Organic Chemistry, 8th Edition

Book Preface

What Sets This Book Apart?

The central message of chemistry is that the properties of a substance come from its structure. What is less obvious, but very powerful, is the corollary. Someone with training in chemistry can look at the structure of a substance and tell you a lot about its properties. Organic chemistry has always been, and continues to be, the branch of chemistry that best connects structure with properties.

The goal of this text, as it has been through seven previous editions, is to provide students with the conceptual tools to understand and apply the relationship between the structures of organic compounds and their properties. Both the organization of the text and the presentation of individual topics were designed with this objective in mind.

A Functional Group Organization

The text is organized according to functional groups—structural units within a molecule that are most closely identifi ed with characteristic properties. This organization offers two major advantages over alternative organizations based on mechanisms or reaction types.

1. The information content of individual chapters is more manageable when organized according to functional groups.
2. Patterns of reactivity are reinforced when a reaction used to prepare a particular functional group reappears as a characteristic reaction of a different functional group.

A Mechanistic Emphasis and Its Presentation

The text emphasizes mechanisms and encourages students to see similarities in mechanisms among different functional groups. Mechanisms are developed from observations; thus, reactions are normally presented fi rst, followed by their mechanism.

In order to maintain consistency with what our students have already learned, this text presents multistep mechanisms in the same way as most general chemistry textbooks; that is, as a series of elementary steps . Additionally, we provide a brief comment about how each step contributes to the overall mechanism.

Section 1.12 “Curved Arrows and Chemical Reactions” introduces the student to the
notational system employed in all of the mechanistic discussions in the text.

Numerous reaction mechanisms are accompanied by potential energy diagrams. Section 4.9 “Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism” shows how the potential energy diagrams for three elementary steps are combined to give the diagram for the overall reaction.

Brief Contents
List of Important Features xvii
Preface xxii
Acknowledgments xxx
1 Structure Determines Properties 2
2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons 56
3 Alkanes and Cycloalkanes: Conformations and cis-trans Stereoisomers 100
4 Alcohols and Alkyl Halides 137
5 Structure and Preparation of Alkenes: Elimination Reactions 184
6 Addition Reactions of Alkenes 226
7 Stereochemistry 278
8 Nucleophilic Substitution 322
9 Alkynes 359
10 Conjugation in Alkadienes and Allylic Systems 388
11 Arenes and Aromaticity 428
12 Reactions of Arenes: Electrophilic and Nucleophilic Aromatic Substitution 478
13 Spectroscopy 538
14 Organometallic Compounds 606
15 Alcohols, Diols, and Thiols 646
16 Ethers, Epoxides, and Sulfi des 686
17 Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 724
18 Carboxylic Acids 776
19 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 812
20 Enols and Enolates 866
21 Amines 930
22 Phenols 988
23 Carbohydrates 1022
24 Lipids 1074
25 Amino Acids, Peptides, and Proteins 1116
26 Nucleosides, Nucleotides, and Nucleic Acids 1174
27 Synthetic Polymers 1216