Organic Chemistry(Robert V. Hoffman)

CONTENTS

1 Functional Groups and Chemical Bonding 
Functional Groups
Orbitals
Bonding Schemes
Antibonding Orbitals
Resonance
Conjugated π Systems
Aromaticity

2 Oxidation States of Organic Compounds 
Oxidation Levels
Oxidation States in Alkanes
Oxidation States in Alkenes
Oxidation States in 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
Electronegativity
Inductive Effects
Resonance Effects

4 Curved-Arrow Notation
Electron Movement
Heterolytic Bond Cleavages
Heterolytic Bond Formation
Homolytic Bond Making and Bond Breaking
Resonance Structures
Depiction of Mechanism

5 Mechanisms of Organic Reactions 
Activation Energy
Activated Complex
Reaction Energetics
Structure of the Activated Complex
Hammond Postulate
Reaction Kinetics
Determining Activation Energies
Isotope Effects
Electronic Effects
Hammett Equation

6 Stereochemical and Conformational Isomerism 
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 Diastereomers
Stereochemistry to Deduce Mechanism
Conformational Analysis
Conformational Energies
A Values
Strain in Ring Systems
Stereoelectronic Effects

7 Functional Group Synthesis 
Functional Group Manipulation
Carboxylic Acids
Esters
Amides
Acid Chlorides
Aldehydes
Ketones
Imines and Imine Derivatives
Alcohols
Amines
Alkenes
Alkanes

8 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
Metal-Catalyzed Carbon–Carbon Bond Formation
Pd(0)-Catalyzed Carbon–Carbon Bond Formation
Heck Reaction
Suzuki Coupling
Stille Coupling
Olefin Metathesis

9 Carbon–Carbon Bond Formation by
Free-Radical Reactions 
Free-Radical Reactions / 272
Free-Radical Polymerization / 277
Nonpolymerization Reactions / 278
Free-Radical Initiation / 280
Free-Radical Cyclization / 283

10 Planning Organic Syntheses
Retrosynthetic Analysis
Carbon Skeleton Synthesis / 296
Umpolung Synthons / 302
Acetylide Nucleophiles / 305
Ring Construction / 306
Robinson Annulation / 310
Diels–Alder Reaction / 312
HOMO–LUMO Interactions / 313
Stereoelectronic Factors / 316
1,3-Dipolar Cycloadditions / 319

11 Structure Determination of Organic Compounds
Structure Determination / 332
Chromatographic Purification / 333
Instrumental Methods / 335
Nuclear Magnetic Resonance / 336
Chemical Shift / 338
Spin–Spin Coupling / 344
Descriptions of Spin Systems / 350
Second-Order Splitting / 354
Structure Identification by 1H NMR / 355
Carbon-13 NMR / 360
Infrared Spectroscopy / 366
IR Stretching Frequencies / 367
Use of IR Spectroscopy for Structure Determination / 371
Mass Spectrometry / 377
Fragmentation Processes / 384



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