Ideal for those who have previously studies organic chemistry but not in great depth and with little exposure to organic chemistry in a formal sense. This text aims to bridge the gap between introductory-level instruction and more advanced graduate-level texts, reviewing the basics as well as presenting the more advanced ideas that are currently of importance in organic chemistry. * Provides students with the organic chemistry background required to succeed in advanced courses. * Practice problems included at the end of each chapter.

ROBERT V. HOFFMAN, PhD, is Professor Emeritus of Chemistry at New Mexico State University in Las Cruces, New Mexico.

Preface	p. xiii
Preface to the First Edition	p. xv
Functional Groups and Chemical Bonding	p. 1
Functional Groups	p. 1
Orbitals	p. 5
Bonding Schemes	p. 7
Antibonding Orbitals	p. 13
Resonance	p. 18
Conjugated [pi] Systems	p. 21
Aromaticity	p. 23
Bibliography	p. 26
Problems	p. 27
Oxidation States of Organic Compounds	p. 32
Oxidation Levels	p. 32
Oxidation States in Alkanes	p. 34
Oxidation States in Alkenes	p. 34
Oxidation States in Common Functional Groups	p. 35
Oxidation Level Changes During Reactions	p. 35
Bibliography	p. 41
Problems	p. 41
Acidity and Basicity	p. 47
Bronsted and Lewis Acids and Bases	p. 47
Acid Strength	p. 49
Acid-Base Equilibria	p. 53
Amphoteric Compounds	p. 56
Structural Effects on Acidity	p. 56
Electronegativity	p. 58
Inductive Effects	p. 59
Resonance Effects	p. 61
Bibliography	p. 63
Problems	p. 63
Curved-Arrow Notation	p. 69
Electron Movement	p. 69
Heterolytic Bond Cleavages	p. 70
Heterolytic Bond Formation	p. 71
Homolytic Bond Making and Bond Breaking	p. 73
Resonance Structures	p. 75
Depiction of Mechanism	p. 76
Bibliography	p. 82
Problems	p. 82
Mechanisms of Organic Reactions	p. 86
Activation Energy	p. 87
Activated Complex	p. 88
Reaction Energetics	p. 89
Structure of the Activated Complex	p. 91
Hammond Postulate	p. 96
Reaction Kinetics	p. 99
Determining Activation Energies	p. 104
Isotope Effects	p. 105
Electronic Effects	p. 110
Hammett Equation	p. 111
Bibliography	p. 118
Problems	p. 118
Stereochemical and Conformational Isomerism	p. 124
Stereochemical Structures	p. 125
Chirality	p. 128
Configuration of Chiral Centers	p. 129
Multiple Stereocenters	p. 132
Optical Activity	p. 137
Absolute Configuration	p. 138
Physical Properties of Enantiomers	p. 139
Resolution of Enantiomers	p. 140
Stereoselective Reactions	p. 144
Formation of Enantiomers	p. 144
Formation of Diastereomers	p. 146
Stereochemistry to Deduce Mechanism	p. 152
Conformational Analysis	p. 157
Conformational Energies	p. 164
A Values	p. 166
Strain in Ring Systems	p. 167
Stereoelectronic Effects	p. 172
Bibliography	p. 176
Problems	p. 176
Functional Group Synthesis	p. 183
Functional Group Manipulation	p. 183
Carboxylic Acids	p. 185
Esters	p. 188
Amides	p. 190
Acid Chlorides	p. 191
Aldehydes	p. 192
Ketones	p. 194
Imines and Imine Derivatives	p. 197
Alcohols	p. 198
Amines	p. 201
Alkenes	p. 203
Alkanes	p. 207
Bibliography	p. 208
Problems	p. 209
Carbon-Carbon Bond Formation between Carbon Nucleophiles and Carbon Electrophiles	p. 216
Synthetic Strategy	p. 217
Nucleophilic Carbon	p. 218
Electrophilic Carbon	p. 220
Reactivity Matching	p. 223
Generation of Nucleophilic Carbon Reagents	p. 224
Generation of Electrophilic Carbon Reagents	p. 227
Matching Nucleophiles with Electrophiles	p. 227
Enolates	p. 228
Enolate Regioisomers	p. 234
Diastereoselection in Aldol Reactions	p. 236
Organometallic Compounds	p. 239
Neutral Carbon Nucleophiles	p. 239
C=C Formation	p. 242
Cyclopropanation Reactions	p. 244
Metal-Catalyzed Carbon--Carbon Bond Formation	p. 246
Pd(0)-Catalyzed Carbon--Carbon Bond Formation	p. 247
Heck Reaction	p. 251
Suzuki Coupling	p. 253
Stille Coupling	p. 254
Olefin Metathesis	p. 256
Bibliography	p. 261
Problems	p. 262
Carbon--Carbon Bond Formation by Free-Radical Reactions	p. 272
Free-Radical Reactions	p. 272
Free-Radical Polymerization	p. 277
Nonpolymerization Reactions	p. 278
Free-Radical Initiation	p. 280
Free-Radical Cyclization	p. 283
Bibliography	p. 288
Problems	p. 288
Planning Organic Syntheses	p. 292
Retrosynthetic Analysis	p. 292
Carbon Skeleton Synthesis	p. 296
Umpolung Synthons	p. 302
Acetylide Nucleophiles	p. 305
Ring Construction	p. 306
Robinson Annulation	p. 310
Diels--Alder Reaction	p. 312
HOMO--LUMO Interactions	p. 313
Stereoelectronic Factors	p. 316
1,3-Dipolar Cycloadditions	p. 319
Bibliography	p. 323
Problems	p. 324
Structure Determination of Organic Compounds	p. 332
Structure Determination	p. 332
Chromatographic Purification	p. 333
Instrumental Methods	p. 335
Nuclear Magnetic Resonance	p. 336
Chemical Shift	p. 338
Spin--Spin Coupling	p. 344
Descriptions of Spin Systems	p. 350
Second-Order Splitting	p. 354
Structure Identification by [superscript 1]H NMR	p. 355
Carbon-13 NMR	p. 360
Infrared Spectroscopy	p. 366
IR Stretching Frequencies	p. 367
Use of IR Spectroscopy for Structure Determination	p. 371
Mass Spectrometry	p. 377
Fragmentation Processes	p. 384
Bibliography	p. 388
Problems	p. 388
Solutions to Chapter Problems	p. 395
Index	p. 471
Table of Contents provided by Rittenhouse. All Rights Reserved.

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