Organic Chemistry 6th Edition Ebook PDF

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Organic
Chemistry
SIXTH EDITION
JANICE GORZYNSKI SMITH

Contents vii
5.9 R and S Assignments in Compounds with Two or More

Stereogenic Centers 201
5.10 Disubstituted Cycloalkanes 202
5.11 Isomers—A Summary 203
5.12 Physical Properties of Stereoisomers 204
5.13 Chemical Properties of Enantiomers 209
Chapter 5 Review 211
Key Concepts 211
Key Skills 213
Problems 215
6 Understanding Organic Reactions 222

6.1 Writing Equations for Organic Reactions 223
6.2 Kinds of Organic Reactions 224
6.3 Bond Breaking and Bond Making 226
6.4 Bond Dissociation Energy 230
6.5 Thermodynamics 234
©Ninikas/Getty Images
6.6 Enthalpy and Entropy 236
6.7 Energy Diagrams 238
6.8 Energy Diagram for a Two-Step Reaction Mechanism 240
6.9 Kinetics 242
6.10 Catalysts 245
6.11 Enzymes 246
Key Concepts 247
Key Equations 248
Key Skills 248
Problems 249
7 Alkyl Halides and Nucleophilic Substitution 256

7.1 Introduction to Alkyl Halides 257
7.2 Nomenclature 258
7.3 Properties of Alkyl Halides 259
7.4 Interesting Alkyl Halides 260
7.5 The Polar Carbon–Halogen Bond 262
Source: Claire Fackler,
CINMS/NOAA 7.6 General Features of Nucleophilic Substitution 263
7.7 The Leaving Group 264
7.8 The Nucleophile 266
7.9 Possible Mechanisms for Nucleophilic Substitution 270
7.10 Two Mechanisms for Nucleophilic Substitution 271
7.11 The SN2 Mechanism 272
7.12 The SN1 Mechanism 277
7.13 Carbocation Stability 282
7.14 The Hammond Postulate 283
7.15 When Is the Mechanism SN1 or SN2? 286
7.16 Biological Nucleophilic Substitution 292
viii Contents
7.17 Vinyl Halides and Aryl Halides 295

7.18 Organic Synthesis 295
Key Concepts 297
Key Skills 299
Key Mechanism Concepts 300
Problems 301
8 Alkyl Halides and Elimination Reactions 308

8.1 General Features of Elimination 309
8.2 Alkenes—The Products of Elimination Reactions 310
8.3 The Mechanisms of Elimination 314
8.4 The E2 Mechanism 314
8.5 The Zaitsev Rule 318
8.6 The E1 Mechanism 320
©Forest & Kim Starr
8.7 SN1 and E1 Reactions 323
8.8 Stereochemistry of the E2 Reaction 324
8.9 When Is the Mechanism E1 or E2? 328
8.10 E2 Reactions and Alkyne Synthesis 328
8.11 When Is the Reaction SN1, SN2, E1, or E2? 330
Key Concepts 334
Key Skills 335
Problems 338
9 Alcohols, Ethers, and Related Compounds 345

9.1 Introduction 346
9.2 Structure and Bonding 347
9.4 Properties of Alcohols, Ethers, and Epoxides 351
9.5 Interesting Alcohols, Ethers, and Epoxides 352
©Daniel C. Smith 9.6 Preparation of Alcohols, Ethers, and Epoxides 355
9.7 General Features—Reactions of Alcohols, Ethers, and Epoxides 357
9.8 Dehydration of Alcohols to Alkenes 359
9.9 Carbocation Rearrangements 362
9.10 Dehydration Using POCl3 and Pyridine 364
9.11 Conversion of Alcohols to Alkyl Halides with HX 365
9.12 Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3 369
9.13 Tosylate—Another Good Leaving Group 372
9.14 Reaction of Ethers with Strong Acid 375
9.15 Thiols and Sulfides 376
9.16 Reactions of Epoxides 379
9.17 Application: Epoxides, Leukotrienes, and Asthma 384
Contents ix
9.18 Application: Benzo[a]pyrene, Epoxides, and Cancer 385

Key Concepts 386
Key Reactions 386
Key Skills 388
Key Mechanism Concepts in Reactions of Alcohols 390
Problems 390
10 Alkenes and Addition Reactions 397

10.2 Calculating Degrees of Unsaturation 399
10.4 Properties of Alkenes 405
10.5 Interesting Alkenes 406
©Adam Gault/ 10.6 Lipids—Part 2 407
Getty Images
10.7 Preparation of Alkenes 409
10.8 Introduction to Addition Reactions 410
10.9 Hydrohalogenation—Electrophilic Addition of HX 411
10.10 Markovnikov’s Rule 413
10.11 Stereochemistry of Electrophilic Addition of HX 415
10.12 Hydration—Electrophilic Addition of Water 417
10.13 Halogenation—Addition of Halogen 418
10.14 Stereochemistry of Halogenation 419
10.15 Halohydrin Formation 421
10.16 Hydroboration–Oxidation 424
10.17 Keeping Track of Reactions 428
10.18 Alkenes in Organic Synthesis 430
Key Concepts 432
Key Reactions 433
Key Skills 433
Problems 435
11 Alkynes and Synthesis 441

11.3 Properties of Alkynes 444
11.4 Interesting Alkynes 445
11.5 Preparation of Alkynes 446
©McGraw-Hill Education/
Chris Kerrigan, 11.6 Introduction to Alkyne Reactions 447
photographer
11.7 Addition of Hydrogen Halides 449
11.8 Addition of Halogen 451
11.9 Addition of Water 451
11.10 Hydroboration–Oxidation 454
11.11 Reaction of Acetylide Anions 456
11.12 Synthesis 460
x Contents

Key Reactions 463
Key Skills 463
Problems 465
12 Oxidation and Reduction 472

12.2 Reducing Agents 474
12.3 Reduction of Alkenes 475
12.4 Application: Hydrogenation of Oils 478
12.5 Reduction of Alkynes 480
©Amarita/Shutterstock 12.6 The Reduction of Polar CX σ Bonds 483
12.7 Oxidizing Agents 484
12.8 Epoxidation 485
12.9 Dihydroxylation 489
12.10 Oxidative Cleavage of Alkenes 491
12.11 Oxidative Cleavage of Alkynes 493
12.12 Oxidation of Alcohols 494
12.13 Green Chemistry 497
12.14 Biological Oxidation 498
12.15 Sharpless Epoxidation 499
Key Concepts 502
Key Reactions 502
Key Skills 504
Problems 505

Spectroscopy A Mass Spectrometry 512
A.1 Mass Spectrometry and the Molecular Ion 513
A.2 Alkyl Halides and the M + 2 Peak 518
A.3 Fragmentation 520
A.4 Fragmentation Patterns of Some Common Functional Groups 523
A.5 Other Types of Mass Spectrometry 525
©atomazul/123RF
Chapter Review 528
Key Concepts 528
Key Skills 528
Problems 529

Spectroscopy B Infrared Spectroscopy 534
B.1 Electromagnetic Radiation 535
B.2 The General Features of Infrared Spectroscopy 537
B.3 IR Absorptions 539
B.4 Infrared Spectra of Common Functional Groups 546
B.5 IR and Structure Determination 554
©T.Daly/Alamy Stock
Photo Chapter Review 556
Key Concepts 556
Key Skills 557
Problems 558
Contents xi

Spectroscopy C Nuclear Magnetic Resonance Spectroscopy 562
C.1 An Introduction to NMR Spectroscopy 563
1
C.2 H NMR: Number of Signals 566
1
C.3 H NMR: Position of Signals 571
C.4 The Chemical Shifts of Protons on sp2 and sp Hybridized Carbons 575
1
C.5 H NMR: Intensity of Signals 577
©Daniel C. Smith
1
C.6 H NMR: Spin–Spin Splitting 578
C.7 More-Complex Examples of Splitting 582
C.8 Spin–Spin Splitting in Alkenes 585
C.9 Other Facts About 1H NMR Spectroscopy 587
C.10 Using 1H NMR to Identify an Unknown 590
13
C.11 C NMR Spectroscopy 593
C.12 Magnetic Resonance Imaging (MRI) 597
Chapter Review 598
Key Concepts 598
Key Skills 598
Problems 602
13 Radical Reactions 611

13.2 General Features of Radical Reactions 613
13.3 Halogenation of Alkanes 615
13.4 The Mechanism of Halogenation 616
13.5 Chlorination of Other Alkanes 619
13.6 Chlorination Versus Bromination 619
©jeep2499/Shutterstock
13.7 Halogenation as a Tool in Organic Synthesis 622
13.8 The Stereochemistry of Halogenation Reactions 623
13.9 Application: The Ozone Layer and CFCs 625
13.10 Radical Halogenation at an Allylic Carbon 627
13.11 Application: Oxidation of Unsaturated Lipids 630
13.12 Application: Antioxidants 631
13.13 Radical Addition Reactions to Double Bonds 632
13.14 Polymers and Polymerization 635
Key Concepts 638
Key Reactions 638
Key Skills 639
Problems 641
14 Conjugation, Resonance, and Dienes 648

14.1 Conjugation 649
14.2 Resonance and Allylic Carbocations 651
14.3 Common Examples of Resonance 653
14.4 The Resonance Hybrid 654
14.5 Electron Delocalization, Hybridization, and Geometry 656
©John Foxx/Getty
Images
xii Contents
14.6 Conjugated Dienes 657

14.7 Interesting Dienes and Polyenes 659
14.8 The Carbon–Carbon σ Bond Length in Buta-1,3-diene 660
14.9 Stability of Conjugated Dienes 660
14.10 Electrophilic Addition: 1,2- Versus 1,4-Addition 661
14.11 Kinetic Versus Thermodynamic Products 663
14.12 The Diels–Alder Reaction 666
14.13 Specific Rules Governing the Diels–Alder Reaction 668
14.14 Other Facts About the Diels–Alder Reaction 672
14.15 Conjugated Dienes and Ultraviolet Light 675
Key Concepts 678
Key Reactions 679
Key Skills 679
Problems 682
15 Benzene and Aromatic Compounds 689

15.1 Background 690
15.2 The Structure of Benzene 691
15.3 Nomenclature of Benzene Derivatives 693
15.4 Spectroscopic Properties 695
15.5 Interesting Aromatic Compounds 696
©Daniel C. Smith 15.6 Benzene’s Unusual Stability 697
15.7 The Criteria for Aromaticity—Hückel’s Rule 699
15.8 Examples of Aromatic Compounds 701
15.9 What Is the Basis of Hückel’s Rule? 708
15.10 The Inscribed Polygon Method for Predicting Aromaticity 711
15.11 Buckminsterfullerene—Is It Aromatic? 713
Key Concepts 715
Key Skills 715
Problems 717
16 Reactions of Aromatic Compounds 725

16.1 Electrophilic Aromatic Substitution 726
16.2 The General Mechanism 727
16.3 Halogenation 728
16.4 Nitration and Sulfonation 730
16.5 Friedel–Crafts Alkylation and Friedel–Crafts Acylation 732
©Jill Braaten
16.6 Substituted Benzenes 739
16.7 Electrophilic Aromatic Substitution of Substituted Benzenes 742
16.8 Why Substituents Activate or Deactivate a Benzene Ring 746
16.9 Orientation Effects in Substituted Benzenes 747
16.10 Limitations on Electrophilic Substitution Reactions with Substituted
Benzenes 750
16.11 Disubstituted Benzenes 752
16.12 Synthesis of Benzene Derivatives 754
Contents xiii
16.13 Nucleophilic Aromatic Substitution 755

16.14 Halogenation of Alkyl Benzenes 759
16.15 Oxidation and Reduction of Substituted Benzenes 761
16.16 Multistep Synthesis 765
Key Concepts 767
Key Reactions 768
Key Skills 769
Problems 772
17 Introduction to Carbonyl Chemistry; Organometallic Reagents;

Oxidation and Reduction 780
17.2 General Reactions of Carbonyl Compounds 782
17.3 A Preview of Oxidation and Reduction 785
©AS Food studio/
17.4 Reduction of Aldehydes and Ketones 787
Shutterstock 17.5 The Stereochemistry of Carbonyl Reduction 789
17.6 Enantioselective Carbonyl Reductions 790
17.7 Reduction of Carboxylic Acids and Their Derivatives 793
17.8 Oxidation of Aldehydes 798
17.9 Organometallic Reagents 799
17.10 Reaction of Organometallic Reagents with Aldehydes and Ketones 802
17.11 Retrosynthetic Analysis of Grignard Products 805
17.12 Protecting Groups 807
17.13 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives 810
17.14 Reaction of Organometallic Reagents with Other Compounds 813
17.15 α,β-Unsaturated Carbonyl Compounds 815
17.16 Summary—The Reactions of Organometallic Reagents 818
17.17 Synthesis 818
Key Reactions 821
Key Skills 823
Problems 825
18 Aldehydes and Ketones—Nucleophilic Addition 833

18.3 Properties of Aldehydes and Ketones 839
18.4 Interesting Aldehydes and Ketones 841
18.5 Preparation of Aldehydes and Ketones 842
©iStock/Getty Images
18.6 Reactions of Aldehydes and Ketones—General Considerations 843
18.7 Nucleophilic Addition of H – and R– —A Review 846
18.8 Nucleophilic Addition of – CN 848
18.9 The Wittig Reaction 850
xiv Contents
18.10 Addition of 1° Amines 855

18.11 Addition of 2° Amines 858
18.12 Addition of H2O—Hydration 861
18.13 Addition of Alcohols—Acetal Formation 863
18.14 Acetals as Protecting Groups 867
18.15 Cyclic Hemiacetals 868
18.16 An Introduction to Carbohydrates 871
Key Concepts 872
Key Reactions 873
Key Skills 874
Problems 876
19 Carboxylic Acids and Nitriles 885

19.3 Physical and Spectroscopic Properties 890
19.4 Interesting Carboxylic Acids and Nitriles 892
19.5 Aspirin, Arachidonic Acid, and Prostaglandins 893
©Sarka Babicka/Getty
Images 19.6 Preparation of Carboxylic Acids 894
19.7 Carboxylic Acids—Strong Organic Brønsted–Lowry Acids 895
19.8 Inductive Effects in Aliphatic Carboxylic Acids 899
19.9 Substituted Benzoic Acids 901
19.10 Extraction 904
19.11 Amino Acids 907
19.12 Nitriles 911
Key Concepts 915
Key Reactions 916
Key Skills 916
Problems 918
20 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl

Substitution 926
©LIKIT SUPASAI/
Shutterstock 20.5 Interesting Esters and Amides 936
20.6 Introduction to Nucleophilic Acyl Substitution 938
20.7 Reactions of Acid Chlorides 941
20.8 Reactions of Anhydrides 943
20.9 Reactions of Carboxylic Acids 945
Contents xv
20.10 Reactions of Esters 950

20.11 Application: Lipid Hydrolysis 952
20.12 Reactions of Amides 955
20.13 Application: The Mechanism of Action of β-Lactam Antibiotics 956
20.14 Summary of Nucleophilic Acyl Substitution Reactions 957
20.15 Natural and Synthetic Fibers 958
20.16 Biological Acylation Reactions 960
Key Concepts 962
Key Reactions 962
Key Skills 964
Problems 964
21 Substitution Reactions of Carbonyl Compounds

at the α Carbon 973
21.2 Enols 975
21.3 Enolates 977
©surachetkhamsuk/
21.4 Enolates of Unsymmmetrical Carbonyl Compounds 982
iStock/Getty Images 21.5 Racemization at the α Carbon 984
21.6 A Preview of Reactions at the α Carbon 985
21.7 Halogenation at the α Carbon 986
21.8 Direct Enolate Alkylation 990
21.9 Malonic Ester Synthesis 993
21.10 Acetoacetic Ester Synthesis 998
Key Reactions 1001
Key Skills 1002
Problems 1003
22 Carbonyl Condensation Reactions 1011

22.1 The Aldol Reaction 1012
22.2 Crossed Aldol Reactions 1016
22.3 Directed Aldol Reactions 1020
22.4 Intramolecular Aldol Reactions 1022
22.5 The Claisen Reaction 1025
©Jill Braaten
22.6 The Crossed Claisen and Related Reactions 1027
22.7 The Dieckmann Reaction 1029
22.8 The Michael Reaction 1030
22.9 The Robinson Annulation 1032
Key Reactions 1036
Key Skills 1037
Problems 1038
xvi Contents
23 Amines 1047
23.5 Interesting and Useful Amines 1054
©Daniel C. Smith
23.6 Preparation of Amines 1057
23.7 Reactions of Amines—General Features 1064
23.8 Amines as Bases 1064
23.9 Relative Basicity of Amines and Other Compounds 1066
23.10 Amines as Nucleophiles 1072
23.11 Hofmann Elimination 1074
23.12 Reactions of Amines with Nitrous Acid 1077
23.13 Substitution Reactions of Aryl Diazonium Salts 1079
23.14 Coupling Reactions of Aryl Diazonium Salts 1084
23.15 Application: Synthetic Dyes and Sulfa Drugs 1085
Key Concepts 1088
Key Reactions 1089
Key Skills 1091
Problems 1093
24 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1102

24.1 Coupling Reactions of Organocuprate Reagents 1103
24.2 Suzuki Reaction 1105
24.3 Heck Reaction 1110
24.4 Carbenes and Cyclopropane Synthesis 1112
24.5 Simmons–Smith Reaction 1115
©DEA/M. Giovanoli/
Getty Images 24.6 Metathesis 1116
Key Reactions 1121
Key Skills 1122
Problems 1123
25 Pericyclic Reactions 1131

25.1 Types of Pericyclic Reactions 1132
25.2 Molecular Orbitals 1133
25.3 Electrocyclic Reactions 1136
25.4 Cycloaddition Reactions 1142
25.5 Sigmatropic Rearrangements 1146
©Nature Picture Library/
Alamy Stock Photo 25.6 Summary of Rules for Pericyclic Reactions 1152
Key Concepts 1153
Key Reactions 1153
Key Skills 1154
Problems 1155
Contents xvii
26 Carbohydrates 1162
26.2 Monosaccharides 1164
26.3 The Family of d-Aldoses 1170
26.4 The Family of d-Ketoses 1171
26.5 Physical Properties of Monosaccharides 1172
©MaraZe/Shutterstock
26.6 The Cyclic Forms of Monosaccharides 1172
26.7 Glycosides 1180
26.8 Reactions of Monosaccharides at the OH Groups 1183
26.9 Reactions at the Carbonyl Group—Oxidation and Reduction 1184
26.10 Reactions at the Carbonyl Group—Adding or Removing
One Carbon Atom 1187
26.11 Disaccharides 1191
26.12 Polysaccharides 1193
26.13 Other Important Sugars and Their Derivatives 1196
Key Reactions 1201
Key Skills 1203
Problems 1206
27 Amino Acids and Proteins 1212

27.1 Amino Acids 1213
27.2 Synthesis of Amino Acids 1217
27.3 Separation of Amino Acids 1220
27.4 Enantioselective Synthesis of Amino Acids 1223
27.5 Peptides 1225
©Daniel C. Smith
27.6 Peptide Sequencing 1229
27.7 Peptide Synthesis 1232
27.8 Automated Peptide Synthesis 1237
27.9 Protein Structure 1239
27.10 Important Proteins 1245
Key Reactions 1248
Key Skills 1250
Problems 1253
28 Synthetic Polymers 1259

28.2 Chain-Growth Polymers—Addition Polymers 1261
28.3 Anionic Polymerization of Epoxides 1268
28.4 Ziegler–Natta Catalysts and Polymer Stereochemistry 1269
28.5 Natural and Synthetic Rubbers 1270
©stuar/Shutterstock
28.6 Step-Growth Polymers—Condensation Polymers 1272
28.7 Polymer Structure and Properties 1276
xviii Contents
28.8 Green Polymer Synthesis 1278

28.9 Polymer Recycling and Disposal 1281
Key Concepts 1284
Key Reactions 1284
Key Skills 1285
Problems 1285
29 Lipids 1292 (Available Online)

29.2 Waxes 1294
29.3 Triacylglycerols 1295
29.4 Phospholipids 1299
29.5 Fat-Soluble Vitamins 1302
©Iconotec/Glowimages
29.6 Eicosanoids 1303
29.7 Terpenes 1306
29.8 Steroids 1312
Key Concepts 1317
Key Reactions 1318
Key Skills 1319
Problems 1319
Appendix A Periodic Table of the Elements A

Appendix B Common Abbreviations, Arrows, and Symbols A-1
Appendix C pKa Values for Selected Compounds A-3
Appendix D Nomenclature A-5
Appendix E B
ond Dissociation Energies for
Some Common Bonds [A–B → A· + ·B] A-9
Appendix F Reactions That Form Carbon–Carbon Bonds A-10
Appendix G Characteristic IR Absorption Frequencies A-11
Appendix H Characteristic NMR Absorptions A-12
Appendix I General Types of Organic Reactions A-14
Appendix J How to Synthesize Particular Functional Groups A-16
Glossary G
Index I-1
Preface
My goal in writing Organic Chemistry was to create a text that showed students the beauty
and logic of organic chemistry by giving them a book that they would use. Organic Chemistry
is my attempt to simplify and clarify a course that intimidates many students—to make organic
chemistry interesting, relevant, and accessible to all students, both chemistry majors and those
interested in pursuing careers in biology, medicine, and other disciplines, without sacrificing
the rigor they need to be successful in the future.
The Basic Features

∙ Style This text is different—by design. The text uses less prose and more diagrams,
equations, tables, and bulleted summaries to introduce and reinforce the major concepts
and themes of organic chemistry.
∙ Content Organic Chemistry accents basic themes in an effort to keep memorization at a
minimum. Relevant examples from everyday life are used to illustrate concepts, and this
material is integrated throughout the chapter rather than confined to a boxed reading. Each
topic is broken down into small chunks of information that are more manageable and easily
learned. Sample problems are used as a tool to illustrate stepwise problem solving. Exceptions
to the rule and older, less useful reactions are omitted to focus attention on the basic themes.
∙ Organization Organic Chemistry uses functional groups as the framework within which
chemical reactions are discussed. Similar reactions are grouped together so that parallels
can be emphasized. These include acid–base reactions (Chapter 2), oxidation and reduction
(Chapters 12 and 17), radical reactions (Chapter 13), and reactions of organometallic
reagents (Chapter 17).
By introducing one new concept at a time, keeping the basic themes in focus, and breaking
complex problems down into small pieces, I have found that many students find organic chem-
istry an intense but learnable subject. Many, in fact, end the year-long course surprised that
they have actually enjoyed their organic chemistry experience.
Organization and Presentation

For the most part, the overall order of topics in the text is consistent with the way most instruc-
tors currently teach organic chemistry. There are, however, some important differences in the
way topics are presented to make the material logical and more accessible. This can especially
be seen in the following areas.
∙ Review material Chapter 1 presents a healthy dose of review material covering Lewis
structures, molecular geometry and hybridization, bond polarity, and types of bonding.
Although many of these topics are covered in general chemistry courses, they are presented
here from an organic chemist’s perspective. I have found that giving students a firm grasp
of these fundamental concepts helps tremendously in their understanding of later material.
∙ Acids and bases Chapter 2 on acids and bases serves two purposes. It gives students experi-
ence with curved arrow notation using some familiar proton transfer reactions. It also illustrates
how some fundamental concepts in organic structure affect a reaction, in this case an acid–base
reaction. Since many mechanisms involve one or more acid–base reactions, I emphasize proton
transfer reactions early and come back to this topic often throughout the text.
∙ Functional groups Chapter 3 uses the functional groups to introduce important properties
of organic chemistry. Relevant examples—PCBs, vitamins, soap, and the cell membrane—
illustrate fundamental solubility concepts. In this way, practical topics that are sometimes
found in the last few chapters of an organic chemistry text (and thus often omitted because
xix
xx Preface
instructors run out of time) are introduced early so that students can better grasp why they
are studying the discipline.
∙ Stereochemistry Stereochemistry (the three-dimensional structure of molecules) is intro-
duced early (Chapter 5) and reinforced often so that students have every opportunity to learn
and understand a crucial concept in modern chemical research, drug design, and synthesis.
∙ Modern reactions While there is no shortage of new chemical reactions to present in
an organic chemistry text, I have chosen to concentrate on new methods that introduce a
particular three-dimensional arrangement in a molecule, so-called asymmetric or enanti-
oselective reactions. Examples include Sharpless epoxidation (Chapter 12), CBS reduction
(Chapter 17), and enantioselective synthesis of amino acids (Chapter 27).
∙ Grouping reactions Because certain types of reactions have their own unique character-
istics and terminology that make them different from the basic organic reactions, I have
grouped these reactions together in individual chapters. These include acid–base reactions
(Chapter 2), oxidation and reduction (Chapters 12 and 17), radical reactions (Chapter 13),
and reactions of organometallic reagents (Chapter 17). I have found that focusing on a group
of reactions that share a common theme helps students to better see their similarities.
∙ Synthesis Synthesis, one of the most difficult topics for a beginning organic student to
master, is introduced in small doses, beginning in Chapter 7 and augmented with a detailed
discussion of retrosynthetic analysis in Chapter 11. In later chapters, special attention is
given to the retrosynthetic analysis of compounds prepared by carbon–carbon bond-form-
ing reactions (for example, Sections 17.11 and 18.9C).
∙ Spectroscopy Because spectroscopy is such a powerful tool for structure determination,
four methods are discussed over three chapters (Spectroscopy A, B, and C).
∙ Chapter Reviews End-of-chapter summaries succinctly summarize the main concepts
and themes of the chapter, making them ideal for review prior to working the end-of-
chapter problems or taking an exam.
New to this Edition

Students sometimes ask me if the facts of organic chemistry have significantly changed since
the last edition. While the basic principles remain the same—carbon forms four bonds in
stable compounds and oppositely charged species attract each other—organic chemistry is a
dynamic subject that is continually refined as new facts are determined, and new editions
reflect current understanding. Each year, novel compounds are discovered and new drugs are
marketed, and these compounds replace older examples to illustrate particular concepts. Also
of significance is how the material in the text is presented. I continue to endeavor to make this
difficult subject as student-friendly as possible, by redesigning sample problems and end-of-
chapter material, and rewriting sentences and paragraphs for improved clarity.
General
Expanded Problem-Solving Approach A central component of each chapter of Organic
Chemistry has always been the Sample Problems, which illustrate how to solve key elements
of the chapter. In this edition, Sample Problems are always paired with a follow-up Problem
to allow students to apply what they have just learned. The Problems are followed by “More
Practice,” a list of end-of-chapter problems that are similar in concept. Students can find
detailed solutions and verify their answers to all of the Problems from the book with the
Organic Chemistry Student Study Guide/Solutions Manual.
Chapter Review The end-of-chapter summary sections have been expanded into parts: Key
Concepts, Key Skills, Key Reactions, and Key Mechanism Concepts, with structures and
examples to illustrate each part, providing students with a broader and more detailed overview
of each chapter’s important concepts and skills. Extensive cross-referencing has also been
added to connect this material with relevant Sample Problems, Problems, Figures, and Tables
within the body of the chapter.
Artwork and Chemical Structures The colors in artwork throughout the text were revised
for emphasis, clarity, and consistency. Color has also been used in many areas to help students
better understand three-dimensional structure, stereochemistry, and reactions.
Preface xxi
Problems Over 300 new problems have been added, increasing the variety of problems for
instructors and students alike.
New How To’s, Sample Problems, and Illustrations Much new content has also been added
throughout the new edition to clarify topics and enhance the student learning experience.
Photos Roughly one-half of the chapter-opening photos have been replaced with photos
emphasizing relevant material within the chapter. More marginal photos of applications have
also been added.
Online Only Content The chapter on Lipids appears online and is available in customizable
versions of the text in McGraw-Hill Create. A supplement covering Imine Derivatives is also
available on the Online Learning Center’s Instructor Resources, via the Library tab in Connect.
Chapter-Specific
Spectroscopy
The revisions to the spectroscopy coverage are designed to allow for more flexibility, making these
chapters more portable to accommodate various lecture and lab arrangements. Three new spec-
troscopy chapters have been created for the sixth edition: Spectroscopy A Mass Spectrometry;
Spectroscopy B Infrared Spectroscopy; and Spectroscopy C Nuclear Magnetic Resonance
Spectroscopy. The coverage and problem sets for these chapters have also been expanded to include
material previously covered in other sections of earlier editions. Extensive cross-referencing has
been added so that whether spectroscopy is covered early or late in an organic chemistry course,
students can readily find the material they need.
∙ Spectroscopy A Mass Spectrometry There has been extensive revision of the molecular
ion, molecular formulas, and fragmentation coverage. A new How To was added on pro-
posing molecular formulas from molecular ions. New Sample Problems on using molecu-
lar ions and degrees of unsaturation to propose molecular formulas and on determining
isomer identity using fragmentation were also added. Several mass spectra have been
added to the text and in problems.
∙ Spectroscopy B Infrared Spectroscopy A new How To on analyzing an IR spectrum
has been added. The chapter also includes a new Sample Problem B.1 on carbonyl absorp-
tions. Section B.3 has been expanded to include the effect of resonance on a carbonyl
absorption, and a new section on IR absorptions based on functional groups also appears
in the chapter. A new Table B.1 summarizes IR absorption by functional group.
∙ Spectroscopy C Nuclear Magnetic Resonance Spectroscopy Section C.7 on complex
splitting was extensively revised to add clarity and deeper understanding for students who
often struggle with this topic. There are also two new sample problems: Sample Problem
C.3 on determining proton equivalency in cyclic compounds and Sample Problem C.8 on
looking for points of difference in the NMR spectra of similar compounds. More complex
NMRs, previously found in later chapters, were imported to expand the breadth of the
problems.
Carbonyls
The coverage of nitriles has been moved to the chapter on carboxylic acids, forming Chapter 19,
Carboxylic Acids and Nitriles. This chapter has been moved to follow Aldehydes and Ketones,
making this coverage closer to the chemistry of acyl derivatives of carboxylic acids. These revi-
sions also allow for the coverage of the nucleophilic addition reactions that occur with nitriles
in closer proximity to the coverage of nucleophilic additions of aldehydes and ketones.
Other New Coverage

Several sections include new material, including Section 4.7, sources of methane in the
atmosphere; Section 5.5, drawing an enantiomer of a complex compound; Section 7.4, drugs
that contain fluorine; Section 13.9, the latest ozone map and updated information on CFC
alternatives now in use; Section 19.4, new drugs that contain nitriles; Section 26.12, human
milk oligosaccharides; and Section 29.7, how isoprene units are connected.
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xxiv Preface
Features of the Text to Make Learning Organic Chemistry Easier

Illustrations Organic Chemistry is supported by a well-developed illustration program.
Besides traditional skeletal (line) structures and condensed formulas, there are numerous ball-
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starch and cellulose (Chapter 5), adrenaline (Chapter 7), partial hydrogenation of vegetable oil
(Chapter 12), and dopamine (Chapter 23).
Spectra Over 100 spectra created specifically for Organic Chemistry are presented mainly
in the spectroscopy chapters. The spectra are color-coded by type and generously labeled. Mass
spectra are green; infrared spectra are red; and proton and carbon nuclear magnetic resonance
spectra are blue.
Mechanisms Curved arrow notation is used extensively to help students follow the movement
of electrons in reactions.
Problem Solving
Sample Problems Sample Problems show students how to solve organic chemistry problems
in a logical, stepwise manner. More than 800 follow-up problems are located throughout the
chapters to test whether students understand concepts covered in the Sample Problems.
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processes.
Applications and Summaries

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provided at the end of each chapter.
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its outlet in unsystematic and uncriticised imaginative construction.
Metaphysics they will certainly have, and if not conscious and
coherent, then unconscious and incoherent Metaphysics. The soul
that is not at rest in itself without some “sight of that immortal sea
which brought it hither,” if hindered from beholding the object of its
quest through the clear glass of rational reflection, will none the less
seek to discern it amid the distorting hazes and mists of superstition.
It is in such seekers after the Infinite that Metaphysics has its natural
and proper followers, and for them the study is its own justification
and its own reward. If a work like the present should prove of any
help to such students, whether by offering positive suggestions
which they can accept, or by assisting them to know definitely why
they reject its conclusions, it will perhaps have achieved as much as
its writer could reasonably expect.
Consult further:—F. H. Bradley, Appearance and Reality, chap. 27;

J. E. McTaggart, Studies m Hegelian Cosmology, chap. 9.
235. I use the epithet in its familiar Platonic sense. The “pure”
pleasure is that which is not dependent, in whole or in part, for its
pleasantness upon a previous ἔνδεια, or actual experience of craving
or desire. I do not mean, as Plato possibly did, that a “mixed”
pleasure, preceded by such ἔνδεια, is a contrast-effect without
positive quality of its own.
236. Compare the argument of Appearance and Reality, chap. 26,
pp. 469-485 (1st ed.), and the famous scholium to Prop. 17 of part 1
of Spinoza’s Ethics, where it is contended that “if intellect and volition
belong to the eternal essence of God, each of these attributes must
at least be understood in a different sense from the current.”
237. I say “finite or infinite” advisedly. The mystic’s condemnation
of the relational scheme as inadequate to express the full nature of
the real, holds good just as much in application to actual finite
experience as in application to the ultimate whole. We may say not
only of “God,” but of human persons, that they are much more than
the “union of thought and will” as such. And in personal human love,
no less than in the saint’s “beatific vision” or the philosopher’s
“intellectual love of God,” we have a type of experience which may
for some psychological purposes be analysed into a combination of
ideational and volitional processes, but emphatically does not, in its
concrete existence, consist of a synthesis of actual ideas and actual
volitions. See ante, p. 152.
238. Studies in Hegelian Cosmology, p. 292.
INDEX
Absolute, meaning of, 53 ff.;

general character of, 60 ff.;
not unknowable, 71 ff.;
not a “self,” 343 ff.;
is it a society? 100, 347 ff.;
a spiritual individual, 98 ff.;
not necessarily the same as “God,” 399 ff.;
not “union of thought and will,” 409 ff.
Activity not identical with conation, 55;
and causation, 169;
empirical nature of, 189.
Agnosticism, 68, 69, 71, 72;
how far justifiable, 412.
Appearance and Reality, connection between, 105 ff.
Aristotle, 6, 42, 97, 266, 361, 386.
Attention, selective, 55, 66, 80;
“span” of, 226, 244.
Avenarius, 35, 45, 80, 121, 174, 298 ff. 315.
Baldwin, J. M., 206.

Berkeley, 26, 64 ff., 75, 184, 185, 201 ff.
Body, my own, as describable object, 282.
Body, my own, and others, 203 ff.
Body and Soul, theories of, 313 ff.;
in what sense the same, 332.
Bosanquet, B., 19, 26, 164.
Bradley, F. H., 9, 11, 23, 26, 55, 67, 88, 90, 131, 146, 199, 227, 243,
259, 289, 318, 326, 335, 338, 355, 364, 370, 384, 411.
Causation, 165 ff.;

cause not identical with ground, 166;
causation a postulate, 167 ff.;
popular as distinguished from scientific sense, 169;
causation and the indefinite regress, 177 ff.;
continuity of causation, 171 ff.;
Immanent and Transeunt Causality, 183 ff.;
psychophysical causation, 322 ff.
Causes, Plurality of, 180 ff.
Chance, “pure,” meaning of, 231, 232;
chance and “free-will,” 378.
Change, 158-164.
Character and freedom, 374.
Choice and motives, 373.
Consciousness, a misleading term, 79.
Consequence (see Ground).
Continuity, nature of, 171
(see Causation);
continuity of space and time, 244, 250.
Contradiction, principle of, 19 ff.
Cosmology Rational, nature of, 43-49, 192-197.
Couturat, L., 149, 260.
Dedekind, 116, 149, 171.

Degrees of Reality, 108 ff.
Descartes, 128, 185, 318, 400 ff.
Description, as scientific ideal, 174;
in physical Science, 280 ff.;
in Psychology, 308 ff.
Determinism, 370-376.
Discontinuity of teleological series, 311.
Distance in space and time, 250.
Ends in Nature, 272, 405, 406.

Energy, conservation of, 292;
kinetic and non-kinetic, 291;
doctrine of, and psychophysical interaction, 322 ff.
Epiphenomenalism, 317, 318-320.
Epistemology and Metaphysics, 16.
Evil, problem of, 391 ff., 395 ff.
Evolution, not identical with mere change, 267;
implies real ends, 268 ff.;
is of finite beings only, 274 ff.;
implies real progress and degeneration, 275;
originates new individuals, 276.
Experience, what, 23 ff., 33 ff.;
“pure,” 35, 54.
Feeling, 23 ff., 55;

in the Absolute, 467 ff.
Freedom, meaning of, 359 ff.
Free-will, origins of belief in, 361 ff.
Geulincx, 184, 185, 186, 317.

Gibson, W. R. B., 288, 329, 366.
God, proofs of being of, 400 ff.
Ground and Consequence, meaning of principle of, 164, 165.
Harmony, Pre-established, 187, 317.
Hegel, 40 ff., 42 ff., 391, 401.
Herbart, 39, 42, 68.
Hobhouse, L. T., 74, 137, 138, 199.
Hume, 29, 7, 133, 169, 172, 183, 400 ff.
Identity, Psychophysical, doctrine of, 102, 321, 331, 332.

Identity, a teleological concept, 335.
(See also Unity of Thing).
Imitation, significance of, for personality, 206.
Immanent Causality, 183 ff.
Immediacy, 32.
“Immortality,” 354 ff.
Indeterminism, 376-379.
Individuality, nature of, 57, 98 ff.;
degrees of, 109 ff.;
infinite and finite, 115 ff.
Infinite Regress, 148 ff., 156;
in space and time, 255 ff., 259;
in causal relation, 177.
Infinity, meaning of, 116.
Interaction, Psychophysical, 317, 329-331.
Introjection, meaning of, 81;
origin of, 81, 299 ff.;
justification of, 301 ff.
James, W., 53, 91, 318, 370, 383, 390, 400.
Kant, 11, 24, 39, 43, 69, 134, 188, 242 ff., 259, 359, 366, 387, 400 ff.
Law, meaning of, 218 ff.

Laws in Nature, 196, 229.
Leibnitz, 68, 82, 86, 91 ff., 117, 187 ff., 317, 366, 401, 404.
Locke, 128, 136, 200, 318, 353, 365, 366.
Lotze, 41, 42, 133, 224, 289.
Mach, E., 174, 175, 192, 223, 228, 283, 290.

Machine, nature of a, 236, 237.
McTaggart, J. E., 345, 357, 391, 398, 413.
Malebranche, 184, 185, 317.
Mass, definition of, 289;
conservation of, 290;
a relative concept, 290, 291.
Matter, meaning of, 198 ff.
Mechanical view of Nature, 233 ff., 237 ff., 283 ff.;
postulates of, 284, 292 ff.
Mechanism, meaning of, 196, 237 ff.
Method of Metaphysics, 38 ff.
Mill, J. S., 24, 180 ff., 370.
Monadism, 86, 91, 94.
Monism, 85.
Münsterberg, H., 45, 67, 198, 283, 303 ff., 315, 318, 321, 324, 329.
Mysticism, 14, 33, 153;
in what sense justifiable, 413.
Necessity and causal relation, 183.

Newton, 128, 200.
Nietzsche, 276.
Number-series, 151 ff., 248-250, 259.
Occasionalism, 184, 317.
Ontology, character of, 42.
Order, a teleological concept, 118;
order in space and time, 251.
Organism, nature of a, 96.
Parallelism, Psychophysical, 317, 320-329.

Pearson, K., 75, 290.
Phenomenalism, 10, 136.
Physical order, nature of the, 194 ff., 198, 208, 282.
Plato, 3, 55, 77, 95, 276, 366, 386, 393, 398, 409.
Pleasure-pain, 55, 344.
Plotinus, 398.
Pluralism, 86 ff.
Position not a principle of individuation, 58;
relativity of, 253.
Pragmatism, 317.
Prediction in science, 219 ff.
Progress not infinite, 387-389.
Psychical order, nature of the, 298 ff.
Psychology, character of, as a science, 296 ff.
Psychology and Physiology, 303 ff.
Psychology, Rational, nature of, 43 ff.
Purpose, nature of, 55 ff.
Qualities, primary and secondary, 128 ff.

Quality and relation, 140 ff.
Quality and substance, 128 ff.
Quality, spatial and temporal, 244.
Rashdall, H., 347, 393, 400.

Realism, Agnostic, 68, 71, 72;
Dogmatic, 69, 72-75.
Relation and quality, 140 ff.
Relations and relatedness, 155.
Religion, metaphysical presuppositions of, 389 ff.
Responsibility and the self, 335.
Royce, J., 13, 33, 51, 56, 76, 116, 145, 148 ff., 206, 226, 239, 263,
270, 277, 307, 398.
Russell, B., 36, 58, 91, 142, 189, 243, 250, 253, 404.
Self, 98, 107;

nature of, 334-340;
a teleological concept, 335;
temporal character of, 341, 342.
Self-consciousness, genuine and fictitious, 79.
Sidgwick, H., 130, 359, 370.
Space, perceptual, 243-245;
conceptual genesis of, 245-249;
infinity of, 247;
divisibility of, 248;
continuity of, 248, 250;
homogeneity of, 251;
relativity of, 251;
is it one or many? 253, 257;
is not ultimate, 254-257;
antinomies of, 259 ff.;
of what is it phenomenal? 260.
Spencer, H., 40, 68.
Spinoza, 62, 101 ff., 318, 399, 411.
Stout, G. F., 33, 67, 135, 154 ff., 208, 247, 318, 324, 332, 378.
Subjectivism, what, 75;
fallacy of, 76-81, 204 ff.
Substance, concept of, 128 ff.;
and quality, 128-140.
Sufficient Reason, principle of, 164.
Teleological description not impossible, 309.

Teleological series, discontinuity of, 311.
Teleology, nature of, 55, 99, 125, 287, 371 ff.;
in Psychology, 305 ff.;
in Biology, 308;
and Psychophysical Parallelism, 326 ff.
Thought and the Absolute, 61;
not ultimate, 409.
Time, perceptual, 243-245;
conceptual, genesis of, 245-249;
infinity of, 247;
divisibility of, 248;
continuity of, 248, 250;
homogeneity of, 251;
relativity of, 251;
is it one or many? 253, 257;
not ultimate, 254-257;
antinomies of, 259 ff.;
of what is it phenomenal? 262;
time and the self, 341, 344.
Truth, degrees of, 214.
Uniformities, statistical, 220 ff.

Uniformity in physical nature, 222, 227.
Unity of things teleological, 123-128.
Ward, J., 45, 64, 174, 225, 228, 289 318, 324, 326-328.
Whole and Part, category of, 96.
Will, nature of, 61, 118;
not ultimate, 410.
Transcriber’s Note
Two words on the first line of p. 70 of this edition
(noted below) were missing (blank). They have been
supplied from the 5th edition, published in 1920.
On p. 226, a footnote at (226.42) refers to Mr. H. G.
Wells’s tale, The New Accumulator, which is certainly a
reference to his 1901 tale “The New Accelerator”.
On p. 340, the first paragraph refers to ‘two points’,
and prefaces the first with ‘(a)’. But there is no ‘(b)’ to
denote the second point. It seems likely that ‘(b)’ should
precede the next paragraph, or perhaps following the
introductory ‘Further’.
The Index reference to p. 467 for ‘Feeling in the
Absolute’ cannot be verified. The page does not exist,
and no other page can be identified with certainty.
Errors deemed most likely to be the printer’s have
been corrected, and are noted here. The references are
to the page and line in the original.
The most common error is missing punctuation: 6.14
purpose[.], 38.29 inquiry[.], 44.12 periphery[.], 44.41
other[.], 56.47 failure[.], 58.27 theory[.], 62.39
“purposive[”], 67.17 life[.], 67.19 subject[.], 79.46
“matter[”], 82.13 it[.], 88.40 exclusive[.], 89.41 facts[.],
99.13 purpose[.], 108.24 admitted[.], 128.23
[“]substance”, 143.19 arisen[.], 215.10 [“]Nature, 224.22
purpose[.], 236.14 based[.], 251.45 series[.], 274.16
advance[.], 320.32 fatum[.], 361.22 considerations[.],
390.5 “temperament[”], 410.22 thing[.]
The name of Professor Hugo Münsterberg is spelled
variably as Münsterberg, Munsterberg, and occasionally
with a partial umlaut. The spelling has been rendered as
Münsterberg to facilitate text searches at 215.5, 305.15,
315.8, 329.40, 418.3.
Other corrected errors are:
xviii.11 to a[s]certain Inserted.
xxiii.12 The concept of [e]volution Restored.
37.9 carry out ou[t/r] programme Replaced.
46.46 Grundz[u/ü]ge der Psychologie Replaced.
66.44 on which it “works.[’/”] Replaced.
70.1.1 a modification of your Restored.
[experience].
70.1.2 to ask what [you] mean Restored.
82.22 to know your own meaning[./,] Replaced.
134.42 too diffuse and technical[,/.] Replaced.
136.24 does no[t] destroy Restored.
149.12 in our illustration 12, [23/22], 32 ... Replaced.
180.46 increases indefinitely[)]. Removed.
215.6 Grundz[u/ü]ge der Psychologie Replaced.
215.12 [“]J. Ward Removed.
229.16 deal only with the problem[,/.] Replaced.
306.4 the physical order was Inserted.
const[r]ucted
318.8 H[o/ö]ffding Replaced.
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Organic Chemistry 6th Edition Ebook PDF

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Organic Chemistry 6th Edition (eBook

JANICE GORZYNSKI SMITH

5.9 R and S Assignments in Compounds with Two or More

6 Understanding Organic Reactions 222

7 Alkyl Halides and Nucleophilic Substitution 256

7.17 Vinyl Halides and Aryl Halides 295

8 Alkyl Halides and Elimination Reactions 308

9 Alcohols, Ethers, and Related Compounds 345

9.18 Application: Benzo[a]pyrene, Epoxides, and Cancer 385

10 Alkenes and Addition Reactions 397

11 Alkynes and Synthesis 441

Chapter 11 Review 463

12 Oxidation and Reduction 472

13 Radical Reactions 611

14 Conjugation, Resonance, and Dienes 648

14.6 Conjugated Dienes 657

15 Benzene and Aromatic Compounds 689

16 Reactions of Aromatic Compounds 725

16.13 Nucleophilic Aromatic Substitution 755

17 Introduction to Carbonyl Chemistry; Organometallic Reagents;

18 Aldehydes and Ketones—Nucleophilic Addition 833

18.10 Addition of 1° Amines 855

19 Carboxylic Acids and Nitriles 885

20 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl

20.10 Reactions of Esters 950

21 Substitution Reactions of Carbonyl Compounds

22 Carbonyl Condensation Reactions 1011

24 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1102

25 Pericyclic Reactions 1131

27 Amino Acids and Proteins 1212

28 Synthetic Polymers 1259

28.8 Green Polymer Synthesis 1278

29 Lipids 1292 (Available Online)

Appendix A Periodic Table of the Elements A

The Basic Features

Organization and Presentation

New to this Edition

Other New Coverage

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Applications and Summaries

Learning Resources for Instructors and Students

Student Study Guide/Solutions Manual

Consult further:—F. H. Bradley, Appearance and Reality, chap. 27;

Absolute, meaning of, 53 ff.;

Baldwin, J. M., 206.

Causation, 165 ff.;

Dedekind, 116, 149, 171.

Ends in Nature, 272, 405, 406.

Feeling, 23 ff., 55;

Geulincx, 184, 185, 186, 317.

Identity, Psychophysical, doctrine of, 102, 321, 331, 332.

James, W., 53, 91, 318, 370, 383, 390, 400.

Law, meaning of, 218 ff.

Mach, E., 174, 175, 192, 223, 228, 283, 290.

Necessity and causal relation, 183.

Parallelism, Psychophysical, 317, 320-329.