Organic Chemistry: A Mechanistic Approach, 1st Edition (Hardback) book cover

Organic Chemistry

A Mechanistic Approach, 1st Edition

By Penny Chaloner

CRC Press

1,284 pages | 3608 Color Illus.

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pub: 2014-12-15
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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


"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

Table of 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

Subject Categories

BISAC Subject Codes/Headings:
MEDICAL / Biochemistry
SCIENCE / Chemistry / Organic
SCIENCE / Chemistry / Physical & Theoretical