Organic Chemistry with Biological Applications, 3rd Edition

Book Preface

What’s New
Text content has been revised substantially for this 3rd edition as a result of user feedback. Most noticeably, two new chapters have been made available for those who want them: Chapter 26 on Pericyclic Reactions and Chapter 27 on Synthetic Polymers. Other changes include:

• Every chapter ends with a brief Something Extra essay that has been repositioned to follow immediately after the last text section where it is more likely to be noticed and read.

• The problems at the ends of chapters are now organized by topic to make it easier for students to find questions on specific subjects.

• New problems have been added in every chapter, 164 in all.

• Text references to all numbered FI GURES and TA BLES are called out in color to help students move more easily between text and art.

• All figure captions have a boldfaced title, and the captions themselves use colored text to make it easier to focus on specific features in the figure art.
New topics in this 3rd edition include:

• A new Something Extra, “Organic Foods: Risk versus Benefit,” in Chapter 1

• A new Something Extra, “Alkaloids: From Cocaine to Dental Anesthetics,” in Chapter 2

• New coverage of bridged bicyclic molecules in Section 4-9

• New coverage of mercury-catalyzed alkyne hydration in Section 8-15

• New coverage of aromatic fluorination and fluorinated drugs in Section 9-6

• New coverage of alcohol to alkyl fluoride conversions in Section 12-3

• A new Section 12-5, “Organometallic Coupling Reactions,” covering both organocopper reactions and the palladium-catalyzed Suzuki–Miyaura reaction

• A new Something Extra, “Naturally Occurring Organohalides,” in Chapter 12

• New coverage of epoxide cleavage by nucleophiles in Section 13-10

• A new Section 13-11, “Crown Ethers and Ionophores”

• New coverage of hydrates of a-keto acids in Section 14-5

• A new Something Extra, “Barbiturates,” in Chapter 17

• Threonine catabolism deleted from Section 20-4

• New coverage of Kiliani–Fischer carbohydrate chain extension and Wohl degradation in Section 21-6

• A new Section 23-7, “Prostaglandins and Other Eicosanoids”

• A new Something Extra, “Statin Drugs,” in Chapter 23

• A new electronic Chapter 26, “Orbitals and Organic Chemistry: Pericyclic Reactions”

• A new electronic Chapter 27, “Synthetic Polymers”

I believe that there is more than enough standard organic chemistry in this book, and that the coverage of biological chemistry far surpasses that found in any other text. My hope is that all the students we teach, including those who worry about