Writing Reaction Mechanisms in Organic Chemistry

ISBN-10: 0124967124
ISBN-13: 9780124967120
Edition: 2nd 2000 (Revised)
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Description: This is a guide to charting the movements of atoms and electrons in the reactions of organic molecules. It shows that understanding organic reactions can be based on applying general principles rather than memorisation of unrelated processes.

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Book details

List price: $86.95
Edition: 2nd
Copyright year: 2000
Publisher: Elsevier Science & Technology Books
Publication date: 11/4/1999
Binding: Paperback
Pages: 471
Size: 7.75" wide x 9.50" long x 1.00" tall
Weight: 1.848
Language: English

This is a guide to charting the movements of atoms and electrons in the reactions of organic molecules. It shows that understanding organic reactions can be based on applying general principles rather than memorisation of unrelated processes.

Audrey Evelyn Miller received her Ph.D. from Columbia University in 1962. She was the National Science Foundation Science Faculty Fellow from 1971-1972. Dr. Miller has served on panels from multiple organizations and societies. She has also given many seminar presentations at various colleges around the U.S. Dr. Miller recently taught chemistry at the University of Connecticut, and is also published under the last names Monahan and Small.

Preface to the Second Edition
Preface to First Edition
Introduction: Molecular Structure and Reactivity
How to Write Lewis Structures and Calculate Formal Charges
Determining the Number of Bonds
Determining the Number of Rings and/or [pi] Bonds (Degree of Unsaturation
Drawing the Lewis Structure
Formal Charge
Representations of Organic Compounds
Geometry and Hybridization
Electronegativities and Dipoles
Resonance Structures
Drawing Resonance Structures
Rules for Resonance Structures
Aromaticity and Antiaromaticity
Aromatic Carbocycles
Aromatic Heterocycles
Antiaromaticity
Tautomers and Equilibrium
Acidity and Basicity
Nucleophiles and Electrophiles
Nucleophilicity
Substrate
Solvent
General Principles for Writing Reaction Mechanisms
Balancing Equations
Using Arrows to Show Moving Electrons
Mechanisms in Acidic and Basic Media
Electron-Rich Species: Bases or Nucleophiles?
Trimolecular Steps
Stability of Intermediates
Driving Forces for Reactions
Leaving Groups
Formation of a Small Stable Molecule
Structural Relationships between Starting Materials and Products
Solvent Effects
A Last Word
Reactions of Nucleophiles and Bases
Nucleophilic Substitution
The S[subscript N]2 Reaction
Nucleophilic Substitution at Aliphatic sp[superscript 2] Carbon (Carbonyl Groups)
Nucleophilic Substitution at Aromatic Carbons
Eliminations at Saturated Carbon
E2 Elimination
Ei Elimination
Nucleophilic Addition to Carbonyl Compounds
Addition of Organometallic Reagents
Reaction of Nitrogen-Containing Nucleophiles with Aldehydes and Ketones
Reactions of Carbon Nucleophiles with Carbonyl Compounds
Base-Promoted Rearrangements
The Favorskii Rearrangement
The Benzilic Acid Rearrangement
Additional Mechanisms in Basic Media
Reactions Involving Acids and Other Electrophiles
Stability of Carbocations
Formation of Carbocations
Ionization
Addition of an Electrophile to a [pi] Bond
Reaction of an Alkyl Halide with a Lewis Acid
The Fate of Carbocations
Rearrangement of Carbocations
The Dienone-Phenol Rearrangement
The Pinacol Rearrangement
Electrophilic Addition
Regiospecificity
Stereochemistry
Acid-Catalyzed Reactions of Carbonyl Compounds
Hydrolysis of Carboxylic Acid Derivatives
Hydrolysis and Formation of Acetals and Orthoesters
1,4-Addition
Electrophilic Aromatic Substitution
Carbenes
Singlet and Triplet Carbenes
Formation of Carbenes
Reactions of Carbenes
Electrophilic Heteroatoms
Electron-Deficient Nitrogen
Rearrangements Involving Electrophilic Nitrogen
Rearrangement Involving Electron-Deficient Oxygen
Radicals and Radical Anions
Introduction
Formation of Radicals
Homolytic Bond Cleavage
Hydrogen Abstraction from Organic Molecules
Organic Radicals Derived from Functional Groups
Radical Chain Processes
Radical Inhibitors
Determining the Thermodynamic Feasibility of Radical Reactions
Addition of Radicals
Intermolecular Radical Addition
Intramolecular Radical Addition: Radical Cyclization Reactions
Fragmentation Reactions
Loss of CO[subscript 2]
Loss of a Ketone
Loss of N[subscript 2]
Loss of CO
Rearrangement of Radicals
The S[subscript RN] 1 Reaction
The Birch Reduction
A Radical Mechanism for the Rearrangement of Some Anions
Pericyclic Reactions
Introduction
Types of Pericyclic Reactions
Theories of Pericyclic Reactions
Electrocyclic Reactions
Selection Rules for Electrocyclic Reactions
Stereochemistry of Electrocyclic Reactions (Conrotatory and Disrotatory Processes)
Electrocyclic Reactions of Charged Species (Cyclopropyl Cations)
Cycloadditions
Terminology of Cycloadditions
Selection Rules for Cycloadditions
Secondary Interactions
Cycloadditions of Charged Species
Sigmatropic Rearrangements
Terminology
Selection Rules for Sigmatropic Rearrangements
The Ene Reaction
A Molecular Orbital View of Pericyclic Processes
Orbitals
Molecular Orbitals
Generating and Analyzing [pi] Molecular Orbitals
HOMOs and LUMOs
Correlation Diagrams
Frontier Orbitals
Additional Problems
Lewis Structures of Common Functional Groups
Symbols and Abbreviations Used in Chemical Notation
Relative Acidities of Common Organic and Inorganic Substances
Index

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