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Organic Chemistry

A Mechanistic Approach

Penny Chaloner
Publication Date:
December 15, 2014
Content Details:
1,284 pages | 3,608 illustrations

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List Price:   $150.00

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  • About the Book

    Book Summary

    Offering a different, more engaging approach to teaching and learning, Organic Chemistry: A Mechanistic Approach classifies organic chemistry according to mechanism rather than by functional group. The book elicits an understanding of the material, by means of problem solving, instead of purely requiring memorization. The text enables a deep understanding of underlying principles that can be applied to a wide range of problems and systems. It also teaches a way of thinking and analysis that will serve students well across many academic disciplines.

    Covering all the key aspects of organic chemistry, this text emphasizes the development of skills through a student-centered approach. In order to provide a contemporary feel to the subject, the author has included some of the more modern synthetic approaches. In addition, later chapters address the biological, environmental, industrial, and forensic aspects of organic chemistry.

    Pedagogical Features:

    • Extensive review problems, which are the central means of integrating the material
    • "Focus boxes" that highlight key points in the chapters
    • An instructors’ website with full lecture notes in animated PowerPoint, a solutions manual in both Word and PowerPoint format, and additional problems for use in tests

    A student website with solutions to review problems, and additional challenging problems and solutions for the ambitious, in animated PowerPoint and text versions


      • Presents a unique text due to the mechanism-led approach
      • Focuses on understanding rather than students having to memorize
      • Offers full lecture notes to faculty, in animated PowerPoint
      • Provides a user friendly, well illustrated textbook
      • Gives solutions to selected problems in word and animated PowerPoint


      "The introduction to each chapter sets its content in the context of the previous chapters. The material is then divided into readable, logical sections interspersed with illustrative problems and their solutions together with summaries of the key points. She writes in a student-friendly style identifying and addressing clearly many of the problems with which students have difficulty. …highly recommended as a reasonably priced textbook particularly to those students who want to understand the mechanistic rationale which underpins modern organic chemistry."
      Science Progress

  • Contents

    Review of Atomic and Molecular Structure
    Atomic and Molecular Structure
    Review Problems

    Alkanes and Friends: Structure, Bonding, Properties, and Nomenclature
    Hybridization in Methane, Ammonia, and Water
    Drawing Molecules
    Introduction to Alkanes
    Stability, Strain, and Properties of Alkanes and Cycloalkanes
    Review Problems

    Alkenes, Alkynes, and Aromatic Compounds
    Aromatic Hydrocarbons
    Alkynes: Hydrocarbons Containing Triple Bonds
    Review Problems

    Heteroatom-Containing Functional Groups
    Compounds Containing sp3 Nitrogen Atoms
    Molecules Containing sp2 Nitrogen Atoms
    Molecules with sp-Hybridized Nitrogen
    Compounds Containing sp3 Oxygen
    Compounds Containing sp2 Oxygen
    Priorities in Nomenclature
    Structure and Bonding in Some Highly Reactive Species
    More Resonance
    Review Problems
    More Challenging Problems

    Purification and Identification of Organic Compounds 1
    Purification of Organic Compounds
    Mass Spectrometry
    UV/Visible Spectroscopy
    Infrared Spectroscopy
    Review Problems
    More Challenging Problems

    Identification of Organic Compounds 2: Nuclear Magnetic Resonance Spectroscopy
    Chemical Shifts
    Spin–Spin Coupling
    Protons Attached to Oxygen and Nitrogen
    13C NMR Spectroscopy
    Review Problems
    More Challenging Problems

    Conformations of Alkanes
    Fischer Projections
    Review Problems
    More Challenging Problems

    Introduction to Mechanism
    Studying Organic Reaction Mechanisms
    Classification of Reactions
    Acids and Bases
    Tautomers: A Slight Digression
    Writing Mechanisms Using Curly Arrows
    Review Problems
    More Challenging Problems

    Nucleophilic Substitution at Saturated Carbon
    Mechanistic Types
    Stereochemical Implications
    Effect of Nucleophile
    Effect of the Leaving Group
    Effect of Substrate Structure
    Effect of Solvents
    Competing Reactions
    Competition between SN1 and SN2 Processes
    Applications and Scope of the Reaction
    Neighboring Group Participation and Intramolecular Reactions
    Review Problems
    More Challenging Problems

    Elimination Reactions
    Effect of Substrate
    Substitution versus Elimination
    Carbocation Rearrangements
    Examples and Applications
    Elimination to Give Alkynes
    Other Elimination Reactions
    Review Problems
    More Challenging Problems

    Addition Reactions
    Electrophilic Reactions
    Radical Addition Reactions
    Multicenter Processes
    Review Problems
    More Challenging Problems

    Electrophilic Aromatic Substitution
    Orientation Effects
    Reactions of Polycyclic Aromatic Compounds
    Heterocyclic Aromatic Compounds
    Review Problems
    More Challenging Problems

    Nucleophilic Aromatic Substitution and Synthesis of Aromatic Compounds
    Unimolecular Nucleophilic Substitution of Aromatic Compounds: The Reactions of Diazonium Salts
    with Simple Nucleophiles
    Azo Coupling Reactions
    Nucleophilic Substitution of Aryl Halides, SN2Ar
    Substitution of Haloheterocycles
    Substitution via Benzyne and Related Intermediates
    Reactions in Side Chains of Aromatic Compounds
    Reduction of Benzene Rings
    Carbon–Aryl Bond Formation
    Aromatic Synthesis
    Review Problems
    More Challenging Problems

    Addition to Carbon–Heteroatom Double Bonds
    Introduction and Review
    Mechanism of Addition Reactions
    Reversible Addition Reactions
    Irreversible Addition Reactions
    Review Problems
    More Challenging Problems

    Substitution of Carbonyl Compounds: Carboxylic Acids and Their Derivatives
    Introduction: Review of Nomenclature
    Substitution Reaction
    Oxygen Nucleophiles
    Nitrogen Nucleophiles
    Synthesis of Acid Chlorides
    Hydride as Nucleophile
    Carbon Nucleophiles
    Review Problems
    More Challenging Problems

    Lipids and Carbohydrates
    Review Problems
    More Challenging Problems

    Substitution α and β to Carbonyl Groups
    Formation of Enols and Enolates
    Isomerizations Involving Enols and Enolates
    Reactions of Enols and Enolates with Electrophiles
    Two Useful Reactions of Nonenolizable Carbonyl Compounds
    Reactions at the β-Position of α,β-Unsaturated Carbonyl Compounds and Other Electron-Poor Alkenes
    Review Problems
    More Challenging Problems

    Rearrangement Reactions
    Migration to Electron-Deficient Carbon
    Migration to Electron-Deficient Nitrogen
    Migration to Electron-Deficient Oxygen: The Baeyer–Villiger Oxidation
    Anionic Rearrangements
    Neutral Rearrangements
    Review Problems
    More Challenging Problems

    Synthesis 1: One-Group Disconnections
    Simple Disconnections and the Retrosynthetic Approach
    One-Group Disconnections
    Review Problems
    More Challenging Problems

    Synthesis 2: Two-Group Disconnections and Protecting Groups
    Introduction to Two-Group Disconnections
    1,2-Difunctionalized Compounds
    1,3-Difunctionalized Compounds
    1,4-Difunctionalized Compounds
    1,5-Difunctionalized Compounds
    Robinson Annulation
    1,6-Difunctionalized Compounds
    Pericyclic Disconnections
    Protecting Group
    Further Reading
    Review Problems
    More Challenging Problems
    More Challenging Problems

    Polymeric Materials
    Polymer Structures
    Preparation of Addition or Chain-Growth Polymers
    Preparation of Step-Reaction Polymers
    Unusual Biopolymers
    Review Problems
    More Challenging Problems

    Amines, Alkaloids, Amino Acids, Peptides, and Nucleic Acids
    Synthesis of Amines
    Amino Acids
    Nucleic Acids
    Review Problems
    More Challenging Problems

    Catalysis of Organic Reactions
    Catalysis by Acids and Bases
    Lewis Acid Catalysis
    Phase-Transfer Catalysis
    Reactions Catalyzed by Metal Surfaces
    Reactions Catalyzed by Transition Metal Complexes
    Enzyme Catalysis
    Review Problems
    More Challenging Problems

    Organic Chemistry in Industry
    Process Chemistry versus Research Chemistry
    Pharmaceutical Industry
    Dyes and Colorants
    Review Problems
    Further Reading

    Organic Chemistry and the Environment
    Endocrine Disruptors
    Chlorofluorocarbons and Their Replacements
    Polycyclic Aromatic Hydrocarbons
    Plastics: Recycle, Degrade, or Burn?
    Is "Green Chemistry" the Future?
    Review Problems
    Further Reading

    Organic Chemistry in Forensic Science
    Drugs of Abuse
    Poisons and Poisoning
    Testing for Blood
    Dyes, Inks, and Paper
    Trace Evidence
    Visualization of Fingerprints
    Review Problems

    Appendix A: Glossary of Abbreviations and Acronyms

    Appendix B: Some Common/Trivial Names You Need to Know