In the newly revised Thirteenth Edition of Organic Chemistry, a team of veteran chemistry educators delivers a practical exploration of the relationship between structure and reactivity. The book combines the most useful features of a functional group approach with an examination of reaction mechanisms. The book emphasizes the common aspects of mechanisms and the unifying features of functional groups. It demonstrates what organic chemistry is, as well as how it works. It relies heavily on examples from living systems and the physical world around us to illustrate crucial concepts.

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 An Introduction to Organic Reactions and Their Mechanisms 104

4 Nomenclature and Conformations of Alkanes and Cycloalkanes 144

5 Stereochemistry Chiral Molecules 193

6 Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides 240

7 Alkenes and Alkynes I Properties and Synthesis. Elimination Reactions of Alkyl Halides 282

8 Alkenes and Alkynes II Addition Reactions 337

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

10 Radical Reactions 448

11 Alcohols and Ethers Synthesis and Reactions 489

12 Alcohols from Carbonyl Compounds Oxidation–Reduction and Organometallic Compounds 534

13 Conjugated Unsaturated Systems 572

14 Aromatic Compounds 617

15 Reactions of Aromatic Compounds 660

16 Aldehydes and Ketones Nucleophilic Addition to the Carbonyl Group 711

17 Carboxylic Acids and Their Derivatives Nucleophilic Addition–Elimination at the Acyl Carbon 761

18 Reactions at the α Carbon of Carbonyl Compounds Enols and Enolates 811

19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds More Chemistry of Enolates 849

20 Amines 890

21 Transition Metal Complexes Promoters of Key Bond-Forming Reactions 938

22 Carbohydrates 965

23 Lipids 1011

24 Amino Acids and Proteins 1045

25 Nucleic Acids and Protein Synthesis 1090

Glossary GL-1

Index I-1

Answers to Selected Problems can be found at www.wiley.com/college/solomons