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Apago PDF Enhancer
smi75625_endppFRONT.indd 2

Periodic Table of the Elements

Group number 1A 8A
1 Key
Period 2
number 1 H 67 He 1
Hydrogen
Atomic number Symbol
Ho
1.0079 Helium
2A 3A 4A 5A 6A 7A 4.0026
3 4 Holmium 5 6 7 8 9 10
Name Atomic weight
Li Be B C N O F Ne
164.9303
2 2
An element
Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon
6.941 9.0122 10.811 12.011 14.0067 15.9994 18.9984 20.1797
11 12 13 14 15 16 17 18

3 Na Mg Al Si P S Cl Ar 3

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Sodium Magnesium Aluminum Silicon Phosphorus Sulfur Chlorine Argon
22.9898 24.3050 3B 4B 5B 6B 7B 8B 8B 8B 1B 2B 26.9815 28.0855 30.9738 32.066 35.4527 39.948
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36

4 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 4
Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton
39.0983 40.078 44.9559 47.88 50.9415 51.9961 54.9380 55.845 58.9332 58.693 63.546 65.41 69.723 72.64 74.9216 78.96 79.904 83.80
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54

5 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 5
Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon
85.4678 87.62 88.9059 91.224 92.9064 95.94 (98) 101.07 102.9055 106.42 107.8682 112.411 114.82 118.710 121.760 127.60 126.9045 131.29
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86

6 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 6
Cesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon
132.9054 137.327 138.9055 178.49 180.9479 183.84 186.207 190.2 192.22 195.08 196.9665 200.59 204.3833 207.2 208.9804 (209) (210) (222)
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116

7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg – – – – – 7
Francium Radium Actinium Rutherfordium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium — — — — —
(223) (226) (227) (267) (268) (271) (272) (270) (276) (281) (280) (285) (284) (289) (288) (293)

58 59 60 61 62 63 64 65 66 67 68 69 70 71

Lanthanides 6 Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 6
Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium
140.115 140.9076 144.24 (145) 150.36 151.964 157.25 158.9253 162.50 164.9303 167.26 168.9342 173.04 174.967
90 91 92 93 94 95 96 97 98 99 100 101 102 103

Actinides 7 Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr 7
Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium
232.0381 231.0359 238.0289 (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (260)
12/2/09 10:14:16 AM
smi75625_endppFRONT.indd 3

COMMON FUNCTIONAL GROUPS

Type of Compound General Structure Example Functional Group Type of Compound General Structure Example Functional Group

O O
Acid – COCl Aromatic compound phenyl group
C C
chloride R Cl CH3 Cl

– OH O O
Alcohol R OH CH3 OH Carboxylic –COOH
hydroxy group acid C C carboxy group
R OH CH3 OH

O O O O

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Aldehyde C C C O Ester C C – COOR
R H CH3 H carbonyl group R OR CH3 OCH3

– OR
Alkane R H CH3CH3 –– Ether R O R CH3 O CH3 alkoxy group

H H O O
C O
Alkene C C C C double bond Ketone C C carbonyl group
R R CH3 CH3
H H

R X –C N
Alkyl halide CH3 Br –X Nitrile R C N CH3 C N
(X = F, Cl, Br, I) halo group cyano group

Alkyne C C H C C H triple bond Sulfide R S R CH3 S CH3 – SR

alkylthio group

O
O – CONH2,
Amide C H (or R) – CONHR, Thiol R SH CH3 SH – SH
R N C
CH3 NH2 – CONR2 mercapto group
H (or R)

O O
Amine R NH2 or CH3 NH2 – NH2 Thioester C C – COSR
R2NH or R3N amino group R SR CH3 SCH3

O O O O O O
12/2/09 10:14:16 AM

Anhydride C C C C C C
R O R CH3 O CH3 O
 Organic Chemistry
Third Edition

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Janice Gorzynski Smith

University of Hawai’i at Ma-noa

TM

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 TM

ORGANIC CHEMISTRY, THIRD EDITION

Published by McGraw-Hill, a business unit of The McGraw-Hill Companies, Inc., 1221 Avenue of the Americas,
New York, NY 10020. Copyright © 2011 by The McGraw-Hill Companies, Inc. All rights reserved. Previous editions
© 2008 and 2006. No part of this publication may be reproduced or distributed in any form or by any means, or stored
in a database or retrieval system, without the prior written consent of The McGraw-Hill Companies, Inc., including, but
not limited to, in any network or other electronic storage or transmission, or broadcast for distance learning.

Some ancillaries, including electronic and print components, may not be available to customers outside the
United States.

This book is printed on acid-free paper.

1 2 3 4 5 6 7 8 9 0 DOW/DOW 1 0 9 8 7 6 5 4 3 2 1 0

ISBN 978–0–07–337562–5
MHID 0–07–337562–4

Vice President & Editor-in-Chief: Marty Lange

Vice President, EDP: Kimberly Meriwether-David
Director of Development: Kristine Tibbetts
Publisher: Ryan Blankenship
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All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.

Library of Congress Cataloging-in-Publication Data

Smith, Janice G.
Organic chemistry / Janice Gorzynski Smith. — 3rd ed.
p. cm.
Includes index.
ISBN 978–0–07–337562–5 — ISBN 0–07–337562–4 (hard copy : alk. paper)
1. Chemistry, Organic–Textbooks. I. Title.
QD253.2.S65 2011
547—dc22 2009034737

www.mhhe.com

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 For Megan Sarah

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smi75625_fm_00i-xxxiv.indd iii 11/17/09 11:21:08 AM

 About the Author

Janice Gorzynski Smith was born in Schenectady, New York, and grew up following
the Yankees, listening to the Beatles, and water skiing on Sacandaga Reservoir. She became
interested in chemistry in high school, and went on to major in chemistry at Cornell University
where she received an A.B. degree summa cum laude. Jan earned a Ph.D. in Organic Chemistry
from Harvard University under the direction of Nobel Laureate E. J. Corey, and she also spent a
year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard. During
her tenure with the Corey group she completed the total synthesis of the plant growth hormone
gibberellic acid.
Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College where
she was employed for 21 years. During this time she was active in teaching organic chemis-
try lecture and lab courses, conducting a research program in organic synthesis, and serving
as department chair. Her organic chemistry class was named one of Mount Holyoke’s “Don’t-
miss courses” in a survey by Boston magazine. After spending two sabbaticals amidst the natu-
ral beauty and diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently
in 2000. She is currently a faculty member at the University of Hawai‘i at Ma- noa, where she
teaches the two-semester organic chemistry lecture and lab courses. In 2003, she received the
Chancellor’s Citation for Meritorious Teaching.
Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician. She has
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four children: Matthew and Zachary, age 14 (margin photo on page 163); Jenna, a student at
Temple University’s Beasley School of Law; and Erin, an emergency medicine physician and
co-author of the Student Study Guide/Solutions Manual for this text. When not teaching, writing,
or enjoying her family, Jan bikes, hikes, snorkels, and scuba dives in sunny Hawai‘i, and time
permitting, enjoys travel and Hawaiian quilting.

The author (far right) and her family from the left: husband Dan,
and children Zach, Erin, Jenna, and Matt.

iv

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 Contents in Brief

Prologue 1
1 Structure and Bonding 6
2 Acids and Bases 54
3 Introduction to Organic Molecules and Functional Groups 81
4 Alkanes 113
5 Stereochemistry 159
6 Understanding Organic Reactions 196
7 Alkyl Halides and Nucleophilic Substitution 228
8 Alkyl Halides and Elimination Reactions 278
9 Alcohols, Ethers, and Epoxides 312
10 Alkenes 358
11 Alkynes 399
12 Oxidation and Reduction 426
13 Mass Spectrometry and Infrared Spectroscopy 463
14 Nuclear Magnetic Resonance Spectroscopy 494
15 Radical Reactions 538
16
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Conjugation, Resonance, and Dienes 571
17 Benzene and Aromatic Compounds 607
18 Electrophilic Aromatic Substitution 641
19 Carboxylic Acids and the Acidity of the O – H Bond 688
20 Introduction to Carbonyl Chemistry; Organometallic Reagents;
Oxidation and Reduction 721
21 Aldehydes and Ketones—Nucleophilic Addition 774
22 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution 825
23 Substitution Reactions of Carbonyl Compounds at the α Carbon 880
24 Carbonyl Condensation Reactions 916
25 Amines 949
26 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1002
27 Carbohydrates 1027
28 Amino Acids and Proteins 1074
29 Lipids 1119
30 Synthetic Polymers 1148
Appendices A-1
Glossary G-1
Credits C-1
Index I-1

smi75625_fm_00i-xxxiv.indd v 11/17/09 11:21:09 AM

 Contents

Preface xviii
Acknowledgments xxiii
List of How To’s xxv
List of Mechanisms xxvii
List of Selected Applications xxx

Prologue 1
What Is Organic Chemistry? 1
Some Representative Organic Molecules 2
Ginkgolide B—A Complex Organic Compound from the Ginkgo Tree 4

1 Structure and Bonding 6

1.1 The Periodic Table 7
1.2 Bonding 10
1.3 Lewis Structures 12
1.4 Apago PDF Enhancer
Lewis Structures Continued 17
1.5 Resonance 18
1.6 Determining Molecular Shape 23
1.7 Drawing Organic Structures 27
1.8 Hybridization 32
1.9 Ethane, Ethylene, and Acetylene 36
1.10 Bond Length and Bond Strength 40
1.11 Electronegativity and Bond Polarity 42
1.12 Polarity of Molecules 44
1.13 L-Dopa—A Representative Organic Molecule 45
Key Concepts 46
Problems 47

2 Acids and Bases 54

2.1 Brønsted–Lowry Acids and Bases 55
2.2 Reactions of Brønsted–Lowry Acids and Bases 56
2.3 Acid Strength and pKa 58
2.4 Predicting the Outcome of Acid–Base Reactions 61
2.5 Factors That Determine Acid Strength 62
2.6 Common Acids and Bases 70
2.7 Aspirin 71
2.8 Lewis Acids and Bases 72
Key Concepts 74
Problems 75
vi

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 Contents vii

3 Introduction to Organic Molecules and

Functional Groups 81
3.1 Functional Groups 82
3.2 An Overview of Functional Groups 83
3.3 Intermolecular Forces 87
3.4 Physical Properties 90
3.5 Application: Vitamins 97
3.6 Application of Solubility: Soap 98
3.7 Application: The Cell Membrane 100
3.8 Functional Groups and Reactivity 102
3.9 Biomolecules 104
Key Concepts 105
Problems 106

4 Alkanes 113
4.1 Alkanes—An Introduction 114
4.2 Cycloalkanes 118
4.3 An Introduction to Nomenclature 119
4.4 Naming Alkanes 120
4.5 Naming Cycloalkanes 125
4.6 Common Names 127
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4.7 Fossil Fuels 128
4.8 Physical Properties of Alkanes 129
4.9 Conformations of Acyclic Alkanes—Ethane 129
4.10 Conformations of Butane 134
4.11 An Introduction to Cycloalkanes 137
4.12 Cyclohexane 138
4.13 Substituted Cycloalkanes 141
4.14 Oxidation of Alkanes 147
4.15 Lipids—Part 1 149
Key Concepts 151
Problems 153

5 Stereochemistry 159
5.1 Starch and Cellulose 160
5.2 The Two Major Classes of Isomers 162
5.3 Looking Glass Chemistry—Chiral and Achiral Molecules 163
5.4 Stereogenic Centers 166
5.5 Stereogenic Centers in Cyclic Compounds 168
5.6 Labeling Stereogenic Centers with R or S 170
5.7 Diastereomers 175
5.8 Meso Compounds 177
5.9 R and S Assignments in Compounds with Two or More Stereogenic
Centers 179
5.10 Disubstituted Cycloalkanes 180

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 viii Contents

5.11 Isomers—A Summary 181

5.12 Physical Properties of Stereoisomers 182
5.13 Chemical Properties of Enantiomers 186
Key Concepts 188
Problems 190

6 Understanding Organic Reactions 196

6.1 Writing Equations for Organic Reactions 197
6.2 Kinds of Organic Reactions 198
6.3 Bond Breaking and Bond Making 200
6.4 Bond Dissociation Energy 203
6.5 Thermodynamics 206
6.6 Enthalpy and Entropy 209
6.7 Energy Diagrams 210
6.8 Energy Diagram for a Two-Step Reaction Mechanism 213
6.9 Kinetics 215
6.10 Catalysts 218
6.11 Enzymes 219
Key Concepts 220
Problems 222

7 Alkyl Halides and Nucleophilic Substitution 228

7.1 Apago PDF Enhancer
Introduction to Alkyl Halides 229
7.2 Nomenclature 230
7.3 Physical Properties 231
7.4 Interesting Alkyl Halides 232
7.5 The Polar Carbon–Halogen Bond 234
7.6 General Features of Nucleophilic Substitution 235
7.7 The Leaving Group 236
7.8 The Nucleophile 238
7.9 Possible Mechanisms for Nucleophilic Substitution 242
7.10 Two Mechanisms for Nucleophilic Substitution 243
7.11 The SN2 Mechanism 244
7.12 Application: Useful SN2 Reactions 250
7.13 The SN1 Mechanism 252
7.14 Carbocation Stability 256
7.15 The Hammond Postulate 258
7.16 Application: SN1 Reactions, Nitrosamines, and Cancer 261
7.17 When Is the Mechanism SN1 or SN2? 262
7.18 Vinyl Halides and Aryl Halides 267
7.19 Organic Synthesis 267
Key Concepts 270
Problems 271

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 Contents ix

8 Alkyl Halides and Elimination Reactions 278

8.1 General Features of Elimination 279
8.2 Alkenes—The Products of Elimination Reactions 281
8.3 The Mechanisms of Elimination 285
8.4 The E2 Mechanism 285
8.5 The Zaitsev Rule 288
8.6 The E1 Mechanism 291
8.7 SN1 and E1 Reactions 294
8.8 Stereochemistry of the E2 Reaction 295
8.9 When Is the Mechanism E1 or E2? 298
8.10 E2 Reactions and Alkyne Synthesis 299
8.11 When Is the Reaction SN1, SN2, E1, or E2? 300
Key Concepts 304
Problems 305

9 Alcohols, Ethers, and Epoxides 312

9.1 Introduction 313
9.2 Structure and Bonding 314
9.3 Nomenclature 314
9.4 Physical Properties 318
9.5 Interesting Alcohols, Ethers, and Epoxides 319
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9.6 Preparation of Alcohols, Ethers, and Epoxides 321
9.7 General Features—Reactions of Alcohols, Ethers, and Epoxides 323
9.8 Dehydration of Alcohols to Alkenes 324
9.9 Carbocation Rearrangements 328
9.10 Dehydration Using POCl3 and Pyridine 330
9.11 Conversion of Alcohols to Alkyl Halides with HX 331
9.12 Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3 335
9.13 Tosylate—Another Good Leaving Group 338
9.14 Reaction of Ethers with Strong Acid 341
9.15 Reactions of Epoxides 343
9.16 Application: Epoxides, Leukotrienes, and Asthma 347
9.17 Application: Benzo[a]pyrene, Epoxides, and Cancer 349
Key Concepts 349
Problems 351

10 Alkenes 358
10.1 Introduction 359
10.2 Calculating Degrees of Unsaturation 360
10.3 Nomenclature 362
10.4 Physical Properties 365
10.5 Interesting Alkenes 366
10.6 Lipids—Part 2 366
10.7 Preparation of Alkenes 369
10.8 Introduction to Addition Reactions 370

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 x Contents

10.9 Hydrohalogenation—Electrophilic Addition of HX 371

10.10 Markovnikov’s Rule 374
10.11 Stereochemistry of Electrophilic Addition of HX 376
10.12 Hydration—Electrophilic Addition of Water 378
10.13 Halogenation—Addition of Halogen 379
10.14 Stereochemistry of Halogenation 381
10.15 Halohydrin Formation 383
10.16 Hydroboration–Oxidation 385
10.17 Keeping Track of Reactions 390
10.18 Alkenes in Organic Synthesis 391
Key Concepts 393
Problems 394

11 Alkynes 399
11.1 Introduction 400
11.2 Nomenclature 401
11.3 Physical Properties 402
11.4 Interesting Alkynes 402
11.5 Preparation of Alkynes 404
11.6 Introduction to Alkyne Reactions 405
11.7 Addition of Hydrogen Halides 406
11.8 Addition of Halogen 409
11.9 Addition of Water 409
11.10 Apago PDF Enhancer
Hydroboration–Oxidation 412
11.11 Reaction of Acetylide Anions 414
11.12 Synthesis 417
Key Concepts 419
Problems 421

12 Oxidation and Reduction 426

12.1 Introduction 427
12.2 Reducing Agents 428
12.3 Reduction of Alkenes 428
12.4 Application: Hydrogenation of Oils 432
12.5 Reduction of Alkynes 434
12.6 The Reduction of Polar C – X σ Bonds 437
12.7 Oxidizing Agents 438
12.8 Epoxidation 439
12.9 Dihydroxylation 442
12.10 Oxidative Cleavage of Alkenes 444
12.11 Oxidative Cleavage of Alkynes 446
12.12 Oxidation of Alcohols 447
12.13 Green Chemistry 450
12.14 Application: The Oxidation of Ethanol 451
12.15 Sharpless Epoxidation 451
Key Concepts 454
Problems 457

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 Contents xi

13 Mass Spectrometry and Infrared Spectroscopy 463

13.1 Mass Spectrometry 464
13.2 Alkyl Halides and the M + 2 Peak 468
13.3 Fragmentation 469
13.4 Other Types of Mass Spectrometry 472
13.5 Electromagnetic Radiation 474
13.6 Infrared Spectroscopy 476
13.7 IR Absorptions 478
13.8 IR and Structure Determination 485
Key Concepts 487
Problems 488

14 Nuclear Magnetic Resonance Spectroscopy 494

14.1 An Introduction to NMR Spectroscopy 495
1
14.2 H NMR: Number of Signals 498
1
14.3 H NMR: Position of Signals 502
14.4 The Chemical Shift of Protons on sp2 and sp Hybridized Carbons 505
1
14.5 H NMR: Intensity of Signals 507
1
14.6 H NMR: Spin–Spin Splitting 508
14.7 More Complex Examples of Splitting 513
14.8 Spin–Spin Splitting in Alkenes 516
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14.9 Other Facts About 1H NMR Spectroscopy 517
14.10 Using 1H NMR to Identify an Unknown 519
13
14.11 C NMR Spectroscopy 522
14.12 Magnetic Resonance Imaging (MRI) 527
Key Concepts 527
Problems 528

15 Radical Reactions 538

15.1 Introduction 539
15.2 General Features of Radical Reactions 540
15.3 Halogenation of Alkanes 541
15.4 The Mechanism of Halogenation 542
15.5 Chlorination of Other Alkanes 545
15.6 Chlorination versus Bromination 546
15.7 Halogenation as a Tool in Organic Synthesis 548
15.8 The Stereochemistry of Halogenation Reactions 549
15.9 Application: The Ozone Layer and CFCs 551
15.10 Radical Halogenation at an Allylic Carbon 552
15.11 Application: Oxidation of Unsaturated Lipids 556
15.12 Application: Antioxidants 557
15.13 Radical Addition Reactions to Double Bonds 558
15.14 Polymers and Polymerization 560
Key Concepts 563
Problems 564

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 xii Contents

16 Conjugation, Resonance, and Dienes 571

16.1 Conjugation 572
16.2 Resonance and Allylic Carbocations 574
16.3 Common Examples of Resonance 575
16.4 The Resonance Hybrid 577
16.5 Electron Delocalization, Hybridization, and Geometry 578
16.6 Conjugated Dienes 580
16.7 Interesting Dienes and Polyenes 581
16.8 The Carbon–Carbon σ Bond Length in 1,3-Butadiene 581
16.9 Stability of Conjugated Dienes 583
16.10 Electrophilic Addition: 1,2- Versus 1,4-Addition 584
16.11 Kinetic Versus Thermodynamic Products 586
16.12 The Diels–Alder Reaction 588
16.13 Specific Rules Governing the Diels–Alder Reaction 590
16.14 Other Facts About the Diels–Alder Reaction 595
16.15 Conjugated Dienes and Ultraviolet Light 597
Key Concepts 599
Problems 601

17 Benzene and Aromatic Compounds 607

17.1 Background 608
17.2 Apago PDF Enhancer
The Structure of Benzene 609
17.3 Nomenclature of Benzene Derivatives 610
17.4 Spectroscopic Properties 613
17.5 Interesting Aromatic Compounds 614
17.6 Benzene’s Unusual Stability 615
17.7 The Criteria for Aromaticity—Hückel’s Rule 617
17.8 Examples of Aromatic Compounds 620
17.9 What Is the Basis of Hückel’s Rule? 626
17.10 The Inscribed Polygon Method for Predicting Aromaticity 629
17.11 Buckminsterfullerene—Is It Aromatic? 632
Key Concepts 633
Problems 633

18 Electrophilic Aromatic Substitution 641

18.1 Electrophilic Aromatic Substitution 642
18.2 The General Mechanism 642
18.3 Halogenation 644
18.4 Nitration and Sulfonation 646
18.5 Friedel–Crafts Alkylation and Friedel–Crafts Acylation 647
18.6 Substituted Benzenes 654
18.7 Electrophilic Aromatic Substitution of Substituted Benzenes 657
18.8 Why Substituents Activate or Deactivate a Benzene Ring 659
18.9 Orientation Effects in Substituted Benzenes 661

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 Contents xiii

18.10 Limitations on Electrophilic Substitution Reactions with Substituted

Benzenes 665
18.11 Disubstituted Benzenes 666
18.12 Synthesis of Benzene Derivatives 668
18.13 Halogenation of Alkyl Benzenes 669
18.14 Oxidation and Reduction of Substituted Benzenes 671
18.15 Multistep Synthesis 675
Key Concepts 678
Problems 680

19 Carboxylic Acids and the Acidity of the O – H Bond 688

19.1 Structure and Bonding 689
19.2 Nomenclature 690
19.3 Physical Properties 692
19.4 Spectroscopic Properties 693
19.5 Interesting Carboxylic Acids 694
19.6 Aspirin, Arachidonic Acid, and Prostaglandins 696
19.7 Preparation of Carboxylic Acids 697
19.8 Reactions of Carboxylic Acids—General Features 699
19.9 Carboxylic Acids—Strong Organic Brønsted–Lowry Acids 700
19.10 Inductive Effects in Aliphatic Carboxylic Acids 703
19.11 Substituted Benzoic Acids 705
19.12 Extraction 707
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19.13 Sulfonic Acids 709
19.14 Amino Acids 710
Key Concepts 713
Problems 714

20 Introduction to Carbonyl Chemistry;

Organometallic Reagents; Oxidation and Reduction 721
20.1 Introduction 722
20.2 General Reactions of Carbonyl Compounds 723
20.3 A Preview of Oxidation and Reduction 726
20.4 Reduction of Aldehydes and Ketones 727
20.5 The Stereochemistry of Carbonyl Reduction 729
20.6 Enantioselective Carbonyl Reductions 731
20.7 Reduction of Carboxylic Acids and Their Derivatives 733
20.8 Oxidation of Aldehydes 738
20.9 Organometallic Reagents 739
20.10 Reaction of Organometallic Reagents with Aldehydes and Ketones 742
20.11 Retrosynthetic Analysis of Grignard Products 746
20.12 Protecting Groups 748
20.13 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives 750
20.14 Reaction of Organometallic Reagents with Other Compounds 753
20.15 α,β-Unsaturated Carbonyl Compounds 755
20.16 Summary—The Reactions of Organometallic Reagents 758

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 xiv Contents

20.17 Synthesis 759

Key Concepts 762
Problems 765

21 Aldehydes and Ketones—Nucleophilic Addition 774

21.1 Introduction 775
21.2 Nomenclature 776
21.3 Physical Properties 779
21.4 Spectroscopic Properties 780
21.5 Interesting Aldehydes and Ketones 783
21.6 Preparation of Aldehydes and Ketones 784
21.7 Reactions of Aldehydes and Ketones—General Considerations 785
21.8 Nucleophilic Addition of H – and R– —A Review 789
21.9 Nucleophilic Addition of – CN 790
21.10 The Wittig Reaction 792
21.11 Addition of 1° Amines 797
21.12 Addition of 2° Amines 800
21.13 Addition of H2O—Hydration 802
21.14 Addition of Alcohols—Acetal Formation 804
21.15 Acetals as Protecting Groups 808
21.16 Cyclic Hemiacetals 809
21.17 An Introduction to Carbohydrates 812
Key Concepts 813
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Problems 815

22 Carboxylic Acids and Their Derivatives—

Nucleophilic Acyl Substitution 825
22.1 Introduction 826
22.2 Structure and Bonding 828
22.3 Nomenclature 830
22.4 Physical Properties 834
22.5 Spectroscopic Properties 835
22.6 Interesting Esters and Amides 836
22.7 Introduction to Nucleophilic Acyl Substitution 838
22.8 Reactions of Acid Chlorides 842
22.9 Reactions of Anhydrides 844
22.10 Reactions of Carboxylic Acids 845
22.11 Reactions of Esters 850
22.12 Application: Lipid Hydrolysis 853
22.13 Reactions of Amides 855
22.14 Application: The Mechanism of Action of β-Lactam Antibiotics 856
22.15 Summary of Nucleophilic Acyl Substitution Reactions 857
22.16 Natural and Synthetic Fibers 858
22.17 Biological Acylation Reactions 860
22.18 Nitriles 862
Key Concepts 867
Problems 870

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 Contents xv

23 Substitution Reactions of Carbonyl Compounds

at the ` Carbon 880
23.1 Introduction 881
23.2 Enols 881
23.3 Enolates 884
23.4 Enolates of Unsymmetrical Carbonyl Compounds 889
23.5 Racemization at the α Carbon 891
23.6 A Preview of Reactions at the α Carbon 892
23.7 Halogenation at the α Carbon 892
23.8 Direct Enolate Alkylation 897
23.9 Malonic Ester Synthesis 900
23.10 Acetoacetic Ester Synthesis 903
Key Concepts 906
Problems 908

24 Carbonyl Condensation Reactions 916

24.1 The Aldol Reaction 917
24.2 Crossed Aldol Reactions 921
24.3 Directed Aldol Reactions 925
24.4 Intramolecular Aldol Reactions 926
24.5 The Claisen Reaction 928
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24.6 The Crossed Claisen and Related Reactions 930
24.7 The Dieckmann Reaction 932
24.8 The Michael Reaction 934
24.9 The Robinson Annulation 936
Key Concepts 940
Problems 941

25 Amines 949
25.1 Introduction 950
25.2 Structure and Bonding 950
25.3 Nomenclature 952
25.4 Physical Properties 954
25.5 Spectroscopic Properties 955
25.6 Interesting and Useful Amines 956
25.7 Preparation of Amines 960
25.8 Reactions of Amines—General Features 966
25.9 Amines as Bases 966
25.10 Relative Basicity of Amines and Other Compounds 968
25.11 Amines as Nucleophiles 975
25.12 Hofmann Elimination 977
25.13 Reaction of Amines with Nitrous Acid 980
25.14 Substitution Reactions of Aryl Diazonium Salts 982
25.15 Coupling Reactions of Aryl Diazonium Salts 986
25.16 Application: Synthetic Dyes 988

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 xvi Contents

25.17 Application: Sulfa Drugs 990

Key Concepts 991
Problems 994

26 Carbon–Carbon Bond-Forming Reactions in Organic

Synthesis 1002
26.1 Coupling Reactions of Organocuprate Reagents 1003
26.2 Suzuki Reaction 1005
26.3 Heck Reaction 1009
26.4 Carbenes and Cyclopropane Synthesis 1012
26.5 Simmons–Smith Reaction 1014
26.6 Metathesis 1015
Key Concepts 1020
Problems 1021

27 Carbohydrates 1027
27.1 Introduction 1028
27.2 Monosaccharides 1028
27.3 The Family of D -Aldoses 1034
27.4 The Family of D -Ketoses 1035
27.5 Physical Properties of Monosaccharides 1036
27.6 The Cyclic Forms of Monosaccharides 1036
27.7
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Glycosides 1042
27.8 Reactions of Monosaccharides at the OH Groups 1046
27.9 Reactions at the Carbonyl Group—Oxidation and Reduction 1047
27.10 Reactions at the Carbonyl Group—Adding or Removing One Carbon
Atom 1049
27.11 The Fischer Proof of the Structure of Glucose 1053
27.12 Disaccharides 1056
27.13 Polysaccharides 1059
27.14 Other Important Sugars and Their Derivatives 1061
Key Concepts 1066
Problems 1068

28 Amino Acids and Proteins 1074

28.1 Amino Acids 1075
28.2 Synthesis of Amino Acids 1078
28.3 Separation of Amino Acids 1081
28.4 Enantioselective Synthesis of Amino Acids 1085
28.5 Peptides 1086
28.6 Peptide Sequencing 1090
28.7 Peptide Synthesis 1094
28.8 Automated Peptide Synthesis 1099
28.9 Protein Structure 1101

smi75625_fm_00i-xxxiv.indd xvi 11/17/09 11:21:38 AM

 Contents xvii

28.10 Important Proteins 1106

Key Concepts 1111
Problems 1113

29 Lipids 1119
29.1 Introduction 1120
29.2 Waxes 1121
29.3 Triacylglycerols 1122
29.4 Phospholipids 1126
29.5 Fat-Soluble Vitamins 1128
29.6 Eicosanoids 1129
29.7 Terpenes 1132
29.8 Steroids 1138
Key Concepts 1143
Problems 1144

30 Synthetic Polymers 1148

30.1 Introduction 1149
30.2 Chain-Growth Polymers—Addition Polymers 1150
30.3 Anionic Polymerization of Epoxides 1156
30.4 Ziegler–Natta Catalysts and Polymer Stereochemistry 1157
30.5 Natural and Synthetic Rubbers 1159
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30.6 Step-Growth Polymers—Condensation Polymers 1160
30.7 Polymer Structure and Properties 1164
30.8 Green Polymer Synthesis 1166
30.9 Polymer Recycling and Disposal 1169
Key Concepts 1172
Problems 1173

Appendix A pKa Values for Selected Compounds A-1

Appendix B Nomenclature A-3
Appendix C Bond Dissociation Energies for Some Common Bonds A-7
Appendix D Reactions that Form Carbon–Carbon Bonds A-9
Appendix E Characteristic IR Absorption Frequencies A-10
Appendix F Characteristic NMR Absorptions A-11
Appendix G General Types of Organic Reactions A-13
Appendix H How to Synthesize Particular Functional Groups A-15

Glossary G-1
Credits C-1
Index I-1

smi75625_fm_00i-xxxiv.indd xvii 11/17/09 11:21:40 AM

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'The platia is crowded already,' said Alexander, looking out.
The hum of the crowd became audible, mingled with the music;
explosions of laughter, and some unexplained applause. The shrill
cry of a seller of iced water rang immediately beneath the window.
The band in the centre continued to shriek remorselessly an
antiquated air of the Paris boulevards.
'At what time is the procession due?' asked Fru Thyregod over
Julian's shoulder.
'At five o'clock; it should arrive at any moment,' Julian said, making
room for the Danish Excellency.
'I adore processions,' cried Fru Thyregod, clapping her hands, and
looking brightly from Julian to Alexander.
Alexander whispered to Julie Lafarge, who had come up,—
'I am sure Fru Thyregod has gone from house to house and from
Legation to Legation, and has had a meal at each to-day.'
Somebody suggested,—
'Let us open the shutters and watch the procession from the
balconies.'
'Oh, what a good idea!' cried Fru Thyregod, clapping her hands
again and executing a pirouette.
Down in the platia an indefinite movement was taking place; the
band stopped playing for the first time that day, and began shuffling
with all its instruments to one side. Voices were then heard raised in
tones of authority. A cleavage appeared in the crowd, which grew in
length and width as though a wedge were being gradually driven
into that reluctant confusion of humanity.
'A path for the procession,' said old Christopoulos, who, although not
pleased at that frivolous flux of his family and guests on to the
balconies of his house, had joined them, overcome by his natural
curiosity.
The path cut in the crowd now ran obliquely across the platia from
the end of the rue Royale to the steps of the cathedral opposite, and
upon it the confetti with which the whole platia was no doubt strewn
became visible. The police, with truncheons in their hands, were
pressing the people back to widen the route still further. They wore
their gala hats, three-cornered, with upright plumes of green and
orange nodding as they walked.
'Look at Sterghiou,' said Alexander.
The Chief of Police rode vaingloriously down the route looking from
left to right, and saluting with his free hand. The front of his uniform
was crossed with broad gold hinges, and plaits of yellow braid
disappeared mysteriously into various pockets. One deduced
whistles; pencils; perhaps a knife. Although he did not wear feathers
in his hat, one knew that only the utmost self-restraint had
preserved him from them.
Here the band started again with a march, and Sterghiou's horse
shied violently and nearly unseated him.
'The troops!' said old Christopoulos with emotion.
Debouching from the rue Royale, the army came marching four
abreast. As it was composed of only four hundred men, and as it
never appeared on any other day of the year, its general
Panaïoannou always mobilised it in its entirety on the national
festival. This entailed the temporary closing of the casino in order to
release the croupiers, who were nearly all in the ranks, and led to a
yearly dispute between the General and the board of administration.
'There was once a croupier,' said Alexander, 'who was admitted to
the favour of a certain grand-duchess until the day when,
indiscreetly coming into the dressing-room where the lady was
arranging and improving her appearance, he said, through sheer
force of habit, "Madame, les jeux sont faits?" and was dismissed for
ever by her reply, "Rien ne va plus."'
The general himself rode in the midst of his troops, in his sky-blue
uniform, to which the fantasy of his Buda-Pesth costumier had
added for the occasion a slung Hussar jacket of white cloth. His gray
moustache was twisted fiercely upwards, and curved like a scimitar
across his face. He rode with his hand on his hip, slowly scanning
the windows and balconies of the platia, which by now were
crowded with people, gravely saluting his friends as he passed.
Around him marched his bodyguard of six, a captain and five men;
the captain carried in one hand a sword, and in the other—nobody
knew why—a long frond of palm.
The entire army tramped by, hot, stout, beaming, and friendly. At
one moment some one threw down a handful of coins from a
window, and the ranks were broken in a scramble for the coppers.
Julian, who was leaning apart in a corner of his balcony, heard a
laugh like a growl behind him as the enormous hand of Grbits
descended on his shoulder.
'Remember the lesson, young man: if you are called upon to deal
with the soldiers of Herakleion, a fistful of silver amongst them will
scatter them.'
Julian thought apprehensively that they must be overheard, but
Grbits continued in supreme unconsciousness,—
'Look at their army, composed of shop-assistants and croupiers. Look
at their general—a general in his spare moments, but in the serious
business of his life a banker and an intriguer like the rest of them. I
doubt whether he has ever seen anything more dead in his life than
a dead dog in a gutter. I could pick him up and squash in his head
like an egg.'
Grbits extended his arm and slowly unfolded the fingers of his
enormous hand. At the same time he gave his great laugh that was
like the laugh of a good-humoured ogre.
'At your service, young man,' he said, displaying the full breadth of
his palm to Julian, 'whenever you stand in need of it. The Stavridists
will be returned to-day; lose no time; show them your intentions.'
He impelled Julian forward to the edge of the balcony and pointed
across to the Davenant house.
'That flag, young man: see to it that it disappears within the hour
after the results of the elections are announced.'
The army was forming itself into two phalanxes on either side of the
cathedral steps. Panaïoannou caracoled up and down shouting his
orders, which were taken up and repeated by the busy officers on
foot. Meanwhile the notables in black coats were arriving in a
constant stream that flowed into the cathedral; old Christopoulos
had already left the house to attend the religious ceremony; the
foreign Ministers and Consuls attended out of compliment to
Herakleion; Madame Lafarge had rolled down the route in her
barouche with her bearded husband; Malteios had crossed the platia
from his own house, and Stavridis came, accompanied by his wife
and daughters. Still the band played on, the crowd laughed,
cheered, or murmured in derision, and the strident cries of the
water-sellers rose from all parts of the platia.
Suddenly the band ceased to play, and in the hush only the hum of
the crowd continued audible.
The religious procession came walking very slowly from the rue
Royale, headed by a banner and by a file of young girls, walking two
by two, in white dresses, with wreaths of roses on their heads. As
they walked they scattered sham roses out of baskets, the gesture
reminiscent of the big picture in the Senate-room. It was customary
for the Premier of the Republic to walk alone, following these young
girls, black and grave in his frock-coat after their virginal white, but
on this occasion, as no one knew who the actual Premier was, a
blank space was left to represent the problematical absentee.
Following the space came the Premier's habitual escort, a posse of
police; it should have been a platoon of soldiers, but Panaïoannou
always refused to consent to such a diminution of his army.
'They say,' Grbits remarked to Julian in this connection, 'that the
general withdraws even the sentries from the frontier to swell his
ranks.'
'Herakleion is open to invasion,' said Julian, smiling.
Grbits replied sententiously, with the air of one creating a new
proverb,—
'Herakleion is open to invasion, but who wants to invade
Herakleion?'
The crowd watched the passage of the procession with the utmost
solemnity. Not a sound was now heard but the monotonous step of
feet. Religious awe had hushed political hilarity. Archbishop and
bishops; archmandrites and papás of the country districts, passed in
a mingling of scarlet, purple and black. All the pomp of Herakleion
had been pressed into service—all the clamorous, pretentious pomp,
shouting for recognition, beating on a hollow drum; designed to
impress the crowd; and perhaps, also, to impress, beyond the
crowd, the silent Islands that possessed no army, no clergy, no
worldly trappings, but that suffered and struggled uselessly, pitiably,
against the tinsel tyrant in vain but indestructible rebellion.
* * * * * *
As five o'clock drew near, the entire population seemed to be
collected in the platia. The white streak that had marked the route
of the procession had long ago disappeared, and the square was
now, seen from above, only a dense and shifting mass of people. In
the Christopoulos drawing-room, where Julian still lingered, talking
to Grbits and listening to the alternate foolishness, fanaticism, and
ferocious good-humour of the giant, the Greeks rallied in numbers
with only one topic on their lips. Old Christopoulos was frankly biting
his nails and glancing at the clock; Alexander but thinly concealed
his anxiety under a dribble of his usual banter. The band had ceased
playing, and the subtle ear could detect an inflection in the very
murmur of the crowd.
'Let us go on to the balcony again,' Grbits said to Julian; 'the results
will be announced from the steps of Malteios' house.'
They went out; some of the Greeks followed them, and all pressed
behind, near the window openings.
'It is a more than usually decisive day for Herakleion,' said old
Christopoulos, and Julian knew that the words were spoken at,
although not to, him.
He felt that the Greeks looked upon him as an intruder, wishing him
away so that they might express their opinions freely, but in a spirit
of contrariness he remained obstinately.
A shout went up suddenly from the crowd: a little man dressed in
black, with a top-hat, and a great many white papers in his hand,
had appeared in the frame of Malteios' front-door. He stood on the
steps, coughed nervously, and dropped his papers.
'Inefficient little rat of a secretary!' cried Alexander in a burst of fury.
'Listen!' said Grbits.
A long pause of silence from the whole platia, in which one thin
voice quavered, reaching only the front row of the crowd.
'Stavridis has it,' Grbits said quietly, who had been craning over the
edge of the balcony. His eyes twinkled maliciously, delightedly, at
Julian across the group of mortified Greeks. 'An immense majority,'
he invented, enjoying himself.
Julian was already gone. Slipping behind old Christopoulos, whose
saffron face had turned a dirty plum colour, he made his way
downstairs and out into the street. A species of riot, in which the
police, having failed successfully to intervene, were enthusiastically
joining, had broken out in the platia. Some shouted for Stavridis,
some for Malteios; some railed derisively against the Islands. People
threw their hats into the air, waved their arms, and kicked up their
legs. Some of them were vague as to the trend of their own
opinions, others extremely determined, but all were agreed about
making as much noise as possible. Julian passed unchallenged to his
father's house.
Inside the door he found Aristotle talking with three islanders. They
laid hold of him, urgent though respectful, searching his face with
eager eyes.
'It means revolt at last; you will not desert us, Kyrie?'
He replied,—
'Come with me, and you will see.'
They followed him up the stairs, pressing closely after him. On the
landing he met Eve and Kato, coming out of the drawing-room. The
singer was flushed, two gold wheat-ears trembled in her hair, and
she had thrown open the front of her dress. Eve hung on her arm.
'Julian!' Kato exclaimed, 'you have heard, Platon has gone?'
In her excitement she inadvertently used Malteios' Christian name.
'It means,' he replied, 'that Stavridis, now in power, will lose no time
in bringing against the Islands all the iniquitous reforms we know he
contemplates. It means that the first step must be taken by us.'
His use of the pronoun ranged himself, Kato, Aristotle, the three
islanders, and the invisible Islands into an instant confederacy. Kato
responded to it,—
'Thank God for this.'
They waited in complete confidence for his next words. He had shed
his aloofness, and all his efficiency of active leadership was to the
fore.
'Where is my father?'
'He went to the Cathedral; he has not come home yet, Kyrie.'
Julian passed into the drawing-room, followed by Eve and Kato and
the four men. Outside the open window, fastened to the balcony,
flashed the green and orange flag of Herakleion. Julian took a knife
from his pocket, and, cutting the cord that held it, withdrew flag and
flag-staff into the room and flung it on to the ground.
'Take it away,' he said to the islanders, 'or my father will order it to
be replaced. And if he orders another to be hung out in its place,' he
added, looking at them with severity, 'remember there is no other
flag in the house, and none to be bought in Herakleion.'
At that moment a servant from the country-house came hurriedly
into the room, drew Julian unceremoniously aside, and broke into an
agitated recital in a low voice. Eve heard Julian saying,—
'Nicolas sends for me? But he should have given a reason. I cannot
come now, I cannot leave Herakleion.'
And the servant,—
'Kyrie, the major-domo impressed upon me that I must on no
account return without you. Something has occurred, something
serious. What it is I do not know. The carriage is waiting at the back
entrance; we could not drive across the platia on account of the
crowds.'
'I shall have to go, I suppose,' Julian said to Eve and Kato. 'I will go
at once, and will return, if possible, this evening. Nicolas would not
send without an excellent reason, though he need not have made
this mystery. Possibly a message from Aphros.... In any case, I must
go.'
'I will come with you,' Eve said unexpectedly.
 V
In almost unbroken silence they drove out to the country-house, in a
hired victoria, to the quick, soft trot of the two little lean horses,
away from the heart of the noisy town; past the race-course with its
empty stands; under the ilex-avenue in a tunnel of cool darkness;
along the road, redolent with magnolias in the warmth of the
evening; through the village, between the two white lodges; and
round the bend of the drive between the bushes of eucalyptus. Eve
had spoken, but he had said abruptly,—
'Don't talk; I want to think,' and she, after a little gasp of astonished
indignation, had relapsed languorous into her corner, her head
propped on her hand, and her profile alone visible to her cousin. He
saw, in the brief glance that he vouchsafed her, that her red mouth
looked more than usually sulky, in fact not unlike the mouth of a
child on the point of tears, a very invitation to inquiry, but, more
from indifference than deliberate wisdom, he was not disposed to
take up the challenge. He too sat silent, his thoughts flying over the
day, weighing the consequences of his own action, trying to forecast
the future. He was far away from Eve, and she knew it. At times he
enraged and exasperated her almost beyond control. His indifference
was an outrage on her femininity. She knew him to be utterly
beyond her influence: taciturn when he chose, ill-tempered when he
chose, exuberant when he chose, rampageous, wild; insulting to her
at moments; domineering whatever his mood, and regardless of her
wishes; yet at the same time unconscious of all these things. Alone
with her now, he had completely forgotten her presence by his side.
Her voice broke upon his reflections,—
'Thinking of the Islands, Julian?' and her words joining like a
cogwheel smoothly on to the current of his mind, he answered
naturally,—
'Yes,'
'I thought as much. I have something to tell you. You may not be
interested. I am no longer engaged to Miloradovitch.'
'Since when?'
'Since yesterday evening. Since you left me, and ran away into the
woods. I was angry, and vented my anger on him.'
'Was that fair?'
'He has you to thank. It has happened before—with others.'
Roused for a second from his absorption, he impatiently shrugged
his shoulders, and turned his back, and looked out over the sea. Eve
was again silent, brooding and resentful in her corner. Presently he
turned towards her, and said angrily, reverting to the Islands,—
'You are the vainest and most exorbitant woman I know. You resent
one's interest in anything but yourself.'
As she did not answer, he added,—
'How sulky you look; it's very unbecoming.'
Was no sense of proportion or of responsibility ever to weigh upon
her beautiful shoulders? He was irritated, yet he knew that his
irritation was half-assumed, and that in his heart he was no more
annoyed by her fantasy than by the fantasy of Herakleion. They
matched each other; their intangibility, their instability, were enough
to make a man shake his fists to Heaven, yet he was beginning to
believe that their colour and romance—for he never dissociated Eve
and Herakleion in his mind—were the dearest treasures of his youth.
He turned violently and amazingly upon her.
'Eve, I sometimes hate you, damn you; but you are the rainbow of
my days.'
She smiled, and, enlightened, he perceived with interest, curiosity,
and amused resignation, the clearer grouping of the affairs of his
youthful years. Fantasy to youth! Sobriety to middle-age! Carried
away, he said to her,—
'Eve! I want adventure, Eve!'
Her eyes lit up in instant response, but he could not read her inward
thought, that the major part of his adventure should be, not Aphros,
but herself. He noted, however, her lighted eyes, and leaned over to
her.
'You are a born adventurer, Eve, also.'
She remained silent, but her eyes continued to dwell on him, and to
herself she was thinking, always sardonic although the matter was of
such perennial, such all-eclipsing importance to her,—
'A la bonne heure, he realises my existence.'
'What a pity you are not a boy; we could have seen the adventure of
the Islands through together.'
('The Islands always!' she thought ruefully.)
'I should like to cross to Aphros to-night,' he murmured, with absent
eyes....
('Gone again,' she thought. 'I held him for a moment.')

When they reached the house no servants were visible, but in reply
to the bell a young servant appeared, scared, white-faced, and, as
rapidly disappearing, was replaced by the old major-domo. He burst
open the door into the passage, a crowd of words pressing on each
other's heels in his mouth; he had expected Julian alone; when he
saw Eve, who was idly turning over the letters that awaited her, he
clapped his hand tightly over his lips, and stood, struggling with his
speech, balancing himself in his arrested impetus on his toes.
'Well, Nicolas?' said Julian.
The major-domo exploded, removing his hand from his mouth,—
'Kyrie! a word alone....' and as abruptly replaced the constraining
fingers.
Julian followed him through the swing door into the servants'
quarters, where the torrent broke loose.
'Kyrie, a disaster! I have sent men with a stretcher. I remained in the
house myself looking for your return. Father Paul—yes, yes, it is he—
drowned—yes, drowned—at the bottom of the garden. Come, Kyrie,
for the love of God. Give directions. I am too old a man. God be
praised, you have come. Only hasten. The men are there already
with lanterns.'
He was clinging helplessly to Julian's wrist, and kept moving his
fingers up and down Julian's arm, twitching fingers that sought
reassurance from firmer muscles, in a distracted way, while his eyes
beseechingly explored Julian's face.
Julian, shocked, jarred, incredulous, shook off the feeble fingers in
irritation. The thing was an outrage on the excitement of the day.
The transition to tragedy was so violent that he wished, in revolt, to
disbelieve it.
'You must be mistaken, Nicolas!'
'Kyrie, I am not mistaken. The body is lying on the shore. You can
see it there. I have sent lanterns and a stretcher. I beg of you to
come.'
He spoke, tugging at Julian's sleeve, and as Julian remained
unaccountably immovable he sank to his knees, clasping his hands
and raising imploring eyes. His fustanelle spread its pleats in a circle
on the stone floor. His story had suddenly become vivid to Julian
with the words, 'The body is lying on the shore'; 'drowned,' he had
said before, but that had summoned no picture. The body was lying
on the shore. The body! Paul, brisk, alive, familiar, now a body,
merely. The body! had a wave, washing forward, deposited it gently,
and retreated without its burden? or had it floated, pale-faced under
the stars, till some man, looking by chance down at the sea from the
terrace at the foot of the garden, caught that pale, almost
phosphorescent gleam rocking on the swell of the water?
The old major-domo followed Julian's stride between the lemon-
trees, obsequious and conciliatory. The windows of the house shone
behind them, the house of tragedy, where Eve remained as yet
uninformed, uninvaded by the solemnity, the reality, of the present.
Later, she would have to be told that a man's figure had been
wrenched from their intimate and daily circle. The situation appeared
grotesquely out of keeping with the foregoing day, and with the wide
and gentle night.
From the paved walk under the pergola of gourds rough steps led
down to the sea. Julian, pausing, perceived around the yellow
squares of the lanterns the indistinct figures of men, and heard their
low, disconnected talk breaking intermittently on the continuous
wash of the waves. The sea that he loved filled him with a sudden
revulsion for the indifference of its unceasing movement after its
murder of a man. It should, in decency, have remained quiet, silent;
impenetrable, unrepentant, perhaps; inscrutable, but at least silent;
its murmur echoed almost as the murmur of a triumph....
He descended the steps. As he came into view, the men's
fragmentary talk died away; their dim group fell apart; he passed
between them, and stood beside the body of Paul.
Death. He had never seen it. As he saw it now, he thought that he
had never beheld anything so incontestably real as its irrevocable
stillness. Here was finality; here was defeat beyond repair. In the
face of this judgment no revolt was possible. Only acceptance was
possible. The last word in life's argument had been spoken by an
adversary for long remote, forgotten; an adversary who had
remained ironically dumb before the babble, knowing that in his own
time, with one word, he could produce the irrefutable answer. There
was something positively satisfying in the faultlessness of the
conclusion. He had not thought that death would be like this. Not
cruel, not ugly, not beautiful, not terrifying—merely unanswerable.
He wondered now at the multitude of sensations that had chased
successively across his mind or across his vision: the elections, Fru
Thyregod, the jealousy of Eve, his incredulity and resentment at the
news, his disinclination for action, his indignation against the
indifference of the sea; these things were vain when here, at his
feet, lay the ultimate solution.
Paul lay on his back, his arms straight down his sides, and his long,
wiry body closely sheathed in the wet soutane. The square toes of
his boots stuck up, close together, like the feet of a swathed
mummy. His upturned face gleamed white with a tinge of green in
the light of the lanterns, and appeared more luminous than they. So
neat, so orderly he lay; but his hair, alone disordered, fell in wet red
wisps across his neck and along the ground behind his head.
At that moment from the direction of Herakleion there came a long
hiss and a rush of bright gold up into the sky; there was a crackle of
small explosions, and fountains of gold showered against the night
as the first fireworks went up from the quays. Rockets soared,
bursting into coloured stars among the real stars, and plumes of
golden light spread themselves dazzlingly above the sea. Faint
sounds of cheering were borne upon the breeze.
The men around the body of the priest waited, ignorant and
bewildered, relieved that some one had come to take command.
Their eyes were bent upon Julian as he stood looking down; they
thought he was praying for the dead. Presently he became aware of
their expectation, and pronounced with a start,—
'Bind up his hair!'
Fingers hastened clumsily to deal with the stringy red locks; the limp
head was supported, and the hair knotted somehow into a
semblance of its accustomed roll. The old major-domo quavered in a
guilty voice, as though taking the blame for carelessness,—
'The hat is lost, Kyrie.'
Julian let his eyes travel over the little group of men, islanders all,
with an expression of searching inquiry.
'Which of you made this discovery?'
It appeared that one of them, going to the edge of the sea in
expectation of the fireworks, had noticed, not the darkness of the
body, but the pallor of the face, in the water not far out from the
rocks. He had waded in and drawn the body ashore. Dead Paul lay
there deaf and indifferent to this account of his own finding.
'No one can explain....'
Ah, no! and he, who could have explained, was beyond the reach of
their curiosity. Julian looked at the useless lips, unruffled even by a
smile of sarcasm. He had known Paul all his life, had learnt from
him, travelled with him, eaten with him, chaffed him lightly, but
never, save in that one moment when he had gripped the priest by
the wrist and had looked with steadying intention into his eyes, had
their intimate personalities brushed in passing. Julian had no genius
for friendship.... He began to see that this death had ended an
existence which had run parallel with, but utterly walled off from, his
own.
In shame the words tore themselves from him,—
'Had he any trouble?'
The men slowly, gravely, mournfully shook their heads. They could
not tell. The priest had moved amongst them, charitable, even
saintly; yes, saintly, and one did not expect confidences of a priest.
A priest was a man who received the confidences of other men.
Julian heard, and, possessed by a strong desire, a necessity, for self-
accusation, he said to them in a tone of urgent and impersonal
Justice, as one who makes a declaration, expecting neither protest
nor acquiescence,—
'I should have inquired into his loneliness.'
They were slightly startled, but, in their ignorance, not over-
surprised, only wondering why he delayed in giving the order to
move the body on to the stretcher and carry it up to the church.
Farther up the coast, the rockets continued to soar, throwing out
bubbles of green and red and orange, fantastically tawdry. Julian
remained staring at the unresponsive corpse, repeating sorrowfully,
—
'I should have inquired—yes, I should have inquired—into his
loneliness.'
He spoke with infinite regret, learning a lesson, shedding a particle
of his youth. He had taken for granted that other men's lives were as
promising, as full of dissimulated eagerness, as his own. He had
walked for many hours up and down Paul's study, lost in an audible
monologue, expounding his theories, tossing his rough head,
emphasising, enlarging, making discoveries, intent on his egotism,
hewing out his convictions, while the priest sat by the table, leaning
his head on his hand, scarcely contributing a word, always listening.
During those hours, surely, his private troubles had been forgotten?
Or had they been present, gnawing, beneath the mask of sympathy?
A priest was a man who received the confidences of other men!
'Carry him up,' Julian said, 'carry him up to the church.'
He walked away alone as the dark cortège set itself in movement,
his mind strangely accustomed to the fact that Paul would no longer
frequent their house and that the long black figure would no longer
stroll, tall and lean, between the lemon-trees in the garden. The fact
was more simple and more easily acceptable than he could have
anticipated. It seemed already quite an old-established fact. He
remembered with a shock of surprise, and a raising of his eyebrows,
that he yet had to communicate it to Eve. He knew it so well himself
that he thought every one else must know it too. He was
immeasurably more distressed by the tardy realisation of his own
egotism in regard to Paul, than by the fact of Paul's death.
He walked very slowly, delaying the moment when he must speak to
Eve. He sickened at the prospect of the numerous inevitable
inquiries that would be made to him by both his father and his uncle.
He would never hint to them that the priest had had a private
trouble. He rejoiced to remember his former loyalty, and to know
that Eve remained ignorant of that extraordinary, unexplained
conversation when Paul had talked about the mice. Mice in the
church! He, Julian, must see to the decent covering of the body. And
of the face, especially of the face.
An immense golden wheel flared out of the darkness; whirled, and
died away above the sea.
In the dim church the men had set down the stretcher before the
iconostase. Julian felt his way cautiously amongst the rush-bottomed
chairs. The men were standing about the stretcher, their fishing caps
in their hands, awed into a whispering mysticism which Julian's voice
harshly interrupted,—
'Go for a cloth, one of you—the largest cloth you can find.'
He had spoken loudly in defiance of the melancholy peace of the
church, that received so complacently within its ready precincts the
visible remains from which the spirit, troubled and uncompanioned
in life, had fled. He had always thought the church complacent,
irritatingly remote from pulsating human existence, but never more
so than now when it accepted the dead body as by right, firstly
within its walls, and lastly within its ground, to decompose and rot,
the body of its priest, among the bodies of other once vital and
much-enduring men.
'Kyrie, we can find only two large cloths, one a dust-sheet, and one
a linen cloth to spread over the altar. Which are we to use?'
'Which is the larger?'
'Kyrie, the dust-sheet, but the altar-cloth is of linen edged with lace.'
'Use the dust-sheet; dust to dust,' said Julian bitterly.
Shocked and uncomprehending, they obeyed. The black figure now
became a white expanse, under which the limbs and features
defined themselves as the folds sank into place.
'He is completely covered over?'
'Completely, Kyrie.'
'The mice cannot run over his face?'
'Kyrie, no!'
'Then no more can be done until one of you ride into Herakleion for
the doctor.'
He left them, re-entering the garden by the side-gate which Paul had
himself constructed with his capable, carpenter's hands. There was
now no further excuse for delay; he must exchange the darkness for
the unwelcome light, and must share out his private knowledge to
Eve. Those men, fisher-folk, simple folk, had not counted as human
spectators, but rather as part of the brotherhood of night, nature,
and the stars.
He waited for Eve in the drawing-room, having assured himself that
she had been told nothing, and there, presently, he saw her come
in, her heavy hair dressed high, a fan and a flower drooping from
her hand, and a fringed Spanish shawl hanging its straight silk folds
from her escaping shoulders. Before her indolence, and her
slumbrous delicacy, he hesitated. He wildly thought that he would
allow the news to wait. Tragedy, reality, were at that moment so far
removed from her.... She said in delight, coming up to him, and
forgetful that they were in the house in obedience to a mysterious
and urgent message,—
'Julian, have you seen the fireworks? Come out into the garden.
We'll watch.'
He put his arm through her bare arm,—
'Eve, I must tell you something.'
'Fru Thyregod?' she cried, and the difficulty of his task became all
but insurmountable.
'Something serious. Something about Father Paul.'
Her strange eyes gave him a glance of undefinable suspicion.
'What about him?'
'He has been found, in the water, at the bottom of the garden.'
'In the water?'
'In the sea. Drowned.'
He told her all the circumstances, doggedly, conscientiously, under
the mockery of the tinsel flames that streamed out from the top of
the columns, and of the distant lights flashing through the windows,
speaking as a man who proclaims in a foreign country a great truth
bought by the harsh experience of his soul, to an audience
unconversant with his alien tongue. This truth that he had won, in
the presence of quiet stars, quieter death, and simple men, was
desecrated by its recital to a vain woman in a room where the very
architecture was based on falsity. Still he persevered, believing that
his own intensity of feeling must end in piercing its way to the
foundations of her heart. He laid bare even his harassing conviction
of his neglected responsibility,—
'I should have suspected ... I should have suspected....'
He looked at Eve; she had broken down and was sobbing, Paul's
name mingled incoherently with her sobs. He did not doubt that she
was profoundly shocked, but with a new-found cynicism he ascribed
her tears to shock rather than to sorrow. He himself would have
been incapable of shedding a single tear. He waited quietly for her to
recover herself.
'Oh, Julian! Poor Paul! How terrible to die like that, alone, in the sea,
at night....' For a moment her eyes were expressive of real horror,
and she clasped Julian's hand, gazing at him while all the visions of
her imagination were alive in her eyes. She seemed to be on the
point of adding something further, but continued to cry for a few
moments, and then said, greatly sobered, 'You appear to take for
granted that he has killed himself?'
He considered this. Up to the present no doubt whatever had existed
in his mind. The possibility of an accident had not occurred to him.
The very quality of repose and peace that he had witnessed had
offered itself to him as the manifest evidence that the man had
sought the only solution for a life grown unendurable. He had
acknowledged the man's wisdom, bowing before his recognition of
the conclusive infallibility of death as a means of escape. Cowardly?
so men often said, but circumstances were conceivable—
circumstances in the present case unknown, withheld, and therefore
not to be violated by so much as a hazarded guess—circumstances
were conceivable in which no other course was to be contemplated.
He replied with gravity,—
'I do believe he put an end to his life.'
The secret reason would probably never be disclosed; even if it
came within sight, Julian must now turn his eyes the other way. The
secret which he might have, nay, should have, wrenched from his
friend's reserve while he still lived, must remain sacred and
unprofaned now that he was dead. Not only must he guard it from
his own knowledge, but from the knowledge of others. With this
resolution he perceived that he had already blundered.
'Eve, I have been wrong; this thing must be presented as an
accident. I have no grounds for believing that he took his life. I must
rely on you to support me. In fairness on poor Paul.... He told me
nothing. A man has a right to his own reticence.'
He paused, startled at the truth of his discovery, and cried out,
taking his head between his hands,—
'Oh God! the appalling loneliness of us all!'
He shook his head despairingly for a long moment with his hands
pressed over his temples. Dropping his hands with a gesture of
discouragement and lassitude, he regarded Eve.
'I've found things out to-night, I think I've aged by five years. I
know that Paul suffered enough to put an end to himself. We can't
tell what he suffered from. I never intended to let you think he had
suffered. We must never let any one else suspect it. But imagine the
stages and degrees of suffering which led him to that state of mind;
imagine his hours, his days, and specially his nights. I looked on him
as a village priest, limited to his village; I thought his long hair
funny; God forgive me, I slightly despised him. You, Eve, you
thought him ornamental, a picturesque appendage to the house.
And all that while, he was moving slowly towards the determination
that he must kill himself.... Perhaps, probably, he took his decision
yesterday, when you and I were at the picnic. When Fru Thyregod....
For months, perhaps, or for years, he had been living with the secret
that was to kill him. He knew, but no one else knew. He shared his
knowledge with no one. I think I shall never look at a man again
without awe, and reverence, and terror.'
He was trembling strongly, discovering his fellows, discovering
himself, his glowing eyes never left Eve's face. He went on talking
rapidly, as though eager to translate all there was to translate into
words before the aroused energy deserted him.
'You vain, you delicate, unreal thing, do you understand at all? Have
you ever seen a dead man? You don't know the meaning of pain.
You inflict pain for your amusement. You thing of leisure, you toy!
Your deepest emotion is your jealousy. You can be jealous even
where you cannot love. You make a plaything of men's pain—you
woman! You can change your personality twenty times a day. You
can't understand a man's slow, coherent progression; he, always the
same person, scarred with the wounds of the past. To wound you
would be like wounding a wraith.'
Under the fury of his unexpected outburst, she protested,—
'Julian, why attack me? I've done, I've said, nothing.'
'You listened uncomprehendingly to me, thinking if you thought at
all, that by to-morrow I should have forgotten my mood of to-night.
You are wrong. I've gone a step forward to-day. I've learnt.... Learnt,
I mean, to respect men who suffer. Learnt the continuity and the
coherence of life. Days linked to days. For you, an episode is an
isolated episode.'
He softened.
'No wonder you look bewildered. If you want the truth, I am angry
with myself for my blindness towards Paul. Poor little Eve! I only
meant half I said.'
'You meant every word; one never speaks the truth so fully as when
one speaks it unintentionally.'
He smiled, but tolerantly and without malice.
'Eve betrays herself by the glibness of the axiom. You know nothing
of truth. But I've seen truth to-night. All Paul's past life is mystery,
shadow, enigma to me, but at the same time there is a central light
—blinding, incandescent light—which is the fact that he suffered.
Suffered so much that, a priest, he preferred the supreme sin to
such suffering. Suffered so much that, a man, he preferred death to
such suffering! All his natural desire for life was conquered. That
irresistible instinct, that primal law, that persists even to the moment
when darkness and unconsciousness overwhelm us—the fight for
life, the battle to retain our birthright—all this was conquered. The
instinct to escape from life became stronger than the instinct to
preserve it! Isn't that profoundly illuminating?'
He paused.
'That fact sweeps, for me, like a great searchlight over an abyss of
pain. The pain the man must have endured before he arrived at such
a reversal of his religion and of his most primitive instinct! His world
was, at the end, turned upside down. A terrifying nightmare. He
took the only course. You cannot think how final death is—so final,
so simple. So simple. There is no more to be said. I had no idea....'
He spoke himself with the simplicity he was trying to express. He
said again, candidly, evenly, in a voice from which all the emotion
had passed,—
'So simple.'
They were silent for a long time. He had forgotten her, and she was
wondering whether she dared now recall him to the personal. She
had listened, gratified when he attacked her, resentful when he
forgot her, bored with his detachment, but wise enough to conceal
both her resentment and her boredom. She had worshipped him in
his anger, and had admired his good looks in the midst of his fire.
She had been infinitely more interested in him than in Paul. Shocked
for a moment by Paul's death, aware of the stirrings of pity, she had
quickly neglected both for the sake of the living Julian.
She reviewed a procession of phrases with which she might recall his
attention.
'You despise me, Julian.'
'No, I only dissociate you. You represent a different sphere. You
belong to Herakleion. I love you—in your place.'
'You are hurting me.'
He put his hands on her shoulders and turned her towards the fight.
She let him have his way, with the disconcerting humility he had
sometimes found in her. She bore his inspection mutely, her hands
dropping loosely by her sides, fragile before his strength. He found
that his thoughts had swept back, away from death, away from Paul,
to her sweetness and her worthlessness.
'Many people care for you—more fools they,' he said. 'You and I,
Eve, must be allies now. You say I despise you. I shall do so less if I
can enlist your loyalty in Paul's cause. He has died as the result of an
accident. Are you to be trusted?'
He felt her soft shoulders move in the slightest shrug under the
pressure of his hands.
'Do you think,' she asked, 'that you will be believed?'
'I shall insist upon being believed. There is no evidence—is there?—
to prove me wrong.'
As she did not answer, he repeated his question, then released her
in suspicion.
'What do you know? tell me!'
After a very long pause, he said quietly,—
'I understand. There are many ways of conveying information. I am
very blind about some things. Heavens! if I had suspected that truth,
either you would not have remained here, or Paul would not have
remained here. A priest! Unheard of.... A priest to add to your
collection. First Miloradovitch, now Paul. Moths pinned upon a board.
He loved you? Oh,' he cried in a passion, 'I see it all: he struggled,
you persisted—till you secured him. A joke to you. Not a joke now—
surely not a joke, even to you—but a triumph. Am I right? A
triumph! A man, dead for you. A priest. You allowed me to talk,
knowing all the while.'
'I am very sorry for Paul,' she said absently.
He laughed at the pitiably inadequate word.
'Have the courage to admit that you are flattered. More flattered
than grieved. Sorry for Paul—yes, toss him that conventional tribute
before turning to the luxury of your gratified vanity. That such things
can be! Surely men and women live in different worlds?'
'But, Julian, what could I do?'
'He told you he loved you?'
She acquiesced, and he stood frowning at her, his hands buried in
his pockets and his head thrust forward, picturing the scenes, which
had probably been numerous, between her and the priest, letting his
imagination play over the anguish of his friend and Eve's
indifference. That she had not wholly discouraged him, he was sure.
She would not so easily have let him go. Julian was certain, as
though he had observed their interviews from a hidden corner, that
she had amusedly provoked him, watched him with half-closed,
ironical eyes, dropped him a judicious word in her honeyed voice,
driven him to despair by her disregard, raised him to joy by her
capricious friendliness. They had had every opportunity for meeting.
Eve was strangely secretive. All had been carried on unsuspected. At
this point he spoke aloud, almost with admiration,—
'That you, who are so shallow, should be so deep!'
A glimpse of her life had been revealed to him, but what secrets
remained yet hidden? The veils were lifting from his simplicity; he
contemplated, as it were, a new world—Eve's world, ephemerally
and clandestinely populated. He contemplated it in fascination,
acknowledging that here was an additional, a separate art, insistent
for recognition, dominating, imperative, forcing itself impudently
upon mankind, exasperating to the straight-minded because it
imposed itself, would not be denied, was subtle, pretended so
unswervingly to dignity that dignity was accorded it by a credulous
humanity—the art which Eve practised, so vain, so cruel, so
unproductive, the most fantastically prosperous of impostors!
She saw the marvel in his eyes, and smiled slightly.
'Well, Julian?'
'I am wondering,' he cried, 'wondering! trying to pierce to your
mind, your peopled memory, your present occupation, your science.
What do you know? what have you heard? What have you seen?
You, so young.... Who are not young. How many secrets like the
secret of Paul are buried away in your heart? That you will never
betray? Do you ever look forward to the procession of your life? You,
so young. I think you have some extraordinary, instinctive, inherited
wisdom, some ready-made heritage, bequeathed to you by
generations, that compensates for the deficiencies of your own
experience. Because you are so young. And so old, that I am afraid.'
'Poor Julian,' she murmured. A gulf of years lay between them, and
she spoke to him as a woman to a boy. He was profoundly shaken,
while she remained quiet, gently sarcastic, pitying towards him, who,
so vastly stronger than she, became a bewildered child upon her
own ground. He had seen death, but she had seen, toyed with,
dissected the living heart. She added, 'Don't try to understand.
Forget me and be yourself. You are annoying me.'
She had spoken the last words with such impatience, that, torn from
his speculations, he asked,—
'Annoying you? Why?'
After a short hesitation she gave him the truth,—
'I dislike seeing you at fault.'
He passed to a further bewilderment.
'I want you infallible.'
Rousing herself from the chair where she had been indolently lying,
she said in the deepest tones of her contralto voice,—
'Julian, you think me worthless and vain; you condemn me as that
without the charity of any further thought. You are right to think me
heartless towards those I don't love. You believe that I spend my life
in vanity. Julian, I only ask to be taken away from my life; I have
beliefs, and I have creeds, both of my own making, but I'm like a
ship without a rudder. I'm wasting my life in vanity. I'm capable of
other things. I'm capable of the deepest good, I know, as well as of
the most shallow evil. Nobody knows, except perhaps Kato a little,
how my real life is made up of dreams and illusions that I cherish.
People are far more unreal to me than my own imaginings. One of
my beliefs is about you. You mustn't ever destroy it. I believe you
could do anything.'
'No, no,' he said, astonished.
But she insisted, lit by the flame of her conviction.
'Yes, anything. I have the profoundest contempt for the herd—to
which you don't belong. I have believed in you since I was a child;
believed in you, I mean, as something Olympian of which I was
frightened. I have always known that you would justify my faith.'
'But I am ordinary, normal!' he said, defending himself. He
mistrusted her profoundly; wondered what attack she was
engineering. Experience of her had taught him to be sceptical.
'Ah, don't you see, Julian, when I am sincere?' she said, her voice
breaking. 'I am telling you now one of the secrets of my heart, if you
only knew it. The gentle, the amiable, the pleasant—yes, they're my
toys. I'm cruel, I suppose. I'm always told so. I don't care; they're
worth nothing. It does their little souls good to pass through the
mill. But you, my intractable Julian....'
'Kyrie,' said Nicolas, appearing, 'Tsantilas Tsigaridis, from Aphros,
asks urgently whether you will receive him?'
'Bring him in,' said Julian, conscious of relief, for Eve's words had
begun to trouble him.
Outside, the fireworks continued to flash like summer lightning.
 VI
Tsigaridis came forward into the room, his fishing cap between his
fingers, and his white hair standing out in bunches of wiry curls
round his face. Determination was written in the set gravity of his
features, even in the respectful bow with which he came to a halt
before Julian. Interrupted in their conversation, Eve had fallen, back,
half lying, in her arm-chair, and Julian, who had been pacing up and
down, stood still with folded arms, a frown cleaving a deep valley
between his brows. He spoke to Tsigaridis,—
'You asked for me, Tsantilas?'
'I am a messenger, Kyrie.'
He looked from the young man to the girl, his age haughty towards
their youth, his devotion submissive towards the advantage of their
birth. He said to Julian, using almost the same words as he had used
once before,—
'The people of Aphros are the people of your people,' and he bowed
again.
Julian had recovered his self-possession; he no longer felt dazed and
bewildered as he had felt before Eve. In speaking to Tsigaridis he
was speaking of things he understood. He knew very well the
summons Tsigaridis was bringing him, the rude and fine old man,
single-sighted as a prophet, direct and unswerving in the cause he
had at heart. He imagined, with almost physical vividness, the hand
of the fisherman on his shoulder, impelling him forward.
'Kyrie,' Tsigaridis continued, 'to-day the flag of Herakleion flew from
the house of your honoured father until you with your own hand
threw it down. I was in Herakleion, where the news was brought to