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Book Details

  • Hardcover + Digital Product License Key Folder
  • Bookstore's Wholesale Price: $165.00
  • Forthcoming: November 2017
  • ISBN: 978-0-393-63074-9
  • 1584 pages
  • Territory Rights: Worldwide
Please Note: Any item that is specified as being a folder is not available for immediate download. You must wait for the registration key folder to be delivered to you.

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Organic Chemistry

Principles and Mechanisms

Second Edition

Hardcover + Digital Product License Key Folder

with Ebook and Smartwork5

See all options and formats starting at

Joel Karty (Author, Elon University)


Understand more, memorize less.

Organic chemistry can overwhelm students and force them to fall back on memorization. But once they understand how to use mechanisms, they can solve just about any problem. With an organization by mechanism, students will understand more, and memorize less. The Second Edition of this groundbreaking text provides a fresh, but proven approach to get students confident using mechanisms.

Smartwork5 online homework supports learning by mirroring the text’s organization and pedagogy. Students use an intuitive drawing tool while receiving instant hints and answer-specific feedback, making practice more productive.


A mechanistic organization

Organic chemistry students often try to memorize their way through the course. An organization by mechanism helps prevent this because each reaction chapter focuses primarily on the importance of understanding reaction mechanisms.
A key to Joel’s organization is Chapter 7: An Overview of the Most Common Elementary Steps. In it, students are introduced to 9 of the 10 mechanisms they will see for most of the course. This lays the foundation for students to build on by foreshadowing what’s to come. It also makes students more comfortable and confident in using mechanisms throughout the course. 

“Think” and “Solve” in the text and Smartwork5

In every worked problem, Joel Karty presents the solution in two steps: Think and Solve. The “Think” step sets this book apart as it promotes active learning and poses the kinds of questions a student should be asking as they approach this type of problem.
Smartwork5 offers a sophisticated, yet user-friendly platform. Tying directly to the text's organization and pedagogy, it includes extensive answer-specific feedback and hints using the “Think” and “Solve” steps.

A variety of interactive question types, including Smartwork5’s intuitive 2D molecular drawing tool, test student understanding and reinforce problem-solving skills. In addition, Smartwork5 can now be used on a tablet and integrates seamlessly with campus LMSs. 

Pedagogy that facilitates active learning

Active-learning exercises, called Your Turn, are integrated into each chapter. These exercises motivate students to work problems and interact with figures as part of their reading. Your Turn questions also act as reality checks to indicate whether a student understands what they just read.
The Your Turn questions are live, clickable links in the ebook, so students can get immediate feedback and determine whether they truly understand the material. In addition, you can click on Solved Problems to reveal the “Think” and then “Solve” steps in the ebook. 

Applications make organic chemistry relevant to non-chemistry majors

Rather than relegating biochemistry to the last chapters of the book, coverage of biochemical material is in self-contained sections at the end of several chapters, beginning with Chapter 1. In each Organic Chemistry of Biomolecules section, Karty draws explicit links to concepts encountered earlier in the chapter. These biochemistry sections are both optional and flexible. 

NEW coverage on contemporary topics and modern reactions

Based on user and reviewer feedback, new material has been added to the Second Edition, including:
• A NEW Green Chemistry section in Chapter 13 presents fundamental ideas behind green chemistry. In subsequent chapters, Green Chemistry boxes highlight green aspects of some reactions and provide examples of green alternatives to others.
• A NEW section on transition metal coupling reactions and alkene metathesis reactions (Section 19.7) gives students access to Nobel prize–winning chemistry. 

    1. Atomic and Molecular Structure
    Interchapter A Nomenclature: The Basic System for Naming Simple Organic Compounds: Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers
    2. Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties
    3. Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals
    Interchapter B Naming Alkenes, Alkynes, and Benzene Derivatives
    4. Isomerism 1: Conformational and Constitutional Isomers
    5. Isomerism 2: Chirality, Enantiomers, and Diastereomers
    Interchapter C Stereochemistry in Nomenclature: R and S Configurations about Asymmetric Carbons and Z and E Configurations about Double Bonds
    6. The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics, and Charge Stability
    7. An Overview of the Most Common Elementary Steps
    Interchapter D Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions
    Interchapter E Naming Compounds with a Functional Group That Calls for a Suffix 1: Alcohols, Amines, Ketones, and Aldehydes
    8. An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions
    Interchapter F Naming Compounds with a Functional Group That Calls for a Suffix 2: Carboxylic Acids and Their Derivatives
    9. Nucleophilic Substitution and Elimination Reactions 1: Competition among SN2, SN1, E2, and E1 Reactions
    10. Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis
    11. Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted Acid
    12. Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving Cyclic Transition States
    13. Organic Synthesis 1: Beginning Concepts
    14. Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity
    15. Structure Determination 1: Ultraviolet–Visible and Infrared Spectroscopies
    16. Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry
    17. Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles
    18. Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid and Base Catalysis
    19. Organic Synthesis 2: Intermediate Topics in Synthesis Design, and Useful Redox and Carbon–Carbon Bond-Formation Reactions
    20. Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involving Strong Nucleophiles

    21. Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles
    22. Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful Accompanying Reactions
    23. Aromatic Substitution 2: Reactions of Substituted Benzene and Other Rings
    24. The Diels–Alder Reaction and Other Pericyclic Reactions
    25. Reactions Involving Free Radicals
    Interchapter G Fragmentation Pathways in Mass Spectrometry
    26. Polymers