Organic Chemistry, 7th Edition

Book Preface

INTRODUCTION

This seventh edition of Organic Chemistry significantly extends the transformation started in the sixth edition. Students taking an organic chemistry course have two objectives: the first is to learn organic chemistry, and the second is to establish the intellectual foundation for other molecular science courses. Most often, these other courses involve biochemistry or specialized topics such as materials science. This textbook addresses these two objectives head-on by first presenting mechanistic and synthetic organic chemistry geared toward giving students a fundamental understanding of organic molecules and reactions as well as their mechanisms and uses in organic synthesis. The text then builds on the fundamentals by emphasizing bridging concepts that will prepare students for subsequent science courses. Several studying and learning features of this text include comprehensive end-of-chapter summaries, a unique paradigm for learning mechanisms, and an enhanced learning tool called Organic Chemistry Reaction Roadmaps.

A FRESH LOOk AT MECHANISMS

This edition refines a revolutionary paradigm for learning organic chemistry mechanisms. Students are introduced to a small set of individual mechanism elements in a special primer section preceding Chapter 6. In addition, a new special primer section just before Chapter 18 describes how to apply this unique approach to construct the mechanisms for the reactions of carboxylic acid derivatives, historically the make-or-break point for students learning to develop and understand complex reaction mechanisms in the organic chemistry course. In both of these new special sections, the mechanism elements are explained in detail, including when they are appropriate to use. Reaction mechanisms throughout the rest of the book are described as combinations of these individual mechanism elements, which are written in stepwise fashion. This new approach not only simplifies the learning of mechanisms for students but also makes it easier to recognize similarities and differences between related reactions. Most important, it makes the prediction of reaction mechanisms simpler, analogous to a multiple-choice situation in which the correct mechanism element is chosen from a menu of choices. Also, Appendix 10, “Common Mistakes in Arrow Pushing,” gives students more hints on writing mechanisms.

To reinforce the mechanism element approach, the uniting concept of nucleophiles reacting with electrophiles is highlighted. Especially helpful is the use of electrostatic potential surface models of reacting molecules. These maps emphasize, in an easily interpreted, color-coded fashion, how the majority of reactions involve areas of higher electron density on one reactant (a nucleophile) interacting with areas of lower electron density on the other reactant (an electrophile).

Contents in Brief

1. Covalent Bonding and Shapes of Molecules / 1
2. Alkanes and Cycloalkanes / 65
3. Stereoisomerism and Chirality / 117
4. Acids and Bases / 157
5. Alkenes: Bonding, Nomenclature, and Properties / 191
Primer I Reaction Mechanisms / 213
6. Reactions of Alkenes / 221
7. Alkynes / 275
8. Haloalkanes, Halogenation, and Radical Reactions / 305
9. Nucleophilic Substitution and b-Elimination / 341
10. Alcohols / 401
11. Ethers, Epoxides, and Sulfides / 451
12. Infrared Spectroscopy / 491
13. Nuclear Magnetic Resonance Spectroscopy / 512
14. Mass Spectrometry / 557
15. An Introduction to Organometallic Compounds / 579
16. Aldehydes and Ketones / 600
17. Carboxylic Acids / 669
Primer II Carboxylic Acid Derivative Reaction Mechanisms / 701
18. Functional Derivatives of Carboxylic Acids / 704
19. Enolate Anions and Enamines / 763
20. Dienes, Conjugated Systems, and Pericyclic Reactions / 831
21. Benzene and the Concept of Aromaticity / 873
22. Reactions of Benzene and Its Derivatives / 926
23. Amines / 967
24. Catalytic Carbon-Carbon Bond Formation / 1021
25. Carbohydrates / 1058
26. Lipids / 1093
27. Amino Acids and Proteins / 1120
28. Nucleic Acids / 1156
29. Organic Polymer Chemistry / 1180