(eBook PDF) Introduction to Organic

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 CONTENTS

Covalent Bonding and Shapes Alkanes and Cycloalkanes 61

1 of Molecules 1 3
1.1 How Do We Describe the Electronic 3.1 What Are Alkanes? 62
Structure of Atoms? 2 3.2 What Is Constitutional Isomerism in
1.2 What Is the Lewis Model Alkanes? 64
of Bonding? 5 3.3 How Do We Name Alkanes? 66
1.3 How Do We Predict Bond 3.4 What Are Cycloalkanes? 71
Angles and the Shapes of
Molecules? 13 3.5 How Is the IUPAC System of
Nomenclature Applied to
1.4 How Do We Predict If a Molecule Molecules that Contain Functional
Is Polar or Nonpolar? 17 Groups? 72
1.5 What Is Resonance? 18 3.6 What Are the Conformations
1.6 What Is the Orbital Overlap of Alkanes and Cycloalkanes? 73
Model of Covalent Bonding? 21 3.7 What Is Cis–Trans Isomerism in
1.7 What Are Functional Cycloalkanes? 80
Groups? 26 3.8 What Are the Physical Properties of Alkanes
Summary of Key Questions 31 and Cycloalkanes? 84
Quick Quiz 32 3.9 What Are the Characteristic Reactions
Problems 34 of Alkanes? 87
Looking Ahead 38 3.10 What Are the Sources of Alkanes? 88
Group Learning Activities 39 Summary of Key Questions 91
Quick Quiz 92
CHEMICAL CONNECTIONS
Key Reactions 93
1A Buckyball: A New Form
of Carbon 16 Problems 93
Looking Ahead 98
Group Learning Activities 99
Putting it Together 99
CHEMICAL CONNECTIONS
Acids and Bases 40
2 3A The Poisonous Puffer Fish 81
3B Octane Rating: What Those Numbers at the
2.1 What Are Arrhenius Acids Pump Mean 90
and Bases? 41
2.2 What Are Brønsted–Lowry Acids
and Bases? 42
2.3 How Do We Measure the Strength
of an Acid or Base? 44 Alkenes and Alkynes 103
2.4 How Do We Determine the Position
4
of Equilibrium in an Acid–Base
Reaction? 46 4.1 What Are the Structures and Shapes
2.5 What Are the Relationships of Alkenes and Alkynes? 105
between Acidity and Molecular 4.2 How Do We Name Alkenes and
Structure? 48 Alkynes? 107
2.6 What Are Lewis Acids 4.3 What Are the Physical Properties of Alkenes
and Bases? 52 and Alkynes? 115
Summary of Key Questions 55 4.4 Why Are 1–Alkynes (Terminal Alkynes) Weak
Quick Quiz 56 Acids? 116
Key Reactions 57 Summary of Key Questions 117
Problems 57 Quick Quiz 118
Looking Ahead 59 Problems 118
Group Learning Activities 60 Looking Ahead 122
Group Learning Activities 122

vi
 CONTENTS vii

CHEMICAL CONNECTIONS Summary of Key Questions 179

4A Ethylene, a Plant Growth Regulator 104 Quick Quiz 180
4B Cis–Trans Isomerism in Vision 106 Problems 181
4C Why Plants Emit Isoprene 115 Chemical Transformations 185
Looking Ahead 186
Group Learning Activities 186
Putting it Together 187
Reactions of Alkenes and Alkynes 123
5 CHEMICAL CONNECTIONS
6A Chiral Drugs 178
5.1 What Are the Characteristic Reactions
of Alkenes? 123
5.2 What Is a Reaction Mechanism? 124
5.3 What Are the Mechanisms of Electrophilic Haloalkanes 190
Additions to Alkenes? 130 7
5.4 What Are Carbocation Rearrangements? 140
5.5 What Is Hydroboration–Oxidation of an 7.1 How Are Haloalkanes Named? 191
Alkene? 143 7.2 What Are the Characteristic Reactions
5.6 How Can an Alkene Be Reduced to an of Haloalkanes? 193
Alkane? 145 7.3 What Are the Products of Nucleophilic Aliphatic
5.7 How Can an Acetylide Anion Be Used to Create Substitution Reactions? 195
a New Carbon–Carbon Bond? 148 7.4 What Are the SN2 and SN1 Mechanisms for
5.8 How Can Alkynes Be Reduced to Alkenes and Nucleophilic Substitution? 197
Alkanes? 150 7.5 What Determines Whether SN1 or SN2
Summary of Key Questions 151 Predominates? 201
Quick Quiz 152 7.6 How Can SN1 and SN2 Be Predicted Based on
Experimental Conditions? 206
Key Reactions 153
7.7 What Are the Products of β‐Elimination? 208
Problems 154
7.8 What Are the E1 and E2 Mechanisms for
Looking Ahead 158 β‐Elimination? 211
Group Learning Activities 158 7.9 When Do Nucleophilic Substitution and
CHEMICAL CONNECTIONS β‐Elimination Compete? 214
5A Catalytic Cracking and the Importance Summary of Key Questions 217
of Alkenes 127 Quick Quiz 218
Key Reactions 218
Problems 219
Chemical Transformations 223
Chirality: The Handedness Looking Ahead 224
6 of Molecules 160 Group Learning Activities 225
CHEMICAL CONNECTIONS
6.1 What Are Stereoisomers? 161 7A The Environmental Impact of
6.2 What Are Enantiomers? 161 Chlorofluorocarbons 193
6.3 How Do We Designate the Configuration 7B The Effect of Chlorofluorocarbon Legislation
of a Stereocenter? 166 on Asthma Sufferers 216
6.4 What Is the 2n Rule? 168
6.5 How Do We Describe the Chirality
of Cyclic Molecules with Two
Stereocenters? 172
6.6 How Do We Describe the Chirality of Alcohols, Ethers, and Thiols 226
Molecules with Three or More 8
Stereocenters? 174
6.7 What Are the Properties of Stereoisomers? 174 8.1 What Are Alcohols? 227
6.8 How Is Chirality Detected in the 8.2 What Are the Characteristic Reactions
Laboratory? 175 of Alcohols? 232
6.9 What Is the Significance of Chirality in the 8.3 What Are Ethers? 245
Biological World? 176 8.4 What Are Epoxides? 249
6.10 How Can Enantiomers Be Resolved? 177 8.5 What Are Thiols? 253
viii CONTENTS

8.6 What Are the Characteristic Reactions 10.5 What Are the Reactions of Amines
of Thiols? 256 with Acids? 325
Summary of Key Questions 257 10.6 How Are Arylamines Synthesized? 327
Quick Quiz 258 10.7 How Do Amines Act as
Key Reactions 259 Nucleophiles? 328
Problems 260 Summary of Key Questions 330
Chemical Transformations 264 Quick Quiz 331
Looking Ahead 264 Key Reactions 331
Group Learning Activities 265 Problems 332
Chemical Transformations 337
CHEMICAL CONNECTIONS
Looking Ahead 337
8A Nitroglycerin: An Explosive and a Drug 230
Group Learning Activities 338
8B Blood Alcohol Screening 245
8C Ethylene Oxide: A Chemical Sterilant 253 Putting it Together 338
CHEMICAL CONNECTIONS
10A Morphine as a Clue in the Design
and Discovery of Drugs 314
10B The Poison Dart Frogs of South
Benzene and Its Derivatives 266
9 America: Lethal Amines 319

9.1 What Is the Structure of Benzene? 267

9.2 What Is Aromaticity? 270
9.3 How Are Benzene Compounds Named, and Spectroscopy 341
What Are Their Physical Properties? 273 11
9.4 What Is a Benzylic Position, and How Does It
Contribute to Benzene Reactivity? 276 11.1 What Is Electromagnetic Radiation? 342
9.5 What Is Electrophilic Aromatic 11.2 What Is Molecular Spectroscopy? 344
Substitution? 278
11.3 What Is Infrared Spectroscopy? 344
9.6 What Is the Mechanism of Electrophilic
11.4 How Do We Interpret Infrared
Aromatic Substitution? 279
Spectra? 347
9.7 How Do Existing Substituents on Benzene Affect
11.5 What Is Nuclear Magnetic
Electrophilic Aromatic Substitution? 288
Resonance? 358
9.8 What Are Phenols? 296
11.6 What Is Shielding? 360
Summary of Key Questions 303
11.7 What Is a 1H-NMR Spectrum? 360
Quick Quiz 304
11.8 How Many Resonance Signals Will
Key Reactions 304 a Compound Yield in Its 1H‐NMR
Problems 305 Spectrum? 362
Chemical Transformations 310 11.9 What Is Signal Integration? 365
Looking Ahead 311 11.10 What Is Chemical Shift? 366
Group Learning Activities 312 11.11 What Is Signal Splitting? 368
CHEMICAL CONNECTIONS
11.12 What Is 13C‐NMR Spectroscopy,
and How Does It Differ from 1H‐NMR
9A Carcinogenic Polynuclear Aromatics Spectroscopy? 371
and Cancer 277 11.13 How Do We Solve an NMR
9B Capsaicin, for Those Who Like It Hot 300 Problem? 374
Summary of Key Questions 378
Quick Quiz 380
Problems 381
Amines 313 Looking Ahead 394
10 Group Learning Activities 395
CHEMICAL CONNECTIONS
10.1 What Are Amines? 313
11A Infrared Spectroscopy: A Window on Brain
10.2 How Are Amines Named? 316
Activity 348
10.3 What Are the Characteristic Physical Properties
of Amines? 319 11B Infrared Spectroscopy: A Window on Climate
Change 354
10.4 What Are the Acid–Base Properties of
Amines? 321 11C Magnetic Resonance Imaging (MRI) 371
 CONTENTS ix

13B Esters as Flavoring Agents 451

Aldehydes and Ketones 396
12 13C Ketone Bodies and Diabetes 456

12.1 What Are Aldehydes and Ketones? 397

12.2 How Are Aldehydes and Ketones Named? 397
12.3 What Are the Physical Properties of Aldehydes Functional Derivatives
and Ketones? 401 14 of Carboxylic Acids 468
12.4 What Is the Most Common Reaction Theme of
Aldehydes and Ketones? 402 14.1 What Are Some Derivatives of
12.5 What Are Grignard Reagents, and How Do They Carboxylic Acids, and How Are They
React with Aldehydes and Ketones? 402 Named? 469
12.6 What Are Hemiacetals and Acetals? 407 14.2 What Are the Characteristic Reactions
12.7 How Do Aldehydes and Ketones React with of Carboxylic Acid Derivatives? 474
Ammonia and Amines? 413 14.3 What Is Hydrolysis? 475
12.8 What Is Keto‐Enol Tautomerism? 417 14.4 How Do Carboxylic Acid Derivatives
12.9 How Are Aldehydes and Ketones React with Alcohols? 480
Oxidized? 420 14.5 How Do Carboxylic Acid Derivatives
12.10 How Are Aldehydes and Ketones React with Ammonia and Amines? 483
Reduced? 423 14.6 How Can Functional Derivatives
Summary of Key Questions 425 of Carboxylic Acids Be Interconverted? 485
Quick Quiz 426 14.7 How Do Esters React with Grignard
Reagents? 486
Key Reactions 427
14.8 How Are Derivatives of Carboxylic Acids
Problems 428
Reduced? 488
Chemical Transformations 434
Summary of Key Questions 492
Spectroscopy 435
Quick Quiz 493
Looking Ahead 435
Key Reactions 493
Group Learning Activities 436
Problems 495
CHEMICAL CONNECTIONS Chemical Transformations 500
12A A Green Synthesis of Adipic Acid 422 Looking Ahead 501
Group Learning Activities 501
Putting it Together 501
CHEMICAL CONNECTIONS
Carboxylic Acids 437 14A Ultraviolet Sunscreens and Sunblocks 470
13 14B From Moldy Clover to a Blood Thinner 471
14C The Penicillins and Cephalosporins:
13.1 What Are Carboxylic Acids? 437 β‐Lactam Antibiotics 472
13.2 How Are Carboxylic Acids Named? 438 14D The Pyrethrins: Natural Insecticides
13.3 What Are the Physical Properties of Carboxylic of Plant Origin 482
Acids? 441 14E Systematic Acquired Resistance
13.4 What Are the Acid–Base Properties of in Plants 485
Carboxylic Acids? 442
13.5 How Are Carboxyl Groups Reduced? 446
13.6 What Is Fischer Esterification? 449
13.7 What Are Acid Chlorides? 453
13.8 What Is Decarboxylation? 455 Enolate Anions 504
15
Summary of Key Questions 459
Quick Quiz 459 15.1 What Are Enolate Anions, and
Key Reactions 460 How Are They Formed? 505
Problems 461 15.2 What Is the Aldol Reaction? 508
Chemical Transformations 466 15.3 What Are the Claisen and Dieckmann
Looking Ahead 466 Condensations? 515
Group Learning Activities 467 15.4 How Are Aldol Reactions and Claisen
Condensations Involved in Biological
CHEMICAL CONNECTIONS Processes? 522
13A From Willow Bark to Aspirin and Beyond 446 15.5 What Is the Michael Reaction? 524
x CONTENTS

Summary of Key Questions 531 Key Reactions 585

Quick Quiz 531 Problems 586
Key Reactions 532 Looking Ahead 589
Problems 533 Group Learning Activities 590
Chemical Transformations 538 Putting it Together 591
Looking Ahead 539 CHEMICAL CONNECTIONS
Group Learning Activities 540 17A Relative Sweetness of Carbohydrate
CHEMICAL CONNECTIONS and Artificial Sweeteners 578
15A Drugs That Lower Plasma Levels 17B A, B, AB, and O Blood‐Group Substances 579
of Cholesterol 523
15B Antitumor Compounds: The Michael
Reaction in Nature 530
Amino Acids and Proteins 595
18
Organic Polymer Chemistry 542 18.1 What Are the Many Functions of Proteins? 595
16 18.2 What Are Amino Acids? 596
18.3 What Are the Acid–Base Properties of Amino
16.1 What Is the Architecture of Polymers? 543 Acids? 599
16.2 How Do We Name and Show 18.4 What Are Polypeptides and Proteins? 606
the Structure of a Polymer? 543 18.5 What Is the Primary Structure of
16.3 What Is Polymer Morphology? a Polypeptide or Protein? 607
Crystalline versus Amorphous 18.6 What Are the Three‐Dimensional Shapes
Materials 545 of Polypeptides and Proteins? 611
16.4 What Is Step‐Growth Polymerization? 546 Summary of Key Questions 618
16.5 What Are Chain‐Growth Polymers? 551 Quick Quiz 619
16.6 What Plastics Are Currently Key Reactions 620
Recycled in Large Quantities? 557 Problems 620
Summary of Key Questions 558 Looking Ahead 623
Quick Quiz 559 Group Learning Activities 623
Key Reactions 560
CHEMICAL CONNECTIONS
Problems 560
18A Spider Silk: A Chemical and Engineering
Looking Ahead 562
Wonder of Nature 616
Group Learning Activities 562
CHEMICAL CONNECTIONS
16A Stitches That Dissolve 551
16B Paper or Plastic? 553
Lipids (Online Chapter) 624
19
19.1 What Are Triglycerides? 624
Carbohydrates 563 19.2 What Are Soaps and Detergents? 628
17 19.3 What Are Phospholipids? 630
19.4 What Are Steroids? 632
17.1 What Are Carbohydrates? 563 19.5 What Are Prostaglandins? 637
17.2 What Are Monosaccharides? 564 19.6 What Are Fat‐Soluble Vitamins? 640
17.3 What Are the Cyclic Structures Summary of Key Questions 643
of Monosaccharides? 568
Quick Quiz 644
17.4 What Are the Characteristic
Reactions of Monosaccharides? 573 Problems 644
17.5 What Are Disaccharides and Looking Ahead 646
Oligosaccharides? 577 Group Learning Activities 647
17.6 What Are Polysaccharides? 581 CHEMICAL CONNECTIONS
Summary of Key Questions 583 19A Snake Venom Phospholipases 632
Quick Quiz 584 19B Nonsteroidal Estrogen Antagonists 636
 CONTENTS xi

21.3 What Are the Ten Reactions of Glycolysis? 678

Nucleic Acids (Online Chapter) 648
20 21.4 What Are the Fates of Pyruvate? 683
21.5 What Are the Reactions of the β‐Oxidation
of Fatty Acids? 685
20.1 What Are Nucleosides and Nucleotides? 648
21.6 What Are the Reactions of the Citric Acid
20.2 What Is the Structure of DNA? 652 Cycle? 689
20.3 What Are Ribonucleic Acids (RNA)? 658 Summary of Key Questions 692
20.4 What Is the Genetic Code? 660 Quick Quiz 693
20.5 How Is DNA Sequenced? 662 Key Reactions 693
Summary of Key Questions 667 Problems 694
Quick Quiz 668 Group Learning Activities 696
Problems 669
Group Learning Activities 671
CHEMICAL CONNECTIONS
20A The Search for Antiviral Drugs 650 Appendix 1 Acid Ionization Constants for the Major
20B DNA Fingerprinting 666 Classes of Organic Acids A.1
Characteristic 1H‐NMR Chemical
Shifts A.1
Appendix 2 Characteristic 13C‐NMR Chemical
Shifts A.2
The Organic Chemistry of Metabolism
21 (Online Chapter) 672
Characteristic Infrared Absorption
Frequencies A.2
Glossary G.1
21.1 What Are the Key Participants in Glycolysis, the
β‐Oxidation of Fatty Acids, and the Citric Acid Answers Section Ans.1
Cycle? 673 Index I.1
21.2 What Is Glycolysis? 678
 P R E FAC E
Goals of This Text
This text is designed for an introductory course in organic
chemistry and assumes, as background, a prior course of general
chemistry. Both its form and content have been shaped by our
experiences in the classroom and by our assessment of the pre-
sent and future direction of the brief organic course.
A brief course in organic chemistry must achieve several
goals. First, most students who elect this course are oriented
toward careers in science, but few if any intend to become pro-
fessional chemists; rather, they are preparing for careers in areas
that require a grounding in the essentials of organic chemistry.
Here is the place to examine the structure, properties, and reac-
tions of rather simple molecules. Students can then build on this
knowledge in later course work and professional life.
Second, an introductory course must portray something of
the scope and content of organic chemistry as well as its tremen-
dous impact on the ways we live and work. To do this, we have
included specific examples of pharmaceuticals, plastics, soaps
and detergents, natural and synthetic textile fibers, petroleum
refining, petrochemicals, pesticides, artificial flavoring agents,
chemical ecology, and so on at appropriate points in the text.
Third, a brief course must convince students that organic
chemistry is more than just a catalog of names and reactions.
There are certain organizing themes or principles, which not only
make the discipline easier to understand, but also provide a way to
analyze new chemistry. The relationship between molecular struc-
ture and chemical reactivity is one such theme. Electronic theory
of organic chemistry, including Lewis structures, atomic orbitals,
the hybridization of atomic orbitals, and the theory of resonance
are presented in Chapter 1. Chapter 2 explores the relationship
between molecular structure and one chemical property, namely,
acidity and basicity. Variations in acidity and basicity among
organic compounds are correlated using the concepts of electron-
egativity, the inductive effect, and resonance. These same con-
cepts are used throughout the text in discussions of molecular
structure and chemical reactivity. Stereochemistry is a second
theme that recurs throughout the text. The concept and impor-
tance of the spatial arrangement of atoms is introduced in
Chapter 3 with the concept of conformations in alkanes and
cycloalkane, followed by cis/trans isomerism in Chapters 3
(in cycloalkanes) and 4 (in alkenes). Molecular symmetry and
asymmetry, enantiomers and absolute configuration, and the sig-
nificance of asymmetry in the biological world are discussed in
Chapter 6. The concept of a mechanistic understanding of the
reactions of organic substances is a third major theme. Reaction
mechanisms are first presented in Chapter 5; they not only help to
minimize memory work but also provide a satisfaction that comes
from an understanding of the molecular logic that governs how
and why organic reactions occur as they do. In this chapter we
present a set of five fundamental patterns that are foundational to
the molecular logic of organic reactions. An understanding and
application of these patterns will not only help to minimize mem-
ory work but also provide a satisfaction that comes from an
understanding of how and why organic reactions occur as they do.
The Audience
This book provides an introduction to organic chemistry for
students who intend to pursue careers in the sciences and who
require a grounding in organic chemistry. For this reason, we
xii
make a special effort throughout to show the interrelation
between organic chemistry and other areas of science, particu-
larly the biological and health sciences. While studying with
this book, we hope that students will see that organic chemis-
try is a tool for these many disciplines, and that organic com-
pounds, both natural and synthetic, are all around them—in
pharmaceuticals, plastics, fibers, agrochemicals, surface coat-
ings, toiletry preparations and cosmetics, food additives, adhe-
sives, and elastomers. Furthermore, we hope that students will
recognize that organic chemistry is a dynamic and ever‐
expanding area of science waiting openly for those who are
prepared, both by training and an inquisitive nature, to ask
questions and explore.
New Features
● Modified Chapter Openers that employ a Guided Inquiry
approach to capture students’ attention, getting them excited
about the material they are about to read.
● Key Concept Videos: Created by co‐author Tom Poon, these
videos are centered on key topics in the text, helping stu-
dents better understand important concepts.
Video lectures are denoted by the following icon which can
be found throughout the text.
● More Practice Problems: We have added over 130 addi-
tional practice problems, while keeping in mind the care
and attention instructors put into their courses by not
changing the basic numbering of problems from the previ-
ous addition.
● More Real World Connections: In order to show the con-
nections between organic chemistry and other disciplines,
we have added over 40 references, either in‐text or via col-
umn elements, to real world products or applications.
● We have reduced the length of the text. Chapter 19, Lipids,
along with Chapter 20 Nucleic Acids, and Chapter 21,
The Organic Chemistry of Metabolism, will be available
in WileyPLUS and on the text website: www.wiley.com/
college/brown.
Hallmark Features
● “Mechanism” boxes for each mechanism in the book. These
Mechanism boxes serve as road maps and present mecha-
nisms using basic steps and recurring themes that are
common to most organic reaction mechanisms. This
approach allows students to see that reactions have many
steps in common, making the reaction easier to understand
and remember.
● “Group Learning Activities” appear with the end‐of‐
chapter problems and provide students with the opportunity
to learn organic chemistry collaboratively, fostering more
active learning.
● “Key Terms and Concepts” appear within the “Summary of
Key Questions.”
● “How To Boxes”: Step‐by‐step How To guides for approach-
ing problems and concepts that students often find difficult.

● Chemical Connection Boxes include applications of
organic chemistry to the world around us, particularly to the
biochemical, health, and biological sciences. The topics
covered in these boxes represent real‐world applications of
organic chemistry and highlight the relevance between
organic chemistry and the students’ future careers.
● “Putting It Together” Cumulative Review Questions: In
this text, end‐of‐chapter problems are organized by section,
allowing students to easily refer back to the appropriate sec-
tion if difficulties arise. We offer a section called Putting It
Together (PIT) at the end of Chapters 3, 6, 10, 14, and 17.
Each PIT section is structured like an exam would be organ-
ized, with questions of varying types (multiple choice, short
answer, naming, mechanism problems, predict the products,
synthesis problems, etc.) and difficulty.
● Problem‐Solving Strategies: To help students overcome the
challenge of knowing where to begin, we include a strategy
step for every worked example in the text. The strategy step
will help students to determine the starting point for each of
the example problems.
● Quick Quizzes: A set of true or false questions, provided at
the end of every chapter, is designed to test students’ under-
standing of the basic concepts presented in the chapter. The
answers to the quizzes are provided at the bottom of the page
so that students can quickly check their progress, and if nec-
essary, return to the appropriate section in the chapter to
review the material.
● Greater Attention to Visual Learning: Research in knowl-
edge and cognition has shown that visualization and organi-
zation can greatly enhance learning. We added over 100
callouts (short dialog bubbles) to highlight important fea-
tures of many of the illustrations throughout the text. This
places most of the important information in one location.
When students try to recall a concept or attempt to solve a
problem, we hope that they will try to visualize the relevant
WileyPLUS for Organic Chemistry
What do students receive with WileyPLUS?
● The complete digital textbook, saving students up to 60%
off the cost of the printed text.
● Question assistance, including links to relevant sections in
the online digital textbook.
● Immediate feedback and proof of progress, 24/7.
W I L EY P L U S A S S E S S M E NT
REACTION EXPLORER
IN CHAPTER/EOC ASSESSMENT
CONCEPT MASTERY
TEST BANK
P R E FA C E xiii
illustration from the text. They may be pleasantly surprised
to find that the visual cues provided by the callouts help
them to remember the content as well as the context of the
illustration.
Organization: An Overview
Chapters 1–10 begin a study of organic compounds by first
reviewing the fundamentals of covalent bonding, the shapes
of molecules, and acid‐base chemistry. The structures and
typical reactions of several important classes of organic com-
pounds are then discussed: alkanes; alkenes and alkynes;
haloalkanes; alcohols and ethers; benzene and its derivatives;
amines, aldehydes, and ketones; and finally carboxylic acids
and their derivatives.
Chapter 11 introduces IR spectroscopy, and 1H‐NMR and
13C‐NMR spectroscopy. Discussion of spectroscopy requires no
more background than what students receive in general chemis-
try. The chapter is freestanding and can be taken up in any order
appropriate to a particular course.
Chapters 12–16 continue the study of organic com-
pounds, including aldehydes and ketones, carboxylic acids, and
finally carboxylic acids and their derivatives. Chapter 15 con-
cludes with an introduction to the aldol, Claisen, and Michael
reactions, all three of which are important means for the forma-
tion of new carbon–carbon bonds. Chapter 16 provides a brief
introduction to organic polymer chemistry.
Chapters 17–20 present an introduction to the organic
chemistry of carbohydrates; amino acids and proteins; nucleic
acids; and lipids. Chapter 21, The Organic Chemistry of
Metabolism, demonstrates how the chemistry developed to this
point can be applied to an understanding of three major meta-
bolic pathways—glycolysis, the β‐oxidation of fatty acids, and
the citric acid cycle.
● Integrated, multi‐media resources that address your students’
unique learning styles, levels of proficiency, and levels of
preparation by providing multiple study paths and encour-
age more active learning.
Four unique silos of assessment are available to instructors for
creating online homework and quizzes and are designed to ena-
ble and support problem‐solving skill development and concep-
tual understanding:
FOR ORGANIC CHEMISTRY
MEANINGFUL PRACTICE OF MECHANISM AND SYNTHESIS
PROBLEMS (A DATABASE OF OVER 100,000 QUESTIONS)
90-100% OF REVIEW PROBLEMS AND END-OF-CHAPTER
QUESTIONS ARE CODED FOR ON LINE ASSESSMENT
PREBUILT CONCEPT MASTERY ASSIGNMENTS
(FROM DATABASE OF OVER 25,000 QUESTIONS)
RICHTESTBANK CONSISTING OF OVER 3,000 QUESTIONS
xiv P R E FA C E
Reaction Explorer—Students’ ability to understand mecha-
nisms and predict synthesis reactions greatly impacts their level
of success in the course. Reaction Explorer is an interactive
system for learning and practicing reactions, syntheses, and
mechanisms in organic chemistry with advanced support for
the automatic generation of random problems and curved arrow
mechanism diagrams.
Mechanism Explorer provides valuable practice of reactions
and mechanisms.

Synthesis Explorer provides meaningful practice of single and
multistep synthesis.
End‐of‐Chapter Problems—A subset of the end‐of‐chapter prob-
lems is included for use in WileyPLUS. Many of the problems are
algorithmic and feature structure drawing/assessment functionality
using MarvinSketch, with immediate answer feedback.
These assignments pull from a unique database of over 25,000
questions, over half of which require students to draw a struc-
ture using MarvinSketch.
Test Bank—A robust Test Bank, containing over 2,000 questions,
is also available within WileyPLUS as an additional resource for
creating assignments or tests.
With WileyPLUS, students receive:
● Key Concept Videos
● Chapter Zero: General Chemistry Refresher: To ensure that
students have mastered the necessary prerequisite content
from General Chemistry, WileyPLUS includes a complete
chapter of core General Chemistry topics with corresponding
assignments.
● Office Hour Videos, Solved Problem Videos, and Video
Mini‐Lectures: In each chapter, several types of video assistance
are included to help students with conceptual understanding
and problem‐solving strategies. The video mini‐lectures focus
on challenging concepts; the Office Hours videos take these
concepts and apply them to example problems, emulating
P R E FA C E xv
Prebuilt Concept Mastery Assignments—Students must con-
tinuously practice and work organic chemistry problems in
order to master the concepts and skills presented in the course.
Prebuilt concept mastery assignments offer students ample
opportunities for practice in each chapter. Each assignment is
organized by topic and features feedback for incorrect answers.
the experience that a student would get if she or he were to
attend office hours and ask for assistance in working a prob-
lem. The Solved Problem videos use the solved problems
from the book, audio, and a whiteboard. The goal is to illus-
trate good problem solving strategies.
● Skill‐Building Exercises that utilize animated exercises, with
instant feedback, to reinforce the key skills required to suc-
ceed in organic chemistry
● 3D Visualization Animations that use the latest visual and
audio technologies to help students understnd concepts.
Instructors can assign quizzes based on these visualizations
in WileyPLUS
With WileyPLUS, instructors receive:
● QuickStart
● Four unique silos of assessment for creating online home-
work and quizzes
● Reliable resources that reinforce course goals inside and out-
side of the classroom
xvi P R E FA C E
● The ability to easily identify those students who are falling
behind by tracking their progress and offering assistance
early, even before they come to office hours. WileyPLUS
simplifies and automates such tasks as student performance
assessment, creating assignments, scoring student work,
keeping grades, and more.
● Media‐rich course materials and assessment content that
allow customization of the classroom presentation with a
wealth of resources and functionality from PowerPoint slides
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and Poon. The Student Solutions Manual contains detailed
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Acknowledgments
While one or a few persons are listed as “authors” of any text-
book, the book is in fact the product of collaboration of many
individuals, some obvious and some not so obvious. It is with
gratitude that we acknowledge the contributions of the many.
We begin with Felix Lee, who has worked with us for so many
years on both the solutions manual and the solutions to prob-
lems in all parts of the text. His keen eye and chemical expertise
has helped to improve this edition in so many ways. A special
thanks go to Professor Robert White of Dalhousie University
for taking the time to inform us of errors that he found in the
previous edition. We also thank Senior Production Editor Patty
Donovan at SPi Global for her incredible organizational skills
and patience. Speaking of patience, the entire Wiley produc-
tion and editorial team is to be commended for their patience,
skill and professionalism on this project including Joan Kakut,
Chemistry Development Editor; Alyson Rentrop, Associate
Development Editor, Mallory Fryc, Chemistry Editorial Assistant;
Sandra Dumas, Senior Production Editor, and Wendy Lai,
Senior Graphic Designer, for her creative contributions to the
covers of both this and the previous edition of the text. We
thank Sophia Brown for a student’s eye view of the PowerPoint
Lecture series. Finally, we thank all our students, both past and
present, for their many positive interactions over the years that
have guided us in creating this textbook.
List of Reviewers
The authors gratefully acknowledge the following reviewers for
their valuable critiques of this book in its many stages as we were
developing the Sixth Edition:
Tammy Davidson, University of Florida
Kimberly Griffin, California Polytechnic State University
Ron Swisher, Oregon Institute of Technology
Felix Lee, University of Western Ontario
Joseph Sumrak, Kansas State University
Lisa Stephens, Marist College
We are also grateful to the many people who provided reviews
that guided preparation of the earlier editions of our book:
Jennifer Batten, Grand Rapids Community College
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Richard Bretz, Miami University
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P R E FA C E xvii
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 Covalent Bonding
A
and Shapes
of Molecules
B
Three forms of elemental carbon,
(A) diamond, (B) graphite, and
(C) buckminsterfullerene, along

1
with their molecular models.
Notice how vastly different their
molecular structures are with
diamond having an intercon-
nected network of atoms, graphite
existing as sheets, and buckmin-
C sterfullerene’s atoms arranged like
(A) James Steidl/Shutterstock, (B) PortiadeCastro/Getty Images, Inc.
a soccer ball.
(C) Charles D. Winters/Science Source Images

KEY QUESTIONS 1.4 How Do We Predict If a Molecule HOW TO

1.1 How Do We Describe the Is Polar or Nonpolar? 1.1 How to Draw Lewis Structures for
Electronic Structure of Atoms? 1.5 What Is Resonance? Molecules and Ions
1.2 What Is the Lewis Model of 1.6 What Is the Orbital Overlap Model
CHEMICAL CONNECTIONS
Bonding? of Covalent Bonding?
1A Buckyball: A New Form of Carbon
1.3 How Do We Predict Bond Angles 1.7 What Are Functional Groups?
and the Shapes of Molecules?

WHAT DO THE FOODS THAT WE EAT , the fragrances that we smell, the medicines that
we take, the tissues that make up all living things, the fuels that we burn, and the many prod-
ucts that constitute our modern conveniences in life have in common? They all contain organic Organic chemistry The study
compounds, compounds that consist of at least one carbon and oftentimes other elements of the chemical and physical
properties of the compounds
such as hydrogen, oxygen, nitrogen, sulfur, and others from the Periodic Table. The study of
of carbon.
these compounds is known as organic chemistry.
You are about to embark on an exploration of organic chemistry, which spans a large
majority of the roughly 88 million chemical substances that have been cataloged. How can
one book cover the chemistry of tens of millions of compounds? It turns out that elements
commonly arrange themselves in ways that are predictable and that consistently exhibit simi-
lar properties. In this chapter, we review how these arrangements of elements such as carbon,
hydrogen, oxygen, and nitrogen are achieved through the sharing of electrons to form mole-
cules. We will then learn chemical trends found in these arrangements and use this knowledge
to make our study of organic chemistry manageable and fun.

1
2 CHAPTER 1 Covalent Bonding and Shapes of Molecules
Shells A region of space
around a nucleus where
electrons are found.
Orbital A region of space
where an electron or pair of
electrons spends 90 to 95%
of its time.
(a)
Nucleus
(protons and
neutrons)
FI G U RE 1. 1 A schematic view of an atom. (a) Most of the mass of an atom is concentrated in its small, dense
nucleus, which has a diameter of 10−14 to 10−15 meter (m). (b) Each shell can contain up to 2n2 electrons, where n
is the number of the shell. Thus, the first shell can hold 2 electrons, the second 8 electrons, the third 18, the fourth
32, and so on (Table 1.1).
the first shell contains a single
orbital called a 1s orbital. The
second shell contains one 2s orbital
and three 2p orbitals. All p orbitals
come in sets of three and can hold
up to 6 electrons. The third shell
contains one 3s orbital, three 3p
orbitals, and five 3d orbitals. All
d orbitals come in sets of five and
can hold up to 10 electrons. All f
orbitals come in sets of seven and
can hold up to 14 electrons
Ground‐state electron
configuration The electron
configuration of lowest
energy for an atom, molecule,
or ion.
1.1 How Do We Describe the Electronic Structure
of Atoms?
You are already familiar with the fundamentals of the electronic structure of atoms from a
previous study of chemistry. Briefly, an atom contains a small, dense nucleus made of neu-
trons and positively charged protons (Figure 1.1a).
Electrons do not move freely in the space around a nucleus, but rather are confined
to regions of space called principal energy levels or, more simply, shells. We number these
shells 1, 2, 3, and so forth from the inside out (Figure 1.1b).
Shells are divided into subshells designated by the letters s, p, d, and f, and within these
subshells, electrons are grouped in orbitals (Table 1.1). An orbital is a region of space that
can hold 2 electrons. In this course, we focus on compounds of carbon with hydrogen,
oxygen, and nitrogen, all of which use only electrons in s and p orbitals for covalent bond-
ing. Therefore, we are concerned primarily with s and p orbitals.
10–10 m
(b)
Nucleus Fourth shell (32 electrons)
Third shell (18 electrons)
Second shell (8 electrons)
Space
occupied by First shell (2 electrons)
electrons
Proton electrons in the first shell are nearest to the
Neutron positively charged nucleus and are held
most strongly by it; these electrons are said
10–15 m to be the lowest in energy
TA B L E 1 . 1 Distribution of Orbitals within Shells
Maximum Number Relative Energies
of Electrons Shell of Electrons in
Shell Orbitals Contained in Each Shell Can Hold Each Shell
4 One 4s, three 4p, five 4d, and seven 4f 2 + 6 + 10 + 14 = 32 Higher
orbitals
3 One 3s, three 3p, and five 3d orbitals 2 + 6 + 10 = 18
2 One 2s and three 2p orbitals 2+6=8
1 One 1s orbital 2 Lower
A. Electron Configuration of Atoms
The electron configuration of an atom is a description of the orbitals the electrons in the
atom occupy. Every atom has an infinite number of possible electron configurations. At this
stage, we are concerned only with the ground‐state electron configuration—the electron
configuration of lowest energy. Table 1.2 shows ground‐state electron configurations
 1. 1 How Do We Describe the Electronic Structure of Atoms? 3

TA B L E 1 . 2 Ground-State Electron Configurations for Elements 1–18* Rule 1. Orbitals in these

1
elements fill in the order
Period H 1 1s
First
1s, 2s, 2p, 3s, and 3p.
He 2 1s2
Li 3 1s2s1 [He] 2s1
Be 4 2
1s 2s 2
[He] 2s2 Rule 2. Notice that
each orbital contains a
1s22s22px1 [He] 2s22px1
Second Period

B 5 maximum of two electrons.

C 6 2
1s 2s 2
2px 2py1
1
[He] 2s22px12py1 In neon, there are six
additional electrons after
N 7 1s22s22px12py12pz1 [He] 2s22px12py12pz1 the 1s and 2s orbitals are
2 2 2 1 1
O 8 1s 2s 2px 2py 2pz [He] 2s22px22py12pz1 filled. These are written as
2px22py22pz2. Alternatively,
F 9 1s22s22px22py22pz1 [He] 2s22px22py22pz1
we can group the three
2 2 2 2 2
Ne 10 1s 2s 2px 2py 2pz [He] 2s22px22py22pz2 filled 2p orbitals and write
Na 11 2 2 2 2
1s 2s 2px 2py 2pz 3s 2 1
[Ne] 3s1 them in a condensed
form as 2p6.
Mg 12 1s22s22px22py22pz23s2 [Ne] 3s2
2 2 2 2 2 2 1
Al 13 1s 2s 2px 2py 2pz 3s 3px [Ne] 3s23px1
Third Period

2 2 2 2 2 2 1 1
Si 14 1s 2s 2px 2py 2pz 3s 3px 3py [Ne] 3s23px13py1 Rule 3. Because the px, py,
P 15 1s22s22px22py22pz23s23px13py13pz1 [Ne] 3s23px13py13pz1 and pz orbitals are equal
in energy, we fill each with
S 16 1s22s22px22py22pz23s23px23py13pz1 [Ne] 3s23px23py13pz1 one electron before adding
2 2
Cl 17 1s 2s 2px22py22pz23s23px23py23pz1 [Ne] 3s23px23py23pz1 a second electron. That is,
only after each 3p orbital
Ar 18 1s22s22px22py22pz23s23px23py23pz2 [Ne] 3s23px23py23pz2
contains one electron do
*Elements are listed by symbol, atomic number, ground-state electron configuration, and we add a second electron
shorthand notation for the ground-state electron configuration, in that order. to the 3px orbital.

for the first 18 elements of the Periodic Table. We determine the ground‐state electron
configuration of an atom with the use of the following three rules:
Rule 1. Orbitals fill in order of increasing energy from lowest to highest (Figure 1.2).
Rule 2. Each orbital can hold up to two electrons with their spins paired. Spin pairing means that
each electron spins in a direction opposite that of its partner (Figure 1.3). We show this
pairing by writing two arrows, one with its head up and the other with its head down.
Rule 3. When orbitals of equivalent energy are available, but there are not enough electrons to fill them
completely, then we add one electron to each equivalent orbital before we add a second electron to any
one of them.

3d
1
3
3 3p a spinning electron spin-paired electrons
generates a tiny are commonly
3s magnetic field represented this way
Order of filling

N S
Energy

2p
2
2s

F I G U R E 1. 2 S N
Relative energies
1 1s when their tiny magnetic
and order of filling 2 F I GU RE 1. 3
Principal fields are aligned N to S,
of orbitals through The pairing of electron
energy level Orbitals the electron spins are paired
the 3d orbitals. spins.

B. Lewis Structures
In discussing the physical and chemical properties of an element, chemists often focus on the Valence electrons Electrons
outermost shell of its atoms, because electrons in this shell are the ones involved in the formation in the valence (outermost)
of chemical bonds and in chemical reactions. We call outer‐shell electrons valence electrons, and shell of an atom.
we call the energy level in which they are found the valence shell. Carbon, for example, with a Valence shell The outermost
ground‐state electron configuration of 1s 22s 22p 2, has four valence (outer‐shell) electrons. electron shell of an atom.
 4 CHAPTER 1 Covalent Bonding and Shapes of Molecules

EXAMPLE 1.1
Write ground‐state electron configurations for these elements: (b) Oxygen (atomic number 8): 1s22s22px22py12pz1. Alter-
(a) Lithium (b) Oxygen (c) Chlorine natively, we can group the four electrons of the 2p
orbitals together and write the ground‐state electron
S T R AT E G Y configuration as 1s22s22p4. We can also write it as [He]
Locate each atom in the Periodic Table and determine its 2s22p4.
atomic number. The order of filling of orbitals is 1s, 2s, 2px, (c) Chlorine (atomic number 17): 1s22s22p63s23p5. Alterna-
2py, 2pz, and so on. tively, we can write it as [Ne] 3s23p5.

See problems 1.17–1.20

SOLUTION
(a) Lithium (atomic number 3): 1s22s1. Alternatively, we can
write the ground‐state electron configuration as [He] 2s1.

PROBLEM 1.1
Write and compare the ground‐state electron configurations (a) Carbon and silicon
for the elements in each set. What can be said about the out- (b) Oxygen and sulfur
ermost shell of orbitals for each pair of elements? (c) Nitrogen and phosphorus

Lewis structure of an
atom The symbol of an
element surrounded by a
number of dots equal to the
number of electrons in the
valence shell of the atom.
UPI/© Corbis
To show the outermost electrons of an atom, we commonly use a representation
called a Lewis structure, after the American chemist Gilbert N. Lewis (1875–1946), who
devised this notation. A Lewis structure shows the symbol of the element, surrounded by
a number of dots equal to the number of electrons in the outer shell of an atom of that
element. In Lewis structures, the atomic symbol represents the nucleus and all filled
inner shells. Table 1.3 shows Lewis structures for the first 18 elements of the Periodic
Table. As you study the entries in the table, note that, with the exception of helium, the
number of valence electrons of the element corresponds to the group number of the
element in the Periodic Table; for example, oxygen, with six valence electrons, is in
Group 6A.
At this point, we must say a word about the numbering of the columns (families or
groups) in the Periodic Table. Dmitri Mendeleev gave them numerals and added the let-
ter A for some columns and B for others. This pattern remains in common use in the
United States today. In 1985, however, the International Union of Pure and Applied

Gilbert N. Lewis (1875–1946)
introduced the theory of the
electron pair that extended
our understanding of
covalent bonding and of the
concept of acids and bases. It
is in his honor that we often
refer to an “electron dot”
structure as a Lewis structure.
Chemistry (IUPAC) recommended an alternative system in which the columns are num-
bered 1 to 18 beginning on the left and without added letters. Although we use the origi-
nal Mendeleev system in this text, the Periodic Table at the front of the text shows both.
Notice from Table 1.3 that, because of the differences in number and kind of valence
shell orbitals available to elements of the second and third periods, significant differences
exist in the covalent bonding of oxygen and sulfur and of nitrogen and phosphorus. For
example, although oxygen and nitrogen can accommodate no more than 8 electrons in
their valence shells, many phosphorus‐containing compounds have 10 electrons in the
valence shell of phosphorus, and many sulfur‐containing compounds have 10 and even 12
electrons in the valence shell of sulfur.

the valence shell

the valence shell of TA B L E 1 . 3 Lewis Structures for Elements 1–18 of the Periodic Table of 3rd period
1st period elements elements contains
contain only s orbitals 1A 2A 3A 4A 5A 6A 7A 8A s, p, and d orbitals.
The d orbitals
H• He
••

the valence shell of allow for expanded

••
•

covalent bonding
•

•
•
•

2nd period elements Li Be B C N O F Ne

••
••

• • •
••

••

••
••

••

••
••
••

•• ••
opportunities for
• •
• •

contains s and p ••
•

Na• Mg Al • Si • P S Cl Ar 3rd period elements

••

••

••

••

••
••

••

••

••

••

orbitals •• ••
•
•
 1. 2 What Is the Lewis Model of Bonding? 5

1.2 What Is the Lewis Model of Bonding?

A. Formation of Ions
In 1916, Lewis devised a beautifully simple model that unified
Noble Noble Gas
many of the observations about chemical bonding and reactions of Gas Notation
the elements. He pointed out that the chemical inertness of the
He 1s2
noble gases (Group 8A) indicates a high degree of stability of
the electron configurations of these elements: helium with a Ne [He] 2s22p6
2
valence shell of two electrons (1s ), neon with a valence shell of Ar [Ne] 3s23p6
2 6
eight electrons (2s 2p ), argon with a valence shell of eight elec-
Kr [Ar] 4s24p63d10
trons (3s 23p6), and so forth.
Xe [Kr] 5s25p64d10
The tendency of atoms to react in ways that achieve an
outer shell of eight valence electrons is particularly common
among elements of Groups 1A–7A (the main‐group elements). We give this tendency the
special name, the octet rule. An atom with almost eight valence electrons tends to gain the Octet rule The tendency
needed electrons to have eight electrons in its valence shell and an electron configura- among atoms of Group 1A–7A
tion like that of the noble gas nearest it in atomic number. In gaining electrons, the atom elements to react in ways that
achieve an outer shell of eight
becomes a negatively charged ion called an anion. An atom with only one or two valence valence electrons.
electrons tends to lose the number of electrons required to have the same electron configu-
ration as the noble gas nearest it in atomic number. In losing one or more electrons, the Anion An atom or group of
atoms bearing a negative
atom becomes a positively charged ion called a cation.
charge.

B. Formation of Chemical Bonds Cation An atom or group

of atoms bearing a positive
According to the Lewis model of bonding, atoms interact with each other in such a way that charge.
each atom participating in a chemical bond acquires a valence‐shell electron configuration
the same as that of the noble gas closest to it in atomic number. Atoms acquire completed
valence shells in two ways:
1. An atom may lose or gain enough electrons to acquire a filled valence shell. An atom that
gains electrons becomes an anion, and an atom that loses electrons becomes a cation. A chemi-
cal bond between an anion and a cation is called an ionic bond. Ionic bond A chemical
bond resulting from the
electrostatic attraction of an
sodium (atomic number chlorine (atomic number anion and a cation.
11) loses an electron to + ‒ 17) gains an electron to
acquire a filled valence Na + Cl Na Cl acquire a filled valence
shell identical to that of shell identical to that of
neon (atomic number 10) argon (atomic number 18)

2. An atom may share electrons with one or more other atoms to acquire a filled valence
shell. A chemical bond formed by sharing electrons is called a covalent bond. Covalent bond A chemical
bond resulting from the
sharing of one or more pairs
each chlorine (atomic of electrons.
number 17) shares an
Cl + Cl Cl Cl electron with another
chlorine atom to effectively
supply each chlorine with
a filled valence shell

We now ask how we can find out whether two atoms in a compound are joined by an
ionic bond or a covalent bond. One way to answer this question is to consider the relative
positions of the two atoms in the Periodic Table. Ionic bonds usually form between a metal
and a nonmetal. An example of an ionic bond is that formed between the metal sodium
and the nonmetal chlorine in the compound sodium chloride, Na+Cl−. By contrast, when
two nonmetals or a metalloid and a nonmetal combine, the bond between them is usually
covalent. Examples of compounds containing covalent bonds between nonmetals include
Cl2, H2O, CH4, and NH3. Examples of compounds containing covalent bonds between a
metalloid and a nonmetal include BF3, SiCl4, and AsH4.
Another random document with
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 weight; 1880-1884, at 40 per cent.; before 1880, at 20 per
cent."

By this mode of reckoning, the table of battleships is

converted to the following exhibit of estimated "naval
strength":

Count adjusted fighting

weight
Great Britain. 70 604,141
France. 35 220,635
Russia. 24 221,988
Germany. 25 152,929
Italy. 19 112,899
United States. 16 176,708
Japan. 7 88,088

This method of depreciating the tonnage on the basis of the

age of a ship causes the respective proportions of Great
Britain, France and Italy, in battle-ships, to become smaller,
while the respective proportions of Russia, Germany, United
States and Japan become larger. The United States lose but 4
per cent. of the nominal value of their battle-ships; Japan, 5
per cent.; Russia, 16; Germany, 20; Great Britain, 26; France,
35; Italy, 42.

Applying the same arithmetic to the returns of armored and

protected cruisers, the writer shows that Japan suffers a loss
of 10 per cent. of their nominal fighting weight, France 14,
United States 14, Italy 18, Great Britain 21, Russia 23,
Germany 24.

Reducing in like manner all the remaining returns, he arrives

at the following summary of "the seven navies arranged in the
order of their strength"—taking the navy of Japan as the unit:
 Degree of strength.
Great Britain, 6.38
France, 2.57
Russia, 1.88
United States, 1.65
Germany, 1.34
Italy, 1.03
Japan, 1.00.

Stated in "tons of fighting weight," his comparison stands:

Great Britain, 1,347,000

France, 543,000
Russia, 397,000
United States, 349,000
Germany, 282,000
Italy, 218,000
Japan, 211,000.

Turning next to the consideration of armaments, the writer has

compiled the following table, which shows "for each class of
gun separately, and for all classes of guns combined, the
number of these guns that are possessed by the seven naval
powers":

POWER Breech Quick Muzzle

Torpedo All Classes
Loading Firing Loading
Tubes of Guns
Guns Guns Guns

Great Britain. 912 7,454 340

1,534 10,240
France. 471 3,653 -
928 5,052
Russia. 393 2,589 -
625 3,607
Germany. 258 1,995 -
611 2,864
Italy. 140 1,791 4
573 2,508
United States. 303 1,791 -
230 2,324
Japan. 110 1,168 -
314 1,592
----------
All the Powers
combined. 2,587 20,441 344
4,815 28,187

In this comparison the United States drops from the fourth

rank to the sixth. For a comparison of the naval expenditure
of the Powers,

See (in this volume)

WAR BUDGETS.

NEBUCHADREZZAR, Exploration of the ruins of the palace of.

See (in this volume)

ARCHÆOLOGICAL RESEARCH: BABYLONIA; GERMAN
EXPLORATION.

NEELY EXTRADITION CASE, The.

See (in this volume)

CUBA: A. D. 1900-1901.

{319}
NEGRITOS.

See (in this volume)

PHILIPPINE ISLANDS: THE NATIVE INHABITANTS.

NEGRO, Disfranchisement of the.

See (in this volume)

MARYLAND, MISSISSIPPI, NORTH CAROLINA: A. D. 1900;
SOUTH CAROLINA: A. D. 1896;
LOUISIANA: A. D. 1898; and
UNITED STATES OF AMERICA: A. D. 1901 (JANUARY).

NEGROS, The island of:

American occupation.

See (in this volume)

PHILIPPINE ISLANDS: A. D. 1899 (JANUARY-NOVEMBER).

Acceptance of American sovereignty.

Establishment of provisional government.

See (in this volume)

PHILIPPINE ISLANDS: A. D. 1899 (MARCH-JULY).

NEMI, Lake: Sunken Roman vessels found in.

See (in this volume)

ARCHÆOLOGICAL RESEARCH: ITALY.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1894.

War in Lombok.

See (in this volume)

DUTCH EAST INDIES: A. D. 1894.
 -------NETHERLANDS, The Kingdom of the (Holland): Start------

NETHERLANDS, The Kingdom of the (Holland): A. D. 1896.

Electoral Reform Act.

A notable extension of the franchise was accomplished by an

Act passed this year by the States General, to have effect in
the elections of 1897. It made voters of all Dutch citizens
not under 25 years of age who present "certain outward and
positive signs of capacity and well-being. The chief sign is
the fact of payment of one or more direct State taxes (for the
land tax an amount of 1 florin is sufficient). Besides these,
the Reform Act admits as electors all those who can prove that
they are householders, and have paid rent of houses or
lodgings during a fixed term, or that they are owners or
tenants of boats of not less than 24 tons capacity, or that
they have been during a fixed term in employment with an
annual wage or salary of at least £22 18s. 4d., or possess a
certificate of State interest of at least 100 florins, or a
State savings bank deposit of at least 50 florins, or the
legal qualifications for any profession or employment."

Statesman's Year-Book,
1899, page 807.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1897.

First election under the new Franchise Law.

The first election in Holland under the new franchise law,

held June 15-25, 1897, returned to the Chamber 47 Liberals, 22
Catholics, 22 Protestant anti-Revolutionists, 4 Radicals, and one
deputy who is styled an Historic Christian.

NETHERLANDS, The Kingdom of the (Holland):A. D. 1898.

Enthronement of Queen Wilhelmina.

Queen Wilhelmina, who succeeded to the crown on the death of

 her father, William III., in 1890, reached the age of 18 on
the 31st of August, 1898, and received the reins of government
from her mother, Queen Emma, who had acted as Regent until
that time. The young Queen was enthroned September 6 in the
New Church at Amsterdam, where she delivered, with a
simplicity and fervor which impressed those present, her
address to the States-General and took her oath of allegiance
to the Constitution. "I am happy and thankful," the Queen
said, "to rule over the people of the Netherlands, who,
although small in numbers, are great in virtue and strong by
nature and character. I esteem it a great privilege that it is
my life's task and duty to dedicate all my powers to the
prosperity and interests of my dear fatherland; and I adopt
the words of my beloved father,—'Yes, Orange can never do
enough for the Netherlands.'" After the Queen and the
Queen-Mother, the most striking figures at the ceremony were
the Princes from the Dutch Indies.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1898 (June).

The Sugar Conference at Brussels.

See (in this volume)

SUGAR BOUNTIES.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1899 (April).

Invitation to the Peace Conference to be held at The Hague.

See (in this volume)

PEACE CONFERENCE.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1899 (May-July).

Representation in the Peace Conference at The Hague.

See,(in this volume)

PEACE CONFERENCE.

NETHERLANDS, The Kingdom of the (Holland): A. D. 1899 (May-

August).
Advice to President Kruger of the South African Republic.

See (in this volume)

SOUTH AFRICA (THE TRANSVAAL): A. D. 1899 (MAY-AuGUST).

NETHERLANDS, The Kingdom of the (Holland):A. D. 1901.

Marriage of Queen Wilhelmina.

Queen Wilhelmina was married, on the 7th of February, to Duke

Henry of Mecklenburg-Schwerin, who received the title of
Prince of the Netherlands by proclamation on the same day.
Both civil and religious ceremonies of marriage were
performed.

--------NETHERLANDS, The Kingdom of the (Holland): End------

NEW BRUNSWICK.

See (in this volume)

CANADA.

NEWEL, Stanford:
American Commissioner to the Peace Conference at The Hague.

See (in this volume)

PEACE CONFERENCE.

NEWFOUNDLAND: A. D. 1895.
Union with Canada refused.

Terms proposed for the union of Newfoundland with the Dominion

of Canada were rejected, and negotiations abandoned.

NEWFOUNDLAND: A. D. 1897.
Conference of colonial premiers with the
British Colonial Secretary.
 See (in this volume)
ENGLAND: A. D. 1897 (JUNE-JULY).

NEWFOUNDLAND: A. D. 1897-1900.
The Reid contract.
The question in politics.

In the fall of 1897 a line of narrow-gauge railway, with

branches over six hundred miles in total length, was completed
and opened to traffic. The main line of rail extends from the
capital, St. Johns, to Port aux Basques, at the southwestern
extremity of the island, and is expected to produce an
important development of resources from the forests and mines,
as well as from agricultural lands. The railway was
constructed by a contractor, Mr. Reid, who agreed to operate
it for seven years at his own expense, receiving therefor a
land grant of 5000 acres per mile. In 1898 a new contract was
made with Mr. Reid, which placed most of the resources of the
island under his control. For an additional land-grant of 2500
acres per mile of road he undertook to operate the road for
fifty years. By a present cash payment of $1,000,000 to the
colony treasury, he purchased the reversion of its right to
the possession of the road at the end of that period. At the
same time he secured the right to purchase from the government
its telegraph lines and the dry-dock at St. Johns, for half a
million of dollars, and was given a monopoly for 30 years of
the coast mail steam service, with an annual subsidy of
$150,000, he undertaking to maintain in it eight steamers,
well equipped. This remarkable contract was bitterly denounced
by a large party in the island, and the Imperial government was
strongly petitioned to nullify the whole transaction: but the
British Colonial Secretary, Mr. Chamberlain, while he
characterized the contract as representing "the most
unparalleled abrogation of its functions by a responsible
government," decided that he could not properly interfere.
{320}
 The "Reid Deal," as it was known, then became a burning issue
in Newfoundland politics, and the Ministry responsible for it,
led by Sir James Winter, was ousted from the government in
February, 1900. Mr. Reid was then arranging to transfer his
Newfoundland contract and franchises to a company, which
required the sanction of the colonial government. The new
(Liberal) Ministry, of which Mr. Robert Bond was Premier,
refused consent to the transfer unless Mr. Reid would amend
his bargain with the colony in several very important
particulars. He offered some concessions, but not to the
extent demanded; and so the question between him and the Bond
Ministry went into the canvass of 1900, for the election of a
new Assembly, and the Conservatives, heavily backed by Mr.
Reid, were defeated overwhelmingly, winning but 4 seats out of
36 in the Lower House of the Legislature. On this result of
the elections the "London Times" of November 26, 1900,
comments as follows: "The course which the victorious Bond
Ministry will now take must be awaited with interest. … A
policy of compromise would certainly appear to be the wisest
and the safest for all parties. Mr. Reid, it seems to be
acknowledged, has carried out his part of the bargain of 1898
fully and even generously, and the colony, it is stated, has
profited largely in consequence. In the absence of actual
fraud or corruption it would be difficult in these
circumstances to justify the rescission or even the material
modification of the agreement, on the faith of which he has
spent his money, without his assent. A repeal of the Act of
1898 against his will would savour of repudiation. It would
assuredly damage the credit of the colony very seriously."

NEWFOUNDLAND: A. D. 1899-1901.
The French Shore Question.
The Modus Vivendi.

"At the period of the negotiation of the Treaty of Utrecht, in

1713, by which the rights of the French fishermen were regulated
[see, in volume 4, NEWFOUNDLAND: A. D. 1713], thousands of
French fishing vessels availed themselves of the inshore
fisheries about the island; and that they might be not
altogether without facilities for the drying and curing of
their fish, they were granted under the Treaty the 'right to
use a strip of the coast seven hundred miles long and half a
mile wide.' Accompanying the Treaty, but, be it noted, not a
part of it, was a declaration of King George, that British
subjects on the island were not to interfere with these French
coast rights by erecting permanent structures upon it,
calculated to obstruct the operations of the French fishermen.
This Royal declaration was harmless and unimportant when the
population of the island was very small, and the French
fishermen resorted to the inshore fisheries of Newfoundland.
But to-day, a different condition exists. The French fishermen
no longer use the inshore fisheries of the island, but
prosecute, instead, their fishing operations on the Grand
Banks, several hundred miles distant, drying their product
either at the French islands of St. Pierre and Miquelon, which
are more adjacent to the Banks, or transporting the fish
direct to France. … The need for which the French shore right
was granted has practically ceased to exist; and inasmuch as
the prohibition to the people of the island from erecting
permanent structures on the island was merely a mandate
emanating from the King, and not an integral part of the
Treaty itself; and because the reason for the observance of
the mandate has thus ceased to exist, it is imperative that,
in the interests of the prosperity of the island, this Royal
concession should be revoked. … But what, it may be asked, on
a perusal of the whole case, has caused the Newfoundland
question to suddenly become paramount? Why is its urgency
greater in 1899 than it was in 1889? Is there not some
concentrated force, some propelling power, at work behind the
scenes? There is—and that power is a millionaire. The name of
this millionaire is Robert Gillespie Reid, who, having
voluntarily assumed, by means of the measure known as the Reid
contract, the responsibility of developing the island's
resources, finds himself, at the outset, confronted by a
situation which precludes all present enterprise. This
gentleman has acquired, in fee simple, some three or four
million acres of land in Newfoundland; and where the islanders
were content to wait patiently for justice, he, as a
business-man, eager to exploit his mines and timber, can
hardly be expected to pin his faith to assurances so frail,
and of fulfilment so remote."

B. Wilson,
Newfoundland's Opportunity
(Fortnightly Review, February, 1899).

A royal commission which lately investigated the situation of

affairs on the Treaty Coast of Newfoundland found that the
coast "is 800 miles in extent, with a permanent population of
13,300, all but 76 of whom are native-born, while the total of
French frequenting the territory during the fishing season
does not exceed 600 men. The French, last year, according to
the official reports furnished to the Admiralty, occupied only
eight cod and nine lobster stations, with a personnel as
above, while their catch of cod was but 18,000 qtls., worth
about 36,000 dollars, and their pack of lobsters about 7,000
cases, of about equal value. And is it not monstrous that, in
order to satisfy vexatious French claims and perpetuate
obsolete treaty claims, the people of the Treaty Coast should
he coerced and victimised, and the development of the whole
colony retarded, as has been the case? The Commissioners
found that, despite the liberal bounties given by France for
fishing on the Treaty Coast, the allowance of 50 francs per
head by the St. Pierre municipality for the same purpose, and
the special appropriation the past two seasons in the French
colonial grant 'for extending operations on the Newfoundland
coast, 4,000 francs,' the number of men frequenting there and
the number of stations operated are steadily declining every
year, and in ten years' time it is doubtful if there would be
a Frenchman on the coast. Still, so powerful is the French
fetish that the shore is tabooed as far as industrial
 development is concerned, and the hinterland likewise. No
grant of land can be given there except with the stipulation
that it is subject to French rights. No permanent building can
be erected within half a mile of high-water mark, because the
French claim the strand for drying their fish. No wharves can
be built by which to load minerals, because they will
interfere with the French fishery. (Only last year they
stopped the erection of one which was twenty-two miles from
their nearest station, and Mr. Reid, the railway contractor,
when he wanted to build a wharf at Bay St. George to land
construction materials, had to seize the opportunity of the
French warship in the Bay leaving to coal and renew stores,
and put an army of men to work, who built it in seventeen
days, so that it was completed when the Frenchmen returned.)
{321}
No mineral developments are permitted because they may hamper
the French. Competition on near-by fishing grounds is
prohibited for the same reason. Illicit (?) lobster packers
are hunted like malefactors for disregarding a 'modus vivendi'
as unjust as it is ridiculous. Bait-selling is only possible
by permission of the French and on their terms. The railway
was deflected 120 miles out of its proper course because of
French objection to a terminus on the shore. In fact, fishing
is only pursued with the greatest difficulty, while the land
is closed to agricultural settlement and mining enterprise.
And that, too, in the face of the fact that the French 'army
of occupation' consists of about one vessel, one station, and
about sixty fishermen on every 100 miles of coast, whose
annual catch is worth about 10,000 dollars."

P. T. McGrath, France in Newfoundland

(Nineteenth Century, January, 1899).

In 1890, a temporary agreement ("modus vivendi") concerning

the lobster packing and other questions, was arranged between
the British and French governments, which has been extended
from time to time, very much to the dissatisfaction of the
Province. The last extension expired at the end of the year
1900, and the Newfoundlanders showed a strong disposition to
resist any renewal of it. A letter from St. Johns, in
December, 1900, stated the feeling of the colony as follows:
"Last year the term of the 'modus vivendi' was allowed to run
out, and a deadlock, such as now seems inevitable, would
doubtless have been created; but when the end of December came
the reverses in South Africa appealed to our patriotism as the
oldest British colony, and the Legislature unanimously passed
at one sitting a Bill renewing the arrangement for another
year. The colony was unable to afford any more substantial aid
at the time, as her naval reserve had not then been
inaugurated, but this course on her part testified to her
sympathy with the Imperial mother, and her readiness to
relieve her from other difficulties. This year Newfoundland is
taking the bit between her teeth, and the result must be a
complication which, however unwelcome to the Imperial Cabinet,
cannot but have been regarded as inevitable sooner or later.
If our case is as strong as we are led to believe that the
Royal Commission represents it to be, there is certainly good
ground for our insisting upon remedial measures. It must not
be forgotten that the French now keep up less than 15 cod and
lobster stations altogether on the treaty coast, and that
about 550 men is the number they had there last season. As
against this the resident population is nearly 14,000, and the
objections which they urged against the 'modus vivendi' in its
early days apply with equal strength now. These people are
shamefully treated, the colony as a whole is humiliated, and
the recognition of such conditions by England without making
an attempt to get rid of them is a cause of reproach which she
should remove without delay."

Much newspaper discussion of the subject has been going on in

both England and France, with an apparent showing of readiness
on the part of the latter country to bargain with the British
for cessions in West Africa or elsewhere. How much of a price
Great Britain is willing to pay for release from the treaty of
 Utrecht is a question the answer to which cannot be forever
postponed.

Despite its reluctance, the Newfoundland Legislature was

prevailed upon, in February, 1901, to pass an Act renewing the
"modus vivendi" for another year. Several members who
supported the measure declared that they did so for the last
time, and only because of an unwillingness to embarrass the
British government during the continuance of the South African
war.

NEWFOUNDLAND: A. D. 1901.
Change of Government.

Early in the year, Sir Henry McCallum was transferred from the
governorship of Newfoundland to that of Natal, and Sir
Cavendish Boyle was appointed to succeed him.

NEW JERSEY: A. D. 1897.

Constitutional Amendments.

On the 28th of September, several proposals of constitutional

amendment were voted on in New Jersey. One prohibitory of
gambling was adopted by a small majority. Another, that would
give the suffrage in school elections to women, was rejected
by about 10,000 majority.

NEW SOUTH WALES.

See (in this volume)

AUSTRALIA; and CONSTITUTION OF AUSTRALIA.

NEW YORK CITY: A. D. 1894-1895.

The Lexow Investigation of Tammany government.
Election of Mayor Strong.

"On the second Sunday in February 1892 the minister of a

 wealthy Presbyterian church, Dr. Charles Parkhurst, startled
his congregation by preaching an outspoken political sermon,
in which he attacked the Tammany administration in most
unmeasured language. 'The mayor and those associated with him
are polluted harpies [he declared]. Under the pretence of
governing this city they are feeding day and night on its
quivering vitals. They are a lying, perjured, rum-soaked, and
libidinous lot. … Every effort to make men respectable,
honest, temperate, and sexually clean is a direct blow between
the eyes of the mayor and his whole gang of lecherous
subordinates, in the sense that while we fight iniquity they
shield and patronise it; while we try to convert criminals
they manufacture them, and they have a hundred dollars
invested in the manufacturing business to every one invested
in converting machinery. … Police and criminals all stand in
with each other. It is simply one solid gang of criminals, one
half in office and the other half out.' This sermon was the
starting point of the new anti-Tammany movement. Dr. Parkhurst
was called before the grand jury to prove his words, but he
was obliged to admit that all he knew was the repeated
accusations that appeared in almost every local newspaper.
Thereupon the grand jury publicly rebuked him, and sent a
formal presentment to the Recorder declaring their
'disapproval and condemnation' of the sermon. Everyone at once
concluded that no more would be heard of Parkhurst in
politics, but they did not know the man. The clergyman called
a couple of detectives to his aid, and personally visited the
lowest resorts, to obtain the necessary evidences of
corruption. A month later he preached a second political
sermon, and this time he took into the pulpit with him a
bundle of affidavits. He repeated and emphasised his former
accusations, and again he was summoned before the grand jury.
This time the result was different. 'The police are either
incompetent or corrupt,' the jury declared, and citizens
generally agreed. …

{322}
"In 1894, the State Senate … appointed a committee, this time
under Senator Lexow, to inquire into New York municipal
affairs. Soon after the committee was appointed Mr. Croker
found it convenient to hastily resign the leadership of
Tammany and go to Europe. The worst accusations of the
bitterest enemies of Crokerism were almost all more than
substantiated by the evidence given before the committee. It
was found that the police were utterly corrupt, that they
extorted blackmail from gambling house keepers, women of ill
fame, saloon keepers, and others, and in return gave them
their protection. Even thieves, in some instances, were found
to be regularly paying their police dues in return for
immunity from arrest. One police justice had to admit that he
received a hundred dollars from a keeper of a disorderly
house. Everywhere that the Lexow Committee probed, or that
other competent critics examined, the same thing was found.
For several years New York had been living under a system of
universal blackmail. Saloon keepers had to pay Tammany to be
allowed to evade the Sunday closing law, merchants to be
granted the simplest conveniences for getting their goods into
their premises. But in the case of Mr. Croker no dishonesty
could be proved. It was known that he had in a few years risen
from a poor man to a millionaire, but in no instance could it be
shown that he had acquired this wealth by corruption. His
friends said he had made his money by horse-racing and real
estate speculation, but unfortunately Mr. Croker did not go
before the witness stand to finally clear up the matter. While
the committee was sitting he remained in Europe.

"The usual storm of indignation followed the 'Lexow' exposure,

and most reputable citizens united once more to overthrow
Tammany. Colonel Strong, a well-known banker, was chosen
reform candidate for mayor, and secured a majority of fifty
thousand. In 1895 he began his administration, and initiated a
vigorous reform movement. The police force was entirely
reorganised; municipal offices were given for merit rather
 than political reward; the streets, for the first time in the
memory of the oldest inhabitant, were really kept clean, and
the whole local government was taken out of politics. Mayor
Strong's time of office has not been without its faults, but
among those faults dishonesty has not been one. Rather the
mistake has been to enforce all laws too rigidly, and make too
few allowances for the weaknesses of human nature in a
cosmopolitan resort. Police President Roosevelt's strict
enforcement of the Sunday closing and social purity laws was
only his duty, but yet it cost the reformers many votes.
Although the report of the 'Lexow' Committee did Tammany much
temporary harm, it recovered quickly. After the mayoral defeat
of 1894 it pulled its forces together again, and rallied
around it all the ambitions men who were disappointed in Mayor
Strong's bestowal of his patronage. In the autumn of 1895 it was
able to score a minor victory at the polls, and it carefully
nursed its strength for the election of November 1897. Mr.
Croker, notwithstanding his repeated declarations that he was
'out of politics,' came back to New York, and at once took
over command of his party."

F. A. McKenzie,
Tammany
(Nineteenth Century, December, 1897).

NEW YORK CITY: A. D. 1895.

Consolidation of the Astor, Lenox and Tilden foundations
to form the New York Public Library.

See (in this volume)

LIBRARY, NEW YORK PUBLIC.

NEW YORK CITY: A. D. 1896-1897.

Consolidation of New York, Brooklyn, and neighboring towns,
in the Greater New York.

"The project of uniting the cities of New York, Brooklyn, and

the cities, towns and villages contiguous to the same, into
one great municipality, although long mooted before 1890,
first took definite form in that year, by the passage on May
8th, by the Legislature, of Laws 1890, Chapter 11, entitled
'An Act to create a commission to inquire into the expediency
of consolidating the various municipalities in the State of
New York, occupying the several islands in the harbor of New
York.' …

Pursuant to the provisions of this act, a commission

consisting of the following members was appointed, viz.:
Andrew H. Green, Frederick W. Devoe, John L. Hamilton, J.
Seaver Page of New York; J. S. T. Stranahan, Edward F. Linton,
William D. Veeder of Brooklyn; John H. Brinkerhoff of Queen's
county; George G. Greenfield of Richmond county; Charles P.
McClelland of Westchester county; and Campbell W. Adams, State
Engineer and Surveyor, ex officio, and Albert E. Henschel
acting as secretary. In 1893, the commission presented to the
Legislature a bill providing for the submission of the
question of consolidation to a vote of the residents of the
various municipalities proposed to be united into one city.
The following year the Legislature provided for the referendum
suggested by the commission. … The following vote was cast
upon the question of consolidation in the ensuing election on
November 6, 1894:

for consolidation; against;

New York, 96,938; 59,959;
Kings, 64,744; 64,467;
Queens, 7,712; 4,741;
Richmond, 5,531; 1,505;
Mount Vernon, 873; 1,603;
Eastchester, 374; 260;
Westchester, 620; 621;
Pelham, 261; 153.
 At the opening of the Legislature in 1895, the Commission of
Municipal Consolidation Inquiry presented a report with a
proposed bill declaring the entire district before mentioned
(with the exception of the city of Mount Vernon) consolidated
with the city of New York. The bill, however, failed of
passage because of the addition of an amendment of referendum
in the last hours of the session of 1895, too late for further
action. The Legislature, as a result no doubt of this vote on
consolidation, did annex to New York city the towns of
Westchester, Eastchester, Pelham and other parts of
Westchester county.

"Early in January, 1896, the Legislature appointed a joint

sub-committee of the Cities Committees of both Houses to
inquire into the subject of the proposed consolidation and
report March 1, 1806. The committee made a report and
submitted a bill favoring consolidation. The bill as reported
was passed by the Legislature and was submitted to the Mayors
of the cities of New York and Brooklyn, and to the Mayor and
Common Council of Long Island City pursuant to the provisions
of the Constitution.
{323}
The bill was returned to the Legislature without the
acceptance of the cities of New York and Brooklyn. The
Legislature repassed the bill over the vetoes of the Mayors of
New York and Brooklyn, and it became a law May 11, 1896, with
the approval of the Governor. This act (L. 1896, ch. 488) is
entitled, 'An Act consolidating the local governments of the
territory within the city and county of New York, the counties
of Kings and Richmond and Long Island City and the towns of
Newtown, Flushing and Jamaica and part of the town of
Hempstead, in the county of Queens, and providing for the
preparation of bills for enactment into laws for the
government thereof.' … Pursuant to the act of consolidation,
the Governor (Levi P. Morton) appointed on June 9, 1896, the
following members of the commission to draft the proposed
charter, viz.: Seth Low, Benjamin F. Tracy, John F. Dillon,
Ashbel P. Fitch, Stewart L. Woodford, Silas B. Dutcher,
William. C. De Witt, George M. Pinney, Jr., Harrison S. Moore.
Mr. Fitch having resigned from the commission, the Governor
appointed Thomas F. Gilroy in his place. By virtue of the act,
the following gentlemen were members of the commission: Andrew
H. Green, president of the commission appointed by L. 1890,
ch. 311; Campbell W. Adams, State Engineer; Theodore E.
Hancock, Attorney-General; William L. Strong, Mayor of New
York; Frederick W. Wurster, Mayor of Brooklyn; and Patrick
Jerome Gleason, Mayor of Long Island City. The commission
organized on June 25, 1896, appointed Benjamin F. Tracy as
president and George M. Pinney, Jr., as secretary, and named
William C. De Witt, John F. Dillon, Thomas F. Gilroy, Seth
Low, Andrew H. Green, Benjamin F. Tracy, and George M. Pinney,
Jr., as a committee on draft of proposed charter."

M. Ash,
The Greater New York Charter,
introduction.

The committee submitted a draft charter to the commission on

the 24th of December, with a report in which a fundamental
feature of its plan is thus set forth: "It is clear that the
work of administering all of the Departments over so large a
space of territory, situated on three islands and partly on
the main land, must be subdivided in order to be successfully
done. The draft, therefore, proposes to divide the city into
the five Boroughs which nature and history have already
formed; that is to say:

(1.) Manhattan, which consists of the island of Manhattan and

the outlying islands naturally related to it.

(2.) The Bronx; that is to say, all that part of the present
City of New York lying north of the Harlem, a territory which
comprises two-thirds of the area of the present City of New
York.