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ORGANIC CHEMISTRY, Second Edition - the first mechanistic-oriented book written at a level that organic chemistry students will understand! Specifically, the focus on mechanisms is a unifying theme, rather then just an organizing principle. Organizationally mainstream, it is unique in bringing in mechanisms as a unifying principle, and reactions are organized by mechanism type not by functional groups. And now, text/media integration has never been so seamless with the introduction of Organic ChemistryNow for ORGANIC CHEMISTRY, Second Edition.

Joe Hornback, University of Denver

Joseph M. Hornback was born and raised in southwestern Ohio. He received a B.S. degree in chemistry, magna cum laude, form the University of Notre Dame in 1965. He then attended the Ohio State University on an NSF traineeship and received his Ph.D. in 1968. He then moved to the University of Wisconsin on an NIH postdoctoral fellowship. In 1970, Joe joined the chemistry faculty at the University of Denver, where he is now Professor of Chemistry and Biochemistry. His research interests are in the areas of synthetic organic chemistry and organic photochemistry. He has served in a number of administrative positions, including Associate Dean for Undergraduate Studies, Associate Dean for Natural Sciences, Mathematics, and Engineering, and Director of the Honors Program. His first love has always been teaching and he has taught organic chemistry nearly every term, even when he was an administrator. He has received the Natural Science Award for Excellence in Teaching and the Outstanding Academic Advising Award.
  • The first three chapters constitute a review of bonding and an introduction to organic compounds. Functional groups are introduced. Resonance is covered extensively, with numerous examples.
  • Chapter 11 covers electrophilic additions to alkenes and alkynes. The behavior of carbocations, presented in Chapter 8, is very useful here. An additional section on synthesis has been added to this chapter.
  • IR spectroscopy is covered in Chapter 13 and hydrogen and carbon NMR spectroscopy are covered in Chapter 14. These topics have been separated to provide a more reasonable chapter size and increase flexibility in order of presentation. Numerous sample spectra and problems are included and all spectra have been redrawn for increase clarity. Because all the functional groups have been introduced early, the spectroscopy of all of them is presented at one time. It is not necessary to return to a discussion of spectra each time a new functional group is introduced. Chapters after Chapter 15 have several spectroscopy-based problems in a separate section of the additional problems.
  • Aromatic chemistry has been moved up and is covered in Chapter 16, which discusses aromaticity, and in Chapter 17, which presents aromatic substitution reactions.
  • The use of reactions to synthesize organic compounds is introduced early and is an important part of every chapter where reactions are presented. The first introduction to synthesis occurs in Chapter 8 with problems such as "What reagent can be used to carry out this transformation?" and "Show how this compound can be prepared from alkyl halides." Chapter 10 introduces the concept of synthetic equivalent (acetate for hydroxide and phthalimide for ammonia). Section 10.15 covers the strategy of organic synthesis and introduces retrosynthetic analysis and here the synthesis problems become more complex. A new section on synthesis in Chapter 11 introduces the retrosynthetic arrow and again raises the level of the problems.
  • Chapter 23 is a unique chapter on synthesis, which brings together most of the reactions presented in earlier chapters, provides additional discussion of synthetic strategy, and the use of protecting groups, and presents some longer, more complex syntheses. Table 23.1 lists the important carbon-carbon bond forming reactions, and Table 23.2 lists most of the reactions presented in the book according to the functional group that is produced. These tables are very useful in designing syntheses and can also be used as a summary of most of the text.
  • Acid-base chemistry is discussed in Chapter 4, and this reaction is used to introduce many of the general features of reactions, including the effect of structure on reactivity. Nomenclature of all of the functional groups is covered in Chapters 5 and 12.
  • NEW! Organic ChemistryNow - a web-based assessment-centered learning tool for the Organic Chemistry course, in concert with this text. Throughout each chapter, icons with captions alert students to media resources that enhance problem-solving skills and improve conceptual understanding. In Organic ChemistryNow, students are provided with a Personalized Learning Plan�based on a diagnostic Pre-Test �that targets their study needs and helps them to visualize, organize, practice, and master the material in the text. An access code for Organic ChemistryNow is packaged FREE with every new copy of the text.
  • In this edition, stereochemistry is covered in two chapters to break up the material: cis-trans isomers and conformations in Chapter 6 and chiral molecules in Chapter 7.
  • Elimination reactions are treated separately in Chapter 9 so that each chapter is more manageable. Chapter 10 discusses synthetic uses of substitution and elimination reactions and introduces retrosynthetic analysis.
  • Each chapter begins with a set of "Mastery Goals." At the end of the chapter, these goals are restated and linked to specific problems for students to test their command of the material. Additionally, "Mastery Goal Quizzes" for each chapter can be found on the web in Organic ChemistryNow.
  • All mechanisms have been carefully examined for inclusion of all steps with arrow pushing, proper reagents, and conditions. Each mechanism is clearly labeled and easily identified by a tan background and steps are numbered and annotated.
  • There are over 1,100 problems in this book, many with multiple parts. Many new, solved in-text "Practice Problems" have been added. Many of these have a "Strategy" section to guide students through the thought process involved.
  • A total new design has made the book visually appealing and pedagogically easier to read. In addition, color is used to highlight parts of molecules and to follow the course of reactions.
  • Since Organic Chemistry is a very visual science, considerable effort has gone into the development of chemical illustrations to make them both clear and informative. Most figures contain structures as well as text. This decreases the need to refer back and forth between the figure and the text.
  • "Focus On� and Focus On Biological Chemistry" boxes illustrate applications of organic chemistry to the world around us and to the health science, explore topics in more depth, or discuss the history of chemical discoveries. Some topics include "DDT-Resistant Insects," "Biological Alkylations" and "Poisons and Environmentally Friendly (Green) Chemistry."
  • The application of organic chemistry to biological chemistry is emphasized within text, in the "Focus on Biological Chemistry" boxes and within problems designated with a Biolink icon.
  • Extensive use of "molecular models" both in-text and on-line help students visualize the shapes of compounds and how the molecules interact in three dimensions. In addition, there are "Model Building Problems" interspersed throughout the text to give students practice building hand-held models and end-of-chapter problems based on on-line models.
  • Animations of key concepts are found on Organic ChemistryNow as Active Figures. Taken straight from the text, Active Figures help students visualize key concepts from the book. The Active Figures also include questions so students can assess their understanding of the concepts. Students can also assess their understanding of each chapter's topics with additional quizzing, conceptual-based problems and tutorials at the Organic ChemistryNow� Web site.
  • Unique to this book are Tables 23.1 and 23.2, which summarize the important carbon-carbon bond forming reactions, and most of the reactions presented in the text. Students can use these tables as an aid in designing the synthesis of more complicated problems.
1. A Simple Model for Chemical Bonds.
2. Organic Compounds: A First Look.
3. Orbitals and Bonding.
4. The Acid-Base Reaction.
5. Functional Groups and Nomenclature I.
6. Stereochemistry I: Cis-Trans Isomers and Conformations.
7. Stereochemistry II: Chiral Molecules.
8. Nucleophilic Substitution Reactions: Reactions of Alkyl Halides, Alcohols, and Related Compounds.
9. Elimination Reactions: Reactions of Alkyl Halides, Alcohols, and Related Compounds.
10. Synthetic Uses of Substitution and Elimination Reactions:Interconverting Functional Groups.
11. Additions to Carbon Carbon Double and Triple Bonds:Reactions of Alkenes and Alkynes.
12. Functional Groups and Nomenclature II.
13. Infrared Spectroscopy.
14. Nuclear Magnetic Resonance Spectroscopy.
15. Ultraviolet-Visible Spectroscopy and Mass Spectrometry.
16. Benzene and Aromatic Compounds.
17. Aromatic Substitution Reactions.
18. Additions to the Carbonyl Group: Reactions of Aldehydes and Ketones.
19. Substitutions at the Carbonyl Group: Reactions of Carboxylic Acids and Derivatives.
20. Enolate and Other Carbon Nucleophiles.
21. The Chemistry of Radicals.
22. Pericyclic Reactions.
23. The Synthesis of Organic Compounds.
24. Synthetic Polymers.
25. Carbohydrates.
26. Amino Acids, Peptides, and Proteins.
27. Nucleotides and Nucleic Acids.
28. Other Natural Products.
Appendix: Answers to In-Chapter Problems.

Textbook Only Options

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  • ISBN-10: 1133384846
  • ISBN-13: 9781133384847
  • STARTING AT $23.49

  • STARTING AT $47.49

  • ISBN-10: 0534389511
  • ISBN-13: 9780534389512
  • Bookstore Wholesale Price $225.00
  • RETAIL $299.95

"Hornback will serve the average students well and also be an excellent foundation for further exploration by more advanced students. Overall the writing style is concise and focused, helping the students stay focused on the most important concepts of the chapter with out becoming lost in details and distractions."

"I share the author’s view that the mechanistic approach is really the only good way to teach the material. I also support the author’s focus on major mechanistic classes, while not covering less important classes of reactions."

"The end-of-chapter problems as well as the problems within the chapters are excellent. Many questions work students through the necessary fundamentals. Only thereafter are more sophisticated problems introduced."

"Hornback’s mechanistic organization is only different from our current approach in that we cover the functional groups as the major topic of most chapters. But our underlying approach is basically mechanistic. Therefore using Hornback would not present any significant challenges."

"I prefer this mechanistic approach as it is the only realistic way to avoid rote memorization by students of the volume of material presented and it exposes them to the inherent logic of the discipline."

Cengage provides a range of supplements that are updated in coordination with the main title selection. For more information about these supplements, contact your Learning Consultant.


Test Bank

ISBN: 9780534397111
A multiple-choice bank of over 1,000 problems for instructors to use for tests, quizzes, or homework assignments.

Student Solutions Manual and Study Guide

ISBN: 9780534397104
Written by Joseph Hornback, this manual contains detailed solutions to all text problems.

Organic ChemistryNOW™ Instant Access Code

ISBN: 9780534466091


Student Solutions Manual and Study Guide

ISBN: 9780534397104
This Student Solutions Manual for ORGANIC CHEMISTRY is your ideal homework companion in your organic chemistry course. It contains detailed solutions to all text problems.

Organic ChemistryNOW™ Instant Access Code

ISBN: 9780534466091
This is an easy-to-use online resource that helps you study in less time to get the grade you want.