Organic Chemistry

Now in a new edition, this book continues its tradition of excellence in teaching and preparing students for success in the organic classroom and beyond. A central theme of the authors′s approach to organic chemistry is to emphasize the relationship between structure and reactivity. To accomplish this, the text is organized in a way that combines the most useful features of a functional group approach with one largely based on reaction mechanisms. Emphasizing mechanisms and their common aspects as often as possible, this book shows students what organic chemistry is, how it works, and what it does in living systems and the physical world around us.

1 The Basics: Bonding and Molecular Structure 1

2 Families of Carbon Compounds: Functional Groups Intermolecular Forces, and Infrared (IR) Spectroscopy 55

3 Acids and Bases: A Introduction to Organic Reactions and Their Mechanisms 104

4 Nomenclature and Corformations of Alkanes and Cycloalkanes 142

5 Stereochemistry: Chiral Molecules 191

6 Ionic Reactions: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides 239

7 Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides 291

8 Alkenes and Alkynes II: Addition Reactions 337

9 Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination 391

10 Radical Reactions 457

11 Alcohols and Ethers: Synthesis and Reactions 498

12 Alcohols from Carbonyl Compounds: Oxidation–Reduction and Organometallic Compounds 542

13 Conjugated Unsaturated Systems 581

14 Aromatic Compounds 626

15 Reactions of Aromatic Compounds 669

16 Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 720

17 Carboxylic Acids and Their Derivatives: Nucleophilic Addition–Elimination at the Acyl Carbon 771

18 Reactions at the α Carbon of Carbonyl Compounds: Enols and Enolates 821

19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds: More Chemistry of Enolates 858

20 Amines 897

21 Phenols and Aryl Halides: Nucleophilic Aromatic Substitution 944

22 Carbohydrates 979

23 Lipids 1027

24 Amino Acids and Proteins 1060

25 Nucleic Acids and Protein Synthesis 1105

Answers to Selected Problems A–1

Glossary GL–1

Index I–1