Organic Chemistry (with Organic ChemistryNOW) (Available Titles OWL), 2nd Edition

Book Preface

This book is intended for use in the first organic chemistry course taken by students majoring in chemistry, biochemistry, biological sciences, and other healthrelated fields. The unique organization of this book sets it apart from many other texts in this area; specifically, this text is organized according to the mechanisms of the presented organic reactions rather than according to functional groups. It covers all of the same material usually found in a book using the functional group approach but in an order based on mechanistic themes.

The organic chemistry course is a pivotal class taken by science students. In addition to the inherent importance of organic reactions in chemistry and biology, organic chemistry introduces and develops a type of reasoning and logic that is new to many students. A solid understanding of this subject is often critical to subsequent success in a science career.

Organic chemistry often has a reputation among students as being a very difficult course, involving an enormous amount of memorization. For students who approach the course by attempting to memorize all of the important information, it is a daunting subject indeed. The goals of this text are to help students be successful in organizing this vast amount of material, to stimulate their interest by making organic chemistry understandable and relevant, to demonstrate the logic and beauty of the field, and to provide a method to remember all of those many reactions.

Using an organization based on reaction mechanisms rather than the approach based on functional groups has always appealed to me. I believe that the mechanism approach encourages students to develop an understanding of why things occur rather than just memorizing what occurs. In writing this book, my goal throughout has been to present organic chemistry in a way that is clear, understandable, and accessible to students. Mechanisms are used as the organizing principle that helps students learn organic chemical behavior, not as the major concept to be learned.

Unlike a graduate-level or advanced undergraduate book, this text is not intended to be an encyclopedia of mechanisms. Those mechanisms that are general and that organize a number of reactions are emphasized, whereas those that are uncommon are often not covered at all.

Brief Contents

1 A Simple Model for Chemical Bonds 1
2 Organic Compounds: A First Look 30
3 Orbitals and Bonding 61
4 The Acid–Base Reaction 103
5 Functional Groups and Nomenclature I 142
6 Stereochemistry I: Cis–Trans Isomers and Conformations 178
7 Stereochemistry II: Chiral Molecules 219
8 Nucleophilic Substitution Reactions: Reactions of Alkyl Halides, Alcohols, and Related Compounds 257
9 Elimination Reactions: Reactions of Alkyl Halides, Alcohols, and Related Compounds 313
10 Synthetic Uses of Substitution and Elimination Reactions: Interconverting Functional Groups 348
11 Additions to Carbon–Carbon Double and Triple Bonds: Reactions of Alkenes and Alkynes 404
12 Functional Groups and Nomenclature II 466
13 Infrared Spectroscopy 500
14 Nuclear Magnetic Resonance Spectroscopy 543
15 Ultraviolet-Visible Spectroscopy and Mass Spectrometry 609
16 Benzene and Aromatic Compounds 642
17 Aromatic Substitution Reactions 671
18 Additions to the Carbonyl Group: Reactions of Aldehydes and Ketones 739
19 Substitutions at the Carbonyl Group: Reactions of Carboxylic Acids and Derivatives 803
20 Enolate and Other Carbon Nucleophiles 858
21 The Chemistry of Radicals 918
22 Pericyclic Reactions 956
23 The Synthesis of Organic Compounds 1011
24 Synthetic Polymers 1053
25 Carbohydrates 1085
26 Amino Acids, Peptides, and Proteins 1123
27 Nucleotides and Nucleic Acids 1162
28 Other Natural Products 1184