Organic Chemistry

Description

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

Preface
1. Functional Groups and Chemical Bonding
Functional Groups
Orbitals
Bonding Schemes
Antibonding Orbitals
Conjugated pi Symbols
Aromaticity
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
Chirality
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
Esters
Amides
Acid Chlorides
Aldehydes
Ketones
Imines and Imine Derivatives
Alcohols
Amines
Alkenes
Alkanes
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
Enolates
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
Stereochemistry
11. Structure Determination of Organic Compounds
Structure Determination
Chromatographic Purification
Instrumental Methods
Nuclear Magnetic Resonance Spectroscopy
Infrared Spectroscopy
Mass Spectrometry
Fragmentation Processes
Index
Each chapter ends with a Bibliography and Problems