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Organic Chemistry

An Intermediate Text

Robert V. Hoffman

Publication Date - November 1996

ISBN: 9780195096187

336 pages
6-1/2 x 9-1/4 inches


Organic Chemistry: An Intermediate Text provides a focused yet rigorous presentation of organic chemistry which bridges the gap between introductory undergraduate texts and advanced graduate level texts. Instead of a functional group approach, the material is presented from a structural and mechanistic point of view. The first five chapters discuss basic principles which are fundamental in understanding organic reactions and reactivity of all types. These principles include structure and bonding, oxidation levels, acidity and basicity, curved arrow notation, and stereochemistry and conformation. Subsequent topics are based on these fundamental principles and include functional group manipulation, strategies and methods for forming carbon-carbon bonds, and retrosynthetic analysis. Chapters on methods for determining reaction mechanisms and methods for organic structure determination round out the subject matter and provide additional insight into modern ways to investigate organic transformations. A large number of practice problems are included at the end of each chapter so that students may effectively learn and organize the information presented in the text.
Clearly written and logically organized, this unique textbook provides senior undergraduate chemistry students and beginning graduate students with the advanced organic foundation necessary to move confidently into advanced graduate level courses or directly into the workplace.

Table of Contents

    1. Functional Groups and Chemical Bonding
    Functional Groups
    Bonding Schemes
    Antibonding Orbitals
    Conjugated pi Symbols
    2. Oxidation States of Organic Compounds
    Oxidation Levels
    Oxidation States in Alkanes
    Oxidation States in Alkenes
    Oxidation States in Other Common Functional Groups
    Oxidation Level Changes During Reactions
    3. Acidity and Basicity
    Bronsted and Lewis Acids and Bases
    Acid Strength
    Acid-Base Equilibria
    Amphoteric Compounds
    Structural Effects on Acidity
    4. Curved Arrow Notation
    Electron Movement
    Heterolytic Bond Cleavages
    Heterolytic Bond Formation
    Homolytic Bond Breaking and Bond Making
    Resonance Structures
    Depiction of Mechanism
    5. Stereochemistry and Conformation
    Stereochemical Structures
    Configuration of Chiral Centers
    Multiple Stereocenters
    Optical Activity
    Absolute Configuration
    Physical Properties of Enantiomers
    Resolution of Enantiomers
    Stereoselective Reactions
    Formation of Enantiomers
    Formation of Disastereomers
    Conformational Analysis
    Conformational Energies
    A Values
    Stereoelectronic Effects
    6. Functional Group Synthesis
    Functional Group Manipulation
    Carboxylic Acids
    Acid Chlorides
    Imines and Imine Derivatives
    7. Carbon-Carbon Bond Formation Between Carbon Nucleophiles and Carbon Electrophiles
    Synthetic Strategy
    Nucleophilic Carbon
    Electrophilic Carbon
    Reactivity Matching
    Generation of Nucleophilic Carbon Reagents
    Generation of Electrophilic Carbon Reagents
    Matching Nucleophiles with Electrophiles
    Enolate Regioisomers
    Diastereoselection in Aldol Reactions
    Organometallic Compounds
    Neutral Carbon Nucleophiles
    C=C Formation
    Cyclopropanation Reactions
    8. Carbon-Carbon Bond Formation by Nonpolar Reactions: Free Radicals and Cycloadditions
    Free Radical Reactions
    Free Radical Polymerization
    Nonpolymerization Reactions
    Free Radical Initiation
    Free Radical Cyclization
    Diels-Alder Reaction
    HOMO-LUMO Interactions
    Stereoelectronic Factors
    1,3-Dipolar Cycloaddition Reactions
    9. Planning Organic Syntheses
    Retrosynthetic Analysis
    Carbon Skeleton Synthesis
    Umpolung Synthons
    Acetylide Nucleophiles
    Ring Construction
    Robinson Annulation
    Diels-Alder Reaction
    10. Mechanisms of Organic Reactions
    Activation Energy
    Activated Complex
    Reaction Energetics
    Structure of the Activated Complex
    The Hammond Postulate
    Reaction Kinetics
    Determining Activation Energies
    Isotope Effects
    Electronic Effects
    The Hammett Equation
    11. Structure Determination of Organic Compounds
    Structure Determination
    Chromatographic Purification
    Instrumental Methods
    Nuclear Magnetic Resonance Spectroscopy
    Infrared Spectroscopy
    Mass Spectrometry
    Fragmentation Processes
    Each chapter ends with a Bibliography and Problems

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