Organic Chemistry 9th Edition

Book Preface

Changes and Additions for This Ninth Edition

Text content has been updated for greater accuracy as a response to user feedback. Discussions of NMR spectroscopy and opportunities to practice mechanism problems have been expanded substantially for this ninth edition.
Changes include:
• Discussions of interpreting mass spectra have been expanded with new spectroscopy problems included throughout the book.
• Discussions of the theory of nuclear magnetic resonance and interpretation of NMR data have been reorganized and expanded with new NMR problems.
• Why This Chapter now precedes the introduction in each chapter, immediately setting the context for what to expect.
• Mechanism problems at the ends of chapters are now grouped together so that they are easily located.
• Many new problems at the ends of chapters have been added, including 108 new mechanism-drawing practice problems and new spectroscopy and NMR problems.
• Deeper Look features have been changed to Something Extra, with updated coverage on each topic.
• Seven new Practice Your Scientific Analysis and Reasoning essays and corresponding questions modeled on professional tests such as the MCAT.

Topics focus on the latest developments in the medical, pharmaceutical, or biological application of organic chemistry. Topics include: The Chiral Drug Thalidomide, From Mustard Gas to Alkylating Anticancer Drugs, Photodynamic Therapy (PDT), Selective Serotonin Reuptake Inhibitors (SSRIs), Thymine in DNA, Melatonin and Serotonin, and The Potent Antibiotic Traits of Endiandric Acid C.

Brief Contents
1 Structure and Bonding 1
2 Polar Covalent Bonds; Acids and Bases 28
3 Organic Compounds: Alkanes and Their Stereochemistry 60
4 Organic Compounds: Cycloalkanes and Their Stereochemistry 89
5 Stereochemistry at Tetrahedral Centers 115
6 An Overview of Organic Reactions 149
Practice Your Scientific Analysis and Reasoning I: The Chiral Drug Thalidomide 182
7 Alkenes: Structure and Reactivity 185
8 Alkenes: Reactions and Synthesis 220
9 Alkynes: An Introduction to Organic Synthesis 263
10 Organohalides 287
11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 309
Practice Your Scientific Analysis and Reasoning II: From Mustard Gas
to Alkylating Anticancer Drugs 351
12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 354
13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 386
14 Conjugated Compounds and Ultraviolet Spectroscopy 420
Practice Your Scientific Analysis and Reasoning III: Photodynamic Therapy (PDT) 448
15 Benzene and Aromaticity 451
16 Chemistry of Benzene: Electrophilic Aromatic Substitution 478
17 Alcohols and Phenols 525
18 Ethers and Epoxides; Thiols and Sulfides 568
• Preview of Carbonyl Chemistry 595
19 Aldehydes and Ketones: Nucleophilic Addition Reactions 604
Practice Your Scientific Analysis and Reasoning IV: Selective Serotonin Reuptake Inhibitors (SSRIs) 649
20 Carboxylic Acids and Nitriles 653
21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 679
22 Carbonyl Alpha-Substitution Reactions
23 Carbonyl Condensation Reactions 753
Practice Your Scientific Analysis and Reasoning V: Thymine in DNA 784
24 Amines and Heterocycles 787
25 Biomolecules: Carbohydrates 832
26 Biomolecules: Amino Acids, Peptides, and Proteins 870
27 Biomolecules: Lipids 907
Practice Your Scientific Analysis and Reasoning VI: Melatonin and Serotonin 939
28 Biomolecules: Nucleic Acids 942
29 The Organic Chemistry of Metabolic Pathways 964
30 Orbitals and Organic Chemistry: Pericyclic Reactions 1013
Practice Your Scientific Analysis and Reasoning VII: The Potent Antibiotic Traits of Endiandric Acid C 1034
31 Synthetic Polymers 1037
Appendix A: Nomenclature of Polyfunctional Organic Compounds A-1
Appendix B: Acidity Constants for Some Organic Compounds A-9
Appendix C: Glossary A-11
Appendix D: Answers to In-Text Problems A-31