Pima County Community William Nguyen, Santa Ana College Patricio Santander, Texas A&M University
College James Nowick, University of California, Gita Sathianathan, California State
Massimiliano Lamberto, Monmouth Irvine University, Fullerton
University Edmond J. O’Connell, Fairfield University Sergey Savinov, Purdue University, West
Cindy Lamberty, Cloud County Community Asmik Oganesyan, Glendale Community Lafayette
College, Geary County Campus College Amber Schaefer, Texas A&M University
Kathleen Laurenzo, Florida State College Kyungsoo Oh, Indiana University, Purdue Kirk Schanze, University of Florida
William Lavell, Camden County College University Indianapolis Paul Schueler, Raritan Valley Community
Iyun Lazik, San Jose City College Greg O’Neil, Western Washington College
Michael Leonard, Washington & Jefferson University Alan Schwabacher, University of Wisconsin,
College Edith Onyeozili, Florida Agricultural & Milwaukee
Sam Leung, Washburn University Mechanical University Pamela Seaton, University of North
Michael Lewis, Saint Louis University Catherine Owens Welder, Dartmouth Carolina, Wilmington
Scott Lewis, James Madison University College Jason Serin, Glendale Community College
Deborah Lieberman, University of Anne B. Padias, University of Arizona Gary Shankweiler, California State
Cincinnati Hasan Palandoken, California Polytechnic University, Long Beach
Harriet Lindsay, Eastern Michigan State University, San Luis Obispo Kevin Shaughnessy, The University of
University Chandrakant Panse, Massachusetts Bay Alabama
Jason Locklin, University of Georgia Community College Emery Shier, Amarillo College
William Loffredo, East Stroudsburg Sapan Parikh, Manhattanville College Richard Shreve, Palm Beach State College
University James Parise Jr., Duke University John Shugart, Coastal Carolina University
Robert Long, Eastern New Mexico Edward Parish, Auburn University Edward Skibo, Arizona State University
University Keith O. Pascoe, Georgia State University Douglas Smith, California State University,
Rena Lou, Cerritos College Michael Pelter, Purdue University, Calumet San Bernadino
Brian Love, East Carolina University Libbie Pelter, Purdue University, Calumet Michelle Smith, Georgia Southwestern State
Douglas Loy, University of Arizona H. Mark Perks, University of Maryland, University
Frederick A. Luzzio, University of Louisville Baltimore County Rhett Smith, Clemson University
xxii PREFACE
Irina Smoliakova, University of North Eric Tillman, Bucknell University Leyte Winfield, Spelman College
Dakota Bruce Toder, University of Rochester Angela Winstead, Morgan State
Timothy Snowden, University of Alabama Ana Tontcheva, El Camino College University
Chad Snyder, Western Kentucky University Jennifer Tripp, San Francisco State Penny Workman, University of Wisconsin,
Scott Snyder, Columbia University University Marathon County
Vadim Soloshonok, University of Oklahoma Adam Urbach, Trinity University Stephen Woski, University of Alabama
John Sowa, Seton Hall University Melissa Van Alstine, Adelphi University Stephen Wuerz, Highland Community
Laurie Starkey, California Polytechnic State Christopher Vanderwal, University of College
University, Pomona California, Irvine Linfeng Xie, University of Wisconsin,
Mackay Steffensen, Southern Utah Aleskey Vasiliev, East Tennessee State Oshkosh
University University Hanying Xu, Kingsborough Community
Mackay Steffensen, Southern Utah Heidi Vollmer-Snarr, Brigham Young College of CUNY
University University Jinsong Zhang, California State University,
Richard Steiner, University of Utah Edmir Wade, University of Southern Chico
Corey Stephenson, Boston University Indiana Regina Zibuck, Wayne State University
Nhu Y Stessman, California State University, Vidyullata Waghulde, St. Louis Community
Stanislaus College C a n ada
Erland Stevens, Davidson College Linda Waldman, Cerritos College Ashley Causton, University of Calgary
James Stickler, Allegany College of Maryland Kenneth Walsh, University of Southern Michael Chong, University of Waterloo
Robert Stockland, Bucknell University Indiana Andrew Dicks, University of Toronto
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Ron Swisher, Oregon Institute of Technology Matthew Weinschenk, Emory University Ian Hunt, University of Calgary
Carole Szpunar, Loyola University Chicago Andrew Wells, Chabot College Norman Hunter, University of Manitoba
Claudia Taenzler, University of Texas at Peter Wepplo, Monmouth University` Michael Pollard, York University
Dallas Lisa Whalen, University of New Mexico Stanislaw Skonieczny, University of
John Taylor, Rutgers University, New Ronald Wikholm, University of Toronto
Brunswick Connecticut, Storrs Jackie Stewart, University of British
Richard Taylor, Miami University Anne Wilson, Butler University Columbia
Cynthia Tidwell, University of Montevallo Michael Wilson, Temple University Shirley Wacowich-Sgarbi, Langara College
This book could not have been created without the incredible efforts of the following peo-
ple at John Wiley & Sons, Inc.
Photo Editor Lisa Gee helped identify exciting photos. Maureen Eide and freelance
designer Anne DeMarinis conceived of a visually refreshing and compelling interior design and
cover. Senior Production Editor Elizabeth Swain kept this book on schedule and was vital to
ensuring such a high-quality product. Joan Kalkut, Sponsoring Editor was invaluable in the
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learn more about
David Klein and
the second edition of the solutions manual. Publisher Petra Recter provided strong vision and
Organic Chemistry, 2e guidance in bringing this book to market.
Despite my best efforts, as well as the best efforts of the reviewers, accuracy checkers, and
class testers, errors may still exist. I take full responsibility for any such errors and would encour-
age those using my textbook to contact me with any errors that you may find.
David R. Klein, Ph.D.
Johns Hopkins University
klein@jhu.edu
A Review of 1
General Chemistry 1.1 Introduction to Organic Chemistry
1.2 The Structural Theory of Matter
ELECTRONS, BONDS, AND MOLECULAR PROPERTIES 1.3 Electrons, Bonds, and Lewis Structures
1.4 Identifying Formal Charges
Did you ever wonder . . . 1.5 Induction and Polar Covalent Bonds
1.6 Atomic Orbitals
what causes lightning?
1.7 Valence Bond Theory
B
1.8 Molecular Orbital Theory
elieve it or not, the answer to this question is still the sub- 1.9 Hybridized Atomic Orbitals
ject of debate (that’s right … scientists have not yet figured out 1.10 VSEPR Theory: Predicting Geometry
everything, contrary to popular belief ). There are various theories
1.11 Dipole Moments and Molecular Polarity
that attempt to explain what causes the buildup of electric charge in
1.12 Intermolecular Forces and
clouds. One thing is clear, though—lightning involves a flow of elec- Physical Properties
trons. By studying the nature of electrons and how electrons flow, it
1.13 Solubility
is possible to control where lightning will strike. A tall building can
be protected by installing a lightning rod (a tall metal column at the
top of the building) that attracts any nearby lightning bolt, thereby
preventing a direct strike on the building itself. The lightning rod on
the top of the Empire State Building is struck over a hundred times
each year.
Just as scientists have discovered how to direct electrons in a bolt
of lightning, chemists have also discovered how to direct electrons
in chemical reactions. We will soon see that although
organic chemistry is literally defined as the study of
compounds containing carbon atoms,
its true essence is actually the
study of electrons, not atoms.
Rather than thinking of reactions
in terms of the motion of atoms, we
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insulted her and is expected to pay damages. If a man meets his
mother-in-law coming along the road and does not recognise her,
she will fall down on the ground as a sign, when he will run away. In
the same way a father-in-law will signal to his daughter-in-law; the
whole idea being that they are unworthy to be noticed till they have
proved that they can beget children.”79.2 However, if a wife should
prove barren for three years, the rules of avoidance between the
young couple and their parents-in-law cease to be observed.79.3
Hence the custom of avoidance among these people is associated in
some way with the wife’s fertility. So among the Awemba, a Bantu
tribe of Northern Rhodesia, “if a young man sees his mother-in-law
coming along the path, he must retreat into the bush and make way
for her, or if she suddenly comes upon him he must keep his eyes
fixed on the ground, and only after a child is born may they converse
together.”79.4 Among the Angoni, another Bantu tribe of British
Central Africa, it would be a gross breach of etiquette if a man were
to enter his son-in-law’s house; he may come within ten paces of the
door, but no nearer. A woman may not even approach her son-in-
law’s house, and she is never allowed to speak to him. Should they
meet accidentally on a path, the son-in-law gives way and makes a
circuit to avoid encountering his mother-in-law face to face.79.5 Here
then we see that a man avoids his son-in-law as well as his mother-
in-law, though not so strictly.
Among the Thonga, a Bantu tribe about
The custom of Delagoa Bay, when a man meets his mother-in-
avoiding mother-in-
law and wife of law or her sister on the road, he steps out of the
wife’s brother road into the forest on the right hand side and sits
among the Thonga down. She does the same. Then they salute each
of Delagoa Bay.
other in the usual way by clapping their hands.
After that they may talk to each other. When a man is in a hut, his
mother-in-law dare not enter it, but must sit down outside without
seeing him. So seated she may salute him, “Good morning, son of
So-and-so.” But she would not dare to pronounce his name.
However, when a man has been married many years, his mother-in-
law has less fear of him, and will even enter the hut where he is and
speak to him. But among the Thonga the woman whom a man is
bound by custom to avoid most rigidly is not his wife’s mother, but
the wife of his wife’s brother. If the two meet on a path, they carefully
avoid each other; he will step out of the way and she will hurry on,
while her companions, if she has any, will stop and chat with him.
She will not enter the same boat with him, if she can help it, to cross
a river. She will not eat out of the same dish. If he speaks to her, it is
with constraint and embarrassment. He will not enter her hut, but will
crouch at the door and address her in a voice trembling with
emotion. Should there be no one else to bring him food, she will do it
reluctantly, watching his hut and putting the food inside the door
when he is absent. It is not that they dislike each other, but that they
feel a mutual, a mysterious fear.80.1 However, among the Thonga,
the rules of avoidance between connexions by marriage decrease in
severity as time passes. The strained relations between a man and
his wife’s mother in particular become easier. He begins to call her
“Mother” and she calls him “Son.” This change even goes so far that
in some cases the man may go and dwell in the village of his wife’s
parents, especially if he has children and the children are grown
up.80.2 Again, among the Ovambo, a Bantu people of German South-
West Africa, a man may not look at his future mother-in-law while he
talks with her, but is bound to keep his eyes steadily fixed on the
ground. In some cases the avoidance is even more stringent; if the
two meet unexpectedly, they separate at once. But after the
marriage has been celebrated, the social intercourse between
mother-in-law and son-in-law becomes easier on both sides.81.1
Thus far our examples of ceremonial avoidance
The custom of between mother-in-law and son-in-law have been
avoiding the
mother-in-law drawn from Bantu tribes. But in Africa the custom,
among other than though apparently most prevalent and most
the Bantu tribes of strongly marked among peoples of the great Bantu
Africa.
stock, is not confined to them. Among the Masai of
British East Africa, “mothers-in-law and their sons-in-law must avoid
one another as much as possible; and if a son-in-law enters his
mother-in-law’s hut she must retire into the inner compartment and
sit on the bed, whilst he remains in the outer compartment; they may
then talk. Own brothers-in-law and sisters-in-law must also avoid one
another, though this rule does not apply to half-brothers-in-law and
sisters-in-law.”81.2 So, too, among the Bogos, a tribe on the outskirts
of Abyssinia, a man never sees the face of his mother-in-law and
never pronounces her name; the two take care not to meet.81.3
Among the Donaglas a husband after marriage “lives in his wife’s
house for a year, without being allowed to see his mother-in-law, with
whom he enters into relations only on the birth of his first son.”81.4 In
Darfur, when a youth has been betrothed to a girl, however intimate
he may have been with her parents before, he ceases to see them
until the ceremony has taken place, and even avoids them in the
street. They, on their part, hide their faces, if they happen to meet
him unexpectedly.81.5
To pass now from Africa to other parts of the
The custom of world, among the Looboos, a primitive tribe in the
avoiding relations
by marriage in tropical forests of Sumatra, custom forbids a
Sumatra and New woman to be in her father-in-law’s company and a
Guinea. man to be in his mother-in-law’s society. For
example, if a man meets his daughter-in-law, he
should cross over to the other side of the road to let her pass as far
as possible from him; but if the way is too narrow, he takes care in
time to get out of it. But no such reserve is prescribed between a
father-in-law and his son-in-law, or between a mother-in-law and her
daughter-in-law.82.1 Among the Bukaua, a Melanesian tribe of
German New Guinea, the rules of avoidance between persons
connected by marriage are very stringent; they may not touch each
other or mention each other’s names. But contrary to the usual
practice the avoidance seems to be quite as strict between persons
of the same sex as between males and females. At least the writer
who reports the custom illustrates it chiefly by the etiquette which is
observed between a man and his daughter’s husband. When a man
eats in presence of his son-in-law, he veils his face; but if
nevertheless his son-in-law should see his open mouth, the father-in-
law is so ashamed that he runs away into the wood. If he gives his
son-in-law anything, such as betel or tobacco, he will never put it in
his hand, but pours it on a leaf, and the son-in-law fetches it away. If
father-in-law and son-in-law both take part in a wild boar hunt, the
son-in-law will abstain from seizing or binding the boar, lest he
should chance to touch his father-in-law. If, however, through any
accident their hands or backs should come into contact, the father-
in-law is extremely horrified, and a dog must be at once killed, which
he gives to his son-in-law for the purpose of wiping out the stain on
his honour. If the two should ever fall out about anything, the son-in-
law will leave the village and his wife, and will stay away in some
other place till his father-in-law, for his daughter’s sake, calls him
back. A man in like manner will never touch his sister-in-law.82.2
Among the low savages of the Californian
The custom of peninsula a man was not allowed for some time to
avoiding relations
by marriage among look into the face of his mother-in-law or of his
the Indian tribes of wife’s other near relations; when these women
America. were present he had to step aside or hide
himself.83.1 Among the Indians of the Isla del
Malhado in Florida a father-in-law and mother-in-law might not enter
the house of their son-in-law, and he on his side might not appear
before his father-in-law and his relations. If they met by accident they
had to go apart to the distance of a bowshot, holding their heads
down and their eyes turned to the earth. But a woman was free to
converse with the father and mother of her husband.83.2 Among the
Indians of Yucatan, if a betrothed man saw his future father-in-law or
mother-in-law at a distance, he turned away as quickly as possible,
believing that a meeting with them would prevent him from begetting
children.83.3 Among the Arawaks of British Guiana a man may never
see the face of his wife’s mother. If she is in the house with him, they
must be separated by a screen or partition-wall; if she travels with
him in a canoe, she steps in first, in order that she may turn her back
to him.83.4 Among the Caribs “the women never quit their father’s
house, and in that they have an advantage over their husbands in as
much as they may talk to all sorts of people, whereas the husband
dare not converse with his wife’s relations, unless he is dispensed
from this observance either by their tender age or by their
intoxication. They shun meeting them and make great circuits for
that purpose. If they are surprised in a place where they cannot help
meeting, the person addressed turns his face another way so as not
to be obliged to see the person, whose voice he is compelled to
hear.”83.5 Among the Araucanian Indians of Chili a man’s mother-in-
law refuses to speak to or even to look at him during the marriage
festivity, and “the point of honour is, in some instances, carried so
far, that for years after the marriage the mother never addresses her
son-in-law face to face; though with her back turned, or with the
interposition of a fence or a partition, she will converse with him
freely.”84.1
It would be easy to multiply examples of similar
The custom of customs of avoidance between persons closely
avoiding relations
by marriage cannot connected by marriage, but the foregoing may
be separated from serve as specimens. Now in order to determine
the similar custom the meaning of such customs it is very important
of avoiding relations
by blood; both are to observe that similar customs of avoidance are
probably practised in some tribes not merely between
precautions to
prevent improper
persons connected with each other by marriage,
relations between but also between the nearest blood relations of
the sexes. different sexes, namely, between parents and
children and between brothers and sisters;84.2 and
the customs are so alike that it seems difficult or impossible to
separate them and to offer one explanation of the avoidance of
connexions by marriage and another different explanation of the
avoidance of blood relations. Yet this is what is done by some who
attempt to explain the customs of avoidance; or rather they confine
their attention wholly to connexions by marriage, or even to mothers-
in-law alone, while they completely ignore blood relations, although
in point of fact it is the avoidance of blood relations which seems to
furnish the key to the problem of such avoidances in general. The
true explanation of all such customs of avoidance appears to be, as I
have already indicated, that they are precautions designed to
remove the temptation to sexual intercourse between persons whose
marriage union is for any reason repugnant to the moral sense of the
community. This explanation, while it has been rejected by theorists
at home, has been adopted by some of the best observers of savage
life, whose opinion is entitled to carry the greatest weight.85.1
That a fear of improper intimacy even between
Mutual avoidance of the nearest blood relations is not baseless among
mother and son, of
father and daughter, races of a lower culture seems proved by the
and of brother and testimony of a Dutch missionary in regard to the
Battas or Bataks of Sumatra, a people who have
sister among the attained to a fairly high degree of barbaric
Battas.
civilization. The Battas “observe certain rules of
avoidance in regard to near relations by blood or marriage; and we
are informed that such avoidance springs not from the strictness but
from the looseness of their moral practice. A Batta, it is said,
assumes that a solitary meeting of a man with a woman leads to an
improper intimacy between them. But at the same time he believes
that incest or the sexual intercourse of near relations excites the
anger of the gods and entails calamities of all sorts. Hence near
relations are obliged to avoid each other lest they should succumb to
temptation. A Batta, for example, would think it shocking were a
brother to escort his sister to an evening party. Even in the presence
of others a Batta brother and sister feel embarrassed. If one of them
comes into the house, the other will go away. Further, a man may
never be alone in the house with his daughter, nor a mother with her
son. A man may never speak to his mother-in-law nor a woman to
her father-in-law. The Dutch missionary who reports these customs
adds that he is sorry to say that from what he knows of the Battas he
believes the maintenance of most of these rules to be very
necessary. For the same reason, he tells us, as soon as Batta lads
have reached the age of puberty they are no longer allowed to sleep
in the family house but are sent away to pass the night in a separate
building (djambon); and similarly as soon as a man loses his wife by
death he is excluded from the house.”85.2
In like manner among the Melanesians of the
Mutual avoidance of Banks’ Islands and the New Hebrides a man must
mother and son and
of brother and sister not only avoid his mother-in-law; from the time
among the when he reaches or approaches puberty and has
Melanesians. begun to wear clothes instead of running about
naked, he must avoid his mother and sisters, and
he may no longer live in the same house with them; he takes up his
quarters in the clubhouse of the unmarried males, where he now
regularly eats and sleeps. He may go to his father’s house to ask for
food, but if his sister is within he must go away before he eats; if she
is not there, he may sit down near the door and eat. If by chance
brother and sister meet in the path, she runs away or hides. If a boy,
walking on the sands, perceives footprints which he knows to be
those of his sister, he will not follow them, nor will she follow his. This
mutual avoidance lasts through life. Not only must he avoid the
persons of his sisters, but he may not pronounce their names or
even use a common word which happens to form part of any one of
their names. In like manner his sisters eschew the use of his name
and of all words which form part of it. Strict, too, is a boy’s reserve
towards his mother from the time when he begins to wear clothes,
and the reserve increases as he grows to manhood. It is greater on
her side than on his. He may go to the house and ask for food and
his mother may bring it out for him, but she will not give it to him; she
puts it down for him to take. If she calls to him to come, she speaks
to him in the plural, in a more distant manner; “Come ye,” she says,
not “Come thou.” If they talk together she sits at a little distance and
turns away, for she is shy of her grown-up son. “The meaning of all
this,” as Dr. Codrington observes, “is obvious.”86.1
Mutual avoidance of
a man and his
When a Melanesian man of the Banks’ Islands
mother-in-law marries, he is bound in like manner to avoid his
among the mother-in-law. “The rules of avoidance are very
Melanesians.
strict and minute. As regards the avoidance of the
person, a man will not come near his wife’s mother; the avoidance is
mutual; if the two chance to meet in a path, the woman will step out
of it and stand with her back turned till he has gone by, or perhaps if
it be more convenient he will move out of the way. At Vanua Lava, in
Port Patteson, a man would not follow his mother-in-law along the
beach, nor she him, until the tide had washed out the footsteps of
the first traveller from the sand. At the same time a man and his
mother-in-law will talk at a distance.”87.1
It seems obvious that these Melanesian
It is significant that customs of avoidance are the same, and must be
mutual avoidance
between blood explained in the same way whether the woman
relations of opposite whom a man shuns is his wife’s mother or his own
sexes begins at or mother or his sister. Now it is highly significant that
near puberty.
just as among the Akamba of East Africa the
mutual avoidance of father and daughter only begins when the girl
has reached puberty, so among the Melanesians the mutual
avoidance of a boy on the one side and of his mother and sisters on
the other only begins when the boy has reached or approached
puberty. Thus in both peoples the avoidance between the nearest
blood relations only commences at the dangerous age when sexual
connexion on both sides begins to be possible. It seems difficult,
therefore, to evade the conclusion that the mutual avoidance is
adopted for no other reason than to diminish as far as possible the
chances of sexual unions which public opinion condemns as
incestuous. But if that is the reason why a young Melanesian boy, on
the verge of puberty, avoids his own mother and sisters, it is natural
and almost necessary to infer that it is the same reason which leads
him, as a full-grown and married man, to eschew the company of his
wife’s mother.
Similar customs of avoidance between mothers
Mutual avoidance of and sons, between fathers and daughters, and
mother and son, of
father and daughter, between brothers and sisters are observed by the
and of brother and natives of the Caroline Islands, and the writer who
sister in the records them assigns the fear of incest as the
Caroline Islands.
motive for their observance. “The prohibition of
marriage,” he says, “and of sexual intercourse between kinsfolk of
the same tribe is regarded by the Central Caroline natives as a
divine ordinance; its breach is therefore, in their opinion, punished by
the higher powers with sickness or death. The law influences in a
characteristic way the whole social life of the islanders, for efforts are
made to keep members of families of different sexes apart from each
other even in their youth. Unmarried men and boys, from the time
when they begin to speak, may therefore not remain by night in the
huts, but must sleep in the fel, the assembly-house. In the evening
their meal (âkot) is brought thither to them by their mothers or
sisters. Only when a son is sick may his mother receive him in the
hut and tend him there. On the other hand entrance to the assembly-
house (fel) is forbidden to women and girls except on the occasion of
the pwarik festival; whereas female members of other tribes are free
to visit it, although, so far as I could observe, they seldom make use
of the permission. Unmarried girls sleep in the huts with their
parents.
“These restrictions, which custom and tradition have instituted
within the family, find expression also in the behaviour of the
members of families toward each other. The following persons,
namely, have to be treated with respect—the daughters by their
father, the sons by their mother, the brothers by their sisters. In
presence of such relations, as in the presence of a chief, you may
not stand, but must sit down; if you are obliged on narrow paths to
pass by one of them you must first obtain permission and then do it
in a stooping or creeping posture. You allow them everywhere to go
in front; you also avoid to drink out of the vessel which they have just
used; you do not touch them, but keep always at a certain distance
from them; the head especially is deemed sacred.”88.1
In all these cases the custom of mutual
Mutual avoidance of avoidance is observed by persons of opposite sex
male and female
cousins in some who, though physically capable of sexual union,
tribes. are forbidden by tradition and public opinion to
have any such commerce with each other. Thus
far the blood relations whom a man is forbidden to marry and
compelled to avoid, are his own mother, his own daughter, and his
own sisters. But to this list some people add a man’s female cousins
or at least certain of them; for many races draw a sharp line of
distinction between cousins according as they are children of two
brothers or of two sisters or of a brother and a sister, and while they
permit or even prefer marriage with certain cousins, they absolutely
forbid marriage with certain others. Now, it is highly significant that
some tribes which forbid a man to marry certain of his cousins also
compel him to adopt towards them the same attitude of social
reserve which in the same or other tribes a man is obliged to
observe towards his wife’s mother, his own mother, and his own
sisters, all of whom in like manner he is forbidden to marry. Thus
among the tribes in the central part of New Ireland
Mutual avoidance of (New Mecklenburg) a male and a female cousin,
male and female
cousins in New the children of a brother and a sister respectively,
Ireland. are most strictly forbidden by custom to marry
each other; indeed this prohibition is described as
the most stringent of all; the usual saying in regard to such relations
is, “The cousin is holy” (i tábu ra kókup). Now, in these tribes a man
is not merely forbidden to marry his female cousin, the daughter of
his father’s sister or of his mother’s brother; he must also avoid her
socially, just as in other tribes a man must avoid his wife’s mother,
his own mother, his own daughter, and his own sisters. The cousins
may not approach each other, they may not shake hands or even
touch each other, they may not give each other presents, they may
not mention each other’s names; but they are allowed to speak to
each other at a distance of some paces. These rules of avoidance,
these social barriers erected between cousins, the children of a
brother and a sister respectively, are interpreted most naturally and
simply as precautions intended to obviate the danger of a criminal
intercourse between persons whose sexual union would be regarded
by public opinion with deep displeasure. Indeed the Catholic
missionary, to whom we are indebted for the information, assumes
this interpretation of the rules as if it were too obvious to call for
serious discussion. He says that all the customs of avoidance “are
observed as outward symbols of this prohibition of marriage”; and he
adds that “were the outward sign of the prohibition of marriage, to
which the natives cleave with genuine obstinacy, abolished or even
weakened, there would be an immediate danger of the natives
contracting such marriages.”90.1 It seems difficult for a rational man
to draw any other inference. If any confirmation were needed, it
would be furnished by the fact that among these tribes of New
Ireland brothers and sisters are obliged to observe precisely the
same rules of mutual avoidance, and that incest between brother
and sister is a crime which is punished with hanging; they may not
come near each other, they may not shake hands, they may not
touch each other, they may not give each other presents; but they
are allowed to speak to each other at a distance of some paces. And
the penalty for incest with a daughter is also death by hanging.90.2
Amongst the Baganda of Central Africa in like
Mutual avoidance of manner a man was forbidden under pain of death
certain male and
female cousins to marry or have sexual intercourse with his
among the cousin, the daughter either of his father’s sister or
Baganda; marriage of his mother’s brother; and such cousins might
or sexual
intercourse not approach each other, nor hand each other
forbidden between anything, nor enter the same house, nor eat out of
these cousins under
pain of death.
the same dish. Were cousins to break these rules
of social avoidance, in other words, if they were to
approach each other or hand each other anything, it was believed
that they would fall ill, that their hands would tremble, and that they
would be unfit for any work.90.3 Here, again, the prohibition of social
intercourse was in all probability merely a precaution against sexual
intercourse, for which the penalty was death. And the same may be
said of the similar custom of avoidance which among these same
Baganda a man had to observe towards his wife’s mother. “No man
might see his mother-in-law, or speak face to face with her; she
covered her face, if she passed her son-in-law, and he gave her the
path and made a detour, if he saw her coming. If she was in the
house, he might not enter, but he was allowed to speak to her from a
distance. This was said to be because he had seen her daughter’s
nakedness. If a son-in-law accidentally saw his mother-in-law’s
breasts, he sent her a barkcloth in compensation, to cover herself,
lest some illness, such as tremor, should come upon him. The
punishment for incest was death; no member of a clan would shield
a person guilty thereof; the offender was disowned by the clan, tried
by the chief of the district, and put to death.”91.1
The prohibition of marriage with certain cousins
Marriage between appears to be widespread among African peoples
certain cousins
forbidden among of the Bantu stock. Thus in regard to the Bantus of
some South African South Africa we read that “every man of a coast
tribes but allowed tribe regarded himself as the protector of those
among others.
females whom we would call his cousins, second
cousins, third cousins, and so forth, on the father’s side, while some
had a similar feeling towards the same relatives on the mother’s side
as well, and classified them all as sisters. Immorality with one of
them would have been considered incestuous, something horrible,
something unutterably disgraceful. Of old it was punished by the
death of the male, and even now a heavy fine is inflicted upon him,
while the guilt of the female must be atoned by a sacrifice performed
with due ceremony by the tribal priest, or it is believed a curse will
rest upon her and her issue.… In contrast to this prohibition the
native of the interior almost as a rule married the daughter of his
father’s brother, in order, as he said, to keep property from being lost
to his family. This custom more than anything else created a disgust
and contempt for them by the people of the coast, who term such
intermarriages the union of dogs, and attribute to them the insanity
and idiocy which in recent times has become prevalent among the
inland tribes.”91.2
Among the Thonga, a Bantu tribe about
Marriage between Delagoa Bay, marriages between cousins are as a
cousins allowed in
some African tribes rule prohibited, and it is believed that such unions
on condition that an are unfruitful. However, custom permits cousins to
expiatory sacrifice marry each other on condition that they perform an
is offered.
expiatory ceremony which is supposed to avert the
curse of barrenness from the wife. A goat is sacrificed, and the
couple are anointed with the green liquid extracted from the half-
digested grass in the animal’s stomach. Then a hole is cut in the
goat’s skin and through this hole the heads of the cousins are
inserted. The goat’s liver is then handed to them, quite raw, through
the hole in the skin, and they must tear it out with their teeth without
using a knife. Having torn it out, they eat it. The word for liver
(shibindji) also means “patience,” “determination.” So they say to the
couple, “You have acted with strong determination. Eat the liver now!
Eat it in the full light of the day, not in the dark! It will be an offering to
the gods.” Then the family priest prays, saying: “You, our gods, So-
and-so, look! We have done it in the daylight. It has not been done
by stealth. Bless them, give them children!” When he has done
praying, the assistants take all the half-digested grass from the
goat’s stomach and place it on the wife’s head, saying, “Go and bear
children!”92.1 Among the Wagogo of German East Africa marriage is
forbidden between cousins who are the children of two brothers or of
two sisters, but is permitted between cousins who are the children of
a brother and sister respectively. However, in this case it is usual for
the wife’s father to kill a sheep and put on a leather armlet, made
presumably from the sheep’s skin; otherwise it is supposed that the
marriage would be unfruitful.92.2 Thus the Wagogo, like the Thonga,
imagine that the marriage of cousins is doomed to infertility unless
an expiatory sacrifice is offered and a peculiar use made of the
victim’s skin. Again, the Akikuyu of British East Africa forbid the
marriage of cousins and second cousins, the children and
grandchildren of brothers and sisters. If such persons married, they
would commit a grave sin, and all their children would surely die; for
the curse or ceremonial pollution (thahu) incurred by such a crime
cannot be purged away. Nevertheless it sometimes happens that a
man unwittingly marries a first or second cousin; for instance, if a
part of the family moves away to another district, it may come about
that a man makes the acquaintance of a girl and marries her before
he discovers the relationship. In such a case, where the sin has
been committed unknowingly, the curse can be averted by the
performance of an expiatory rite. The elders take a sheep and place
it on the woman’s shoulders; there it is killed and the intestines taken
out. Then the elders solemnly sever the intestines with a sharp
splinter of wood taken from a bush of a certain sort (mukeo), “and
they announce that they are cutting the clan kutinyarurira, by which
they mean that they are severing the bond of relationship which
exists between the pair. A medicine man then comes and purifies the
couple.”93.1 In all these cases we may assume with a fair degree of
probability that the old prohibition of marriage between cousins is
breaking down, and that the expiatory sacrifice offered when such a
marriage does take place is merely a salve to the uneasy conscience
of those who commit or connive at a breach of the ancient taboo.
Thus the prohibition of marriage between
The mutual cousins, and the rules of ceremonial avoidance
avoidance of male
and female cousins observed in some tribes between persons who
is probably a stand in that relationship to each other, appear
precaution against both to spring from a belief, right or wrong, in the
a criminal intimacy
between them. injurious effects of such unions and from a desire
to avoid them. The mutual avoidance of the
cousins is merely a precaution to prevent a closer and more criminal
intimacy between them. If that is so, it furnishes a confirmation of the
view that all the customs of ceremonial avoidance between blood
relations or connexions by marriage of opposite sexes are based
simply on a fear of incest.
The theory is perhaps confirmed by the
The mutual observation that in some tribes the avoidance
avoidance between
a man and his between a man and his wife’s mother lasts only
wife’s relations until he has had a child by his wife;94.1 while in
seems to be partly
grounded on a fear others, though avoidance continues longer, it
of rendering the gradually wears away with time as the man and
wife infertile.
woman advance in years,94.2 and in others, again,
it is observed only between a man and his future mother-in-law, and
comes to an end with his marriage.94.3 These customs suggest that
in the minds of the people who practise them there is a close
connexion between the avoidance of the wife’s relations and the
dread of an infertile marriage. The Indians of Yucatan, as we saw,
believe that if a betrothed man were to meet his future mother-in-law
or father-in-law, he would thereby lose the power of begetting
children. Such a fear seems to be only an extension by false analogy
of that belief in the disastrous consequences of illicit sexual relations
which we dealt with in an earlier part of this chapter,94.4 and of which
we shall have more to say presently.94.5 From thinking, rightly or
wrongly, that sexual intercourse between certain persons is fraught
with serious dangers, the savage jumped to the conclusion that
social intercourse between them may be also perilous by virtue of a
sort of physical infection acting through simple contact or even at a
distance; or if, in many cases, he did not go so far as to suppose that
for a man merely to see or touch his mother-in-law sufficed to blast
the fertility of his wife’s womb, yet he may have thought, with much
better reason, that intimate social converse between him and her
might easily lead to something worse, and that to guard against such
a possibility it was best to raise a strong barrier of etiquette between
them. It is not, of course, to be supposed that these rules of
avoidance were the result of deliberate legislation; rather they were
the spontaneous and gradual growth of feelings and thoughts of
which the savages themselves perhaps had no clear consciousness.
In what precedes I have merely attempted to sum up in language
intelligible to civilized man the outcome of a long course of moral and
social evolution.
These considerations perhaps obviate to some extent the only
serious difficulty which lies in the way of the theory here advocated.
If the custom of avoidance was adopted in order to
The mutual guard against the danger of incest, how comes it
avoidance between
persons of the that the custom is often observed towards persons
same sex was of the same sex, for example, by a man towards
probably an his father-in-law as well as towards his mother-in-
extension by false
analogy of the law? The difficulty is undoubtedly serious: the only
mutual avoidance way of meeting it that I can suggest is the one I
between persons of
different sexes.
have already indicated. We may suppose that the
deeply rooted beliefs of the savage in the fatal
effects of marriage between certain classes of persons, whether
relations by blood or connexions by marriage, gradually spread in his
mind so as to embrace the relations between men and men as well
as between men and women; till he had worked himself into the
conviction that to see or touch his father-in-law, for example, was
nearly or quite as dangerous as to touch or have improper relations
with his mother-in-law. It is no doubt easy for us to detect the flaw in
this process of reasoning; but we should beware of casting stones at
the illogical savage, for it is possible or even probable that many of
our own cherished convictions are no better founded.
Viewed from this standpoint the customs of
The custom of ceremonial avoidance among savages assume a
mutual avoidance
between near serious aspect very different from the appearance
relations has of arbitrariness and absurdity which they are apt to
probably had the present to the civilized observer who does not look
effect of checking
the practice of below the surface of savage society. So far as
inbreeding. these customs have helped, as they probably
have done, to suppress the tendency to
inbreeding, that is, to the marriage of near relations, we must
conclude that their effect has been salutary, if, as many eminent
biologists hold, long-continued inbreeding is injurious to the stock,
whether animal or vegetable, by rendering it in the end infertile.95.1
However, men of science are as yet by no means agreed as to the
results of consanguineous marriages, and a living authority on the
subject has recently closed a review of the evidence as follows:
“When we take into account such evidence as there is from animals
and plants, and such studies as those of Huth,95.2 and the instances
and counter-instances of communities with a high degree of
consanguinity, we are led to the conclusion that the prejudices and
laws of many peoples against the marriage of near kin rest on a
basis not so much biological as social.”96.1 Whatever may be the
ultimate verdict of science on this disputed question, it will not affect
the result of the present enquiry, which merely affirms the deep and
far-reaching influence which in the long course of human history
superstition has exercised on morality. Whether the influence has on
the whole been for good or evil does not concern us. It suffices for
our purpose to shew that superstition has been a crutch to morality,
whether to support it in the fair way of virtue or to precipitate it into
the miry pit of vice. To return to the point from which we wandered
into this digression, we must leave in suspense the question whether
the Australian savages were wise or foolish who forbade a man
under pain of death to speak to his mother-in-law.
I will conclude this part of my subject with a few
Other examples of more instances of the extreme severity with which
the severe
punishment of certain races have visited what they deemed
sexual crime. improper connexions between the sexes.
Among the Indians who inhabited the coast of
The Indians of Brazil near Rio de Janeiro about the middle of the
Brazil. sixteenth century, a married woman who gave
birth to an illegitimate child was either killed or
abandoned to the caprice of the young men who could not afford to
keep a wife. Her child was buried alive; for they said that were he to
grow up he would only serve to perpetuate his mother’s disgrace; he
would not be allowed to go to war with the rest for fear of the
misfortunes and disasters he might draw down upon them, and no
one would eat any food, whether venison, fish, or what not, which
the miserable outcast had touched.96.2 In Ruanda,
The natives of
Ruanda.
a district of Central Africa, down to recent years
any unmarried woman who was got with child
used to be put to death with her baby, whether born or unborn. A
spot at the mouth of the Akanyaru river was the place of execution,
where the guilty women and their innocent offspring were hurled into
the water. As usual, this Puritanical strictness of morality has been
relaxed under European influence; illegitimate children are still killed,
but their mothers escape with the fine of a cow.97.1
The Saxons.
Among the Saxons down to the days of St.
Boniface the adulteress or the maiden who had dishonoured her
father’s house was compelled to hang herself, was burned, and her
paramour hung over the blazing pile; or she was scourged or cut to
pieces with knives by all the women of the village till she was
dead.97.2 Among the Slav peoples of the Balkan
The Southern
Slavs.
peninsula women convicted of immoral conduct
used to be stoned to death. About the year 1770 a
young betrothed couple were thus executed near Cattaro in
Dalmatia, because the girl was found to be with child. The youth
offered to marry her, and the priest begged that the sentence of
death might be commuted to perpetual banishment; but the people
declared that they would not have a bastard born among them; and
the two fathers of the luckless couple threw the first stones at them.
When Miss M. Edith Durham related this case to some Montenegrin
peasantry, they all said that in the old days stoning was the proper
punishment for unchaste women; the male paramours were shot by
the relations of the girls whom they had seduced. When “that
modern Messalina,” Queen Draga of Servia, was murdered, a
decent peasant woman remarked that “she ought to be under the
cursed stone heap” (pod prokletu gomilu). The country-folk of
Montenegro, who heard the news of the murder from Miss Durham,
“looked on it as a cleansing—a casting out of abominations—and
genuinely believed that Europe would commend the deed, and that
the removal of this sinful woman would bring prosperity to the
land.”97.3 Even down to the second half of the nineteenth century in
cases of seduction among the Southern Slavs the people proposed
to stone both the culprits to death.98.1 This happened, for example, in
Herzegovina in the year 1859, when a young man named Milutin
seduced or (to be more exact) was seduced by three unmarried girls
and got them all with child. The people sat in judgment upon the
sinners, and, though an elder proposed to stone them all, the court
passed a milder sentence. The young man was to marry one of the
girls, to rear the infants of the other two as his legitimate children,
and next time there was a fight with the Turks he was to prove his
manhood by rushing unarmed upon the enemy and wresting their
weapons from them, alive or dead. The sentence was fulfilled to the
letter, though many years passed before the culprit could carry out
the last part of it. However, his time came in 1875, when
Herzegovina revolted against the Turks. Then Milutin ran unarmed
upon a regiment of the enemy and found among the Turkish
bayonets a hero’s death.98.2 Even now the Old Catholics among the
South Slavs believe that a village in which a seducer is not
compelled to marry his victim will be punished with hail and
excessive rain. For this article of faith, however, they are ridiculed by
their enlightened Catholic neighbours, who hold the far more
probable view that thunder and lightning are caused by the village
priest to revenge himself for unreasonable delays in the payment of
his salary. A heavy hail-storm has been known to prove almost fatal
to the local incumbent, who was beaten within an inch of his life by
his enraged parishioners.98.3
It is difficult to believe that in these and similar
Inference from the cases the community would inflict such severe
severe punishments
inflicted for sexual punishment for sexual offences if it did not believe
offences. that its own safety, and not merely the interest of a
few individuals, was imperilled thereby.
If now we ask why illicit relations between the
Why should illicit sexes should be supposed to disturb the balance
relations between
the sexes be of nature and particularly to blast the fruits of the
thought to disturb earth, a partial answer may be conjecturally
the balance of suggested. It is not enough to say that such
nature?
relations are displeasing to the gods, who punish
indiscriminately the whole community for the sins of a few. For we
must always bear in mind that the gods are creations of man’s fancy;
he fashions them in human likeness, and endows them with tastes
and opinions which are merely vast cloudy projections of his own. To
affirm, therefore, that something is a sin because the gods will it so,
is only to push the enquiry one stage farther back and to raise the
further question, Why are the gods supposed to dislike and punish
these particular acts? In the case with which we
The reason why the are here concerned, the reason why so many
gods of savages
are supposed to savage gods prohibit adultery, fornication, and
punish sexual incest under pain of their severe displeasure may
crimes so severely
may perhaps be perhaps be found in the analogy which many
found in a mistaken savage men trace between the reproduction of the
belief that human species and the reproduction of animals
irregularities of the
human sexes and plants. The analogy is not purely fanciful, on
prevent the the contrary it is real and vital; but primitive
reproduction of peoples have given it a false extension in a vain
edible animals and
plants and thereby attempt to apply it practically to increasing the food
supply. They have imagined, in fact, that by
strike a fatal blow at
the food supply. performing or abstaining from certain sexual acts
they thereby directly promoted the reproduction of
animals and the multiplication of plants.99.1 All such acts and
abstinences, it is obvious, are purely superstitious and wholly fail to
effect the desired result. They are not religious but magical; that is,
they compass their end, not by an appeal to the gods, but by
manipulating natural forces in accordance with certain false ideas of
physical causation. In the present case the principle on which
savages seek to propagate animals and plants is that of magical
sympathy or imitation: they fancy that they assist the reproductive
process in nature by mimicking or performing it among themselves.
Now in the evolution of society such efforts to control the course of
nature directly by means of magical rites appear to have preceded
the efforts to control it indirectly by appealing to the vanity and
cupidity, the good-nature and pity of the gods; in short, magic seems
to be older than religion.100.1 In most races, it is true, the epoch of
unadulterated magic, of magic untinged by religion, belongs to such
a remote past that its existence, like that of our ape-like ancestors,
can be a matter of inference only; almost everywhere in history and
the world we find magic and religion side by side, at one time allies,
at another enemies, now playing into each other’s hands, now
cursing, objurgating, and vainly attempting to exterminate one
another. On the whole the lower intelligences cling closely, though
secretly, to magic, while the higher intelligences have discerned the
vanity of its pretensions and turned to religion instead. The result has
been that beliefs and rites which were purely magical in origin often
contract in course of time a religious character; they are modified in
accordance with the advance of thought, they are translated into
terms of gods and spirits, whether good and beneficent, or evil and
malignant. We may surmise, though we cannot prove, that a change
of this sort has come over the minds of many races with regard to
sexual morality. At some former time, perhaps, straining a real
analogy too far, they believed that those relations of the human
sexes which for any reason they regarded as right and natural had a
tendency to promote sympathetically the propagation of animals and
plants and thereby to ensure a supply of food for the community;
while on the contrary they may have imagined that those relations of
the human sexes which for any reason they deemed wrong and
unnatural had a tendency to thwart and impede the propagation of
animals and plants and thereby to diminish the common supply of
food.
Such a belief, it is obvious, would furnish a
Such a belief would sufficient motive for the strict prohibition of what
account both for the
horror with which were deemed improper relations between men
many savages and women; and it would explain the deep horror
regard such crimes, and detestation with which sexual irregularities are
and for the severity
with which they viewed by many, though certainly not by all,
punish them. savage tribes. For if improper relations between
the human sexes prevent animals and plants from
multiplying, they strike a fatal blow at the existence of the tribe by
cutting off its supply of food at the roots. No wonder, therefore, that
wherever such superstitions have prevailed the whole community,
believing its very existence to be put in jeopardy by sexual
immorality, should turn savagely on the culprits, and beat, burn,
drown or otherwise exterminate them in order to rid itself of so
dangerous a pollution. And when with the advance of knowledge
men began to perceive the mistake they had made in imagining that
the commerce of the human sexes could affect the propagation of
animals and plants, they would still through long habit be so inured
to the idea of the wickedness of certain sexual relations that they
could not dismiss it from their minds, even when they discerned the
fallacious nature of the reasoning by which they had arrived at it. The
old practice would therefore stand, though the old theory had fallen:
the old rules of sexual morality would continue to be observed, but if
they were to retain the respect of the community, it was necessary to

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Edition by David Klein

PRACTICALLY SPEAKING An Introduction 6.3 Gibbs Free Energy 243

5.9 Resolution of Enantiomers 226 7.7 Drawing the Complete Mechanism

Addition Reactions of Alkenes 404

11.7 Allylic Bromination 522 13.5 Preparation of Diols 595

18.6 Reactions at the Benzylic Position 854 20.2 Nomenclature 933

24.5 Cyclic Structures of Monosaccharides 1158 26.4 Reactions of Triglycerides 1245

MEDICALLY SPEAKING Lactose Intolerance 1176 26.5 Phospholipids 1254

PRACTICALLY SPEAKING Artificial Sweeteners 1177 MEDICALLY SPEAKING Selectivity of Antifungal

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