1st Edition

Organic Chemistry
A Mechanistic Approach

ISBN 9781482206906
Published December 15, 2014 by CRC Press
1284 Pages 3608 Color Illustrations

USD $170.00

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Book Description

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

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

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"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