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Organic Chemistry
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 Organic Chemistry
Demystified

DANIEL R. BLOCH

McGRAW-HILL
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DOI: 10.1036/0071459200
To Nan for her assistance, patience, and helpful comments.
This page intentionally left blank
 For more information about this title, click here

CONTENTS

Preface xvii
Acknowledgments xix
CHAPTER 1 Structure and Bonding 1
Atomic Structure 1
Atomic Number and Atomic Mass (Weight) 3
Electron Energy Levels 4
The Octet Rule 7
Valences 8
Lewis Structures 9
Orbital Shapes 15
Quantum Mechanics 15
Bond Formation 18
Valence Bond Theory 20
Molecular Orbitals 21
Bonding and Antibonding MOs 21
Bonding and 3-D Molecular Shape 23
Curved Arrows 30
Electronegativity and Bond Polarity 31
Dipole Moments 33
Formal Charges 34
Resonance Structures 36
Intermolecular Forces 37
Quiz 39

CHAPTER 2 Families and Functional Groups 43

vii
viii CONTENTS

CHAPTER 3 Acids and Bases 46

Introduction 46
Arrhenius Definition 47
Brønsted-Lowry Definition 47
Conjugate Acids and Bases 47
Equilibrium Reactions 49
Weak Hydrocarbon Acids 53
Lewis Acids and Bases 54
Quiz 56

CHAPTER 4 Alkanes and Cycloalkanes 59

Introduction 59
Sources of Alkanes 60
Acyclic and Cyclic Alkanes 60
Nomenclature 61
Formulas 62
Structures 62
Constitutional Isomers 64
Cycloalkanes 66
Alkyl Groups 67
Nomenclature—Naming Compounds
by the IUPAC System 70
Physical Properties 74
Chemical Properties 75
Conformations of Alkanes 76
Conformations of Cylcoalkanes 84
Quiz 94

CHAPTER 5 Stereochemistry 99
Isomers 99
Chiral Compounds 100
Stereocenters 101
Chirality Centers 102
Enantiomers 105
Racemic Mixtures 109
CONTENTS ix

The R/S System 110

When the Lowest Priority Group Is Not
in the Back 113
Molecules with Multiple Asymmetric
Centers 115
Enantiomers 116
Diastereomers 116
Meso Compounds 117
Fisher Projections 119
Rotating Fisher Projections/Structures 120
Cyclic Stereoisomers 122
Naming Cyclic Stereoisomers 125
Prochiral Carbons (Wanabees) 126
Quiz 126

CHAPTER 6 Structure and Properties of Alkenes 129

Introduction 129
Structure 130
Naming Alkenes 132
Common Names 134
Cis and Trans Isomers 134
The E/Z (Easy) System 135
Degrees of Unsaturation 136
Stability of Alkenes 140
Physical Properties of Alkenes 141
Chemical Properties 141
The Curved Arrow 142
Quiz 142

CHAPTER 7 Reaction Mechanisms 145

Introduction 145
Thermodynamics 145
Kinetics 148
Carbocations 150
Stereochemistry 151
x CONTENTS

The Hammond Postulate 152

Regiochemical Reactions 154
The Markovnikov Rule 155
Stereochemistry 156
Rearrangement Reactions of Carbocations 157
Quiz 159

CHAPTER 8 Reactions of Alkenes 161

Reaction with Hydrogen Halides in Inert
Solvents 161
Reaction with Hydrogen Halides in Protic
Solvents 162
Oxymercuration-Demercuration Reactions 165
Hydroboration-Reduction 167
Halogenation in Inert Solvents 171
Stereochemistry Halogenation 173
Halogenation in Reactive Solvents 174
Radical Bromination 175
Formation of Diols 177
Double Bond Cleavage 178
Hydrogenation 180
Epoxides 180
Cyclopropanes 181
Quiz 182

CHAPTER 9 Alkynes 185

Introduction 185
Structure 185
Nomenclature 186
Physical Properties 188
Chemical Properties 188
Reactions with Brønsted-Lowry Acids 189
CONTENTS xi

Reactions with HBr and Peroxides 193

Reaction with Halogens 195
Hydration Reactions 195
Hydroboration-Oxidation Reactions 198
Hydrogenation/Reduction Reactions 199
Oxidation Reactions 200
Acidity of Alkynes 201
Alkylation Reactions 202
Preparation of Alkynes 204
Quiz 204

CHAPTER 10 Characterization 207

Introduction 207
Chromatography 207
Spectroscopy 212
UV Spectroscopy 222
Nuclear Magnetic Resonance Spectroscopy 226
Nuclear Properties 226
NMR Spectrometers 228
1 H NMR Spectroscopy 230
13 C NMR Spectroscopy 243
Mass Spectrometry 246
Quiz 251

CHAPTER 11 Organohalides 256

Introduction 256
Nomenclature 256
Properties 257
Preparation of Halides 258
Radical Halogenation 258
Isomeric Products 260
Allylic Halogenation 263
Reactions of Organohalides 265
Quiz 266
xii CONTENTS

CHAPTER 12 Nucleophilic Substitution and

Elimination Reactions 269
Introduction 269
Properties of Nucleophiles 270
Properties of Bases 271
Properties of Substrates/Electrophiles 272
Properties of Leaving Groups 272
Properties of Solvents 273
Second-Order Nucleophilic Substitution
(SN 2) Reactions 276
First-Order Nucleophilic Substitution
(SN 1) Reactions 279
Summary of SN 1 and SN 2 Reactions 284
Second-Order Elimination (E2)
Reactions 284
First-Order Elimination (E1) Reactions 289
Summary of E1 and E2 Reactions 291
Competition between Substitution and
Elimination Reactions 291
Quiz 292

CHAPTER 13 Alcohols 295

Introduction 295
Properties of Alcohols 296
Nomenclature 297
Acidity and Basicity of Alcohols 299
Reactions with Active Metals 301
Preparation of Alcohols 301
Organometallic Compounds 306
Preparation of Alcohols Using
Organometallic Reagents 307
Reactions of Alcohols 310
Conversion of Alcohols to Alkyl Halides 311
Dehydration Reactions 313
Quiz 313
CONTENTS xiii

CHAPTER 14 Ethers 317

Introduction 317
Nomenclature 317
Properties 318
Preparation of Ethers 319
Reactions of Ethers 321
Three-Membered Ether Rings 323
Quiz 327

CHAPTER 15 Sulfur Compounds 330

Nomenclature 330
Properties 331
Reactions of Sulfur Compounds 333
Quiz 335

CHAPTER 16 Conjugated Systems 337

Introduction 337
Stability of Dienes 337
Electrophilic Addition to Conjugated Dienes 344
Allylic Cations, Radicals, and Anions 347
Diels-Alder Reactions 349
Quiz 355

CHAPTER 17 Aromatic Compounds 358

Introduction 358
Reactivity of Aromatic Compounds 358
Nomenclature 359
Kekulé Structures 361
Stability of Benzene 362
The Resonance Model 364
Molecular Orbital Description of Aromaticity 365
Properties of Aromatic, Nonaromatic, and
Antiaromatic Compounds 369
Hückel’s Rule 370
Heterocyclic Compounds 371
xiv CONTENTS

Aromatic Ions 372

Polycyclic Aromatic Compounds 374
Quiz 375

CHAPTER 18 Reactions of Benzene and other

Aromatic Compounds 378
Introduction 378
Electrophilic Aromatic Substitution 379
Nucleophilic Aromatic Substitution 386
More Derivatives of Benzene 388
Multiple Substitution Reactions 392
Electrophilic Substitution in Disubstituted
Benzenes 399
Quiz 400

CHAPTER 19 Aldehydes and Ketones 404

Introduction 404
Nomenclature 405
Physical Properties 408
Chemical Properties 408
Preparation of Aldehydes and Ketones 410
Hydration of Alkynes 412
Reduction of Acid Chlorides 414
Reactions of Aldehydes and Ketones with
Nucleophiles 418
Wittig Reactions 424
Oxidation and Reduction Reactions 425
Quiz 427

CHAPTER 20 Carboxylic Acids 430

Introduction 430
Nomenclature 431
Three-Dimensional Structure 434
Molecular Orbital (MO) Description 434
Physical Properties 435
CONTENTS xv

Acidity of Carboxylic Acids 437

Preparation of Carboxylic Acids 439
Derivatives of Carboxylic Acids 444
Quiz 444

CHAPTER 21 Derivatives of Carboxylic Acids 447

Introduction 447
Carboxylic Acid Halides 450
Carboxylic Acid Anhydrides 454
Carboxylic Esters 458
Amides 463
Cyclic Amides 466
Imides 467
Nitriles 468
Quiz 470

CHAPTER 22 Alpha-Substitution Reactions in

Carbonyl Compounds 474
Introduction 474
Enol and Enolate Anions 475
Alpha Monohalogenation of Aldehydes
and Ketones 477
α,β Unsaturated Ketones 479
α-Bromination of Carboxylic Acids 479
Acidity of α-Hydrogen Atoms 479
Malonic Ester Synthesis 483
Acetoacetic Ester Synthesis 485
Additional Condensation Reactions 486
Quiz 488

CHAPTER 23 Carbonyl Condensation Reactions 490

Introduction 490
Aldol Reactions 491
Dehydration of Aldol Compounds 492
Mixed or Crossed Aldol Reactions 493
xvi CONTENTS

Intramolecular Aldol Reactions 494

Claisen Condensation Reactions 495
α-Substitution Reactions 499
Quiz 502

Final Exam 504

Quiz and Exam Solutions 531

Appendix A / Periodic Table

of the Elements 537

Bibliography 539

Index 541
 PREFACE

Organic chemistry is the chemistry of carbon-containing compounds. Every

living organism, plant and animal, is composed of organic compounds. Anyone
with an interest in life and living things needs to have a basic understanding of
organic chemistry.
Articles continue to appear in newspapers and magazines describing the
development of new medicines and diagnostic tests. These new products and
technologies are results of a better understanding of the structure and function
of DNA, proteins, and other organic biological molecules. The reactions and
interactions of these complex molecules are the same reactions and interactions
that occur in more simple organic molecules.
This text was written to help those who are intimidated by the words organic
chemistry. Those who have never had a formal course in organic chemistry and
students currently taking or planning to take a formal course will find this text
an easy-to-read introduction and supplement to other texts.
The chapters are written in the same general order as found in most college
textbooks. It would be helpful, but not necessary, if the reader had a course in
introductory chemistry. The first three chapters cover the background material
typically covered in general chemistry courses. It is not necessary that chapters
be read sequentially, but since material tends to build on previous concepts it will
be easier to understand the material if the chapters are read in sequential order.
Key terms and concepts are italicized. Be sure you understand these concepts
as they will continue to appear in other sections of this book. Questions (and
answers) are given within each chapter to help you measure your understanding.
Each chapter ends with a quiz covering the material presented. Use each quiz
to check your comprehension and progress. The answers to quizzes are given
in the back of the text. Review those problems (immediately) you did not get
correct. Be sure you understand the concepts before going to the next chapter
as new material often builds upon previous concepts.

xvii

Copyright © 2006 by The McGraw-Hill Companies, Inc. Click here for terms of use.
xviii PREFACE

As you read each chapter, take frequent breaks (you can munch on the extra
gum drops used to make models in Chapter 5). The book contains a lot of figures
and diagrams. Follow these as you read the text. It is often easier to understand
a reaction mechanism in a diagram than to describe it in words.
Yes, there is some memorization. New terms will appear that you probably
have never heard before. For a series of terms I recommend making a mnemonic
and I suggested a few. Reaction mechanisms are not as difficult as they may
appear. You can predict most reactions in that negative species will be attracted
to positive species (opposites attract). Atoms with electrons to share will be
attracted to species that want more electrons—it is just that simple.
There is a multiple-choice final exam at the end of the text. The final exam
has more general, but similar, questions than those in the quizzes. Answers are
given in the back of the book. If you are able to answer 80% of the final exam
questions correctly (the first time), you will have a good understanding of the
material.
I hope you will enjoy reading about organic chemistry as much as I have
enjoyed writing about it.

Daniel R. Bloch
 ACKNOWLEDGMENTS

The author expresses his appreciation to Nan for her assistance, patience, and
helpful comments during the preparation of this book.
The following individuals were kind enough to review various chapters in
this book:
Vaughn Ausman, Marquette University
Kate Bichler, University of Wisconsin Center—Manitowoc
Peter Conigliaro (retired), S.C. Johnson
Sheldon Cramer (emeritus), Marquette University
Timothy Eckert, Carthage College
Sharbil Firson, Sigma-Aldrich
Kevin Glaeske, Wisconsin Lutheran College
Bruce Holman
Shashi Jasti, Sigma-Aldrich
Steven Levsen, Mount Mary College
Julie Lukesh, University of Wisconsin—Green Bay
Kevin Morris, Carthage College
Patt Nylen, University of Wisconsin—Milwaukee
Stephen Templin, Cardinal Stritch University

A special thanks to Priyanka Negi and Judy Bass who assisted with the
technical editing of this book.

xix

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This page intentionally left blank
 Organic Chemistry
Demystified

xxi

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This page intentionally left blank
 1
CHAPTER

Structure and
Bonding

Introduction
The study of organic chemistry involves the reactions and interactions of
molecules. Since molecules are composed of atoms, it is necessary to review
the structure of atoms and how they contribute to the properties of molecules.

Atomic Structure
Atoms are composed of a nucleus surrounded by electrons, as shown in Fig. 1-1.
The nucleus consists of positively charged protons and neutral neutrons. Al-
though the nucleus consists of other subatomic particles, the proton, neutron,
and electron are the only subatomic particles that will be discussed in this text.

Copyright © 2006 by The McGraw-Hill Companies, Inc. Click here for terms of use.
2 CHAPTER 1 Structure and Bonding

Nucleus contains
protons and neutrons and is
about 0.0001 angstrom in diameter

Electron cloud

1Å
diameter

Fig. 1-1. Structure of an atom.

The atom is extremely small. It has a diameter of about 10−10 m

(0.000,000,000,1 m or 0.000,000,004 in.). These small dimensions are usu-
ally expressed in angstroms (Å), where 1 Å equals 1 ×10−10 m, or pm where
1 pm equals 1 × 10−12 m. The nucleus is about 1/10,000th the diameter of the
atom, or about 10−4 Å. A key point: most of the volume of an atom is occupied
by the electrons. To put this in terms that are easier to understand, if the atom
was magnified so that the nucleus was the size of a marble, the area occupied by
the electrons would be the size of a football stadium. Take a minute to visualize
that. The area occupied by electrons is huge relative to that of the nucleus. The
area occupied by electrons is referred to as the electron cloud.

MASSES OF ATOMS
The mass of an atom is concentrated in the nucleus. A proton and a neutron
each have a mass of about 1.66 × 10−24 g. An electron has a mass of 1/1800th
that of a proton. Since these are such very small numbers, it is more convenient
to give the mass of a proton and a neutron in atomic mass units (amu). One
amu is equal to 1.66 × 10−24 g. The mass of individual atoms is also given in
a.m.u. The mass of 1 mole of atoms (a mole is a specific number, approximately
6.022 × 1023 ) is the atomic mass, which we usually call the atomic weight, of
an element. The atomic weight is expressed in grams/mol.

ELECTRON CLOUDS
Structures of molecules are usually written as shown in Fig. 1-2. Structure 1-2a
implies that atoms are quite far apart, relative to their size. This is certainly true
for the nuclei, but not for the electron clouds. The distance between a hydrogen
nucleus and a carbon nucleus in a carbon-hydrogen bond is about 1.14 Å. The
CHAPTER 1 Structure and Bonding 3

1.14 Å Electron cloud

H H overlap

H C H H C H

H H

1-2a 1-2b

Fig. 1-2. Bond formation resulting from electron cloud overlap.

radius of the electron cloud of an isolated hydrogen atom is calculated to be 0.79

Å and the radius of an isolated carbon atom is calculated to be 0.91 Å. Since the
sum of the radii of the two atoms is 1.70 Å and the actual bond length is only
1.14 Å, the electron clouds must overlap to form the C H bond. Generally, the
greater the electron cloud overlap, the greater the electron density in the bond
and the stronger the bond. The area occupied by the electrons, the electron cloud,
is much greater than implied in the structures typically drawn (such as Structure
1-2a) in this book and other organic chemistry textbooks. The area occupied by
electrons in a molecule is more accurately represented by Structure 1-2b.
Why do we need to be so concerned with electrons and electron clouds?
Organic chemistry involves physical interactions and chemical reactions be-
tween molecules. Electrons are primarily responsible for these interactions and
reactions.
QUESTION 1-1
Atoms consist of which three subatomic particles?
ANSWER 1-1
Protons, neutrons, and electrons.

Atomic Number and Atomic Mass (Weight)

The atomic number (Z ) for an element is equal to the number of protons in the
nucleus of an atom of a given element. The sum of the number of protons and
neutrons is the mass number (A). If the number of protons changes (a nuclear
reaction), a new element results. There are no changes in the number of protons
in an atom in chemical reactions.
An element is identified with a symbol. The symbol is an abbreviation for an
element: H stands for hydrogen, C for carbon, He for helium, and Na for sodium.
Symbols are not always the first letters of a current name as some symbols are
 4 CHAPTER 1 Structure and Bonding

derived from historical or non-English names. A symbol is often shown with a

superscript indicating the atomic weight and a subscript indicating the atomic
number, e.g., ZA He or 42 He.

ISOTOPES
The number of neutrons may vary for a particular element. About 99% of
carbon atoms have six neutrons, about 1% have seven neutrons, and a very small
percentage contain eight neutrons. Atoms with the same atomic number (and
thus the same number of protons) but different mass numbers (the sum of protons
and neutrons) are called isotopes. The average mass of carbon is 12.0107 g/mol,
the element’s atomic weight. Note that the atomic weights (we should really say
atomic masses, but organic chemists usually use the term weight) of elements
in the periodic table (Appendix A) are not whole numbers as they represent the
average of the isotopic composition. The number of electrons in a neutral atom,
one without a charge, equals the number of protons. Electrons also contribute
to an atom’s molecular weight, but an electron’s total weight is about 1/2000th
that of a proton and their weight contribution is usually ignored.

QUESTION 1-2
A sample consists of three atoms of chlorine: one has a mass of 35.0 amu and
two have masses of 36.0 amu. How many protons, neutrons, and electrons are
in each atom? What is the average mass of the sample?

ANSWER 1-2
The atom of 35.0 amu has 17 electrons, 17 protons, and 18 neutrons. The other
atoms have 17 electrons, 17 protons, and 19 neutrons. The average mass is
(1 × 35.0 + 2 × 36.0)/3 = 35.7 amu.

Electron Energy Levels

Electrons occupy concentric shells and subshells around a nucleus. The shells
are given numbers called principle quantum numbers of 1, 2, 3, etc., to identify
the levels. The energy of each shell and distance between the electrons in a shell
and the nucleus increases with increasing principle quantum number. Level 1 is
the lowest energy level and the electrons in that shell are nearest to the nucleus.
Level 2 is higher in energy and the electrons in this level are found further from
the nucleus than are the electrons in Level 1. Shells are composed of subshells.
Subshells have designations s, p, d, and f. The energy of the shells and subshells
increases as shown in Fig. 1-3. The electron configurations for hydrogen, helium,
CHAPTER 1 Structure and Bonding 5

3d Subshells
3p
Increasing 3s
energy
2p
Shells
2s
1s

Fig. 1-3. Energy levels of shells and subshells.

carbon, nitrogen, and oxygen atoms are shown in Fig. 1-4. Electrons prefer to
occupy the lowest energy levels available to them. This represents their most
stable state called their ground state.

AUFBAU PRINCIPLE
Figure 1-4 is a more concise method showing how electrons fill the subshells as
the atomic number of the element increases. Each additional electron goes into
the lowest energy subshell available to it. This is called the aufbau (building
up) principle. Figure 1-4 shows the electron lowest-energy configuration of six
common elements. Each s subshell consists of one orbital. Each p subshell
consists of three orbitals. Note the term orbital, not orbit, is used. An orbital is
defined in a following section.
Each orbital can hold a maximum of two electrons. When the orbitals in
a subshell are filled, electrons go into the next higher-energy subshell. Each
principle shell has only one s orbital: 1s, 2s, 3s, etc. Each principle shell of
Level 2 and higher has three p orbitals, px , p y , and pz . All p orbitals in the same
subshell (2px , 2p y , and 2pz ) are of equal energy. Orbitals of equal energy are

2p 2p 2p
2s 2s 2s
1s 1s 1s
Hydrogen, 1H Helium, 2He Carbon, 6C

2p 2p 2p
2s 2s 2s
1s 1s 1s
Nitrogen, 7N Oxygen, 8O Neon, 10Ne

Fig. 1-4. Electron configuration of elements.

6 CHAPTER 1 Structure and Bonding

called degenerate orbitals. The maximum number of electrons in a main shell

is 2n 2 , where n is the principle quantum number, 1, 2, 3, etc.

PAULI EXCLUSION PRINCIPLE

Since electrons have negative charges, there is some resistance for two electrons
to occupy the same orbital, that is, to pair up. Species of like charge (two negative
charges) repel each other. The helium atom has two electrons to be placed in
orbitals. (See the electron configuration of helium in Fig. 1-4.) One electron can
be put into the lowest energy orbital, the 1s orbital. The second electron can
go into the 1s orbital or the 2s orbital. The energy required to put the second
electron into the higher energy 2s orbital is greater than the energy required
(electron-electron repulsion) to pair the electrons in the 1s orbital. Therefore
the second electron goes into the 1s orbital. Each electron is said to have a spin,
like a top, and the spin can be clockwise or counterclockwise. The spin direction
is indicated by an arrow pointing up or down. Two electrons in the same orbital
must have opposite spins (Pauli exclusion principle). Helium’s two electrons
are shown with opposite spins (↑↓) in Fig. 1-4.

HUND’S RULE
Consider the carbon atom with six electrons. The electron configuration is shown
in Fig. 1-4. Using the aufbau principle, the first two electrons go into the 1s
orbital. The next two electrons go into the next higher energy 2s orbital. Then
the last two electrons go into the higher energy 2p orbitals. The last two electrons
could go into one p orbital or each could go into two different p orbitals. For
degenerate (equal energy) orbitals, it is more energy efficient for electrons to
go into different degenerate orbitals until they must pair up (Hund’s rule).
Now consider oxygen with eight electrons. When seven electrons are added
by the aufbau principle, the electron configuration will be the same as shown for
nitrogen (see Fig. 1-4). The last electron added pairs with an electron already in
a 2p orbital. Their spins must be opposite (Pauli exclusion principle) as shown
in Fig. 1-4.

ELECTRON CONFIGURATIONS
A short-hand method for writing the electron configurations of atoms is shown
for oxygen as 1s2 2s2 2p4 . Verbally one would say one s two, two s two, two
p four. The prefix indicates the principle energy level (1, 2, 3, etc.), the letter
(s, p, d, or f) gives the type of orbital, and the exponent is the number of electrons
in that orbital.
CHAPTER 1 Structure and Bonding 7

QUESTION 1-3
Draw the short-hand electron configuration for the sodium atom.

ANSWER 1-3
The sodium atom has 11 electrons: 1s2 2s2 2p6 3s1 .

VALENCE ELECTRONS
The electrons in the outermost shell are called the valence electrons. Elements
in the first row (period) in the periodic table, hydrogen and helium, have only a
1s orbital. The maximum number of electrons these two elements can accom-
modate is 2. A 2-electron configuration will be called a duet. When hydrogen
has 2 valence electrons in its 1s orbital it will be called duet happy. Elements in
the second row (period) in the periodic table, from lithium to neon, can hold a
maximum of 10 electrons. The outermost shell, the valence shell, has a principle
quantum number of 2 and can hold a maximum of 8 electrons, 2s2 , 2p6 . When
the valence shell orbitals are filled, the atom will be called octet happy. The
number of valence electrons in the elements in the first three rows of the
periodic table is equal to their group number (see the periodic table in Appendix
A). Hydrogen in Group IA has 1 valence electron, carbon in Group IVB has
4 valence electrons, and fluorine in Group VIIB has 7 valence electrons. An
atom can gain valence electrons from, or loose electrons to, other atoms. Valence
electrons are important since they are involved in forming chemical bonds.

QUESTION 1-4
How many electrons does a nitrogen atom have? How many valence electrons
does it have?

ANSWER 1-4
It has seven electrons and five valence electrons.

The Octet Rule

Neon, argon, and the other elements in column VIIIB in the periodic table are
called the noble gases. They have eight electrons in their valence shell. Helium
is an exception since its valence shell (1s) can hold only two electrons. Noble
gases are so called because they are, of course, gases and tend to be unreactive
or inert. There is a special stability associated with atoms with eight electrons in
their valence shell (except for the elements in row 1). The octet rule states that
elements will gain, lose, or share electrons to achieve eight electrons in their
 8 CHAPTER 1 Structure and Bonding

outermost (valence) shell. An explanation for this special stability is beyond the
scope of this book.
There are some exceptions to the octet rule. Third row elements (such as
sulfur and phosphorus) can hold up to 18 electrons in their outermost valence
shell (3s, 3p, and 3d orbitals). Beryllium and boron atoms can have less than
8 electrons in their valence shells. An example of a boron compound will be
discussed in a following section.

Valences
The bonding capacity or the number of bonds to an atom is called its valence.
(It would be helpful to look at the periodic table in Appendix A as you read
this paragraph.) The valence of atoms in Groups IA to IVA is the same as
the group number. Lithium (Group IA) has a valence of one and will have a
single bond to another atom. Carbon (Group IVB) has a valence of four and
there will be four bonds to each carbon atom. Carbon is called tetravalent. The
valence of elements in Groups VB to VIIB is 3, 2, and 1 (or eight minus the
group number) respectively. Elements in Groups VB to VIIB can have multiple
positive valences, but those situations will not be discussed here.

QUESTION 1-5
What valence does oxygen have? What is the bonding capacity for oxygen?
What is the bonding capacity for boron?

ANSWER 1-5
Oxygen has a valence and bonding capacity of 2. Boron has a bonding capacity
of 3.

Atoms in the second row tend to gain or lose electrons to achieve the electron
structure of the nearest noble gas. They want to be duet or octet happy as are
the noble gases. Thus, lithium tends to lose one electron to achieve the helium
electron configuration. Fluorine tends to gain an electron to achieve the neon
electron configuration.

QUESTION 1-6
How many electrons must oxygen gain to become octet happy?

ANSWER 1-6
Oxygen will gain 2 electrons to have a full octet in its valence shell.
CHAPTER 1 Structure and Bonding 9

BOND FORMATION
Atoms form bonds by transferring or sharing electrons with other atoms. An
atom that loses an electron has a positive charge and is called a cation. If an
atom gains an electron, it has a negative charge and is called an anion. Atoms of
elements in Groups IA and IIA tend to transfer electrons to elements in Groups
VIB and VIIB. The resulting cation from Group IA or IIA forms an ionic bond
with the resulting anion from Group VIB or VIIB. Elements in Groups VIB and
VIIB tend to share electrons if they react with elements in Groups IVB to VIIB.
Sharing electrons result in covalent bonds.
Carbon, in Group IVB, tends to form bonds with many other elements. One
reason there are so many organic compounds is that carbon atoms can form
bonds with other carbon atoms, resulting in a large number of compounds.

Lewis Structures
Lewis structures are a convenient way of showing an atom’s valence electrons.
Dots are used to indicate the valence electrons. The inner electrons, the core
electrons, are not shown. Lewis structures for carbon, nitrogen, and fluorine
atoms are shown in Fig. 1-5.

LEWIS STRUCTURE FOR CH4

The Lewis structures of some compounds are shown in Fig. 1-6. Bonds in
compounds are shown by a pair of dots or a solid line representing two electrons.
How does one know where to put the electrons? First consider methane, CH4 .
There are four simple rules to follow:
1. Sum the valence electrons of all the atoms in a molecule.
CH4 has eight valence electrons, four from the carbon atom and four
from the hydrogen atoms (one from each).
2. Show the structure of the compound by connecting the atoms with a
single (two electron) bond. You may have to be told how the atoms are
connected if they can be connected in more than one way. Methane is

• •• •

C• • N• • F
••

••

• •
••

4 valence 5 valence 7 valence

electrons electrons electrons

Fig. 1-5. Lewis structures.

10 CHAPTER 1 Structure and Bonding

H H Bonding electrons
H
•• ••

H C H or H C H H C O H

••

••
•• ••

H H
H Nonbonding electrons
1-6a 1-6b

Electron pair
•• movement ••

O O
••

••

••
•• •• •• ••

H O C O H H O C O H
•• •• •• ••

1-6c 1-6d

••
••
O

••
O
••

••

•• ••
•• ••
O N O

••

••
O N O
••

••

•• •• •• ••

1-6e 1-6f
NO3−

Fig. 1-6. Lewis structures for molecules and ions.

shown as Structure 1-6a. Each hydrogen atom is bonded to the carbon

atom with a single bond.
3. Each bond consists of two electrons. Subtract the number of bond-
ing electrons from the total number of valence electrons. There are
eight electrons in the bonds and eight valence electrons. In this case,
all valence electrons are assigned to the four C H bonds in CH4 .
4. If there are additional unassigned electrons, place them on the second
row elements to give full octets. Pairs of electrons not involved in bond-
ing are called nonbonding electrons, as shown in Structures 1-6b–1-6f.
(In CH4 there are no nonbonding electrons and all atoms are duet or octet
happy.)
5. Move electrons in pairs (shown by the curved arrow in Structures 1-6c
and 1-6e) to make all atoms duet or octet happy, if possible.

LEWIS STRUCTURE FOR CH3 OH

Three examples using CH3 OH, H2 CO3 , and NO3− will help explain how to
draw Lewis structures. Atom connectivity is shown in Fig. 1-6. First consider
CH3 OH. There are 14 valence electrons: 4 from the carbon atom, 4 from the
four hydrogen atoms, and 6 from the oxygen atom. The atoms are connected as
CHAPTER 1 Structure and Bonding 11

shown in Structure 1-6b. The five bonds use 10 electrons (2 electrons in each
bond). There are 4 valence electrons left to assign. Put these electrons on the
oxygen atom to make it octet happy. All atoms are now duet or octet happy. The
Lewis structure is shown as Structure 1-6b.
A key point: the total number of valence electrons for an atom in a compound
is the sum of all bonding and nonbonding electrons. Both electrons in a bond
are counted as valence electrons for each atom connected by that bond. In a
C H bond the two electrons are counted as valence electrons for H and for C.
Thus electrons in bonds are double counted as valence electrons.

LEWIS STRUCTURE FOR H2 CO3

Now consider H2 CO3 , Structures 1-6c and 1-6d. There are 24 valence electrons,
2 from the two hydrogen atoms, 4 from the carbon atom, and 18 from the three
oxygen atoms. Ten electrons are used in the five bonds connecting the atoms.
The remaining 14 electrons are put on the oxygen atoms. Four electrons are put
on the two oxygen atoms bonded to H and C. Six electrons are put on the third
oxygen atom bonded only to C, as shown in Structure 1-6c. All atoms are octet
happy except the carbon atom. Move one electron pair, as shown by the curved
arrow in Structure 1-6c, to be shared by the oxygen atom and the carbon atom.
This results in two bonds (a double bond) between the oxygen and carbon atoms
as shown in Structure 1-6d. Now every atom is duet or octet happy.

LEWIS STRUCTURE FOR NO3 −

There is an additional step to consider for ions and ionic compounds that have
a net charge. If the ion has a negative charge, an additional valence electron
needs to be added for each negative charge. If the ion has a positive charge, one
valence electron has to be removed for each positive charge.
The nitrate anion, NO3 − , has a net negative charge. There are 24 valence
electrons, 5 from the nitrogen atom, 18 from the three oxygen atoms, and an
additional electron due to the negative charge. The atoms are connected as shown
in Structure 1-6e. Six electrons are used in the three bonds. The remaining 18
electrons are put on the oxygen atoms, 6 electrons on each. All atoms are octet
happy, except nitrogen. Move an electron pair, as shown by the curved arrow
in Structure 1-6e, between any one of the three oxygen atoms and the nitrogen
atom. This results in two bonds between one oxygen atom and the nitrogen atom
(Structure 1-6f). Now each atom is octet happy.
QUESTION 1-7
Draw the Lewis structures for CH3 F, ICl, H2 O, HCN, and CH3 CO2 − .
12 CHAPTER 1 Structure and Bonding

ANSWER 1-7

H H O

••
••
•• •• •• •• ••
F I N

••
••

••
H C Cl O H C H C C O

••
H H

••
•• •• •• •• ••
H H

KEKULÉ STRUCTURES
Kekulé structures are similar to the Lewis structures but exclude the nonbonding
electrons. All bonds are shown as lines and not dot pairs.

CONDENSED STRUCTURES
Condensed structures are another way of drawing chemical structures. Follow
along in Fig. 1-7 as you read this paragraph. Structures 1-7a–c represent the
same compound written in different ways. The carbon atoms are usually (but

Substituents with a single bond

CH Bond shown for substituent or branch
3

CH3CH2CHCH2CH2CH3 Main chain

1-7a Bonds between atoms not shown

Atoms generally follow the atom they are bonded to

CH3
CH3CH2CH(CH2)2CH3
1-7b Repeating units may be combined

CH3CH2CH(CH3)CH2CH2CH3

1-7c
Substituent may be written in main chain

Substituents with a double bond

CH2
CH3CCH3 or CH3C(CH2)CH3
1-7d Group or atom bonded to the
O preceding atom with a double bond
CH3CCH3 or CH3C(O)CH3
1-7e

Fig. 1-7. Condensed structures.

 Another Random Document on
Scribd Without Any Related Topics
 p p g ,
But better late than never—You know I love you,
As you, I know, love me, and loyally
Have follow’d me thus far in my wild venture:
Well! now then—having seen me safe thus far—
Safe if not wholly sound—over the rocks
Into the country where my business lies—
Why should not you return the way we came,
The storm all clear’d away, and, leaving me
(Who now shall want you, though not thank you, less,
Now that our horses gone) this side the ridge,
Find your way back to dear old home again;
While I—Come, come!—
What, weeping, my poor fellow?—
Fife. Leave you here
Alone—my Lady—Lord! I mean my Lord—
In a strange country—among savages—
Oh, now I know—you would be rid of me
For fear my stumbling speech—
Ros. Oh, no, no, no!—
I want you with me for a thousand sakes
To which that is as nothing—I myself
More apt to let the secret out myself
Without your help at all—Come, come, cheer up!
And if you sing again, ‘Come weal, come woe,’
Let it be that; for we will never part
Until you give the signal.
Fife. ’Tis a bargain.
Ros. Now to begin, then. ‘Follow, follow me,
You fairy elves that be.’
Fife. Ay, and go on—
Something of ‘following darkness like a dream,’
For that we’re after.
Ros. No, after the sun;
Trying to catch hold of his glittering skirts
Trying to catch hold of his glittering skirts
That hang upon the mountain as he goes.
Fife. Ah, he’s himself past catching—as you spoke
He heard what you were saying, and—just so—
Like some scared water-bird,
As we say in my country, dōve below.
Ros. Well, we must follow him as best we may.
Poland is no great country, and, as rich
In men and means, will but few acres spare
To lie beneath her barrier mountains bare.
We cannot, I believe, be very far
From mankind or their dwellings.
Fife. Send it so!
And well provided for man, woman, and beast.
No, not for beast. Ah, but my heart begins
To yearn for her—
Ros. Keep close, and keep your feet
From serving you as hers did.
Fife. As for beasts,
If in default of other entertainment,
We should provide them with ourselves to eat—
Bears, lions, wolves—
Ros. Oh, never fear.
Fife. Or else,
Default of other beasts, beastlier men,
Cannibals, Anthropophagi, bare Poles
Who never knew a tailor but by taste.
Ros. Look, look! Unless my fancy misconceive
With twilight—down among the rocks there, Fife—
Some human dwelling, surely—
Or think you but a rock torn from the rocks
In some convulsion like to-day’s, and perch’d
Quaintly among them in mock-masonry?
 Fife. Most likely that, I doubt.
Ros. No, no—for look!
A square of darkness opening in it—
Fife. Oh,
I don’t half like such openings!—
Ros. Like the loom
Of night from which she spins her outer gloom—
Fife. Lord, Madam, pray forbear this tragic vein
In such a time and place—
Ros. And now again
Within that square of darkness, look! a light
That feels its way with hesitating pulse,
As we do, through the darkness that it drives
To blacken into deeper night beyond.
Fife. In which could we follow that light’s example,
As might some English Bardolph with his nose,
We might defy the sunset—Hark, a chain!
Ros. And now a lamp; a lamp! And now the hand
That carries it.
Fife. Oh, Lord! that dreadful chain!
Ros. And now the bearer of the lamp; indeed
As strange as any in Arabian tale,
So giant-like, and terrible, and grand,
Spite of the skin he’s wrapt in.
Fife. Why, ’tis his own:
Oh, ’tis some wild man of the woods; I’ve heard
They build and carry torches—
Ros. Never Ape
Bore such a brow before the heavens as that—
Chain’d as you say too!—
Fife Oh that dreadful chain!
 Fife. Oh, that dreadful chain!
Ros. And now he sets the lamp down by his side,
And with one hand clench’d in his tangled hair
And with a sigh as if his heart would break—
[During this Segismund has entered from the fortress, with a torch.
 Segismund. Once more the storm has roar’d itself away,
Splitting the crags of God as it retires;
But sparing still what it should only blast,
This guilty piece of human handiwork,
And all that are within it. Oh, how oft,
How oft, within or here abroad, have I
Waited, and in the whisper of my heart
Pray’d for the slanting hand of heaven to strike
The blow myself I dared not, out of fear
Of that Hereafter, worse, they say, than here,
Plunged headlong in, but, till dismissal waited,
To wipe at last all sorrow from men’s eyes,
And make this heavy dispensation clear.
Thus have I borne till now, and still endure,
Crouching in sullen impotence day by day,
Till some such out-burst of the elements
Like this rouses the sleeping fire within;
And standing thus upon the threshold of
Another night about to close the door
Upon one wretched day to open it
On one yet wretcheder because one more;—
Once more, you savage heavens, I ask of you—
I, looking up to those relentless eyes
That, now the greater lamp is gone below,
Begin to muster in the listening skies;
In all the shining circuits you have gone
About this theatre of human woe,
What greater sorrow have you gazed upon
Than down this narrow chink you witness still;
And which, did you yourselves not fore-devise,
You register’d for others to fulfil!
Fife. This is some Laureate at a birth-day ode;
No wonder we went rhyming.
Ros. Hush! And now
See, starting to his feet, he strides about
See, starting to his feet, he strides about
Far as his tether’d steps—
Seg. And if the chain
You help’d to rivet round me did contract
Since guiltless infancy from guilt in act;
Of what in aspiration or in thought
Guilty, but in resentment of the wrong
That wreaks revenge on wrong I never wrought
By excommunication from the free
Inheritance that all created life,
Beside myself, is born to—from the wings
That range your own immeasurable blue,
Down to the poor, mute, scale-imprison’d things,
That yet are free to wander, glide, and pass
About that under-sapphire, whereinto
Yourselves transfusing you yourselves englass!
Ros. What mystery is this?
Fife. Why, the man’s mad:
That’s all the mystery. That’s why he’s chain’d—
And why—
Seg. Nor Nature’s guiltless life alone—
But that which lives on blood and rapine; nay,
Chartered with larger liberty to slay
Their guiltless kind, the tyrants of the air
Soar zenith-upward with their screaming prey,
Making pure heaven drop blood upon the stage
Of under earth, where lion, wolf, and bear,
And they that on their treacherous velvet wear
Figure and constellation like your own,[13]
With their still living slaughter bound away
Over the barriers of the mountain cage,
Against which one, blood-guiltless, and endued
With aspiration and with aptitude
Transcending other creatures, day by day
Beats himself mad with unavailing rage!
 g g
Fife. Why, that must be the meaning of my mule’s
Rebellion—
Ros. Hush!
Seg. But then if murder be
The law by which not only conscience-blind
Creatures, but man too prospers with his kind;
Who leaving all his guilty fellows free,
Under your fatal auspice and divine
Compulsion, leagued in some mysterious ban
Against one innocent and helpless man,
Abuse their liberty to murder mine:
And sworn to silence, like their masters mute
In heaven, and like them twiring through the mask
Of darkness, answering to all I ask,
Point up to them whose work they execute!
Ros. Ev’n as I thought, some poor unhappy wretch,
By man wrong’d, wretched, unrevenged, as I!
Nay, so much worse than I, as by those chains
Clipt of the means of self-revenge on those
Who lay on him what they deserve. And I,
Who taunted Heaven a little while ago
With pouring all its wrath upon my head—
Alas! like him who caught the cast-off husk
Of what another bragg’d of feeding on,
Here’s one that from the refuse of my sorrows
Could gather all the banquet he desires!
Poor soul, poor soul!
Fife. Speak lower—he will hear you.
Ros. And if he should, what then? Why, if he would,
He could not harm me—Nay, and if he could,
Methinks I’d venture something of a life
I care so little for—
Seg. Who’s that? Clotaldo? Who are you, I say,
 g y , y,
That, venturing in these forbidden rocks,
Have lighted on my miserable life,
And your own death?
Ros. You would not hurt me, surely?
Seg. Not I; but those that, iron as the chain
In which they slay me with a lingering death,
Will slay you with a sudden—Who are you?
Ros. A stranger from across the mountain there,
Who, having lost his way in this strange land
And coming night, drew hither to what seem’d
A human dwelling hidden in these rocks,
And where the voice of human sorrow soon
Told him it was so.
Seg. Ay? But nearer—nearer—
That by this smoky supplement of day
But for a moment I may see who speaks
So pitifully sweet.
Fife. Take care! take care!
Ros. Alas, poor man, that I, myself so helpless,
Could better help you than by barren pity,
And my poor presence—
Seg. Oh, might that be all!
But that—a few poor moments—and, alas!
The very bliss of having, and the dread
Of losing, under such a penalty
As every moment’s having runs more near,
Stifles the very utterance and resource
They cry for quickest; till from sheer despair
Of holding thee, methinks myself would tear
To pieces—
Fife. There, his word’s enough for it.
Seg. Oh, think, if you who move about at will,
dl h k d
And live in sweet communion with your kind,
After an hour lost in these lonely rocks
Hunger and thirst after some human voice
To drink, and human face to feed upon;
What must one do where all is mute, or harsh,
And ev’n the naked face of cruelty
Were better than the mask it works beneath?—
Across the mountain then! Across the mountain!
What if the next world which they tell one of
Be only next across the mountain then,
Though I must never see it till I die,
And you one of its angels?
Ros. Alas! alas!
No angel! And the face you think so fair,
’Tis but the dismal frame-work of these rocks
That makes it seem so; and the world I come from—
Alas, alas, too many faces there
Are but fair vizors to black hearts below,
Or only serve to bring the wearer woe!
But to yourself—If haply the redress
That I am here upon may help to yours.
I heard you tax the heavens with ordering,
And men for executing, what, alas!
I now behold. But why, and who they are
Who do, and you who suffer—
Seg. (pointing upwards). Ask of them,
Whom, as to-night, I have so often ask’d,
And ask’d in vain.
Ros. But surely, surely—
Seg. Hark!
The trumpet of the watch to shut us in.
Oh, should they find you!—Quick! Behind the rocks!
To-morrow—if to-morrow—
Ros. (flinging her sword toward him). Take my sword!
 Rosaura and Fife hide in the rocks; enter Clotaldo.

Clotaldo. These stormy days you like to see the last of

Are but ill opiates, Segismund, I think,
For night to follow: and to-night you seem
More than your wont disorder’d. What! A sword?
Within there!

Enter Soldiers with black vizors and torches.

 Fife. Here’s a pleasant masquerade!
Clo. Whosever watch this was
Will have to pay head-reckoning. Meanwhile,
This weapon had a wearer. Bring him here,
Alive or dead.
Seg. Clotaldo! good Clotaldo!—
Clo. (to Soldiers who enclose Segismund; others searching the
rocks). You know your duty.
Soldiers (bringing in Rosaura and Fife). Here are two of them,
Whoever more to follow—
Clo. Who are you,
That in defiance of known proclamation
Are found, at night-fall too, about this place?
Fife. Oh, my Lord, she—I mean he—
Ros. Silence, Fife,
And let me speak for both.—Two foreign men,
To whom your country and its proclamations
Are equally unknown; and, had we known,
Ourselves not masters of our lawless beasts
That, terrified by the storm among your rocks,
Flung us upon them to our cost.
Fife. My mule—
Clo. Foreigners? Of what country?
Ros. Muscovy.
Clo. And whither bound?
Ros. Hither—if this be Poland;
But with no ill design on her, and therefore
Taking it ill that we should thus be stopt
Upon her threshold so uncivilly.
Clo. Whither in Poland?
 Ros. To the capital.
Clo. And on what errand?
Ros. Set me on the road,
And you shall be the nearer to my answer.
Clo. (aside). So resolute and ready to reply,
And yet so young—and—— (Aloud) Well,—
Your business was not surely with the man
We found you with?
Ros. He was the first we saw,—
And strangers and benighted, as we were,
As you too would have done in a like case,
Accosted him at once.
Clo. Ay, but this sword?
Ros. I flung it toward him.
Clo. Well, and why?
Ros. And why?
But to revenge himself on those who thus
Injuriously misuse him.
Clo. So—so—so!
’Tis well such resolution wants a beard—
And, I suppose, is never to attain one.
Well, I must take you both, you and your sword,
Prisoners.
Fife. (offering a cudgel). Pray take mine, and welcome, sir;
I’m sure I gave it to that mule of mine
To mighty little purpose.
Ros. Mine you have;
And may it win us some more kindliness
Than we have met with yet.
Clo. (examining the sword). More mystery!
How came you by this weapon?
How came you by this weapon?
Ros. From my father.
Clo. And do you know whence he?
Ros. Oh, very well:
From one of this same Polish realm of yours,
Who promised a return, should come the chance,
Of courtesies that he received himself
In Muscovy, and left this pledge of it—
Not likely yet, it seems, to be redeem’d.
Clo. (aside). Oh, wondrous chance—or wondrous Providence:
The sword that I myself in Muscovy,
When these white hairs were black, for keepsake left
Of obligation for a like return
To him who saved me wounded as I lay
Fighting against his country; took me home;
Tended me like a brother till recover’d,
Perchance to fight against him once again—
And now my sword put back into my hand
By his—if not his son—still, as so seeming,
By me, as first devoir of gratitude,
To seem believing, till the wearer’s self
See fit to drop the ill-dissembling mask.
(Aloud) Well, a strange turn of fortune has arrested
The sharp and sudden penalty that else
Had visited your rashness or mischance:
In part, your tender youth too—pardon me,
And touch not where your sword is not to answer—
Commends you to my care; not your life only,
Else by this misadventure forfeited;
But ev’n your errand, which, by happy chance,
Chimes with the very business I am on,
And calls me to the very point you aim at.
Ros. The capital?
Clo. Ay, the capital; and ev’n
Th t it l f it l th C t
That capital of capitals, the Court:
Where you may plead, and, I may promise, win
Pardon for this, you say unwilling, trespass,
And prosecute what else you have at heart,
With me to help you forward all I can;
Provided all in loyalty to those
To whom by natural allegiance
I first am bound to.
Ros. As you make, I take
Your offer: with like promise on my side
Of loyalty to you and those you serve,
Under like reservation for regards
Nearer and dearer still.
Clo. Enough, enough;
Your hand; a bargain on both sides. Meanwhile,
Here shall you rest to-night. The break of day
Shall see us both together on the way.
Ros. Thus then what I for misadventure blamed,
Directly draws me where my wishes aim’d.
[Exeunt.

Scene II.—The Palace at Warsaw.

Enter on one side Astolfo, Duke of Muscovy, with his train; and, on
the other, the Princess Estrella, with hers.
 Astolfo. My royal cousin, if so near in blood,
Till this auspicious meeting scarcely known,
Till all that beauty promised in the bud
Is now to its consummate blossom blown,
Well met at last; and may—
Estrella. Enough, my Lord,
Of compliment devised for you by some
Court tailor, and, believe me, still too short
To cover the designful heart below.
Ast. Nay, but indeed, fair cousin—
Est. Ay, let Deed
Measure your words, indeed your flowers of speech
Ill with your iron equipage atone;
Irony indeed, and wordy compliment.
Ast. Indeed, indeed, you wrong me, royal cousin,
And fair as royal, misinterpreting
What, even for the end you think I aim at,
If false to you, were fatal to myself.
Est. Why, what else means the glittering steel, my Lord,
That bristles in the rear of these fine words?
What can it mean, but, failing to cajole,
To fight or force me from my just pretension?
Ast. Nay, might I not ask ev’n the same of you,
The nodding helmets of whose men at arms
Out-crest the plumage of your lady court?
Est. But to defend what yours would force from me.
Ast. Might not I, lady, say the same of mine?
But not to come to battle, ev’n of words,
With a fair lady, and my kinswoman;
And as averse to stand before your face,
Defenceless, and condemn’d in your disgrace,
Till the good king be here to clear it all—
Will h f t h ?
Will you vouchsafe to hear me?
Est. As you will.
Ast. You know that, when about to leave this world,
Our royal grandsire, King Alfonso, left
Three children; one a son, Basilio,
Who wears—long may he wear!—the crown of Poland;
And daughters twain: of whom the elder was
Your mother, Clorileña, now some while
Exalted to a more than mortal throne;
And Recisunda, mine, the younger sister,
Who, married to the Prince of Muscovy,
Gave me the light which may she live to see
Herself for many, many years to come.
Meanwhile, good King Basilio, as you know,
Deep in abstruser studies than this world,
And busier with the stars than lady’s eyes,
Has never by a second marriage yet
Replaced, as Poland ask’d of him, the heir
An early marriage brought and took away;
His young queen dying with the son she bore him:
And in such alienation grown so old
As leaves no other hope of heir to Poland
Than his two sisters’ children; you, fair cousin,
And me; for whom the Commons of the realm
Divide themselves into two several factions;
Whether for you, the elder sister’s child;
Or me, born of the younger, but, they say,
My natural prerogative of man
Outweighing your priority of birth.
Which discord growing loud and dangerous,
Our uncle, King Basilio, doubly sage
In prophesying and providing for
The future, as to deal with it when come,
Bids us here meet to-day in solemn council
Our several pretensions to compose.
And but the martial out burst that proclaims
And, but the martial out-burst that proclaims
His coming, makes all further parley vain,
Unless my bosom, by which only wise
I prophesy, now wrongly prophesies,
By such a happy compact as I dare
But glance at till the Royal Sage declare.
Trumpets, etc. Enter King Basilio with his Council.

All. The King! God save the King!

Estrella. Oh, Royal Sir!—

} (Kneeling)
Astolfo. God save your Majesty!—
 King. Rise, both of you,
Rise to my arms, Astolfo and Estrella;
As my two sisters’ children always mine,
Now more than ever, since myself and Poland
Solely to you for our succession look’d.
And now give ear, you and your several factions,
And you, the Peers and Princes of this realm,
While I reveal the purport of this meeting
In words whose necessary length I trust
No unsuccessful issue shall excuse.
You and the world who have surnamed me ‘Sage’
Know that I owe that title, if my due,
To my long meditation on the book
Which ever lying open overhead—
The book of heaven, I mean—so few have read;
Whose golden letters on whose sapphire leaf,
Distinguishing the page of day and night,
And all the revolution of the year;
So with the turning volume where they lie
Still changing their prophetic syllables,
They register the destinies of men:
Until with eyes that, dim with years indeed,
Are quicker to pursue the stars than rule them,
I get the start of Time, and from his hand
The wand of tardy revelation draw.
Oh, had the self-same heaven upon his page
Inscribed my death ere I should read my life
And, by fore-casting of my own mischance,
Play not the victim but the suicide
In my own tragedy!—But you shall hear.
You know how once, as kings must for their people,
And only once, as wise men for themselves,
I woo’d and wedded: know too that my Queen
In childing died; but not, as you believe,
With her, the son she died in giving life to.
For as the hour of birth was on the stroke
For, as the hour of birth was on the stroke,
Her brain conceiving with her womb, she dream’d
A serpent tore her entrail. And too surely
(For evil omen seldom speaks in vain)
The man-child breaking from that living tomb
That makes our birth the antitype of death,
Man-grateful, for the life she gave him paid
By killing her: and with such circumstance
As suited such unnatural tragedy;
He coming into light, if light it were
That darken’d at his very horoscope,
When heaven’s two champions—sun and moon I mean—
Suffused in blood upon each other fell
In such a raging duel of eclipse
As hath not terrified the universe
Since that which wept in blood the death of Christ:
When the dead walk’d, the waters turn’d to blood,
Earth and her cities totter’d, and the world
Seem’d shaken to its last paralysis.
In such a paroxysm of dissolution
That son of mine was born; by that first act
Heading the monstrous catalogue of crime,
I found fore-written in his horoscope;
As great a monster in man’s history
As was in nature his nativity;
So savage, bloody, terrible, and impious,
Who, should he live, would tear his country’s entrails,
As by his birth his mother’s; with which crime
Beginning, he should clench the dreadful tale
By trampling on his father’s silver head.
All which fore-reading, and his act of birth
Fate’s warrant that I read his life aright;
To save his country from his mother’s fate,
I gave abroad that he had died with her
His being slew; with midnight secrecy
I had him carried to a lonely tower
Hewn from the mountain-barriers of the realm
Hewn from the mountain-barriers of the realm,
And under strict anathema of death
Guarded from men’s inquisitive approach,
Save from the trusty few one needs must trust;
Who while his fasten’d body they provide
With salutary garb and nourishment,
Instruct his soul in what no soul may miss
Of holy faith, and in such other lore
As may solace his life-imprisonment,
And tame perhaps the Savage prophesied
Toward such a trial as I aim at now,
And now demand your special hearing to.
What in this fearful business I have done,
Judge whether lightly or maliciously,—
I, with my own and only flesh and blood,
And proper lineal inheritor!
I swear, had his foretold atrocities
Touch’d me alone, I had not saved myself
At such a cost to him; but as a king,—
A Christian king,—I say, advisedly,
Who would devote his people to a tyrant
Worse than Caligula fore-chronicled?
But even this not without grave mis-giving,
Lest by some chance mis-reading of the stars,
Or mis-direction of what rightly read,
I wrong my son of his prerogative,
And Poland of her rightful sovereign.
For, sure and certain prophets as the stars,
Although they err not, he who reads them may;
Or rightly reading—seeing there is One
Who governs them, as, under Him, they us,
We are not sure if the rough diagram
They draw in heaven and we interpret here,
Be sure of operation, if the Will
Supreme, that sometimes for some special end
The course of providential nature breaks
By miracle may not of these same stars
By miracle, may not of these same stars
Cancel his own first draft, or overrule
What else fore-written all else overrules.
As, for example, should the Will Almighty
Permit the Free-will of particular man
To break the meshes of else strangling fate—
Which Free-will, fearful of foretold abuse,
I have myself from my own son for-closed
From ever possible self-extrication;
A terrible responsibility,
Not to the conscience to be reconciled
Unless opposing almost certain evil
Against so slight contingency of good.
Well—thus perplex’d, I have resolved at last
To bring the thing to trial: whereunto
Here have I summon’d you, my Peers, and you
Whom I more dearly look to, failing him,
As witnesses to that which I propose;
And thus propose the doing it. Clotaldo,
Who guards my son with old fidelity,
Shall bring him hither from his tower by night
Lockt in a sleep so fast as by my art
I rivet to within a link of death,
But yet from death so far, that next day’s dawn
Shall wake him up upon the royal bed,
Complete in consciousness and faculty,
When with all princely pomp and retinue
My loyal Peers with due obeisance
Shall hail him Segismund, the Prince of Poland.
Then if with any show of human kindness
He fling discredit, not upon the stars,
But upon me, their misinterpreter,
With all apology mistaken age
Can make to youth it never meant to harm,
To my son’s forehead will I shift the crown
I long have wish’d upon a younger brow;
And in religious humiliation
And in religious humiliation,
For what of worn-out age remains to me,
Entreat my pardon both of Heaven and him
For tempting destinies beyond my reach.
But if, as I misdoubt, at his first step
The hoof of the predicted savage shows;
Before predicted mischief can be done,
The self-same sleep that loosed him from the chain
Shall re-consign him, not to loose again.
Then shall I, having lost that heir direct,
Look solely to my sisters’ children twain
Each of a claim so equal as divides
The voice of Poland to their several sides,
But, as I trust, to be entwined ere long
Into one single wreath so fair and strong
As shall at once all difference atone,
And cease the realm’s division with their own.
Cousins and Princes, Peers and Councillors,
Such is the purport of this invitation,
And such is my design. Whose furtherance
If not as Sovereign, if not as Seer,
Yet one whom these white locks, if nothing else,
To patient acquiescence consecrate,
I now demand and even supplicate.
Ast. Such news, and from such lips, may well suspend
The tongue to loyal answer most attuned;
But if to me as spokesman of my faction
Your Highness looks for answer; I reply
For one and all—Let Segismund, whom now
We first hear tell of as your living heir,
Appear, and but in your sufficient eye
Approve himself worthy to be your son,
Then we will hail him Poland’s rightful heir.
What says my cousin?
Est. Ay, with all my heart.
But if my youth and sex upbraid me not
But if my youth and sex upbraid me not
That I should dare ask of so wise a king—
King. Ask, ask, fair cousin! Nothing, I am sure,
Not well consider’d; nay, if ’twere, yet nothing
But pardonable from such lips as those.
Est. Then, with your pardon, Sir—if Segismund,
My cousin, whom I shall rejoice to hail
As Prince of Poland too, as you propose,
Be to a trial coming upon which
More, as I think, than life itself depends,
Why, Sir, with sleep-disorder’d senses brought
To this uncertain contest with his stars?
King. Well ask’d indeed! As wisely be it answer’d!—
Because it is uncertain, see you not?
For as I think I can discern between
The sudden flaws of a sleep-startled man,
And of the savage thing we have to dread;
If but bewilder’d, dazzled, and uncouth,
As might the sanest and the civilest
In circumstance so strange—nay, more than that,
If moved to any out-break short of blood,
All shall be well with him; and how much more,
If ’mid the magic turmoil of the change,
He shall so calm a resolution show
As scarce to reel beneath so great a blow!
But if with savage passion uncontroll’d
He lay about him like the brute foretold,
And must as suddenly be caged again;
Then what redoubled anguish and despair,
From that brief flash of blissful liberty
Remitted—and for ever—to his chain!
Which so much less, if on the stage of glory
Enter’d and exited through such a door
Of sleep as makes a dream of all between.
Est. Oh kindly answer, Sir, to question that
To charitable courtesy less wise
Might call for pardon rather! I shall now
Gladly, what, uninstructed, loyally
I should have waited.
Ast. Your Highness doubts not me,
Nor how my heart follows my cousin’s lips,
Whatever way the doubtful balance fall,
Still loyal to your bidding.
Omnes. So say all.
King. I hoped, and did expect, of all no less—
And sure no sovereign ever needed more
From all who owe him love or loyalty.
For what a strait of time I stand upon,
When to this issue not alone I bring
My son your Prince, but ev’n myself your King:
And, whichsoever way for him it turn,
Of less than little honour to myself.
For if this coming trial justify
My thus withholding from my son his right,
Is not the judge himself justified in
The father’s shame? And if the judge proved wrong,
My son withholding from his right thus long,
Shame and remorse to judge and father both:
Unless remorse and shame together drown’d
In having what I flung for worthless found.
But come—already weary with your travel,
And ill refresh’d by this strange history,
Until the hours that draw the sun from heaven
Unite us at the customary board,
Each to his several chamber: you to rest;
I to contrive with old Clotaldo best
The method of a stranger thing than old
Time has as yet among his records told.
[Exeunt.
 ACT II

Scene I.—A Throne-room in the Palace. Music within.

Enter King and Clotaldo, meeting a Lord in waiting.

 King. You, for a moment beckon’d from your office,
Tell me thus far how goes it. In due time
The potion left him?
Lord. At the very hour
To which your Highness temper’d it. Yet not
So wholly but some lingering mist still hung
About his dawning senses—which to clear,
We fill’d and handed him a morning drink
With sleep’s specific antidote suffused;
And while with princely raiment we invested
What nature surely modell’d for a Prince—
All but the sword—as you directed—
King. Ay—
Lord. If not too loudly, yet emphatically
Still with the title of a Prince address’d him.
King. How bore he that?
Lord. With all the rest, my liege,
I will not say so like one in a dream
As one himself misdoubting that he dream’d.
King. So far so well, Clotaldo, either way,
And best of all if tow’rd the worse I dread.
But yet no violence?—
Lord. At most, impatience;
Wearied perhaps with importunities
We yet were bound to offer.
King. Oh, Clotaldo!
Though thus far well, yet would myself had drunk
The potion he revives from! such suspense
Crowds all the pulses of life’s residue
Into the present moment; and, I think,
Whichever way the trembling scale may turn,
Will leave the crown of Poland for some one
T it l th th tti !
To wait no longer than the setting sun!
Clo. Courage, my liege! The curtain is undrawn,
And each must play his part out manfully,
Leaving the rest to heaven.
King. Whose written words
If I should misinterpret or transgress!
But as you say—
(To the Lord, who exit.) You, back to him at once;
Clotaldo, you, when he is somewhat used
To the new world of which they call him Prince,
Where place and face, and all, is strange to him,
With your known features and familiar garb
Shall then, as chorus to the scene, accost him,
And by such earnest of that old and too
Familiar world, assure him of the new.
Last in the strange procession, I myself
Will by one full and last development
Complete the plot for that catastrophe
That he must put to all; God grant it be
The crown of Poland on his brows!—Hark! hark!—
Was that his voice within?—Now louder—Oh,
Clotaldo, what! so soon begun to roar!—
Again! above the music—But betide
What may, until the moment, we must hide.
[Exeunt King and Clotaldo.

Segismund (within). Forbear! I stifle with your perfume! cease

Your crazy salutations! peace, I say—
Begone, or let me go, ere I go mad
With all this babble, mummery, and glare,
For I am growing dangerous—Air! room! air!—

[He rushes in. Music ceases.

Oh but to save the reeling brain from wreck
With its bewilder’d senses!—

[He covers his eyes for a while.

 What! Ev’n now
That Babel left behind me, but my eyes
Pursued by the same glamour, that—unless
Alike bewitch’d too—the confederate sense
Vouches for palpable: bright-shining floors
That ring hard answer back to the stamp’d heel,
And shoot up airy columns marble-cold,
That, as they climb, break into golden leaf
And capital, till they embrace aloft
In clustering flower and fruitage over walls
Hung with such purple curtain as the West
Fringes with such a gold; or over-laid
With sanguine-glowing semblances of men,
Each in his all but living action busied,
Or from the wall they look from, with fix’d eyes
Pursuing me; and one most strange of all
That, as I pass’d the crystal on the wall,
Look’d from it—left it—and as I return,
Returns, and looks me face to face again—
Unless some false reflection of my brain,
The outward semblance of myself—Myself?
How know that tawdry shadow for myself,
But that it moves as I move; lifts his hand
With mine; each motion echoing so close
The immediate suggestion of the will
In which myself I recognize—Myself!—
What, this fantastic Segismund the same
Who last night, as for all his nights before,
Lay down to sleep in wolf-skin on the ground
In a black turret which the wolf howl’d round,
And woke again upon a golden bed,
Round which as clouds about a rising sun,
In scarce less glittering caparison,
Gather’d gay shapes that, underneath a breeze
Of music, handed him upon their knees
The wine of heaven in a cup of gold
The wine of heaven in a cup of gold,
And still in soft melodious under-song
Hailing me Prince of Poland!—‘Segismund,’
They said, ‘Our Prince! The Prince of Poland!’ and
Again, ‘Oh, welcome, welcome, to his own,
Our own Prince Segismund—’
Oh, but a blast—
One blast of the rough mountain air! one look
At the grim features—— (He goes to the window)
What they disvizor’d also! shatter’d chaos
Cast into stately shape and masonry,
Between whose channel’d and perspective sides
Compact with rooted towers, and flourishing
To heaven with gilded pinnacle and spire,
Flows the live current ever to and fro
With open aspect and free step!—Clotaldo!
Clotaldo!—calling as one scarce dares call
For him who suddenly might break the spell
One fears to walk without him—Why, that I,
With unencumber’d step as any there,
Go stumbling through my glory—feeling for
That iron leading-string—ay, for myself—
For that fast-anchor’d self of yesterday,
Of yesterday, and all my life before,
Ere drifted clean from self-identity
Upon the fluctuation of to-day’s
Mad whirling circumstance!—And, fool, why not?
If reason, sense, and self-identity
Obliterated from a worn-out brain,
Art thou not maddest striving to be sane,
And catching at that Self of yesterday
That, like a leper’s rags, best flung away!
Or if not mad, then dreaming—dreaming?—well—
Dreaming then—Or, if self to self be true,
Not mock’d by that, but as poor souls have been
By those who wrong’d them, to give wrong new relish?
Or have those stars indeed they told me of