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 Organic Chemistry, Ninth Edition © 2016, 2012, Cengage Learning
John McMurry WCN: 02-200-203
Product Director: Mary Finch ALL RIGHTS RESERVED. No part of this work covered by the copyright herein
Product Manager: Maureen Rosener may be reproduced, transmitted, stored, or used in any form or by any means
Content Developers: Nat Chen, Lisa Weber graphic, electronic, or mechanical, including but not limited to photocopying,
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Content Project Manager: Teresa Trego written permission of the publisher.
Art Director: Andrei Pasternak
For product information and technology assistance, contact us at
Manufacturing Planner: Judy Inouye
Cengage Learning Customer & Sales Support, 1-800-354-9706.
Production Service: Graphic World Inc. For permission to use material from this text or product,
Photo Researcher: Lumina Datamatics submit all requests online at www.cengage.com/permissions.
Further permissions questions can be e-mailed to
Text Researcher: Lumina Datamatics
[email protected].
Copy Editor: Graphic World Inc.
Text Designer: Parallelogram Graphics Library of Congress Control Number: 2014960022
Cover Designer: Cheryl Carrington
Student Edition:
Cover Image: Imagebroker.net/SuperStock
ISBN: 978-1-305-08048-5
Compositor: Graphic World Inc.
Loose-leaf Edition:
ISBN: 978-1-305-63871-6

Cengage Learning
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Boston, MA 02210
USA

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office locations around the globe, including Singapore, the United Kingdom,
Australia, Mexico, Brazil, and Japan. Locate your local office at
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Printed in the United States of America

Print Number: 01 Print Year: 2015

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Brief Contents

1 Structure and Bonding 1

2 Polar Covalent Bonds; Acids and Bases 28

3 Organic Compounds: Alkanes and Their Stereochemistry 60

4 Organic Compounds: Cycloalkanes and Their Stereochemistry 89

5 Stereochemistry at Tetrahedral Centers 115

6 An Overview of Organic Reactions 149

Practice Your Scientific Analysis and Reasoning I: The Chiral Drug Thalidomide 182

7 Alkenes: Structure and Reactivity 185

8 Alkenes: Reactions and Synthesis 220

9 Alkynes: An Introduction to Organic Synthesis 263

10 Organohalides 287

11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 309

 ractice Your Scientific Analysis and Reasoning II: From Mustard Gas
P
to Alkylating Anticancer Drugs 351

12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 354

13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 386

14 Conjugated Compounds and Ultraviolet Spectroscopy 420

Practice Your Scientific Analysis and Reasoning III: Photodynamic Therapy (PDT) 448

15 Benzene and Aromaticity 451

16 Chemistry of Benzene: Electrophilic Aromatic Substitution 478

17 Alcohols and Phenols 525

18 Ethers and Epoxides; Thiols and Sulfides 568

• Preview of Carbonyl Chemistry 595

19 Aldehydes and Ketones: Nucleophilic Addition Reactions 604

 ractice Your Scientific Analysis and Reasoning IV: Selective Serotonin

P
Reuptake Inhibitors (SSRIs) 649

20 Carboxylic Acids and Nitriles 653

21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 679

22 Carbonyl Alpha-Substitution Reactions 727

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Brief Contents

23 Carbonyl Condensation Reactions 753

Practice Your Scientific Analysis and Reasoning V: Thymine in DNA 784

24 Amines and Heterocycles 787

25 Biomolecules: Carbohydrates 832

26 Biomolecules: Amino Acids, Peptides, and Proteins 870

27 Biomolecules: Lipids 907

Practice Your Scientific Analysis and Reasoning VI: Melatonin and Serotonin 939

28 Biomolecules: Nucleic Acids 942

29 The Organic Chemistry of Metabolic Pathways 964

30 Orbitals and Organic Chemistry: Pericyclic Reactions 1013

 ractice Your Scientific Analysis and Reasoning VII: The Potent Antibiotic
P
Traits of Endiandric Acid C 1034

31 Synthetic Polymers 1037

Appendix A: Nomenclature of Polyfunctional Organic Compounds A-1

Appendix B: Acidity Constants for Some Organic Compounds A-9

Appendix C: Glossary A-11

Appendix D: Answers to In-Text Problems A-31

Index I-1

vi

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 D e ta i l e d C o n t e n t s

Structure and Bonding | 1

1-1 Atomic Structure: The Nucleus 3

1-2 Atomic Structure: Orbitals 4
1-3 Atomic Structure: Electron Configurations 6
c h ap t e r
1-4 Development of Chemical Bonding Theory

1
7
1-5 Describing Chemical Bonds: Valence Bond Theory 10
1-6 sp3 Hybrid Orbitals and the Structure of Methane 12
1-7 sp3 Hybrid Orbitals and the Structure of Ethane 13
1-8 sp2 Hybrid Orbitals and the Structure of Ethylene 14
1-9 sp Hybrid Orbitals and the Structure of Acetylene 17
1-10 Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur 18
1-11 Describing Chemical Bonds: Molecular Orbital Theory 20
1-12 Drawing Chemical Structures 21

Something Extra Organic Foods: Risk versus Benefit 25

Summary 26
Key words 26
Working Problems 27
Exercises 27a

Polar Covalent Bonds; Acids and Bases | 28

2-1 Polar Covalent Bonds: Electronegativity

Shutterstock.com

28
©Kostyantyn
Ivanyshen/

2-2 Polar Covalent Bonds: Dipole Moments 31

2-3 Formal Charges 33
c h ap t e r
2-4 Resonance

2
36
2-5 Rules for Resonance Forms 37
2-6 Drawing Resonance Forms 39
2-7 Acids and Bases: The Brønsted–Lowry Definition 42

vii

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 viii contents

2-8 Acid and Base Strength 44

2-9 Predicting Acid–Base Reactions from pKa Values 46
2-10 Organic Acids and Organic Bases 47
2-11 Acids and Bases: The Lewis Definition 50
2-12 Noncovalent Interactions between Molecules 54

Something Extra  lkaloids: From Cocaine

A
to Dental Anesthetics  56

Summary 58
Key words 58
Exercises 59

Organic Compounds: Alkanes and

Their Stereochemistry | 60
3-1 Functional Groups
Shutterstock.com

60
©tactilephoto/

3-2 Alkanes and Alkane Isomers 66

3-3 Alkyl Groups 70
c h ap t e r
3-4 Naming Alkanes

3
73
3-5 Properties of Alkanes 78
3-6 Conformations of Ethane 80
3-7 Conformations of Other Alkanes 82

Something Extra Gasoline 86

Summary 87
Key words 87
Exercises 88

Organic Compounds: Cycloalkanes and

Their Stereochemistry | 89
4-1 Naming Cycloalkanes 90
Indiapicture /

4-2 Cis–Trans Isomerism in Cycloalkanes 92

Alamy

4-3 Stability of Cycloalkanes: Ring Strain 95

c h ap t e r
4-4 Conformations of Cycloalkanes

4
97
4-5 Conformations of Cyclohexane 99
4-6 Axial and Equatorial Bonds in Cyclohexane 101

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Contents ix

4-7 Conformations of Monosubstituted Cyclohexanes 104

4-8 Conformations of Disubstituted Cyclohexanes 107
4-9 Conformations of Polycyclic Molecules 110

Something Extra Molecular Mechanics 113

Summary 114
Key words 114
Exercises 114a

Stereochemistry at Tetrahedral Centers | 115

5-1 Enantiomers and the Tetrahedral Carbon

Shutterstock.com

116
©Bart Brouwer/

5-2 The Reason for Handedness in Molecules: Chirality 117

5-3 Optical Activity 121
c h ap t e r
5-4 Pasteur’s Discovery of Enantiomers

5
123
5-5 Sequence Rules for Specifying Configuration 124
5-6 Diastereomers 131
5-7 Meso Compounds 133
5-8 Racemic Mixtures and the Resolution of Enantiomers 135
5-9 A Review of Isomerism 138
5-10 Chirality at Nitrogen, Phosphorus, and Sulfur 140
5-11 Prochirality 141
5-12 Chirality in Nature and Chiral Environments 145

Something Extra Chiral Drugs 147

Summary 148
Key words 148
Exercises 148a

An Overview of Organic Reactions | 149

6-1 Kinds of Organic Reactions

Shutterstock.com

149
©Aspen Photo/

6-2 How Organic Reactions Occur: Mechanisms 151

6-3 Radical Reactions 152
c h ap t e r
6-4 Polar Reactions

6
155
6-5 An Example of a Polar Reaction: Addition of HBr to Ethylene 159
6-6 Using Curved Arrows in Polar Reaction Mechanisms 162

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 x contents

6-7 Describing a Reaction: Equilibria, Rates, and Energy Changes 165

6-8 Describing a Reaction: Bond Dissociation Energies 169
6-9 Describing a Reaction: Energy Diagrams and Transition States 171
6-10 Describing a Reaction: Intermediates 174
6-11 A Comparison Between Biological Reactions
and Laboratory Reactions 177

Something Extra Where Do Drugs Come From? 179

Summary 181
Key words 181
Exercises 181a

Practice Your Scientific Analysis and Reasoning I 

The Chiral Drug Thalidomide | 182

Alkenes: Structure and Reactivity | 185

7-1 Industrial Preparation and Use of Alkenes

Shutterstock.com

186
©JIANHAO

7-2 Calculating Degree of Unsaturation 187

GUAN/

7-3 Naming Alkenes 189

c h ap t e r
7-4 Cis–Trans Isomerism in Alkenes

7
192
7-5 Alkene Stereochemistry and the E,Z Designation 194
7-6 Stability of Alkenes 198
7-7 Electrophilic Addition Reactions of Alkenes 201
7-8 Orientation of Electrophilic Additions: Markovnikov’s Rule 205
7-9 Carbocation Structure and Stability 208
7-10 The Hammond Postulate 211
7-11 Evidence for the Mechanism of Electrophilic
Additions: Carbocation Rearrangements 214

Something Extra Bioprospecting: Hunting

for Natural Products  217

Summary 218
Key words 218
Exercises 219

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Contents xi

Alkenes: Reactions and Synthesis | 220

8-1 Preparing Alkenes: A Preview of Elimination Reactions 221

Science Faction/
Getty Images
Ed Darack/

8-2 Halogenation of Alkenes: Addition of X2 222

8-3 Halohydrins from Alkenes: Addition of HOX 225
c h ap t e r
8-4 Hydration of Alkenes: Addition of H2O by Oxymercuration

8
227
8-5 Hydration of Alkenes: Addition of H2O by Hydroboration 230
8-6 Reduction of Alkenes: Hydrogenation 235
8-7 Oxidation of Alkenes: Epoxidation and Hydroxylation 239
8-8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds 242
8-9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis 245
8-10 Radical Additions to Alkenes: Chain-Growth Polymers 247
8-11 Biological Additions of Radicals to Alkenes 251
8-12 Reaction Stereochemistry: Addition of H2O to an Achiral Alkene 252
8-13 Reaction Stereochemistry: Addition of H2O to a Chiral Alkene 255

Something Extra Terpenes: Naturally Occurring Alkenes 257

Summary 259
Key words 259
Learning Reactions 260
Summary of Reactions 260
Exercises 262

Alkynes: An Introduction to Organic Synthesis | 263

9-1 Naming Alkynes

Shutterstock.com

264
©Igor Bulgarin/

9-2 Preparation of Alkynes: Elimination Reactions of Dihalides 265

9-3 Reactions of Alkynes: Addition of HX and X2 265
c h ap t e r
9-4 Hydration of Alkynes

9
268
9-5 Reduction of Alkynes 272
9-6 Oxidative Cleavage of Alkynes 275
9-7 Alkyne Acidity: Formation of Acetylide Anions 275
9-8 Alkylation of Acetylide Anions 277
9-9 An Introduction to Organic Synthesis 279

Something Extra The Art of Organic Synthesis 283

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 xii contents

Summary 284
Key words 284
Summary of Reactions 285
Exercises 286a

Organohalides | 287
Sebastián Crespo

10-1 Names and Structures of Alkyl Halides 288

Photography/
Getty Images

10-2 Preparing Alkyl Halides from Alkanes: Radical Halogenation 290

10-3 Preparing Alkyl Halides from Alkenes: Allylic Bromination 292
c h ap t e r
10-4 Stability of the Allyl Radical: Resonance Revisited

10
294
10-5 Preparing Alkyl Halides from Alcohols 297
10-6 Reactions of Alkyl Halides: Grignard Reagents 298
10-7 Organometallic Coupling Reactions 300
10-8 Oxidation and Reduction in Organic Chemistry 303

Something Extra Naturally Occurring Organohalides 305

Summary 307
Key words 307
Summary of Reactions 307
Exercises 308

Reactions of Alkyl Halides: Nucleophilic

Substitutions and Eliminations | 309
11-1 The Discovery of Nucleophilic Substitution Reactions 310
Martin Harvey/
Getty Images

11-2 The SN2 Reaction 313

11-3 Characteristics of the SN2 Reaction 316
c h ap t e r
11-4 The SN1 Reaction

11
323
11-5 Characteristics of the SN1 Reaction 327
11-6 Biological Substitution Reactions 333
11-7 Elimination Reactions: Zaitsev’s Rule 335
11-8 The E2 Reaction and the Deuterium Isotope Effect 338
11-9 The E2 Reaction and Cyclohexane Conformation 341
11-10 The E1 and E1cB Reactions 343
11-11 Biological Elimination Reactions 345
11-12 A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2 345

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Contents xiii

Something Extra Green Chemistry 347

Summary 349
Key words 349
Summary of Reactions 350
Exercises 350a

Practice Your Scientific Analysis and Reasoning II 

From Mustard Gas to Alkylating Anticancer Drugs | 351

Structure Determination: Mass Spectrometry

and Infrared Spectroscopy | 354
12-1 Mass Spectrometry of Small Molecules:
MakiEni’s photo/
Getty Images

Magnetic-Sector Instruments 355

12-2 Interpreting Mass Spectra 357
c h ap t e r 12-3 Mass Spectrometry of Some Common Functional Groups 362

12 12-4 Mass Spectrometry in Biological Chemistry:

Time-of-Flight (TOF) Instruments 367
12-5 Spectroscopy and the Electromagnetic Spectrum 368
12-6 Infrared Spectroscopy 371
12-7 Interpreting Infrared Spectra 373
12-8 Infrared Spectra of Some Common Functional Groups 376

Something Extra X-Ray Crystallography 384

Summary 385
Key words 385
Exercises 385

Structure Determination: Nuclear Magnetic

Resonance Spectroscopy | 386
13-1 Nuclear Magnetic Resonance Spectroscopy
Shutterstock.com

386
©EM Karuna/

13-2 The Nature of NMR Absorptions 389

13-3 The Chemical Shift 392
c h ap t e r
13-4 Chemical Shifts in 1H NMR Spectroscopy

13
394
13-5 Integration of 1H NMR Absorptions: Proton Counting 396

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 xiv contents

13-6 Spin–Spin Splitting in 1H NMR Spectra 397

13-7 1H NMR Spectroscopy and Proton Equivalence 402
13-8 More Complex Spin–Spin Splitting Patterns 404
13-9 Uses of 1H NMR Spectroscopy 407
13-10 13C NMR Spectroscopy: Signal Averaging and FT–NMR 408
13-11 Characteristics of 13C NMR Spectroscopy 410
13-12 DEPT 13C NMR Spectroscopy 413
13-13 Uses of 13C NMR Spectroscopy 416

Something Extra Magnetic Resonance Imaging (MRI) 417

Summary 418
Key words 418
Exercises 419

Conjugated Compounds and Ultraviolet

Spectroscopy | 420
14-1 Stability of Conjugated Dienes: Molecular Orbital Theory
Shutterstock.com

421
©DemarK/

14-2 Electrophilic Additions to Conjugated Dienes:

Allylic Carbocations 425
c h ap t e r 14-3 Kinetic versus Thermodynamic Control of Reactions 428

14 14-4
14-5
The Diels–Alder Cycloaddition Reaction
Characteristics of the Diels–Alder Reaction
430
431
14-6 Diene Polymers: Natural and Synthetic Rubbers 437
14-7 Ultraviolet Spectroscopy 438
14-8 Interpreting Ultraviolet Spectra: The Effect of Conjugation 441
14-9 Conjugation, Color, and the Chemistry of Vision 442

Something Extra Photolithography 444

Summary 446
Key words 446
Summary of Reactions 447
Exercises 447a

Practice Your Scientific Analysis and Reasoning III 

Photodynamic Therapy (PDT) | 448

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Contents xv

Benzene and Aromaticity | 451

15-1 Naming Aromatic Compounds

Shutterstock.com
452
©Handmade

15-2 Structure and Stability of Benzene 456

Pictures/

15-3 Aromaticity and the Hückel 4n 1 2 Rule 459

c h ap t e r
15-4 Aromatic Ions

15
461
15-5 Aromatic Heterocycles: Pyridine and Pyrrole 464
15-6 Polycyclic Aromatic Compounds 467
15-7 Spectroscopy of Aromatic Compounds 469

Something Extra Aspirin, NSAIDs, and COX-2 Inhibitors 474

Summary 476
Key words 476
Exercises 477

Chemistry of Benzene: Electrophilic

Aromatic Substitution | 478
16-1 Electrophilic Aromatic Substitution Reactions: Bromination 479
Library / Alamy
Niday Picture

16-2 Other Aromatic Substitutions 482

16-3 Alkylation and Acylation of Aromatic Rings:
c h ap t e r The Friedel–Crafts Reaction 488

16 16-4
16-5
Substituent Effects in Electrophilic Substitutions
Trisubstituted Benzenes: Additivity of Effects 503
493

16-6 Nucleophilic Aromatic Substitution 505

16-7 Benzyne 508
16-8 Oxidation of Aromatic Compounds 510
16-9 Reduction of Aromatic Compounds 513
16-10 Synthesis of Polysubstituted Benzenes 514

Something Extra Combinatorial Chemistry 519

Summary 521
Key words 521
Summary of Reactions 522
Exercises 524

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 xvi contents

Alcohols and Phenols | 525

17-1 Naming Alcohols and Phenols

Shutterstock.com

526
©JManuel

17-2 Properties of Alcohols and Phenols 528

Murillo/

17-3 Preparation of Alcohols: A Review 533

c h ap t e r
17-4 Alcohols from Carbonyl Compounds: Reduction

17
535
17-5 Alcohols from Carbonyl Compounds: Grignard Reaction 539
17-6 Reactions of Alcohols 543
17-7 Oxidation of Alcohols 550
17-8 Protection of Alcohols 553
17-9 Phenols and Their Uses 555
17-10 Reactions of Phenols 557
17-11 Spectroscopy of Alcohols and Phenols 559

Something Extra Ethanol: Chemical, Drug, Poison 563

Summary 564
Key words 564
Summary of Reactions 565
Exercises 567

Ethers and Epoxides; Thiols and Sulfides | 568

18-1 Names and Properties of Ethers

Shutterstock.com

569
©Heiko Kiera/

18-2 Preparing Ethers 570

18-3 Reactions of Ethers: Acidic Cleavage 573
c h ap t e r
18-4 Reactions of Ethers: Claisen Rearrangement

18
575
18-5 Cyclic Ethers: Epoxides 577
18-6 Reactions of Epoxides: Ring-Opening 578
18-7 Crown Ethers 583
18-8 Thiols and Sulfides 584
18-9 Spectroscopy of Ethers 588

Something Extra Epoxy Resins and Adhesives 591

Summary 592
Key words 592
Summary of Reactions 593
Exercises 594a

Copyright 2016 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
 Contents xvii

Preview of Carbonyl Chemistry | 595

I Kinds of Carbonyl Compounds 595

II Nature of the Carbonyl Group 597
III General Reactions of Carbonyl Compounds 597
IV Summary 603

Aldehydes and Ketones: Nucleophilic

Addition Reactions | 604
19-1 Naming Aldehydes and Ketones
Shutterstock.com

605
©Loskutnikov/

19-2 Preparing Aldehydes and Ketones 607

19-3 Oxidation of Aldehydes and Ketones 609
c h ap t e r
19-4 Nucleophilic Addition Reactions of Aldehydes and Ketones

19
610
19-5 Nucleophilic Addition of H2O: Hydration 614
19-6 Nucleophilic Addition of HCN: Cyanohydrin Formation 616
19-7 Nucleophilic Addition of Hydride and Grignard Reagents:
Alcohol Formation 617
19-8 Nucleophilic Addition of Amines: Imine and Enamine Formation 619
19-9 Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction 624
19-10 Nucleophilic Addition of Alcohols: Acetal Formation 626
19-11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction 630
19-12 Biological Reductions 633
19-13 Conjugate Nucleophilic Addition to a,b-Unsaturated
Aldehydes and Ketones 635
19-14 Spectroscopy of Aldehydes and Ketones 640

Something Extra Enantioselective Synthesis 644

Summary 646
Key words 646
Summary of Reactions 646
Exercises 648a

Practice Your Scientific Analysis and Reasoning IV

Selective Serotonin Reuptake Inhibitors (SSRIs) | 649

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 HENRY W. GRADY.

From the “New Orleans Times-Democrat.”

Henry W. Grady, editor of the Atlanta Constitution, died
yesterday, after a short illness, from typhoid pneumonia, at the early
age of thirty-six. Perhaps no man in the South has been more often
mentioned in the last few years or attracted more attention than he.
His famous speech before the New England Society had the effect of
bringing him before the country as the representative of that New
South which is building up into prosperity and greatness.
Mr. Grady was a native of Georgia. His father was Colonel of a
Confederate regiment during the late war, and to that father he paid
the highest tribute a son could pay in several of his speeches. He
had a hard struggle at first, like nearly every Southern boy, but he
fought his way up to the top by pluck, energy and determination.
Mr. Grady’s first journalistic venture was, we believe, in his native
town. He ran a small paper there, moved thence to Atlanta, carrying
on another newspaper venture in the Georgia capital. In the course
of events this paper was swallowed up by the Constitution, then
pushing itself to the front of the Georgia press, and Mr. Grady was
selected as co-editor of the latter.
Under him that paper became one of the leading exponents of
Southern opinion, a representative of the progressive South, not
lingering over dead memories, but living in the light of the present
and laboring to build up this section.
Mr. Grady and his paper were always the defenders of the South,
yet not afraid to expose and condemn its errors and mistakes. He
had the courage to speak out whenever this was necessary, and
when, some few months ago, regulators attempted to introduce into
Georgia, in the immediate vicinity of Atlanta, the same practices as
in Lafayette parish in this State, Mr. Grady, through the Constitution,
denounced it vigorously. There were threats, but it did not affect the
Constitution, which insisted that the New South must be a South of
peace, law and order.
We cannot at this time review Mr. Grady’s entire journalistic career.
It is sufficient to say that with his colleagues he built up his paper to
be a power in Georgia and the South. His ability was recognized
throughout this section, but it was not until his famous speech at the
New England dinner that his reputation became national.
When at that dinner, speaking for the New South he so well
represented, he pledged his brethren of the North the patriotic
devotion of the Southern people, he created a sensation. Some of
the most famous orators of the country were present, but without a
dissenting voice it was declared that Mr. Grady’s speech was the
event of the day. It sent a thrill throughout the Union. The Southern
people rose to declare that Mr. Grady had fully explained their views
and ideas, and before his eloquent words the prejudice which had
lingered since the war in many portions of the North disappeared.
Perhaps no single event tended more to bring the sections closer
together than that speech, which so eloquently voiced the true
sentiments of the Southern people. A wave of fraternal feeling swept
through the country, and although the Republican politicians
managed to counteract some of the good accomplished, much of it
remained. Mr. Grady deserves remembrance, for in a few words,
burning with eloquence, he swept away the prejudices of years.
The country discovered that it contained an orator of whom it had
known but little, a statesman who helped to remove the sectional
hatred which had so long retarded its progress. Mr. Grady became at
once one of the best-known men in the Union. He was spoken of for
United States Senator, he was mentioned as Vice-President, and it
looked as though he could be elevated to any position to which he
aspired; but he wisely clung to his journalistic career, satisfied that
he could thereby best benefit his State and section.
Mr. Grady was not a one-speech man. He has made many
addresses since then, and while it is true that his other speeches did
not create the same sensation as his first, they were all eloquent,
able and patriotic.
 His career so auspiciously begun, which promised so much to
himself and the country, has been brought suddenly and prematurely
to a close. Mr. Grady was a young man, and we had every reason to
believe that he would play a leading part in the South and in the
country. Although his career is thus cut short, he had accomplished
much, and the New South for which he spoke will carry on the good
work he began of uniting the entire country on one broad and
patriotic platform.
 SECOND TO NONE.

From the “Louisville Courier-Journal.”

Henry W. Grady died at his home in Atlanta yesterday. There is
that in the very announcement which is heart-breaking. He was the
rose and expectancy of the young South, the one publicist of the
New South, who, inheriting the spirit of the old, yet had realized the
present, and looked into the future, with the eyes of a statesman and
the heart of a patriot. His own future was fully assured. He had made
his place; had won his spurs; and he possessed the gifts, not merely
to hold them, but greatly to magnify their importance. That he should
be cut down upon the threshold of a career, for whose brilliant
development and broad usefulness all was prepared, is almost as
much a public calamity as it is a private grief. We tender to his family,
and to Georgia, whom he loved with the adoration of a true son for a
mother, the homage of our respectful and profound sympathy.
Mr. Grady became a writer for the Courier-Journal when but little
more than a boy and during the darkest days of the Reconstruction
period. There was in those days but a single political issue for the
South. Our hand was in the lion’s mouth, and we could do nothing,
hope for nothing, until we got it out. The young Georgian was ardent,
impetuous, the son of a father slain in battle, the offspring of a
section, the child of a province; yet he rose to the situation with
uncommon faculties of courage and perception; caught the spirit of
the struggle against reaction with perfect reach; and threw himself
into the liberal and progressive movements of the time with the
genius of a man born for both oratory and affairs. He was not long
with us. He wished a wider field of duty, and went East, carrying
letters in which he was commended in terms which might have
seemed extravagant then, but which he more than vindicated. His
final settlement in the capital of his native State and in a position
where he could speak directly and responsibly, gave him the
opportunity he had sought to make a fame for himself, and an
audience of his own. Here he carried the policy with which, in the
columns of the Courier-Journal, he had early identified himself, to its
finest conclusions; coming at once to the front as a champion of a
free South and a united country, second to none in efficiency,
equaled by none in eloquence.
He was eager and aspiring, and, in the heedlessness of youth,
with its aggressive ambitions, may not have been at all times
discriminating and considerate in the objects of his attacks; but he
was generous to a fault, and, as he advanced upon the highway, he
broadened with it and to it, and, if he had lived, would have realized
the fullest measure of his own promise and the hopes of his friends.
The scales of error, when error he felt he had committed, were fast
falling from his eyes, and he was frank to own his changed, or
changing view. The vista of the way ahead was opening before him
with its far perspective clear to his mental sight. He had just
delivered an utterance of exceeding weight and value, at once
rhetorically fine and rarely solid, and was coming home to be
welcomed by his people with open arms, when the Messenger of
Death summoned him to his last account. The tidings of the fatal
termination of his disorder are startling in their suddenness and
unexpectedness, and will be received North and South with sorrow
deep and sincere, and far beyond the bounds compassed by his
personality.
The Courier-Journal was always proud of him, hailed him as a
young disciple who had surpassed his elders in learning and power,
recognized in him a master voice and soul, followed his career with
admiring interest, and recorded his triumphs with ever-increasing
sympathy and appreciation. It is with poignant regret that we record
his death. Such spirits are not of a generation, but of an epoch; and
it will be long before the South will find one to take the place made
conspicuously vacant by his absence.
 A LOSS TO THE SOUTH.

From the “Louisville Post.”

The death of Henry W. Grady, of Atlanta, after so brief an illness
and in the very prime of a vigorous young manhood, will startle the
whole country and will be an especial affliction to the South. Mr.
Grady was a brilliant journalist, a man of brain and heart, and by his
sensible and enthusiastic policy has identified himself with the
interests of the New South. In fact, few men have been more largely
instrumental in bringing about that salutary sentiment, now
prevailing, that it is best for the South to look with hope and courage
to the future, rather than to live in sad inactivity amid the ruins of the
past. Mr. Grady was a warm and confident advocate of industrial
advancement in the land of his birth. He wanted to see the South
interlaced with railroads, her rich mineral deposits opened to
development, her cities teeming with factories, her people busy,
contented and prosperous. This was his mission as a man and as a
journalist, and his influence has been widespread. Just at this time
his loss will be doubly severe.
One morning Henry Grady, who had possessed little more than a
sectional reputation, woke up to find himself famous throughout the
nation. By his speech at a New York banquet he sounded the key-
note of fraternal Union between North and South, and his appeal for
mutual trust and confidence, with commerce and industry to cement
more strongly than ever the two great sections of the country, met
with a response from both sides of Mason and Dixon’s line more
hearty than ever before. Many another man from the South felt the
same sentiments and would have expressed them gladly. Many a
man in the North felt that in the South those sentiments were
sincerely held. But Grady had a peculiar opportunity, and right well
did he improve it. He expressed eloquently and forcibly the feelings,
the purposes, the very spirit of the New South, and in that very
moment he made a reputation that is national. It was his good
fortune to express to the business men as well as to the politicians of
the nation the idea of an indivisible union of interests, of sentiments
and of purposes, as well as of territory.
In Mr. Grady’s own State his death will be most felt. What he has
done for Georgia can only be appreciated by those who compare its
present activity and prosperity with the apathy and discontent which
existed there a few years ago. The dead man will be sincerely
mourned, but the idea which he made the fundamental one of his
brief career will continue to work out the welfare of the New South.
 THE DEATH OF HENRY W. GRADY.

The most brilliant journalist of the South is no more. When the

news was sent over the country yesterday morning that Henry W.
Grady, the editor of the Atlanta Constitution, was dead, there were
sighs of regret which, if they could have been gathered together into
one mass, would have been heard across the Atlantic. He was
peculiarly gifted. With an imagery and wealth of language that
enabled him to clothe the most uninteresting subject in a pleasing
garb, he had at the same time the genius of common sense more
fully developed than most men now prominently before the public.
He was born in 1851 in the town of Athens, Georgia, and was
therefore less than forty years of age. At college he was remarkable
among his fellows for those gifts of speech and pen which made him
famous. To his eternal honor, it can be said that in neither the
sanctum or the forum were his powers used in a way to add to any
one’s sorrow or distress. His writings were clean and pure and in
every line gave token of the kind heart that beat in his bosom. Mr.
Grady was a lovable man. Those who knew him well entertained for
him the deepest affection. His face was itself a fair type of his nature,
which was essentially of the sunshine character.
He was restlessly energetic and always agitating matters that he
believed would be promotive of the public good. The Cotton States’
Exposition and the Piedmont Exposition, both held in Atlanta, were
literally the creations of his energy and enthusiasm and pluck. It will
no doubt be readily admitted by his associates of the Constitution
that he was its moving spirit, and by his powers largely made it the
grand and magnificent success that it undeniably is.
The Young Men’s Christian Association building, costing $100,000,
arose as by magic under the persuasive powers of his tongue and
pen. The list of his works of a practical kind that now add to Atlanta’s
character and position could be indefinitely extended. When he
appealed to Atlanta he never spoke in vain, for in addition to brains
and energy he had those rare qualities of personal magnetism,
which made his originality and zeal wonderfully effective. He entered
into everything his big head conceived with his whole heart and soul.
He was loyal to his city and State, and never missed an
opportunity for aiding in their advancement. He was sought out by
the young and the old, and enjoyed the full confidence of all who
knew him.
His name and fame, however, were not confined to Georgia. In the
Lone Star State, thousands flocked to the city of Dallas to hear his
great speech at the Texas State Fair. His New York speech, a year or
two ago, fairly thrilled the country and caused the enactment of
scenes never before witnessed on similar occasions. No orator had
ever received such an ovation in that great city, and none such has
been since extended to any speaker. His recent speech at Boston
was calculated to do more good for the entire country than anything
that has fallen from the lips of any man in the last decade. It will be a
monument to his memory more enduring than brass. It made a
profound impression on those who heard it. The sentiments and
truths he so boldly uttered are echoing and re-echoing among the
hills of New England and over the prairies of the great West, and
they will bear rich fruit in the near future. They were things known to
us all here, but those who did not know and did not care have been
set to thinking by his eloquent presentation of the Southern situation.
That speech, perhaps, cost him his life; but if it produces the effect
on the Northern mind and heart which it deserves, the great sacrifice
will not have been in vain. His death will cause a more earnest
attention to the great truths he uttered, and result in an emphasis of
them that could not have been attained otherwise, sad as that
emphasis may be. The death of such a man is a national calamity.
He had entered upon a career that would have grown more brilliant
each year of his life. His like will not soon be seen and heard again.
 UNIVERSAL SORROW.

From the “Nashville American.”

The news of Mr. Grady’s death is received with universal sorrow.
No man of his age in the South or in the Union has achieved such
prominence or given promise of greater usefulness or higher honors.
His reputation as a journalist was deservedly high; but he won
greater distinction, perhaps, by his public speeches. He was
intensely, almost devoutly Southern, but he had always the
respectful attention of the North when he spoke for the land of his
nativity. There was the ring of sincerity in his fervid utterances, and
his audiences, whether in the North or in the South, felt that every
word came hot from the heart. He has done as much as any man to
put the South right before the world; and few have done more to
promote its progress and prosperity. He was a man of tremendous
energy, bodily and mental, and always worked at high tension.
Whatever subject interested him took his mind and body captive, and
into whatever cause he enlisted he threw all the powers of his
intellect and all the force of a nature ardent, passionate, and
enthusiastic in the extreme. It is probable that the disease which laid
hold of him found him an easier prey because of the restless energy
which had pushed his physical powers beyond their capacity. His
nervous and impetuous temperament showed no mercy to the
physical man and made it impossible for him to exercise a prudent
self-restraint even when the danger of a serious illness was present
with him.
Mr. Grady’s personal traits were such as won the love of all who
knew him. All knew the brilliant intellect; but few knew the warm,
unselfish heart. The place which he held in public esteem was but
one side of his character; the place which he held in the hearts of his
friends was the other.
The South has other men of genius and of promise; but none who
combine the rare and peculiar qualities which made Henry W. Grady,
at the age of thirty-eight, one of the most conspicuous men of his
generation.
 THE HIGHEST PLACE.

From the “Charleston News and Courier.”

The death of Henry W. Grady has removed from earth the most
prominent figure among the younger generation of public men in
America. He held unquestionably the highest place in the admiration
and regard of the people of the South that was accorded to any man
of his years, and had won, indeed, by his own efforts and
attainments a place among the older and the most honored
representatives of the people of the whole country. It was said of him
by a Northern writer, a few days before his death, that no other
Southern man could command so large a share of the attention of
the Northern people, and his death was the result of a visit to New
England, whither he went in response to an earnest invitation to
speak to the people of that section upon a question of the gravest
national concern.
The people of Georgia both honored and loved Henry Grady, and
would have elected him to any office within their gift. It is probable
that, had he lived but a little while longer, he would have been made
Governor of the State, or commissioned to represent it in the Senate
of the United States. He would have filled either of these positions
acceptably and with credit to himself; and perhaps even higher
honors awaited him. When his name was mentioned a few months
ago in connection with the nomination for the second highest office
in the gift of the people of the whole country, the feeling was general
and sincere that he was fully worthy, at least, of the great dignity
which it was proposed to confer upon him. Certainly no other
evidence is required to prove that the brave and brilliant young
Georgian was a marked man, and that he had already made a deep
impression on the events and the men of his time when he was so
suddenly stricken down in the flower of useful and glorious
manhood.
It is inexpressibly saddening to contemplate the untimely ending of
so promising a career. Only a few days ago the brightest prospect
that could open before the eyes of any young man in all this broad
land lay before the eyes of Henry Grady. To-day his eyes are closed
to all earthly scenes. To-morrow the shadows of the grave will close
around him forever. But it will be long before his influence will cease
to be felt. The memory of his kindly, gracious presence, of his
eloquent words and earnest work, of his generous deeds and noble
example in the discharge of all the duties of citizenship, will ever
remain with those who knew him best and loved him most.
To his wife and children he has left a rich inheritance in his
honored name, though he had left them nothing else. The people of
his State and of the South owe him a large debt of gratitude. He
served them faithfully and devotedly. What he said so well, only a
few months ago, of one who served with him, and who like him was
stricken down in the prime of his life, can be said of Henry Grady
himself. It is true of him also that “his leadership has never been
abused, its opportunities never wasted, its power never prostituted,
its suggestions never misdirected.” Georgia surely is a better and
more prosperous State “because he lived in it and gave his life freely
and daily to her service.”
And surely, again, “no better than this could be said of any man,”
as he said, and for as much to be written, in truth and sincerity, over
his grave, the best and proudest man might be willing to toil through
life and to meet death at last, as he met it, “unfearing and tranquil.”
His own life, and the record and the close of his life, are best
described in these his own words, written ten months ago, and,
perhaps, no more fitting epitaph could be inscribed on his tomb than
the words which he spoke, almost at the last, in the hour of his
death: “Send word to mother to pray for me. Tell her if I die, that I
died while trying to serve the South—the land I love so well.”
 A BRILLIANT CAREER.

From the “Baltimore Sun.”

The death yesterday at Atlanta of Henry W. Grady, editor of the
Constitution of that city, is a distressing shock to the thousands North
and South who had learned to admire his vigorous and impressive
utterances on public subjects. Young, enterprising, industrious and
devoted to the material advancement of his State and section, he
was a type of the progressive Southern man of our day. In the face
of the greatest possible difficulties and discouragements he achieved
success, intellectual and financial, of a most substantial character.
Mr. Grady’s career was brief and meteoric, but it was also a useful
career. His strong grasp of present facts enabled him to guide and
stimulate the energies of those about him into profitable channels.
Full of ideas, which his intense, nervous nature fused into sentiment,
he exerted an influence which greatly promoted the progress and
prosperity of his section. Outside his own State Mr. Grady will be
best known, however, as a brilliant and eloquent speaker. For some
years past his speeches at social gatherings of a semi-public
character in Northern cities have attracted a great deal of attention
North and South. His earlier utterances were a trifle effusive,
conceding overmuch, perhaps, under the inspiration of the moment,
to the prejudices of his audience. In discussing fiscal measures he
was sometimes at fault, political economy not being his strongest
point, but as regards the relations of the sections, and especially as
regards the so-called Southern problem, he was a beacon of light to
his Northern auditors. His last speech at Boston the other day—the
delivery of which may be said to have brought about his death—is a
fitting monument of his genius and impassioned eloquence. It thrilled
the country with its assertion of the right of the white race of the
South to intelligent government and its determination never again to
submit to the misrule of the African. Mr. Grady’s speech on this
occasion was remarkable not only for its fervor and frankness—
which conciliated his most unrelenting political opponents—but also
for its wealth of recent fact, concisely stated and conclusive upon the
point he had in view. Is the full vote, as shown by the census, not
always cast in Southern elections? Neither is it cast in Northern
States, Mr. Grady showed, appealing to the facts of the elections of
November last. “When,” President Harrison asked in his last
message, referring to the colored voter of the South—“when is he to
have those full civic rights which have so long been his in law?” He
will have them, Mr. Grady answered, when the poor, ignorant, and
dependent employé everywhere gets his. The colored voter of the
South cannot be reasonably expected, he pointed out, to exercise
his civil rights to a greater extent than such rights are exercised by
persons in his position in the North and West. The point of view here
taken was new to Mr. Grady’s audience and new to the Northern
press. The effect of his speech, as a whole, upon Northern opinion
has been, it is believed, most beneficial. In the South it was
welcomed as an effort to put the Northern partisan in a position to
see in their true light the hardship and danger with which the South
is perpetually confronted. In some remarks made later at the Bay
State Club, in Boston, Mr. Grady adverted to a larger problem—one
that confronts the whole country. “It seems to me,” he said, “that the
great struggle in this country is a fight against the consolidation of
power, the concentration of capital, the domination of local
sovereignty and the dwarfing of the individual citizen. It is the
democratic doctrine that the citizen is master, and that he is best
fitted to carry out the diversified interests of the country. It is the
pride, I believe, of the South that her simple and sturdy faith, the
homogeneous nature of her people, elevate her citizens above party.
We teach the man that his best guide is the consciousness of his
sovereignty; that he may not ask the national government for
anything the State can do for him, and not ask anything of the State
that he can do for himself.” These views mark the breadth of the
speaker’s statesmanship, and show that it embraced interests wider
than those of his own section—as wide, in fact, as the continent
itself. Mr. Grady died of pneumonia, complicated with nervous
prostration. His early death, at the outset of a most promising career,
is a warning to others of our public men who are under a constant
nervous tension. Attempting too much, they work under excessive
pressure, and when, owing to some accident, they need a margin of
strength, there is none.
 A PUBLIC CALAMITY.

From the “Selma Times and Mail.”

At forty minutes past three o’clock on Monday morning Henry W.
Grady, the distinguished editor of the Atlanta Constitution, died at his
home of pneumonia. No announcement of the death of any leading
man of the South has ever created a more profound impression, or
caused more genuine and universal sorrow than will the sad news of
the demise of this brilliant young Georgian, coming as it does when
he was at the very zenith of his fame and usefulness. The death of
Mr. Grady is a public calamity that will be mourned by the entire
country. It is no exaggeration to say that no orator in the United
States since the days of S. S. Prentiss has had such wonderful
power over his audiences as Henry W. Grady. This fact has been
most forcibly illustrated by his two memorable speeches at the North,
the first in New York something over a year ago, the second recently
delivered in Boston and with the praises of which the country is still
ringing. Sad, sad indeed to human perception that such a brilliant
light should have been extinguished when it was shining the
brightest and doing the most to dispel the mists of prejudice. But an
All-wise Providence knows best. His servant had run his course, he
had fulfilled his destiny. The heart of the South has been made sad
to overflowing in a short space of time. Davis—Grady, types of the
past and the present, two noble representatives of the highest order
of Southern manhood and intelligence, representing two notable
eras, have passed away and left a brilliant mark on the pages of
history.
Henry W. Grady was a native Georgian. He was born in Athens in
1851, and consequently was too young to participate in the late war,
but his father lost his life in defense of the Confederate cause, and
the son was an ardent lover of the South. At an early age he
developed remarkable talent for journalism and entered the
profession as the editor of the Rome, Ga., Commercial. After
conducting this paper for several years he moved to Atlanta, and
established the Daily Herald. When Mr. Grady came to the
Constitution in 1880 he soon became famous as a correspondent,
and his letters were read far and wide, and when he assumed
editorial control of the Constitution, the paper at once felt the impulse
of his genius, and from that day has pushed steadily forward in
popular favor and in influence until both it and its brilliant editor
gained national reputation. No agencies have been more potent for
the advancement of Atlanta than Grady and the Constitution, the
three indissolubly linked together, and either of the three names
suggests the other.
As a type of the vigorous young Southerner of the so-called New
South Mr. Grady has won the admiration of the country and gone far
to the front, but he has been the soul of loyalty to his section, and
has ever struck downright and powerful blows for the Democratic
cause and for the rule of intelligence in the South. From the Potomac
to the Rio Grande all over our beautiful Southland to-day, there will
be mourning and sympathy with Georgia for the loss of her gifted
son.
 GRIEF TEMPERS TO-DAY’S JOY.

From the “Austin, Tex., Statesman.”

When an old man, full of years, and smitten with the decrepitude
they bring, goes down to the grave, the world, though saddened,
bows its acquiescence. It is recognized that lonely journey is a thing
foredoomed from the foundation of the world—it is the way of all
things mortal. But when a young man, full of the vigor of a sturdy life
growing into its prime, is suddenly stricken from the number of the
quick, a nation is startled and, resentful of the stroke, would rebel,
but that such decrees come from a Power that earth cannot reach,
and which, though working beyond the ken of fallible understanding,
yet doeth all things well.
For the second time within the past two weeks the South has been
called upon to mourn the demise of a chosen and well-beloved son.
The two men may be classified according to an analysis first of all
instituted by him whose funeral to-day takes place in Atlanta.
Jefferson Davis was typical of the Old South—Henry W. Grady of the
New. And by this we mean not that the South has put away those
things that, as a chosen and proud people, they have cherished
since first there was a State government in the South. They have the
same noble type of manhood, the same chivalrous ambitions, the
same love of home and state and country, they are as determined in
purpose, as unswerving in the application of principle. But what is
meant is that the material conditions of the South have changed, the
economics of an empire of territory have been radically altered. Not
only has a new class of field labor taken the place of the long-
accustomed slave help, but industries unknown in the South before
the war have invaded our fair lands, and the rush and whir of
manufactories are all around us. It is in this that the South has
changed. Jefferson Davis, in his declining years ushered into the
reign of peace, was never truly identified with the actualities of the
living present, in the sense of a man who, from the present, was for
himself carving out a future. His life was past, and for him the past
contained the most of earthly life—his was an existence of history,
not of activity—he was the personification of the Old South.
Mr. Grady was too young to have participated in the Civil War. He
was then but a boy, and has grown into manhood and power since
the time when the issues that gave birth to that war were settled. His
has been a life of the realistic present. He brought to a study of the
changes that were going on around him a keenly perceptive and a
well-trained mind—he studied the problems that surrounded him
thoroughly and conscientiously, and his conclusions were almost
invariably the soundest. He realized the importance and
responsibility of his position as the editor of a widely circulating
newspaper, and he was unfaltering in his zeal to discharge his every
duty with credit to himself and profit to his people. He was the
champion of the Southern people through the columns of his paper
and upon the rostrum—and when he fell beneath the unexpected
stroke of the grim reaper, the South lost a true and valiant friend, the
ablest defender with pen and word retort this generation has known.
As two weeks ago the South bowed in sorrow over the last leaf
that had fluttered down from the tree of the past, so to-day, as the
mortal remains of Henry W. Grady are lowered into the tomb, she
should cease from the merriment of the gladsome holiday season,
and drop a tear upon the grave of him who, though so young in
years, had in such brilliant paragraphs bidden defiance to ancient
prejudice, scoffed at partisan bigotry, and proudly invited the closest
scrutiny and criticism of the South. That South in him has lost a
warm-hearted friend whom manhood bids us mourn.