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Principles of Organic Chemistry
This page intentionally left blank
Principles of Organic Chemistry

Robert J. Ouellette
Professor Emeritus
Department of Chemistry
The Ohio State University

J. David Rawn
Professor Emeritus
Department of Chemistry
Towson University

AMSTERDAM • BOSTON • HEIDELBERG • LONDON • NEW YORK • OXFORD

PARIS • SAN DIEGO • SAN FRANCISCO • SINGAPORE • SYDNEY • TOKYO
Elsevier
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 Table of Contents
CHAPTER 1 STRUCTURE OF ORGANIC COMPOUNDS 1
1.1 ORGANIC AND INORGANIC COMPOUNDS 1
1.2 ATOMIC STRUCTURE 1
1.3 TYPES OF BONDS 4
1.4 FORMAL CHARGE 7
1.5 RESONANCE STRUCTURES 8
1.6 PREDICTING THE SHAPES OF SIMPLE MOLECULES 10
1.7 ORBITALS AND MOLECULAR SHAPES 11
1.8 FUNCTIONAL GROUPS 15
1.9 STRUCTURAL FORMULAS 18
1.10 ISOMERS 23
1.11 NOMENCLATURE 25
EXERCISES 27

CHAPTER 2 PROPERTIES OF ORGANIC COMPOUNDS 33

2.1 STRUCTURE AND PHYSICAL PROPERTIES 33
2.2 CHEMICAL REACTIONS 38
2.3 ACID-BASE REACTIONS 39
2.4 OXIDATION-REDUCTION REACTIONS 41
2.5 CLASSIFICATION OF ORGANIC REACTIONS 44
2.6 CHEMICAL EQUILIBRIUM AND EQUILIBRIUM CONSTANTS 45
2.7 EQUILIBRIA IN ACID-BASE REACTIONS 47
2.8 EFFECT OF STRUCTURE ON ACIDITY 49
2.9 INTRODUCTION TO REACTION MECHANISMS 51
2.10 REACTION RATES 54
EXERCISES 58

CHAPTER 3 ALKANES AND CYCLOALKANES 65

3.1 CLASSES OF HYDROCARBONS 65
3.2 ALKANES 65
3.3 NOMENCLATURE OF ALKANES 68
3.4 CONFORMATIONS OF ALKANES 72
3.5 CYCLOALKANES 75
3.6 CONFORMATIONS OF CYCLOALKANES 78
3.7 PHYSICAL PROPERTIES OF ALKANES 81
3.8 OXIDATION OF ALKANES AND CYCLOALKANES 83
3.9 HALOGENATION OF SATURATED ALKANES 84

v
 3.10 NOMENCLATURE OF HALOALKANES 87
SUMMARY OF REACTIONS 89
EXERCISES 90

CHAPTER 4 ALKENES AND ALKYNES 95

4.1 UNSATURATED HYDROCARBONS 95
4.2 GEOMETRIC ISOMERISM 99
4.3 E,Z NOMENCLATURE OF GEOMETRICAL ISOMERS 101
4.4 NOMENCLATURE OF ALKENES AND ALKYNES 103
4.5 ACIDITY OF ALKENES AND ALKYNES 106
4.6 HYDROGENATION OF ALKENES AND ALKYNES 107
4.7 OXIDATION OF ALKENES AND ALKYNES 110
4.8 ADDITION REACTIONS OF ALKENES AND ALKYNES 111
4.9 MECHANISM OF ADDITION REACTIONS 113
4.10 HYDRATION OF ALKENES AND ALKYNES 115
4.11 PREPARATION OF ALKENES AND ALKYNES 116
4.12 ALKADIENES (DIENES) 119
4.13 TERPENES 120
SUMMARY OF REACTIONS 124
EXERCISES 126

CHAPTER 5 AROMATIC COMPOUNDS 133

5.1 AROMATIC COMPOUNDS 133
5.2 AROMATICITY 134
5.3 NOMENCLATURE OF AROMATIC COMPOUNDS 137
5.4 ELECTROPHILIC AROMATIC SUBSTITUTION 139
5.5 STRUCTURAL EFFECTS IN ELECTROPHILIC AROMATIC SUBSTITUTION 143
5.6 INTERPRETATION OF RATE EFFECTS 145
5.7 INTERPRETATION OF DIRECTING EFFECTS 148
5.8 REACTIONS OF SIDE CHAINS 150
5.9 FUNCTIONAL GROUP MODIFICATION 152
5.10 SYNTHESIS OF SUBSTITUTED AROMATIC COMPOUNDS 154
SUMMARY OF REACTIONS 156
EXERCISES 158

CHAPTER 6 STEREOCHEMISTRY 163

6.1 CONFIGURATION OF MOLECULES 163
6.2 MIRROR IMAGES AND CHIRALITY 163
6.3 OPTICAL ACTIVITY 167

vi
6.4 FISCHER PROJECTION FORMULAS 168
6.5 ABSOLUTE CONFIGURATION 170
6.6 MOLECULES WITH MULTIPLE STEREOGENIC CENTERS 173
6.7 SYNTHESIS OF STEREOISOMERS 178
6.8 REACTIONS THAT PRODUCE STEREOGENIC CENTERS 179
6.9 REACTIONS THAT FORM DIASTEREOMERS 182
EXERCISES 184

CHAPTER 7 NUCLEOPHILIC SUBSTITUTION

AND ELIMINATION REACTIONS 189
7.1 REACTION MECHANISMS AND HALOALKANES 189
7.2 NUCLEOPHILIC SUBSTITUTION REACTIONS 192
7.3 NUCLEOPHILICITY VERSUS BASICITY 194
7.4 MECHANISMS OF SUBSTITUTION REACTIONS 197
7.5 SN2 VERSUS SN1 REACTIONS 200
7.6 MECHANISMS OF ELIMINATION REACTIONS 201
7.7 EFFECT OF STRUCTURE ON COMPETING REACTIONS 203
SUMMARY OF REACTIONS 206
EXERCISES 206

CHAPTER 8 ALCOHOLS AND PHENOLS 209

8.1 THE HYDROXYL GROUP 209
8.2 PHYSICAL PROPERTIES OF ALCOHOLS 212
8.3 ACID-BASE REACTIONS OF ALCOHOLS 214
8.4 SUBSTITUTION REACTIONS OF ALCOHOLS 215
8.5 DEHYDRATION OF ALCOHOLS 216
8.6 OXIDATION OF ALCOHOLS 218
8.7 SYNTHESIS OF ALCOHOLS 221
8.8 PHENOLS 226
8.9 SULFUR COMPOUNDS: THIOLS AND THIOETHERS 229
SUMMARY OF REACTIONS 231
EXERCISES 232

CHAPTER 9 ETHERS AND EPOXIDES 239

9.1 STRUCTURE OF ETHERS 239
9.2 NOMENCLATURE OF ETHERS 240
9.3 PHYSICAL PROPERTIES OF ETHERS 241
9.4 THE GRIGNARD REAGENT AND ETHERS 242
9.5 SYNTHESIS OF ETHERS 244

vii
 9.6 REACTIONS OF ETHERS 245
9.7 SYNTHESIS OF EPOXIDES 246
9.8 REACTIONS OF EPOXIDES 246
SUMMARY OF REACTIONS 254
EXERCISES 255

CHAPTER 10 ALDEHYDES AND KETONES 259

10.1 THE CARBONYL GROUP 259
10.2 NOMENCLATURE OF ALDEHYDES AND KETONES 261
10.3 PHYSICAL PROPERTIES OF ALDEHYDES AND KETONES 263
10.4 OXIDATION-REDUCTION REACTIONS OF CARBONYL COMPOUNDS 265
10.5 ADDITION REACTIONS OF CARBONYL COMPOUNDS 267
10.6 SYNTHESIS OF ALCOHOLS FROM CARBONYL COMPOUNDS 269
10.7 ADDITION REACTIONS OF OXYGEN COMPOUNDS 272
10.8 FORMATION OF ACETALS AND KETALS 274
10.9 ADDITION OF NITROGEN COMPOUNDS 275
10.10 REACTIVITY OF THE a-CARBON ATOM 278
10.11 THE ALDOL CONDENSATION 279
SUMMARY OF REACTIONS 282
EXERCISES 284

CHAPTER 11 CARBOXYLIC ACIDS AND ESTERS 287

11.1 CARBOXYLIC ACIDS AND ACYL GROUPS 287
11.2 NOMENCLATURE OF CARBOXYLIC ACIDS 289
11.3 PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS 292
11.4 ACIDITY OF CARBOXYLIC ACIDS 294
11.5 SYNTHESIS OF CARBOXYLIC ACIDS 297
11.6 NUCLEOPHILIC ACYL SUBSTITUTION 300
11.7 REDUCTION OF ACYL DERIVATIVES 304
11.8 ESTERS AND ANHYDRIDES OF PHOSPHORIC ACID 305
11.9 THE CLAISEN CONDENSATION 308
SUMMARY OF REACTIONS 309
EXERCISES 311

CHAPTER 12 AMINES AND AMIDES 315

12.1 ORGANIC NITROGEN COMPOUNDS 315
12.2 BONDING AND STRUCTURE OF AMINES 316
12.3 STRUCTURE AND CLASSIFICATION OF AMINES AND AMIDES 317
12.4 NOMENCLATURE OF AMINES AND AMIDES 319

viii
12.5 PHYSICAL PROPERTIES OF AMINES 322
12.6 BASICITY OF NITROGEN COMPOUNDS 325
12.7 SOLUBILITY OF AMMONIUM SALTS 328
12.8 NUCLEOPHILIC REACTIONS OF AMINES 328
12.9 SYNTHESIS OF AMINES 331
12.10 HYDROLYSIS OF AMIDES 333
12.11 SYNTHESIS OF AMIDES 334
SUMMARY OF REACTIONS 334
EXERCISES 336

CHAPTER 13 CARBOHYDRATES 343

13.1 CLASSIFICATION OF CARBOHYDRATES 343
13.2 CHIRALITY OF CARBOHYDRATES 344
13.3 HEMIACETALS AND HEMIKETALS 349
13.4 CONFORMATIONS OF MONOSACCHARIDES 353
13.5 REDUCTION OF MONOSACCHARIDES 354
13.6 OXIDATION OF MONOSACCHARIDES 354
13.7 GLYCOSIDES 356
13.8 DISACCHARIDES 358
13.9 POLYSACCHARIDES 362
SUMMARY OF REACTIONS 365
EXERCISES 366

CHAPTER 14 AMINO ACIDS, PEPTIDES, AND PROTEINS 371

14.1 PROTEINS AND POLYPEPTIDES 371
14.2 AMINO ACIDS 371
14.3 ACID-BASE PROPERTIES OF α-AMINO ACIDS 372
14.4 ISOIONIC POINT 376
14.5 PEPTIDES 377
14.6 PEPTIDE SYNTHESIS 380
14.7 DETERMINATION OF PROTEIN STRUCTURE 382
14.8 PROTEIN STRUCTURE 386
EXERCISES 393

CHAPTER 15 SYNTHETIC POLYMERS 397

15.1 NATURAL AND SYNTHETIC MACROMOLECULES 397
15.2 STRUCTURE AND PROPERTIES OF POLYMERS 397
15.3 CLASSIFICATION OF POLYMERS 399
15.4 METHODS OF POLYMERIZATION 401

ix
 15.5 ADDITION POLYMERIZATION 404
15.6 COPOLYMERIZATION OF ALKENES 405
15.7 CROSS-LINKED POLYMERS 406
15.8 STEREOCHEMISTRY OF ADDITION POLYMERIZATION 408
15.9 CONDENSATION POLYMERS 410
15.10 POLYESTERS 411
15.11 POLYCARBONATES 413
15.12 POLYAMIDES 414
15.13 POLYURETHANES 415
EXERCISES 416

CHAPTER 16 SPECTROSCOPY 421

16.1 SPECTROSCOPIC STRUCTURE DETERMINATION 421
16.2 SPECTROSCOPIC PRINCIPLES 422
16.3 ULTRAVIOLET SPECTROSCOPY 424
16.4 INFRARED SPECTROSCOPY 425
16.5 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 431
16.6 SPIN-SPIN SPLITTING 435
16.7 13
C NMR SPECTROSCOPY 439
EXERCISES 442

Solutions to In-Chapter Problems 447

Index 477

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x
1 Structure
of
Organic Compounds

1.1 ORGANIC AND Organic chemistry began to emerge as a science about 200 years ago. By the late eighteenth cen-
INORGANIC COMPOUNDS tury, substances were divided into two classes called inorganic and organic compounds. Inorganic
compounds were derived from mineral sources, whereas organic compounds were obtained only
from plants or animals. Organic compounds were more difficult to work with in the laboratory, and
decomposed more easily, than inorganic compounds. The differences between inorganic and organic
compounds were attributed to a “vital force” associated with organic compounds. This unusual attri-
bute was thought to exist only in living matter. It was believed that without the vital force, organic
compounds could not be synthesized in the laboratory. However, by the mid-nineteenth century,
chemists had learned both how to work with organic compounds and how to synthesize them.
Organic compounds always contain carbon and a limited number of other elements, such as hy-
drogen, oxygen, and nitrogen. Compounds containing sulfur, phosphorus, and halogens are known
but are less prevalent. Most organic compounds contain many more atoms per structural unit than
inorganic compounds and have more complex structures. Common examples of organic compounds
include the sugar sucrose (C12H22O11), vitamin B2 (C117H120N4O6), cholesterol (C27H46O), and the
fat glycerol tripalmitate (C51H98O6). Some organic molecules are gigantic. DNA, which stores genet-
ic information, has molecular weights that range from 3 million in Escherichia coli to 2 billion for
mammals.
Based on the physical characteristics of compounds, such as solubility, melting point, and boil-
ing point, chemists have proposed that the atoms of the elements are bonded in compounds in two
principal ways—ionic bonds and covalent bonds. Both types of bonds result from a change in the
electronic structure of atoms as they associate with each other. Thus, the number and type of bonds
formed and the resultant shape of the molecule depend on the electron configuration of the atoms.
Therefore, we will review some of the electronic features of atoms and the periodic properties of the
elements before describing the structures of organic compounds.

1.2 ATOMIC STRUCTURE Each atom has a central, small, dense nucleus that contains protons and neutrons; electrons are
located outside the nucleus. Protons have a +1 charge; electrons have a −1 charge. The number of
protons, which determines the identity of an atom, is given as its atomic number. Since atoms
have an equal number of protons and electrons and are electrically neutral, the atomic number also
indicates the number of electrons in the atom. The number of electrons in the hydrogen, carbon,
nitrogen, and oxygen atoms are one, six, seven, and eight, respectively.
The periodic table of the elements is arranged by atomic number. The elements are arrayed in
horizontal rows called periods and vertical columns called groups. In this text, we will emphasize
hydrogen in the first period and the elements carbon, nitrogen, and oxygen in the second period.
The electronic structure of these atoms is the basis for their chemical reactivity.

Principles of Organic Chemistry. http://dx.doi.org/10.1016/B978-0-12-802444-7.00001-X

Copyright © 2015 Elsevier Inc. All rights reserved. 1
 Atomic Orbitals

Electrons around the nucleus of an atom are found in atomic orbitals. Each orbital can contain
a maximum of two electrons. The orbitals, designated by the letters s, p, d, and f, differ in energy,
shape, and orientation. We need to consider only the s and p orbitals for elements such as carbon,
oxygen, and nitrogen.
Orbitals are grouped in shells of increasing energy designated by the integers n = 1, 2, 3, 4, · · ·, n.
These integers are called principal quantum numbers. With few exceptions, we need consider only the
orbitals of the first three shells for the common elements found in organic compounds.
Each shell contains a unique number and type of orbitals. The first shell contains only one or-
bital—the s orbital. It is designated 1s. The second shell contains two types of orbitals—one s orbital
and three p orbitals.
An s orbital is a spherical region of space centered around the nucleus (Figure 1.1). The elec-
trons in a 2s orbital are higher in energy than those in a 1s orbital. The 2s orbital is larger than the
1s orbital, and its electrons on average are farther from the nucleus. The three p orbitals in a shell
are shaped like “dumbbells.” However, they have different orientations with respect to the nucleus
(Figure 1.1). The orbitals are often designated px, py, and pz to emphasize that they are mutually per-
pendicular to one another. Although the orientations of the p orbitals are different, the electrons in
each p orbital have equal energies.
Orbitals of the same type within a shell are often considered as a group called a subshell. There
is only one orbital in an s subshell. An s subshell can contain only two electrons, but a p subshell can
contain a total of six electrons within its px, py, and pz orbitals. Electrons are located in subshells of
successively higher energies so that the total energy of all electrons is as low as possible. The order of
increasing energy of subshells is 1s< 2s < 2p < 3s < 3p for elements of low atomic number. If there
is more than one orbital in a subshell, one electron occupies each with parallel spins until all are
half full. A single electron within an orbital is unpaired; two electrons with opposite spins within
an orbital are paired and constitute an electron pair. The number and location of electrons for the
first 18 elements are given in Table 1.1. The location of electrons in atomic orbitals is the electron
configuration of an atom.

Figure 1.1 z 2pz

Shapes of 2s and 2p Orbitals
Electrons are pictured within a volume
called an orbital. A “cloud” of negative
charge surrounds the nucleus, which is
x 2px
located at the origin of the intersecting
axes. (a) The s orbital is pictured as a
sphere. (b) The three orbitals of the p y 2py
subshell are arranged perpendicular to
one another. Each orbital may contain
s orbital 2p orbitals
two electrons. (c) Molecular model of a
2pz orbital. (a) (b)

(c)

2pz orbital
(molecular model)

2 Chapter 1 Structure of Organic Compounds

 Table 1.1
Electron Configurations of First and Second Period Elements
Element Atomic Number 1s 2s 2px 2py 2pz Electron Configuration
H 1 1 1s1
He 2 2 1s2
Li 3 2 1 1s2 2s1
Be 4 2 2 1s2 2s2
B 5 2 2 1(↑) 1s2 2s2 2p1
C 6 2 2 1 (↑) 1 (↑) 1s2 2s2 2p2
N 7 2 2 1 (↑) 1 (↑) 1 (↑) 1s2 2s2 2p3
O 8 2 2 2(↑↓) 1 (↑) 1 (↑) 1s2 2s2 2p4
F 9 2 2 2 (↑↓) 2 (↑↓) 1 (↑) 1s2 2s2 2p5
Ne 10 2 2 2 (↑↓) 2 (↑↓) 2 (↑↓) 1s2 2s2 2p6

Valence Shell Electrons

Electrons in filled, lower energy shells of atoms have no role in determining the structure of
molecules, nor do they participate in chemical reactions. Only the higher energy electrons located in
the outermost shell, the valence shell, participate in chemical reactions. Electrons in the valence shell
are valence electrons. For example, the single electron of the hydrogen atom is a valence electron.
The number of valence electrons for the common atoms contained in organic molecules is given by
their group number in the periodic table. Thus carbon, nitrogen, and oxygen atoms have four, five,
and six valence electrons, respectively. With this information we can understand how these elements
combine to form the structure of organic compounds.
The physical and chemical properties of an element may be estimated from its position in the
periodic table. Two principles that help us to explain the properties of organic compounds are atomic
radius and electronegativity. The overall shape of an isolated atom is spherical, and the volume of
the atom depends on the number of electrons and the energies of the electrons in occupied orbitals.
The sizes of some atoms expressed as the atomic radius, in picometers, are given in Figure 1.2. The
atomic radius for an atom does not vary significantly from one compound to another. Atomic radii
increase from top to bottom in a group of the periodic table. Each successive member of a group has
one additional energy level containing electrons located at larger distances from the nucleus. Thus,
the atomic radius of sulfur is greater than that of oxygen, and the radii of the halogens increase in
the order F < Cl < Br.
The atomic radius decreases from left to right across a period. Although electrons are located
in the same energy level within the s and p orbitals of the elements, the nuclear charge increases
from left to right within a period. As a result, the nucleus draws the electrons inward and the radius
decreases. The radii of the common elements in organic compounds are in the order C > N > 0.

Figure 1.2 H
Atomic radii in picometers, 37
pm (10-12 m) Li Be B C N O F
152 111 88 77 70 66 64
Na Mg Al Si P S Cl
186 160 143 117 110 104 99
Br
114
I
133

1.2 Atomic Structure 3

 Electronegativity

Electronegativity is a measure of the attraction of an atom for bonding electrons in molecules com-
pared to that of other atoms. The electronegativity values devised by Linus Pauling, an American
chemist, are dimensionless quantities that range from slightly less than one for the alkali metals to
a maximum of four for fluorine. Large electronegativity values indicate a stronger attraction for
electrons than small electronegativity values.
Electronegativities increase from left to right across the periodic table (Figure 1.3). Elements
on the left of the periodic table have low electronegativities and are often called electropositive ele-
ments. The order of electronegativities F > O > N > C is an important property that we will use to
explain the chemical properties of organic compounds. Electronegativities decrease from top to bot-
tom within a group of elements. The order of decreasing electronegativities F > Cl > Br > I is another
sequence that we will use to interpret the chemical and physical properties of organic compounds.

Figure 1.3 H
Electronegativity 2.1
Li Be B C N O F
1.0 1.5 2.0 2.5 3.0 3.5 4.0
Na Mg Al Si P S Cl
0.9 1.2 1.5 1.8 2.1 2.5 3.0
Br
2.8
I
2.5

1.3 TYPES OF BONDS In 1916, the American chemist G.N. Lewis proposed that second period elements tend to react
to obtain an electron configuration of eight electrons so that they electronically resemble the inert
gases. This hypothesis is summarized in the Lewis octet rule: Second period atoms tend to combine
and form bonds by transferring or sharing electrons until each atom is surrounded by eight electrons
in its highest energy shell. Note that hydrogen requires only two electrons to complete its valence
shell.
Ionic Bonds

Ionic bonds form between two or more atoms by the transfer of one or more electrons between at-
oms. Electron transfer produces negative ions called anions and positive ions called cations. These
ions attract each other.
Let’s examine the ionic bond in sodium chloride. A sodium atom, which has 11 protons and 11
electrons, has a single valence electron in its 3s subshell. A chlorine atom, which has 17 protons and
17 electrons, has seven valence electrons in its third shell, represented as 3s23p5. In forming an ionic
bond, the sodium atom, which is electropositive, loses its valence electron to chlorine. The resulting
sodium ion has the same electron configuration as neon (ls22s22p6) and has a +1 charge, because
there are 11 protons in the nucleus, but only 10 electrons about the nucleus of the ion.
The chlorine atom, which has a high electronegativity, gains an electron and is converted into
a chloride ion that has the same electron configuration as argon ( ls22s22p63s23p6). The chloride ion
has a −1 charge because there are 17 protons in the nucleus, but there are 18 electrons about the
nucleus of the ion. The formation of sodium chloride from the sodium and chlorine atoms can be
shown by Lewis structures. Lewis structures represent only the valence electrons; electron pairs are
shown as pairs of dots.

Na + Cl Na + Cl

Note that by convention, the complete octet is shown for anions formed from electronegative ele-
ments. However, the filled outer shell of cations that results from loss of electrons by electropositive
elements is not shown.

4 Chapter 1 Structure of Organic Compounds

Metals are electropositive and tend to lose electrons, whereas nonmetals are electronegative and tend
to gain electrons. A metal atom loses one or more electrons to form a cation with an octet. The same
number of electrons are accepted by the appropriate number of atoms of a nonmetal to form an octet
in the anion, producing an ionic compound. In general, ionic compounds result from combinations
of metallic elements, located on the left side of the periodic table, with nonmetals, located on the
upper right side of the periodic table.

Covalent Bonds

A covalent bond consists of the mutual sharing of one or more pairs of electrons between two atoms.
These electrons are simultaneously attracted by the two atomic nuclei. A covalent bond forms when
the difference between the electronegativities of two atoms is too small for an electron transfer to
occur to form ions. Shared electrons located in the space between the two nuclei are called bonding
electrons. The bonded pair is the “glue” that holds the atoms together in molecular units.
The hydrogen molecule is the simplest substance having a covalent bond. It forms from two
hydrogen atoms, each with one electron in a ls orbital. Both hydrogen atoms share the two electrons
in the covalent bond, and each acquires a helium-like electron configuration.

H +H H H

A similar bond forms in Cl2. The two chlorine atoms in the chlorine molecule are joined by a shared
pair of electrons. Each chlorine atom has seven valence electrons in the third energy level and requires
one more electron to form an argon-like electron configuration. Each chlorine atom contributes one
electron to the bonding pair shared by the two atoms. The remaining six valence electrons of each
chlorine atom are not involved in bonding and are concentrated around their respective atoms. These
valence electrons, customarily shown as pairs of electrons, are variously called nonbonding electrons,
lone pair electrons, or unshared electron pairs.

Cl Cl nonbonding electrons

The covalent bond is drawn as a dash in a Lewis structure to distinguish the bonding pair from the
lone pair electrons. Lewis structures show the nonbonding electrons as pairs of dots located about the
atomic symbols for the atoms. The Lewis structures of four simple organic compounds—methane,
methylamine, methanol, and chloromethane—are drawn here to show both bonding and nonbond-
ing electrons. In these compounds carbon, nitrogen, oxygen, and chlorine atoms have four, three,
two, and one bonds, respectively.

H H H H

H C H H C N H H C O H H C Cl

H H H H H
methane aminomethane methanol chloromethane

The hydrogen atom and the halogen atoms form only one covalent bond to other atoms in most
stable neutral compounds. However, the carbon, oxygen, and nitrogen atoms can simultaneously
bond to more than one atom. The number of such bonds is the valence of the atom. The valences of
carbon, nitrogen, and oxygen are four, three, and two, respectively.

Multiple Covalent Bonds

In some molecules more than one pair of electrons is shared between pairs of atom. If four electrons
(two pairs) or six electrons (three pairs) are shared, the bonds are called double and triple bonds, re-
spectively. A carbon atom can form single, double, or triple bonds with other carbon atoms as well as

1.3 Types of Bonds 5

 with atoms of some other elements. Single, double, and triple covalent bonds link two carbon atoms
in ethane, ethylene, and acetylene, respectively. Each carbon atom in these compounds shares one,
two, and three electrons, respectively, with the other. The remaining valence electrons of the carbon
atoms are contained in the single bonds with hydrogen atoms.

1 electron pair 2 electron pairs 3 electron pairs

H H H
H
H C C H C C H C C H

H H H H
ethane ethene ethyne

Polar Covalent Bonds

A polar covalent bond exists when atoms with different electronegativities share electrons in a covalent
bond. Consider the hydrogen chloride (HCl) molecule. Each atom in HCl requires one more electron
to form an inert gas electron configuration. Chlorine has a higher electronegativity than hydrogen,
but the chlorine atom’s attraction for electrons is not sufficient to remove an electron from hydrogen.
Consequently, the bonding electrons in hydrogen chloride are shared unequally in a polar covalent
bond. The molecule is represented by the conventional Lewis structure, even though the shared elec-
tron pair is associated to a larger extent with chlorine than with hydrogen. The unequal sharing of the
bonding pair results in a partial negative charge on the chlorine atom and a partial positive charge on
the hydrogen atom. The symbol d (Greek lowercase delta) denotes these fractional charges.

δ δ
H Cl

Table 1.2 The hydrogen chloride molecule has a dipole (two poles), which consists of a pair of opposite charges
Average Dipole Moments (D) separated from each other. The dipole is shown by an arrow with a cross at one end. The cross is near
Structural Unit1 Bond Moments the end of the molecule that is partially positive, and the arrowhead is near the partially negative end
(D) of the molecule.
H—C 0.4
H—N 1.3 H Cl

H—O 1.5
H—F 1.7 Single or multiple bonds between carbon atoms are nonpolar. Hydrogen and carbon have similar
H—S 0.7 electronegativity values, so the C-H bond is not normally considered a polar covalent bond. Thus
ethane, ethylene, and acetylene have nonpolar covalent bonds, and the compounds are nonpolar.
H—Cl 1.1
Bonds between carbon and other elements such as oxygen and nitrogen are polar. The polarity
H—Br 0.8 of a bond depends on the electronegativities of the bonded atoms. Large differences between the
H—I 0.4 electronegativities of the bonded atoms increase the polarity of bonds. The direction of the polarity
C—C 0.0 of common bonds found in organic molecules is easily predicted. The common nonmetals are more
electronegative than carbon. Therefore, when a carbon atom is bonded to common nonmetal atoms,
C—N 0.2
it has a partial positive charge.
C—O 0.7
C—F 1.4
C—Cl 1.5 C N C O C F C Cl
C—Br 1.4
C—I 1.2 Hydrogen is also less electronegative than the common nonmetals. Therefore, when a hydrogen atom
C=O 2.3 is bonded to common nonmetals, the resulting polar bond has a partial positive charge on the hydro-
gen atom.
C≡N 3.5
1. The more negative element is on the right.
H N H O

6 Chapter 1 Structure of Organic Compounds

 The magnitude of the polarity of a bond is the dipole moment, (D). The dipole moments of several
bond types are given in Table 1.2. The dipole moment of a specific bond is relatively constant from
compound to compound. When carbon forms multiple bonds to other elements, these bonds are
polar. Both the carbon-oxygen double bond in formaldehyde (methanal) and the carbon–nitrogen
triple bond in acetonitrile (cyanomethane) are polar.

δ-
O H
δ+ δ-
C C C N
H δ+ H
H H
methanal cyanomethane

1.4 FORMAL CHARGE Although most organic molecules are represented by Lewis structures containing the “normal” num-
ber of bonds, some organic ions and even some molecules contain less than or more than the cus-
tomary number of bonds. First let’s review the structures of some “inorganic” ions. The valence
of the oxygen atom is two—it normally forms two bonds. However, there are three bonds in the
hydronium ion and one in the hydroxide ion.

How do we predict the charge of the ions? Second, what atoms bear the charge? There is a useful
formalism for answering both of these question. Each atom is assigned a formal charge by a book-
keeping method that involves counting electrons. The method is also used for neutral molecules
that have unusual numbers of bonds. In such cases, centers of both positive and negative charge are
located at specific atoms.
The formal charge of an atom is equal to the number of its valence electrons as a free atom
minus the number of electrons that it “owns” in the Lewis structure.

number of valence
formal charge = electrons in free atom - number of valence
electrons in bonded atom

The question of ownership is decided by two simple rules. Unshared electrons belong exclusively to
the parent atom. One-half of the bonded electrons between a pair of atoms is assigned to each atom.
Thus, the total number of electrons “owned” by an atom in the Lewis structure equals the number of
nonbonding electrons plus half the number of bonding electrons. Therefore, we write the following:

H O H O

formal charge =
number of valence
electrons in free atom - number of valence
electrons in bonded atom - 1/2 number of bonded electrons

The formal charge of each atom is zero in most organic molecules. However, the formal charge may
also be negative or positive. The sum of the formal charges of each atom in a molecule equals zero;
the sum of the formal charges of each atom in an ion equals the charge of the ion. Let’s consider
the molecule hydrogen cyanide, HCN, and calculate the formal charges of the carbon and nitrogen
atoms bonded in a triple bond.
H C N lone pair electrons: assign both to nitrogen

two bonding electrons: 6 bonding electrons:

assign 1 to hydrogen assign 3 to carbon
assign 1 to carbon assign 3 to nitrogen

1.4 Formal Charge 7

 The formal charge of each atom is calculated by substitution into the formula shown below:
Formal charge of hydrogen = 1 – 0 – 1/2(2) = 0
Formal charge of carbon = 4 – 2 – 1/2(6) = −1
Formal charge of nitrogen = 5 – 0 – 1/2(8) = +1

The formal charge of carbon is −1 and the formal charge of nitrogen is +1. However, the sum of the
formal charges of these atoms equals the net charge of the species, which in this case is zero.
There are often important chemical consequences when a neutral molecule contains centers
whose formal charges are not zero. There are often important chemical consequences when a neutral
molecule contains centers whose formal charges are not zero. It is important to be able to recognize
these situations, which allow us to understand the chemical reactivity of such molecules.

1.5 RESONANCE In the Lewis structures for the molecules shown to this point, the electrons have been pictured as
STRUCTURES either between two nuclei or about a specific atom. These electrons are localized. The electronic
structures of molecules are written to be consistent with their physical properties. However, the elec-
tronic structures of some molecules cannot be represented adequately by a single Lewis structure. For
example, the Lewis structure of the acetate ion has one double bond and one single bond to oxygen
atoms. Note that the formal charge of the single-bonded oxygen atom is −1 whereas that of the dou-
ble-bonded oxygen atom is zero.

O
CH3 C
O

However, single and double bonds are known to have different bond lengths—a double bond between
two atoms is shorter than a single bond. The Lewis structure shown implies that there is one “long”
C-O bond and a “short” C=O bond in the acetate ion. But both carbon–oxygen bond lengths in
the acetate ion have been shown experimentally to be equal. Moreover, both oxygen atoms bear equal
amounts of negative charge. Therefore, the preceding Lewis structure with single and double bonds
does not accurately describe the acetate ion. Under these circumstances, the concept of resonance is
used. We say that a molecule is resonance stabilized if two or more Lewis structures can be written
that have identical arrangements of atoms but different arrangements of electrons. The real structure
of the acetate ion can be represented better as a hybrid of two Lewis structures, neither of which is
completely correct.

O O
CH3 C CH3 C
O O

A double-headed arrow between two Lewis structures indicates that the actual structure is similar in
part to the two simple structures but lies somewhere between them. The individual Lewis structures
are called contributing structures or resonance structures.
Curved arrows can be used to keep track of the electrons when writing resonance structures.
The tail of the arrow is located near the bonding or nonbonding pair of electrons to be “moved” or
“pushed,” and the arrowhead shows the “final destination” of the electron pair in the Lewis structure.

O “Pushing” electrons gives O

either of two Lewis structures
CH3 C CH3 C
O O
Structure 1 Structure 2

In resonance structure 1, the nonbonding pair of electrons on the bottom oxygen atom is moved to
form a double bond with the carbon atom. A bonding pair of electrons of the carbon–oxygen double

8 Chapter 1 Structure of Organic Compounds

bond is also moved to form a nonbonding pair of electrons on the top oxygen atom. The result is
resonance structure 2. This procedure of “pushing” electrons from one position to another is only a
bookkeeping formalism. Electrons do not really move this way! The actual ion has delocalized electrons
distributed over three atoms—a phenomenon that cannot be shown by a single Lewis structure.
Electrons can be delocalized over many atoms. For example, benzene, C6H6, consists of six equiv-
alent carbon atoms contained in a ring in which all carbon–carbon bonds are identical. Each carbon
atom is bonded to a hydrogen atom. A single Lewis structure containing alternating single and dou-
ble bonds can be written to satisfy the Lewis octet requirements.
H

H H

H H

H
benzene

However, single and double bonds have different bond lengths. In benzene, all carbon–carbon bonds
have been shown to be the same length. Like the acetate ion, benzene is represented by two con-
tributing resonance structures separated by a double-headed arrow. The positions of the alternating
single and double bonds are interchanged in the two resonance structures.
H H

H H H H

H H H H

H H
equivalent contributing structures for the resonance hybrid of benzene

The electrons in benzene are delocalized over the six carbon atoms in the ring, resulting in a unique
structure. There are no carbon–carbon single or double bonds in benzene; its bonds are of an inter-
mediate type that cannot be represented with a single structure.

Problem 1.1
Consider the structure of nitromethane, a compound used to increase the power in some specialized
race car engines. A nitrogen-oxygen single bond length is 136 pm; a nitrogen-oxygen double bond
length is 114 pm. The nitrogen-oxygen bonds in nitromethane are equal and are 122 pm. Explain.
O

CH3 N
O
Solution
The actual nitrogen–oxygen bonds are neither single nor double bonds. Two resonance forms can be
written to represent nitromethane. They result from “moving” a nonbonding pair of electrons from
the single-bonded oxygen atom to form a double bond with the nitrogen atom. One of the bonding
pairs of electrons from the nitrogen-oxygen double bond is moved to the other oxygen atom. The
structures differ only in the location of the single and double bonds.

O O
CH3 N CH3 N
O O

1.5 Resonance Structures 9

Exploring the Variety of Random
Documents with Different Content
—
"No, I will not go on. Do you suppose I have been thinking of
myself? Take back your order. There is no obedience due to a sinful
command, and this command is sinful. It is wicked, it is mad, it is
abominable. You are asking me to commit murder—that's it—murder
—and I will not commit it. There's your order—take it back and
damn it!"
So saying, he crushed the paper in his hands and flung it on the
desk.
At the next instant everybody in the room had risen. There was
consternation on every face, and the General, who was choking with
anger, was saying in a half-stifled voice—
"You are no fool—you know what you have done now. You have
not only refused to obey orders—you have insulted your General and
been guilty of deliberate insubordination. Therefore you are
unworthy of bearing arms—give me your sword."
Gordon hesitated for a moment, and the General said—
"Give it me—give it me."
Then with a rapid gesture Gordon unbuckled his sword from the
belt and handed it to the General.
The General held it in both his hands, which were vibrating like
the parts of an engine from the moving power within, while he said,
in the same half-stifled voice as before—
"You have had the greatest opportunity that ever came to an
English soldier and—thrown it away. You have humiliated your father,
outraged the love of your intended wife, and insulted England.
Therefore you are a traitor!"
 Gordon quivered visibly at that word, and seeing this, the
General hurled it at him again.
"A traitor, I say. A traitor who has consorted with the enemies of
his country." With that he drew the sword from its scabbard, broke it
across his knee, and flung the fragments at Gordon's feet.
Helena turned and fled from the room in agony at the harrowing
scene, and the Consul-General, unable to bear the sight of it, rose
and walked to the window, his face broken up with pain as no one
had ever seen it before.
Then the General, who had been worked up to a towering rage
by his own words and acts, lost himself utterly, and saying—
"You are unfit to wear the decorations of an English soldier. Take
them off, take them off!" he laid hold of Gordon's medals—the
Distinguished Service Order, the South African Medal with its four
clasps, the British Soudan Medal, the Medjidieh, and the Khedive's
star—and tore them from his tunic, ripping pieces of the cloth away
with them, and threw them on the ground.
Then in a voice like the scream of a wild bird, he cried—
"Now go! Go back to your quarters and consider yourself under
arrest. Or take my advice and be off altogether. Quit the army you
have dishonoured and the friends you have disgraced and hide your
infamous conduct in some foreign land. Leave the room at once!"
Gordon had stood through this gross indignity bolt upright and
without speaking. His face had become deadly white and his
colourless lower lip had trembled. At the end, while the old General
was taking gusts of breath, he tried to say something, but his
tongue refused to speak. At length he staggered rather than walked
to the door, and with his hand on the handle he turned and said
quietly, but in a voice which his father never forgot—
"General, the time may come when it will be even more painful
to you to remember all this than it has been to me to bear it."
Then he stumbled out of the room.
 CHAPTER XXIV

Out in the hall he had an impulse to turn towards Helena's room on

the right, but through his half-blind eyes he saw Helena herself on
the left, standing by the open entrance to the garden, with her
handkerchief at her mouth.
"Helena!"
She made a little nervous cry, but stifling it in her throat she
turned hotly round on him.
"You told me that love was above everything," she said, "and
this is how you love me!"
Torn as he was to his heart's core, outraged as he believed
himself to be, he made a feeble effort to excuse himself.
"I couldn't help it, Helena,—it was impossible for me to act
otherwise."
"Oh, I know! I know!" she said. "You were doing what you
thought to be right. But I am no match for you. You have duties that
are higher than your duty to me."
Her tone cut him to the quick, and he tried to speak but could
not. Like a drowning man he stretched out his hand to her, but she
made no response.
He stretched out his hand to her, but she
made no response
 "It was not to be, I see that now," she said, while her eyes filled
and her bosom heaved. "I am not worthy of you. But I loved you
and I thought you loved me, and I believed you when you told me
that nothing could come between us."
Again he tried to speak, to explain, to protest, but his tongue
would not utter a sound.
"If you had really loved me you would have been ready to ...
even to.... But I was mistaken and I am punished, and this is how it
is to end!"
"Helena, for God's sake—" he began, but he could bear no
more. He did not see that the girl's love was fighting with her pride.
The hideous injustice of it all was working like madness in his brain,
and after a moment he turned to go.
As he walked across the garden the ground under his feet
sounded hollow in his ears like the ground above a new-covered
grave. When he reached the gate he thought he heard Helena
calling in a pleading, sobbing voice—
"Gordon!"
But when he turned to look back she had disappeared. Then
bareheaded, without helmet or sword, with every badge of rank and
honour gone, he pulled the gate open and staggered into the
square.

CHAPTER XXV
Helena returned to her father's room, and found the two old men
getting ready to go. In the Pasha's face there were traces of that
impulse to smile which comes to shallow natures in the presence of
another person's troubles. But the face of the Consul-General was a
tragic sight. The square-set jaw hung low, and the eyes were heavy
as with unshed tears. It was easy to see that the iron man was
deeply moved—that the depths of his ice-bound soul were utterly
broken up.
Only in short, disjointed sentences did he speak at all. It was
about his enemies—the corrupt, cruel, and hypocritical upholders of
the old dark ways. They had bided their time; they had taken their
revenge; they had hit him at last where he could least bear a blow;
they had struck him in the face with the hand of his only son.
"There is no shame left in them," he said, and then he turned to
Helena as if intending to say some word of sympathy. He wanted to
tell her that he had hoped for other things, and would have been
happy if they had come to pass. But when he saw the girl standing
before him with her red eyes and pale cheeks, he hesitated, grasped
her hand, held it for a moment, and then walked away without a
word.
The Military Secretary accompanied the Consul-General and the
Pasha to their carriages, and so father and daughter were left
together. The General, labouring under the most painful of all
senses, the sense of having done an unworthy thing, walked for
some minutes about the room, and talked excitedly, while Helena sat
on the sofa in silence, and, resting her chin on her hand, looked
fixedly before her.
 "Well, well, it's all over, thank God! It couldn't be helped, either!
It had to be! Better as it is, too, than if it had come later on.... How
hot I am! My throat is like fire. Get me a drink of water, girl."
"Let me give you your medicine, father. It's here on the desk,"
said Helena.
"No, no! Water, girl, water! That's right! There! ... He has gone,
I suppose? Has he gone? Yes? Good thing too! Hope I'll never see
him again! I never will—never! ... How my head aches! No wonder
either!"
"You're ill, father—let me run for the doctor."
"Certainly not. I'm all right. Sit down, girl. Sit down and don't
worry.... You mustn't mind me. I'm a bit put out—naturally! It's hard
for you, I know, but don't cry, Helena!"
"I'm not crying, father—you see I'm not."
"That's right! That's right, dear! It's hard for you, I say, but then
it isn't easy for me either. I liked him. I did, I confess it. I really liked
him, and to ... to do that was like cutting off one's own son. But ...
give me another drink of water, Helena ... or perhaps if you think
you ought to run ... no, give me the medicine and I'll be better
presently."
She poured out a dose and he drank it off.
"Now I'll lie down and close my eyes. I soon get better when I
lie down and close my eyes, you know. And don't fret, dear. Think
what an escape you've had! Merciful heavens! A traitor! Think if you
had married a traitor! A man who had sold himself to the enemies of
England! I was proud of you when you showed him that—come
what would—you must stand by your country. Splendid! Just what I
expected of you, Helena! Splendid!"
 After a while his excited speech and gusty breathing softened
down to silence and to something like sleep, and then Helena sat on
a stool beside the sofa and covered her face with her hands. A hot
flush mounted to her pale cheeks when she remembered that it had
not been for England that she had acted as she had, but first for her
father and next for herself.
Perhaps she ought to have told Gordon why she could not leave
her father. If she had done so he might have acted otherwise. But
the real author of the whole trouble had been the Egyptian. How she
hated that man! With all the bitterness of her tortured heart she
hated him!
As for Gordon, traitor or no traitor, he had been above them all!
Far, far above everybody! Even the Consul-General, now she came to
think of it, had been a little man compared with his son.
With her face buried in both hands and the tears at last trickling
through her fingers, she saw everything over again, and one thing
above all—Gordon standing in silence while her father insulted and
degraded him.
The General opened his eyes, and seeing Helena at his feet he
tried to comfort her, but every word he spoke went like iron into her
soul.
"I'm sorry for you, Helena—very sorry! We must bear this
trouble together, dear. Only ourselves again now, you know, just as
it was five years ago at home. Your dark hour, this time, darling, but
I'll make it up to you. Come, kiss me, Helena," and, drying her
weary eyes, she kissed him.
The afternoon sun was then reddening the alabaster walls of
the mosque outside, and they heard a surging sound as of a crowd
approaching. A moment later little black Mosie ran in to say that the
new Mahdi was coming, and almost before the General and Helena
could rise to their feet a tall man in white Oriental costume entered
the room. He came in slowly, solemnly, and with head bent, saying—
"Excuse me, sir, if I come without ceremony."
"Ishmael Ameer?" asked the General.
"My name is Ishmael—you are the Commander of the British
forces. May I speak with you alone?"
The General stood still for a moment, measuring his man from
head to foot, and then said—
"Leave us, Helena."
Helena hesitated, and the General said, "I'm better now—leave
us."
With that she went out reluctantly, turning at the door to look at
her enemy, who stood in his great height in the middle of the floor
and never so much as glanced in her direction.

CHAPTER XXVI

Both men continued to stand during the interview that followed—the

one in his white robes by the end of the sofa, resting two tapering
fingers upon it, the other in his General's uniform by the side of the
desk, except when in the heat of his anger he strode with heavy
step and the jingling of spurs across the space between.
"Now, sir, now," said the General. "I have urgent work to do,
and not much time to give you. What is it?"
 "I come," said Ishmael, who was outwardly very calm, though
his large black eyes were full of fire and light, "I come to speak to
you about the order to close El Azhar."
"Then you come to the wrong place," said the General sharply.
"You should go to the Agency—the British Agency."
"I have seen the English lord already. He refuses to withdraw his
order. Therefore I am here to ask you—forgive me—I am here to ask
you not to obey it."
The General tried to laugh. "Wonderful!" he said. "Your Eastern
ideas of discipline are wonderful! Please understand, sir, I am here
as the instrument of authority—that and that only."
"An instrument has its responsibility," said Ishmael. "If there
were no instruments to do evil deeds would evil deeds be done? It is
not your fault, sir, that the order has been issued, but it will be your
fault if it is carried into effect."
"Really!" said the General, again trying to laugh. "Permit me to
tell you, sir, that in this case there will be no fault in question,
neither of mine nor anybody else's. El Azhar is a hotbed of sedition,
and it is high time the Government cleared it out."
"El Azhar," said Ishmael, "is the heart of the Moslem faith. Take
their religion away from them and the Moslems have nothing left.
You are a Christian, and when your great Master was on earth He
fed the souls of the people first."
"Yes, and He whipped the rascals out of the temple, and that's
what the Government is going to do now—to drive out the
pretentious impostors who are putting a lying spirit into the mouth
of the people and making it impossible to govern them."
 The Egyptian showed no anger. "I am here only to plead for the
people, sir. Do not harden your heart against them. Do not send
armed men among an unarmed populace. It will be slaughter."
"Tell them to submit to the Government and there will be no
harm done to any one. It's their duty, isn't it? Whatever the
Government may be, isn't it their duty to submit to it?"
"Yes," said Ishmael. "We who are Moslems are taught by the
Prophet (blessed be his name!) that even if a negro slave is
appointed to rule over us we ought to obey him."
"Deuce take it, sir, what do you mean by that?" said the
General.
"But Government is a trust from God," said the Egyptian, "and
at the Day of Resurrection the Most High will ask you what you have
done to His children."
"Damn it, sir, have you come here to preach me a sermon?"
"I have come to plead with you for justice—the justice you look
for from your Saviour. 'Be merciful to the weak,' He taught, and it is
for the weak I appeal to you. He was meek and lowly—will you
forget His precepts? 'Love one another'—will you make strife
between man and man? He is dead—shall it be said that His spirit
has died out among those who call Him their Redeemer?"
The General brought his fist heavily down on the desk as if to
command silence.
"Listen here, sir," he said. "If you imagine for one moment that
this tall talk will have any effect upon me, let me advise you to drop
it. Being a plain soldier who has received a plain command, I shall
take whatever military steps are necessary to see it faithfully carried
out, and if the precious leaders of the people, playing on their
credulity and fanaticism, should instigate rebellion, I shall have the
honour—understand me plainly—I shall have the honour to lodge
them in safe quarters, whosoever they are and whatsoever their
pretensions may be."
The Egyptian's eyes showed at that moment that he was a man
capable of wild frenzy, but he controlled himself and answered—
"I am not here to defend myself, sir. You can take me now if you
choose to do so. But if I cannot plead with you for the people let me
plead with you for yourself—your family."
The General, who had turned away from Ishmael, swung round
on him.
"My family?"
"He that troubleth his own house, saith the Koran, shall inherit
the wind. Will you, my brother, allow your daughter to be separated
from the brave man who loves her? A woman is tender and sweet;
all she wants is love; and love is a sacred thing, sir. Your daughter is
your flesh and blood—will you make her unhappy? I see a day when
you are dead—will it comfort you in the grave that two who should
be together are apart?"
"They're apart already, so that's over and done with," said the
General. "But listen to me again, sir. My girl needs none of your pity.
She has done her duty as a soldier's daughter, and cut off the traitor
whom you, and men like you, appear to have corrupted. Look here—
and here," he cried, pointing to the broken sword and the medals
which were still lying where he had flung them on the floor. "The
man has gone—gone in disgrace and shame. That's what you've
done for him, if it's any satisfaction to you to know it. As for my
daughter," he said, raising his voice in his gathering wrath and
striding up to Ishmael with heavy steps and the jingling of his spurs,
"As for my daughter, Helena, I will ask you to be so good as to keep
her name out of it—do you hear? Keep her name out of it, or else
——"
 "Look here—and here," he cried, pointing to the
broken sword

At that moment the men heard the door open and a woman's
light footsteps behind them. It was Helena coming into the room.
"Did you call me, father?" she asked.
"No; go back immediately."
She looked doubtfully at the two men, who were now face to
face as if in the act of personal quarrel, hesitated, seemed about to
speak, and then, went out slowly.
There was silence for a moment after she was gone, and then
Ishmael said—
"Do I understand you to say, sir, that Colonel Lord has gone in
disgrace?"
"Yes, for consorting with the enemies of his country and
refusing to obey the order of his General."
"Lost his place and rank as a soldier?"
"Soon will, and then he will be alone and have you to thank for
it."
The Egyptian drew himself up to his full height and answered,
"You are wrong, sir. He who has no one has God, and if that brave
man has suffered rather than do an evil act, will God forget him?
No!"
"God will do as He thinks best without considering either you or
me, sir," said the General. "But I have something to do and I will ask
you to leave me.... Or wait one moment! Lest you should carry away
the impression that because Colonel Lord has refused to obey his
General's order the order will not be obeyed—wait and see."
He touched the bell and called for his Aide-de-camp.
"Tell Colonel Macdonald to come to me immediately," said the
General, and when the Aide-de-camp had gone he turned to his
desk for papers.
The Egyptian, who had never moved from his place by the sofa,
now took one step forward and said in a low, quivering voice—
"General, I have appealed to you on behalf of my people and on
your own behalf, but there is one thing more."
"What is it?"
"Your country."
The General made an impatient gesture, and the Egyptian said,
"Hear me, I beg, I pray! Real as life, real as death, real as wells of
water in a desert place, is their religion to the Muslemeen, and if you
lay so much as your finger upon it your Government will die."
He raised his hand and with one trembling finger pointed
upwards. "Do you think your swords will govern them? What can
your swords do to their souls? By the Most High God I swear to you
that I have only to speak the word and the rule of England in Egypt
will end."
At that moment Colonel Macdonald, a large man in khaki, a
Highlander, with a ruddy face and a glass in his left eye, opened the
door and stood by it, while the General, whose own face was scarlet
with anger, said—
"So! So that's how you talked to Colonel Lord, I presume—how
you darkened the poor devil's understanding! Now see—see what
effect your threats have upon me. Step forward, Colonel
Macdonald."
The Colonel saluted and stepped up to the General, who
repeated to him word for word the order he had given to Gordon,
and then said—
"You will arrest all who resist you, and if any resist with violence
you will compel obedience—you understand?"
"Perfectly," said the Colonel, and saluting again he left the
room.
"Now, sir, you can go," said the General to Ishmael, whereupon
the Egyptian, whose face had taken on an extreme pallor, replied—
"Very well! I have warned you and you will not hear me. But I
tell you that at this moment Israfil has the trumpet to his mouth and
is only waiting for God's order to blow it! I tell you, too, that I see
you—you—on the Day of Judgment, and there are black marks on
your face."
"Silence, sir!" said the General, bringing his clenched fist heavily
down on the desk. Then he struck the bell, and in a choking voice
called first for his servant and afterwards for his Aide-de-camp.
"Robson! See this man out of the Citadel! This damnable,
presumptuous braggart! Robson! Where are you?" But the servant
did not appear and the Aide-de-camp did not answer.
"No matter," said the Egyptian. "I will go of myself. I will try to
forget the hard words you have said of me. I will not retort them
upon you. You are a Christian, and it was a Christian who said 'Resist
not evil.' That is a commandment as binding upon us as upon you.
God's will be done."
 With that Ishmael went out as he had entered, slowly, solemnly,
with head bent and eyes on the ground.

CHAPTER XXVII

The General was now utterly exhausted. Being left alone he leaned
against the desk, intending to wait until his breathing had become
more regular and he could reach the sofa. Standing there, he heard
the surging noise of the crowd that had been waiting outside for
their Arab prophet and were now going away with him. He wanted
to call Helena, but restrained himself, remembering how often she
had warned him.
"Robson!" he called again but again the Aide-de-camp did not
answer—he must have gone off on some errand for Colonel
Macdonald.
The General took up his medicine and gulped down a large
dose, drinking from the neck of the bottle, and then sank on to the
sofa.
Some minutes passed and he began to feel better. The sunset
was deflected into his face from the alabaster walls of the mosque
outside, but he could not get up to pull down the blind of his
window. So he closed his eyes and thought of what had happened.
It seemed to him that Gordon had been to blame for everything.
But for Gordon's monstrous conduct they would have been spared all
this trouble—Lord Nuneham's crushing blow, his own humiliating
action, so wickedly forced upon him, and above all, Helena's sorrow.
 In the delirium of his anger against Gordon he felt as if he
would choke. Thinking of Helena and her ruined happiness, he
wondered why he had let Gordon off so lightly, and he wanted to
follow and punish him.
Then he heard the door open, and thinking Helena was coming
into the room, he rose to his feet and faced around, when before
him, with a haggard face, stood Gordon himself.

CHAPTER XXVIII

When Gordon Lord, after parting with Helena, had left the Citadel,
his mental anguish had been so intense as to deaden all his
faculties. His reason was clogged, his ideas were obscure, he could
not see or hear properly. Passing the sentry in his lodge by the gate,
he did not notice the man's bewildered stare or acknowledge his
abbreviated salute. The whole event of the last hour had
overwhelmed him as with a terrible darkness, and in this darkness
he plodded on, until he came into the streets, dense with people and
clamorous with all the noises of an Eastern city—the clapping of
water-carriers, the crying of lemonade-sellers, the braying of
donkeys, and the ruckling of camels.
"Where am I going?" he asked himself at one moment, and
when he remembered that he was going back to his quarters—for
that was what he had been ordered to do, that he might be under
arrest and in due course tried by court-martial—he told himself that
he had been tried and condemned and punished already. At that
thought, though clouded and obscure, he bit his lip until it bled, and
muttered, "No, I cannot go back to quarters—I will not!"
At the next moment a certain helplessness came over him, and
up from the deep place where the strongest man is as a child, by the
pathetic instinct that keeps the boy alive in him to the last dark day
of his life and in the hour of death, came a desire to go home—to
his mother. But when he thought of his mother's pleading voice as
she begged him to keep peace with his father, and then, by some
juggling twist of torturing memory, of the first evening after his
return to Egypt, when he wore his medals and she fingered them on
his breast with a pride that no queen ever had in the jewels in her
crown, he said to himself, "No, I can never go home again."
His mind was oscillating among these agonising thoughts when
he became aware that he was walking in the Esbekiah district, the
European quarter of Cairo, where the ooze of the gutter of the city is
flung up under the public eye; and there under the open piazza,
containing a line of drinking places, in an atmosphere that was thick
with tobacco smoke, the reek of alcohol, the babel of many tongues,
the striking of matches, and the popping of corks, he sat down at a
table and called for a glass of brandy.
The brandy seemed to clear his faculties for a moment, and his
aimless and wandering thoughts began to concentrate themselves.
Then the scene in the General's office came back to him—the
drawing of his sword from its scabbard, the breaking of it across the
knee, the throwing of the wretched fragments at his feet, the ripping
away of his medals and the trampling of them under foot. The
hideous memory of it all, so illegal, so un-English, made his blood to
boil, and when his beaten brain swung back to the scenes in which
he had won his honours at the risk of his life—Omdurman,
Ladysmith, Pretoria—the rank injustice he had suffered almost stifled
him with rage, and he swore and struck the table.
All his anger was against the General, not against his father, of
whom he had hardly thought at all, but the cruellest agony he
passed through came at the moment when his wrath rose against
Helena. As he thought of her he became dizzy; his brain reeled with
a dance of ideas, in which no picture lasted longer than an instant,
and no emotion would stay. At one moment he was seeing her as he
saw her first, with her big eyes, black as a sloe, the joyous smile
that was one of her greatest charms, the arched brow, the silken
lashes, the gleam of celestial fire, the "Don't go yet" that came into
her look, and then his quickening pulse, the thrill that passed
through him, and the mysterious voice that whispered, "It is She!"
Without knowing it he groaned aloud as he thought of the ruin
all this had come to, and at the next moment he was in the midst of
another memory—a memory of the future as he had imagined it
would be. They were to be married soon, and then, realising one of
the dreams of his life, they were to visit America, for his mother's
blood called to him to go there, to see the great new world—yes, but
above all to stand, with Helena's quivering hand in his, on that rock
at Plymouth, where a handful of fearless men and women had
landed on a bleak and hungry coast, afraid of no fate, for God was
with them, and in two short centuries had peopled a vast continent
and created one of the mightiest empires of the earth. Remembering
this as a vanished dream, his wretched soul was on the edge of a
vortex of madness, and he laughed outright with a laugh that
shivered the air around him.
 Then he was conscious that somebody was speaking to him. It
was a young girl in a gaudy silk dress, with a pasty face, lips painted
very red, eyebrows darkened, a flower in her full bosom which was
covered with transparent lace, and a little satchel swinging on her
wrist.
"Overdoing it a bit, haven't you, dear?" she said in French, and
she smiled at him, a poor sidelong smile, out of her crushed and
crumpled soul.
At the same moment he became aware that three men at a
table behind him were winking at the girl and joking at his expense.
One of them, a little fat American Jew with puffy cheeks, chewing
the end of a cigar, was saying—
"Guess a man don't have no use for a hat in a climate like this—
sun so soft, and only ninety-nine in the shade."
Whereupon an Englishman with a ripped and ragged mouth and
a miscellaneous nose, half pug and half Roman, answered—
"Been hanging himself up on a nail by the breast of his coat,
too, you bet."
Putting his hand to his hair and looking down at the torn cloth
of his tunic, Gordon realised for the first time that he was
bareheaded, having left his helmet at the Citadel, and that to the
unclean consciousness of the people about him he was drunk.
At that moment he started up suddenly, and coming into
collision with the American, who was swinging on the back legs of
his chair, he sent him sprawling on the ground, where he yelled—
"Here, I say, you blazing——"
But the third man at the table, a dragoman in a fez, whispered
—
 "Hush! I know that gentleman. Leave him alone, sirs, please.
Let him go."
With heart and soul aflame, Gordon walked away, intending to
take the first cab that came along and then forgetting to do so. One
wild thought now took possession of him and expelled all other
thoughts. He must go back to the Citadel and accuse the General of
his gross injustice. He must say what he meant to say when he
stood by the door as he was going out.
The General should hear it—he should, and by —— he must!
The brandy was working in his brain by this time, and in the
blind leading of passion everything that happened on the way
seemed to fortify his resolve. The streets of the native city were now
surging with people, as a submerged mine surges with the water
that runs through it. He knew where they were going—they were
going to El Azhar—and when he came to the great mosque he had
to fight his way through a crowd that was coming from the opposite
direction, with the turbaned head of a very tall man showing
conspicuously in the midst of the multitude, who were chanting
verses from the Koran and crying in chorus, "La ilaha illa-llah."
At sight of this procession, knowing what it meant—that the
Moslems were going to the doomed place, to defend it or to die—a
thousand confused forms danced before Gordon's eyes. His
impatience to reach the Citadel became feverish, and he began to
run, but again at the foot of the hill on which the fortress stands he
was kept back. This time it was by a troop of cavalry who were
trotting hard towards El Azhar. He saw his deputy, Macdonald, with
his blotchy face and his monocle, but he was himself seen by no
one, and in the crush he was almost ridden down.
 The Citadel, when he reached it, seemed to be deserted, even
the sentry standing with his back to him in the sentry-box as he
hurried through. There was nobody in the square of the mosque or
yet at the gate to the General's garden, which was open, and the
door of the house, when he came to it, was open too. With the hot
blood in his head, his teeth compressed, and his nostrils quivering,
he burst into the General's office and came face to face with the old
soldier as he was rising from the sofa. Thus in the blind swirl of
circumstance the two men met at the moment when the heart of
each was full of hatred for the other.
They were brave men both of them, and never for one instant
had either of them known what it was to feel afraid. They were not
afraid now, but they had loved each other once, and up from what
deep place in their souls God alone can say, there came a wave of
feeling that fought with their hate. The General no longer wanted to
punish Gordon, but only that Gordon should go away, while Gordon's
rage, which was to have thundered at the General, broke into an
agonising cry.
"What are you doing here? Didn't I order you to your quarters?
Do you wish me to put you under close arrest? Get off!"
"Not yet. You and I have to settle accounts first. You have
behaved like a tyrant. A tyrant—that's the only word for it! If I was
guilty of insubordination, you were guilty of outrage. You had a right
to arrest me, and to order that I should be court-martialled, but
what right had you to condemn me before I was tried and punish
me before I was sentenced? Before or after, what right had you to
break my sword and tear off my medals? Degradation is obsolete in
the British Army—what right had you to degrade me? Before my
father, too, and before Helena—what right had you?"
"Leave my house instantly; leave it, leave it!" said the General,
his voice coming thick and hoarse.
"Not till you hear what I've come to tell you," said Gordon, and
then he repeated the threat—who knows on what inherited cell of
his brain imprinted—which his father had made forty years before.
"I've come to tell you that I'll go back to my quarters and you
shall court-martial me to-morrow if you dare. Before that, England
may know by what is done to-night that I refused to obey your order
because I'm a soldier, not a murderer. But if she never knows," he
cried, in his breaking voice, "and you try me and condemn me and
degrade me even to the ranks, I'll get up again—do you hear me?—
I'll get up again, and win back all I've lost and more—until I'm your
own master and you'll have to obey me."
The General's face became scarlet, and lifting his hand as if to
strike Gordon, he cried, in a choking voice—
"Go, before I do something——"
But Gordon in the delirium of his rage heard nothing except the
sound of his own quivering voice.
"More than that," he said, "I'll win back Helena. She was mine,
and you have separated her from me and broken her heart as well
as my own. Was that the act of a father, or of a robber and a tyrant?
But she will come back to me, and when you are dead and in your
grave we shall be together, because ... Stop that! Stop it, I say!"
The General, unable to command himself any longer, had
snatched up the broken sword from the floor and was making for
Gordon as if to smite him.
 "Stand away! You are an old man and I am not a coward. Drop
that, or by God you——"
But the General, losing himself utterly, flung himself on Gordon
with the broken sword, his voice gone in a husky growl and his
breath coming in hoarse gusts.
The struggle was short but terrible. Gordon in the strength of
his young manhood first laid hold of the General by the upper part of
the breast to keep him off, and then, feeling that his hand was
wounded, he gripped at the old man's throat with fingers that clung
like claws. At the next moment he snatched the sword from the
General, and at the same instant, with a delirious laugh, he flung the
man himself away.
The General fell heavily with a deep groan and a gurgling cry.
Gordon, with a contemptuous gesture, threw the broken sword on
the floor, and then with the growl of a wild creature he turned to go.
"Fight me—would you, eh! Kill me, perhaps! We've settled
accounts at last—haven't we?"
But hearing no answer he turned at the door to look back and
saw the General lying where he had fallen, outstretched and still. At
that sight the breath seemed to go out of his body at one gasp. His
head turned giddy, and the red gleams of the sunset which were
deflected into the room appeared to his half-blind eyes to cover
everything with blood.

CHAPTER XXIX
Gordon stood with his mouth open, the brute sense struck out of
him by the dead silence. Then he said—
"Get up! Why don't you get up?" hardly knowing what he was
saying.
He got no answer, and a horrible idea began to take shape in
his mind. Though so hot a moment ago, he shivered and his teeth
began to chatter. He looked around him for a moment in the dazed
way of a man awakening from a nightmare, and then stepped up on
tiptoe to where the General lay.
Raising his head he looked at him, and found it hard to believe
that what he vaguely feared had happened. There was no sign of
injury anywhere. The eyes were open, and they looked fixedly at
him with so fierce a stare that they seemed to jump out of their
sockets.
"Stunned—that's all—stunned by the fall," he thought, and
seeing a bottle of brandy on the shelf of the desk he got up and
poured a little into the medicine glass, and then, kneeling and lifting
the General's head again, he forced the liquor through the tightly
compressed lips.
It ran out as it went in, and, with gathering fear and fumbling
fingers, Gordon unbuttoned the General's frock coat and laid a
trembling hand over his heart. At one moment he thought he felt a
beat, but at the next he knew it was only the throb of his own pulse.
At that the world seemed for a moment to be blotted out, and
when he came to himself again he was holding the General in his
arms and calling to him—
"General! General! Speak to me! For God's sake speak to me."
 In the torrent of his remorse he was kissing the General's
forehead, and crying over his face, but there was no response.
Then a great trembling shook his whole body, and dropping the
head gently back to the floor he rose to his feet. The General was
dead, and he knew it.
He had seen death a hundred times before, but only on the
battlefield, amid the boom of cannon, the wail of shell, the snap of
rifles, and the oaths of men, but now it filled him with terror.
The silence was awful. A minute ago the General had been a
living man, face to face with him, and the room had been ringing
with the clashing of their voices; but now this breathless hush, this
paralysing stillness, in which the very air seemed to be dead, for
something was gone as by the stroke of an almighty hand, and there
was nothing left but the motionless figure at his feet.
"What have I done?" he asked, and when he told himself that in
his headstrong wrath he had killed a man, his head spun round and
round. He, who had refused to obey orders because he would not
commit murder was guilty of murder himself! What devil out of hell
had ordered things so that as the very consequence of refusing to
commit a crime he had become a criminal?
"God have pity upon me and tell me it is not true," he thought.
But he knew it was true, and when he told himself that the man
he had killed was his General his pain increased tenfold. The General
had loved him and favoured him, been proud of him and upheld him,
and never, down to the coming of this trouble, had their friendship
been darkened by a cloud.
"Oh, forgive me! God forgive me!" he thought.
 In his blind misery, which hardly saw itself yet for what it was,
the impulse came to him to carry the burden of his sin, too heavy for
himself, to Helena, that she might help him to bear it; and he had
taken some steps towards the door leading to her room when it
struck him as a blow on the brain that she was the daughter of the
dead man, and he was going to her for comfort after killing her
father.
At that thought he stopped and laid hold of the desk for
support, being so weak that he could scarcely keep on his legs. He
remembered Helena's love for the General, how much of her young
life she had given to him, and how the quarrel that had divided
himself from her had come of her determination not to leave her
father as long as he lived. And now he had killed him!
Beads of sweat started from his forehead, but after a moment
he told himself that if he could not expect comfort from Helena it
was his duty to comfort her—to break the news to her. He saw
himself doing so. "Helena, listen, dear; be brave." "What is it?" "Your
father—is—is dead." "Dead?" "Worse, a thousandfold worse—he is
murdered." "Murdered?" "It was all in the heat of blood—the man
didn't know what he was doing." "Who was it—who was it?" "Don't
you see, Helena—it was I."
He had turned again to the door leading to Helena's room when
another blow from an invisible hand seemed to fall upon him. He
saw Helena's eyes fixed on his face in the intensity of her hate, and
he heard her voice driving him away. "Go, let me never see you
again!" That was more than he could bear, and staggering to the
sofa he sat down.
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