Organic Chemistry: An Intermediate Text

✍ Scribed by Robert V. Hoffman

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Leaves: 495
• Edition: 2
• Category: Library

✦ Synopsis

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.

✦ Table of Contents

ORGANIC CHEMISTRY SECOND EDITION......Page 4
CONTENTS......Page 10
Preface......Page 16
Preface to the First Edition......Page 18
Functional Groups......Page 20
Orbitals......Page 24
Bonding Schemes......Page 26
Antibonding Orbitals......Page 32
Resonance......Page 37
Conjugated π Systems......Page 40
Aromaticity......Page 42
Bibliography......Page 45
Problems......Page 46
Oxidation Levels......Page 51
Oxidation States in Alkenes......Page 53
Oxidation Level Changes During Reactions......Page 54
Problems......Page 60
Bronsted and Lewis Acids and Bases......Page 66
Acid Strength......Page 68
Acid–Base Equilibria......Page 72
Structural Effects on Acidity......Page 75
Electronegativity......Page 77
Inductive Effects......Page 78
Resonance Effects......Page 80
Problems......Page 82
Electron Movement......Page 88
Heterolytic Bond Cleavages......Page 89
Heterolytic Bond Formation......Page 90
Homolytic Bond Making and Bond Breaking......Page 92
Resonance Structures......Page 94
Depiction of Mechanism......Page 95
Problems......Page 101
5 Mechanisms of Organic Reactions......Page 105
Activation Energy......Page 106
Activated Complex......Page 107
Reaction Energetics......Page 108
Structure of the Activated Complex......Page 110
Hammond Postulate......Page 115
Reaction Kinetics......Page 118
Determining Activation Energies......Page 123
Isotope Effects......Page 124
Electronic Effects......Page 129
Hammett Equation......Page 130
Problems......Page 137
6 Stereochemical and Conformational Isomerism......Page 143
Stereochemical Structures......Page 144
Chirality......Page 147
Configuration of Chiral Centers......Page 148
Multiple Stereocenters......Page 151
Optical Activity......Page 156
Absolute Configuration......Page 157
Physical Properties of Enantiomers......Page 158
Resolution of Enantiomers......Page 159
Formation of Enantiomers......Page 163
Formation of Diastereomers......Page 165
Stereochemistry to Deduce Mechanism......Page 171
Conformational Analysis......Page 176
Conformational Energies......Page 183
A Values......Page 185
Strain in Ring Systems......Page 186
Stereoelectronic Effects......Page 191
Problems......Page 195
Functional Group Manipulation......Page 202
Carboxylic Acids......Page 204
Esters......Page 207
Amides......Page 209
Acid Chlorides......Page 210
Aldehydes......Page 211
Ketones......Page 213
Imines and Imine Derivatives......Page 216
Alcohols......Page 217
Amines......Page 220
Alkenes......Page 222
Alkanes......Page 226
Bibliography......Page 227
Problems......Page 228
8 Carbon–Carbon Bond Formation between Carbon Nucleophiles and Carbon Electrophiles......Page 235
Synthetic Strategy......Page 236
Nucleophilic Carbon......Page 237
Electrophilic Carbon......Page 239
Reactivity Matching......Page 242
Generation of Nucleophilic Carbon Reagents......Page 243
Matching Nucleophiles with Electrophiles......Page 246
Enolates......Page 247
Enolate Regioisomers......Page 253
Diastereoselection in Aldol Reactions......Page 255
Neutral Carbon Nucleophiles......Page 258
C=C Formation......Page 261
Cyclopropanation Reactions......Page 263
Metal-Catalyzed Carbon–Carbon Bond Formation......Page 265
Pd(0)-Catalyzed Carbon–Carbon Bond Formation......Page 266
Heck Reaction......Page 270
Suzuki Coupling......Page 272
Stille Coupling......Page 273
Olefin Metathesis......Page 275
Bibliography......Page 280
Problems......Page 281
Free-Radical Reactions......Page 291
Free-Radical Polymerization......Page 296
Nonpolymerization Reactions......Page 297
Free-Radical Initiation......Page 299
Free-Radical Cyclization......Page 302
Problems......Page 307
Retrosynthetic Analysis......Page 311
Carbon Skeleton Synthesis......Page 315
Umpolung Synthons......Page 321
Acetylide Nucleophiles......Page 324
Ring Construction......Page 325
Robinson Annulation......Page 329
Diels–Alder Reaction......Page 331
HOMO–LUMO Interactions......Page 332
Stereoelectronic Factors......Page 335
1,3-Dipolar Cycloadditions......Page 338
Bibliography......Page 342
Problems......Page 343
Structure Determination......Page 351
Chromatographic Purification......Page 352
Instrumental Methods......Page 354
Nuclear Magnetic Resonance......Page 355
Chemical Shift......Page 357
Spin–Spin Coupling......Page 363
Descriptions of Spin Systems......Page 369
Second-Order Splitting......Page 373
Structure Identification by (1)H NMR......Page 374
Carbon-13 NMR......Page 379
Infrared Spectroscopy......Page 385
IR Stretching Frequencies......Page 386
Use of IR Spectroscopy for Structure Determination......Page 390
Mass Spectrometry......Page 396
Fragmentation Processes......Page 403
Problems......Page 407
Solutions to Chapter Problems......Page 414
Index......Page 490