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Organic Chemistry, 9th edition

Published by Pearson (July 17, 2024) © 2025

  • Paula Yurkanis Bruice University of California, Santa Barbara

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For courses in 2-semester organic chemistry.

Understand and apply the foundations of organic chemistry

Organic Chemistry provides the conceptual foundations, chemical logic and problem-solving skills students need to reason their way to solutions for problems in synthetic organic chemistry, biochemistry and medicine. By building an organic chemistry framework, students can understand and apply learning rather than relying on memorization.

The 9th Edition presents a wealth of problem-solving strategies, over 300 new problems (now totaling over 2,000), updated content and organizational changes to support the unique ways students acquire knowledge, study, practice and master organic chemistry.

Hallmark features of this title

  • Synthetic and retrosynthetic chemistry are introduced early to help students grasp multistep synthesis from the beginning.
  • Problem Sets and Reaction Summaries review key topics and reinforce essential skills at the end of each chapter.
  • Learn the Strategy labels guide students on how to approach problems and develop critical-thinking skills.
  • Reactions of Organic Compounds Table organizes reactions by similar chemical behavior into 4 groups that emphasize key characteristics of each group.
  • Applications boxes connect discussions to medical, environmental, biological and pharmaceutical applications, relating content to real life and future careers.
  • MCAT learning outcomes and MCAT-style questions in the Study Guide/Solutions Manual prepare students for the MCAT exam.

New and updated features of this title

  • EXPANDED: Study Guide/Solutions Manual provides answers to all problems with explanation when needed. Author-written solutions ensure consistency with the text. A digital version is available in the Mastering Study Area.
  • 7 Special synthesis design sections appear at appropriate intervals with 2 new tutorials on synthesis and retrosynthetic analysis added.
  • 65 Spectroscopy problems with worked-out answers in the Study Guide/Solutions Manual supplement the 170 existing spectroscopy problems. Problems are paired with assignable NMR/IR simulations in Mastering.
  • Solved Problems (Determining Electronic Configuration, Predicting Whether a Species Exists) and Problem-Solving Strategies (How to Calculate Formal Charge, Identifying Compounds with Dipole Moments) appear in all chapters.
  • Reflecting greater diversity, equity, and inclusion, visuals, language and terminology have been meaningfully revised throughout.
  • NEW & UPDATED Content: over 300 new problems (in-chapter and end-of-chapter), new Synthetic Polymers sections in Ch 11 (chain-growth) and Ch 14 (step-growth); updated Chs 12 and 13 for IR and NMR spectra; new section on benzyne in Ch 17; new palladium-catalyzed coupling reactions plus alkene/alkyne metathesis in Ch 19.

Features of Mastering Chemistry for the 9th Edition

  • NEW: Key Concept Interactives break down key topics and guide students through a series of interactive screens and questions that must be answered to progress.
  • NEW: 6 Tutorials follow relevant chapters to help students master essential skills.
  • Organic Chemistry Dynamic Study Modules focus on general chemistry remediation, acid-base chemistry, functional groups, nomenclature and key mechanisms.
  • Mechanism Practice Problems feature 1-step hints and predict the product functionality on any step of selected problems where students struggle, so students learn through practice.
  • 6 NMR/IR Spectroscopy Simulations provide access to limitless spectral analysis with guided activities.
  • 120 Organic Chemistry-specific tutorials built around the most challenging topics in Organic Chemistry provide wrong-answer feedback and hints.

Features of Pearson+ eTextbook for the 9th Edition

  • NEW: Key Concept Interactives in the Pearson+ eTextbook break down key topics and guide students through an interactive experience with opportunities for practice. Questions provide wrong-answer feedback.
  • Video assets give students easy access to visual explanations of mechanisms, nomenclature, and reaction summaries through embedded links in Pearson eText.

PART 1: AN INTRODUCTION TO THE STUDY OF ORGANIC CHEMISTRY

  • 1. Remembering General Chemistry: Electronic Structure and Bonding
  • 2. Acids and Bases: Central to Understanding Organic Chemistry
  • TUTORIAL: Acids and Bases
  • 3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Rotation About Single Bonds

PART 2: ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION

  • TUTORIAL: Using Molecular Models to Understand Structure
  • 4. Isomers: The Arrangement of Atoms in Space
  • TUTORIAL: Interconverting Structural Representations
  • 5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics
  • TUTORIAL: Drawing Curved Arrows
  • TUTORIAL: Kinetics
  • 6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions
  • TUTORIAL: An Overview of Functional Groups and How They React
  • 7. The Reactions of Alkynes • An Introduction to Multistep Synthesis
  • 8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity • Electronic Effects
  • TUTORIAL: Drawing Resonance Contributors

PART 3: SUBSTITUTION AND ELIMINATION REACTIONS

  • 9. Substitution and Elimination Reactions
  • 10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds • An Introduction to Organometallic Compounds
  • 11. Radicals
  • TUTORIAL: Drawing Curved Arrows in Radical Systems
  • TUTORIAL: Synthesizing Organic Compounds I

PART 4: IDENTIFICATION OF ORGANIC COMPOUNDS

  • 12. Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy
  • 13. NMR Spectroscopy

PART 5: CARBONYL COMPOUNDS

  • 14. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
  • 15. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
  • TUTORIAL: Predicting Mechanisms
  • 16. Reactions at the alpha-Carbon
  • TUTORIAL: Synthesizing Organic Compounds II

PART 6: AROMATIC COMPOUNDS

  • 17. Reactions of Benzene and Substituted Benzenes
  • 18. More About Amines • Reactions of Heterocyclic Aromatic Compounds
  • 19. Coupling Reactions and Metathesis

PART 7: BIOORGANIC COMPOUNDS

  • 20. The Organic Chemistry of Carbohydrates
  • 21. Amino Acids, Peptides, and Proteins
  • 22. Catalysis in Organic Reactions and in Enzymatic Reactions
  • 23. The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins
  • 24. The Organic Chemistry of the Metabolic Pathways
  • 25. The Organic Chemistry of Lipids
  • 26. The Chemistry of the Nucleic Acids

PART 8: SPECIAL TOPICS IN ORGANIC CHEMISTRY

  • 27. Synthetic Polymers
  • 28. Pericyclic Reactions

APPENDICES

  • I. pKa Values
  • II. Summary of Methods Used to Synthesize a Particular Functional Group
  • III. Summary of Methods Employed to Form Carbon-Carbon Bonds
  • IV. Spectroscopy Tables
  • V. Physical Properties of Organic Compounds
  • VI. Answers to Selected Problems

MATH AND CHEMISTRY-BASED GLOSSARY

USEFUL REFERENCES

  • Organizing What We Know About the Reactions of Organic Chemistry
  • Periodic Table of the Elements
  • Common Functional Groups
  • Approximate pKa Values
  • Common Symbols and Abbreviations

About our author

Paula Yurkanis Bruice was raised primarily in Massachusetts. After graduating from the Girls' Latin School in Boston, she earned an A.B. from Mount Holyoke College and a Ph.D. in chemistry from the University of Virginia. She then received an NIH postdoctoral fellowship for study in the Department of Biochemistry at the University of Virginia Medical School and held a postdoctoral appointment in the Department of Pharmacology at the Yale School of Medicine.

Paula spent most of her career at the University of California, Santa Barbara, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, two Mortar Board Professor of the Year Awards, and the UCSB Alumni Association Teaching Award. Her research interests center on the mechanism and catalysis of organic reactions, particularly those of biological significance. Paula has a daughter and a son who are physicians and a son who is a lawyer. Her main hobbies are reading mysteries and biographies and enjoying her pets (three dogs, two cats, and two parrots).

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