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<p>Preface xvii</p> <p>About the Campanion Website xxiii</p> <p><b>1 Bonding and Structure of Organic Compounds 1</b></p> <p>1.1 Introduction 1</p> <p>1.2 Electronic Structure of Atoms 4</p> <p>1.3 Chemical Bonds 9</p> <p>1.4 Chemical Formulas 18</p> <p>1.5 The Covalent Bond 20</p> <p>1.6 Bonding– Concept Summary and Applications 28</p> <p>1.7 Intermolecular Attractions 29</p> <p>1.8 Intermolecular Molecular Interactions – Concept Summary and Applications 31</p> <p>End of Chapter Problems 34</p> <p><b>2 Carbon Functional Groups and Organic Nomenclature 39</b></p> <p>2.1 Introduction 39</p> <p>2.2 Functional Groups 39</p> <p>2.3 Saturated Hydrocarbons 41</p> <p>2.4 Organic Nomenclature 45</p> <p>2.5 Structure and Nomenclature of Alkanes 45</p> <p>2.6 Unsaturated Hydrocarbons 54</p> <p>2.7 Structure and Nomenclature of Alkenes 56</p> <p>2.8 Structure and Nomenclature of Substituted Benzenes 58</p> <p>2.9 Structure and Nomenclature of Alkynes 60</p> <p>End of Chapter Problems 61</p> <p><b>3 Heteroatomic Functional Groups and Organic Nomenclature 63</b></p> <p>3.1 Properties and Structure of Alcohols, Phenols, and Thiols 63</p> <p>3.2 Nomenclature of Alcohols 66</p> <p>3.3 Nomenclature of Thiols 68</p> <p>3.4 Structure and Properties of Aldehydes and Ketones 69</p> <p>3.5 Nomenclature of Aldehydes 70</p> <p>3.6 Nomenclature of Ketones 71</p> <p>3.7 Structure and Properties of Carboxylic Acids 73</p> <p>3.8 Nomenclature of Carboxylic Acids 75</p> <p>3.9 Structure and Properties of Esters 78</p> <p>3.10 Structure and Properties of Acid Chlorides 82</p> <p>3.11 Structure and Properties of Anhydrides 83</p> <p>3.12 Structure and Properties of Amines 84</p> <p>3.13 Structure and Properties of Amides 88</p> <p>3.14 Structure and Properties of Nitriles 90</p> <p>3.15 Structure and Properties of Ethers 91</p> <p>3.16 An Overview of Spectroscopy and the Relationship to Functional Groups 94</p> <p><b>4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities 103</b></p> <p>4.1 Introduction 103</p> <p>4.2 Structural Isomers 103</p> <p>4.3 Conformational Isomers of Alkanes 104</p> <p>4.4 Conformational Isomers of Cycloalkanes 108</p> <p>4.5 Geometric Isomers 114</p> <p>4.6 Stability of Alkanes 119</p> <p>4.7 Stability of Alkenes 121</p> <p>4.8 Stability of Alkynes 122</p> <p>End of Chapter Problems 123</p> <p><b>5 Stereochemistry 125</b></p> <p>5.1 Introduction 125</p> <p>5.2 Chiral Stereoisomers 126</p> <p>5.3 Significance of Chirality 129</p> <p>5.4 Nomenclature of the Absolute Configuration of Chiral Molecules 131</p> <p>5.5 Properties of Stereogenic Compounds 133</p> <p>5.6 Compounds with More Than One Stereogenic Carbon 134</p> <p>5.7 Resolution of Enantiomers 137</p> <p>End of Chapter Problems 140</p> <p><b>6 An Overview of the Reactions of Organic Chemistry 145</b></p> <p>6.1 Introduction 145</p> <p>6.2 Acid–Base Reactions 145</p> <p>6.3 Addition Reactions 149</p> <p>6.4 Reduction Reactions 150</p> <p>6.5 Oxidation Reactions 153</p> <p>6.6 Elimination Reactions 154</p> <p>6.7 Substitution Reactions 156</p> <p>6.8 Pericyclic Reactions 158</p> <p>6.9 Catalytic Coupling Reactions 158</p> <p>End of Chapter Problems 159</p> <p><b>7 Acid–Base Reactions in Organic Chemistry 165</b></p> <p>7.1 Introduction 165</p> <p>7.2 Lewis Acids and Bases 165</p> <p>7.3 Relative Strengths of Acids and Conjugate Bases 166</p> <p>7.4 Predicting the Relative Strengths of Acids and Bases 169</p> <p>7.5 Factors That Affect Acid and Base Strengths 170</p> <p>7.6 Applications of Acid–Bases Reactions in Organic Chemistry 176</p> <p>End of Chapter Problems 180</p> <p><b>8 Addition Reactions Involving Alkenes and Alkynes 183</b></p> <p>8.1 Introduction 183</p> <p>8.2 The Mechanism for Addition Reactions Involving Alkenes 183</p> <p>8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes) 185</p> <p>8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes) 196</p> <p>8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation) 198</p> <p>8.6 Addition of Water to Alkenes (Hydration of Alkenes) 199</p> <p>8.7 Addition of Carbenes to Alkenes 207</p> <p>8.8 The Mechanism for Addition Reactions Involving Alkynes 209</p> <p>8.9 Applications of Addition Reactions to Synthesis 213</p> <p>End of Chapter Problems 214</p> <p><b>9 Addition Reactions Involving Carbonyls and Nitriles 223</b></p> <p>9.1 Introduction 223</p> <p>9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds 223</p> <p>9.3 Addition of HCN to Carbonyl Compounds 224</p> <p>9.4 Addition of Water to Carbonyl Compounds 226</p> <p>9.5 Addition of Alcohols to Carbonyl Compounds 230</p> <p>9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction) 235</p> <p>9.7 Addition of Enolates to Carbonyl Compounds 237</p> <p>9.8 Addition of Amines to Carbonyl Compounds 240</p> <p>9.9 Mechanism for Addition Reactions Involving Imines 241</p> <p>9.10 Mechanism for Addition Reactions Involving Nitriles 242</p> <p>9.11 Applications of Addition Reactions to Synthesis 244</p> <p>End of Chapter Problems 246</p> <p><b>10 Reduction Reactions in Organic Chemistry 251</b></p> <p>10.1 Introduction 251</p> <p>10.2 Reducing Agents of Organic Chemistry 252</p> <p>10.3 Reduction of C=O and C=S Containing Compounds 255</p> <p>10.4 Reduction of Imines 263</p> <p>10.5 Reduction of Oxiranes 266</p> <p>10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes 268</p> <p>End of Chapter Problems 272</p> <p><b>11 Oxidation Reactions in Organic Chemistry 275</b></p> <p>11.1 Introduction 275</p> <p>11.2 Oxidation 275</p> <p>11.3 Oxidation of Alcohols and Aldehydes 279</p> <p>11.4 Oxidation of Alkenes Without Bond Cleavage 288</p> <p>11.5 Oxidation of Alkenes with Bond Cleavage 293</p> <p>11.6 Applications of Oxidation Reactions of Alkenes 296</p> <p>11.7 Oxidation of Alkynes 299</p> <p>11.8 Oxidation of Aromatic Compounds 300</p> <p>11.9 Autooxidation of Ethers and Alkenes 301</p> <p>11.10 Applications of Oxidation Reactions to Synthesis 302</p> <p>End of Chapter Problems 304</p> <p><b>12 Elimination Reactions of Organic Chemistry 309</b></p> <p>12.1 Introduction 309</p> <p>12.2 Mechanisms of Elimination Reactions 309</p> <p>12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation) 316</p> <p>12.4 Elimination of Water (Dehydration) 319</p> <p>12.5 Applications of Elimination Reactions to Synthesis 323</p> <p>End of Chapter Problems 326</p> <p><b>13 Spectroscopy Revisited, A More Detailed Examination 331</b></p> <p>13.1 Introduction 331</p> <p>13.2 The Electromagnetic Spectrum 331</p> <p>13.3 UV‐Vis Spectroscopy and Conjugated Systems 334</p> <p>13.4 Infrared Spectroscopy 337</p> <p>13.5 Mass Spectrometry 343</p> <p>13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy 346</p> <p>End of Chapter Problems 367</p> <p><b>14 Free Radical Substitution Reactions Involving Alkanes 369</b></p> <p>14.1 Introduction 369</p> <p>14.2 Types of Alkanes and Alkyl Halides 371</p> <p>14.3 Chlorination of Alkanes 376</p> <p>14.4 Bromination of Alkanes 380</p> <p>14.5 Applications of Free Radical Substitution Reactions 386</p> <p>14.6 Free Radical Inhibitors 388</p> <p>14.7 Environmental Impact of Organohalides and Free Radicals 389</p> <p>End of Chapter Problems 391</p> <p><b>15 Nucleophilic Substitution Reactions at sp³ Carbons 393</b></p> <p>15.1 Introduction 393</p> <p>15.2 The Electrophile 393</p> <p>15.3 The Leaving Group 394</p> <p>15.4 The Nucleophile 397</p> <p>15.5 Nucleophilic Substitution Reactions 397</p> <p>15.6 Bimolecular Substitution Reaction Mechanism (S_N2 Mechanism) 400</p> <p>15.7 Unimolecular Substitution Reaction Mechanism (S_N1 Mechanism) 406</p> <p>15.8 Applications of Nucleophilic Substitution Reactions – Synthesis 414</p> <p>End of Chapter Problems 420</p> <p><b>16 Nucleophilic Substitution Reactions at Acyl Carbons 425</b></p> <p>16.1 Introduction 425</p> <p>16.2 Mechanism for Acyl Substitution 426</p> <p>16.3 Substitution Reactions Involving Acid Chlorides 428</p> <p>16.4 Substitution Reactions Involving Anhydrides 436</p> <p>16.5 Substitution Reactions Involving Esters 442</p> <p>16.6 Substitution Reactions Involving Amides 451</p> <p>16.7 Substitution Reactions Involving Carboxylic Acids 454</p> <p>16.8 Substitution Reactions Involving Oxalyl Chloride 458</p> <p>16.9 Substitution Reactions Involving Sulfur Containing Compounds 458</p> <p>16.10 Applications of Acyl Substitution Reactions 460</p> <p>End of Chapter Problems 462</p> <p><b>17 Aromaticity and Aromatic Substitution Reactions 467</b></p> <p>17.1 Introduction 467</p> <p>17.2 Structure and Properties of Benzene 468</p> <p>17.3 Nomenclature of Substituted Benzene 470</p> <p>17.4 Stability of Benzene 473</p> <p>17.5 Characteristics of Aromatic Compounds 475</p> <p>17.6 Electrophilic Aromatic Substitution Reactions of Benzene 478</p> <p>17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene 484</p> <p>17.8 Applications– Synthesis of Substituted Benzene Compounds 491</p> <p>17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds 494</p> <p>17.10 Electrophilic Substitution Reactions of Pyrrole 496</p> <p>17.11 Electrophilic Substitution Reactions of Pyridine 497</p> <p>17.12 Nucleophilic Aromatic Substitution 499</p> <p>End of Chapter Problems 504</p> <p><b>18 Conjugated Systems and Pericyclic Reactions 511</b></p> <p>18.1 Conjugated Systems 511</p> <p>18.2 Pericyclic Reactions 513</p> <p>End of Chapter Problems 522</p> <p><b>19 Catalytic Carbon–Carbon Coupling Reactions 525</b></p> <p>19.1 Introduction 525</p> <p>19.2 Reactions of Transition Metal Complexes 525</p> <p>19.3 Palladium‐ Catalyzed Coupling Reactions 528</p> <p>End of Chapter Problems 535</p> <p><b>20 Synthetic Polymers and Biopolymers 537</b></p> <p>20.1 Introduction 537</p> <p>20.2 Cationic Polymerization of Alkenes 537</p> <p>20.3 Anionic Polymerization of Alkenes 540</p> <p>20.4 Free Radical Polymerization of Alkenes 540</p> <p>20.5 Copolymerization of Alkenes 542</p> <p>20.6 Properties of Polymers 543</p> <p>20.7 Biopolymers 544</p> <p>20.8 Amino Acids, Monomers of Peptides and Proteins 545</p> <p>20.9 Acid–Base Properties of Amino Acids 547</p> <p>20.10 Synthesis of α‐Amino Acids 547</p> <p>20.11 Reactions of α‐Amino Acids 550</p> <p>20.12 Primary Structure and Properties of Peptides 556</p> <p>20.13 Secondary Structure of Proteins 558</p> <p>20.14 Monosaccharides, Monomers of Carbohydrates 559</p> <p>20.15 Reactions of Monosaccharides 560</p> <p>20.16 Disaccharides and Polysaccharides 566</p> <p>20.17 N‐Glycosides and Amino Sugars 567</p> <p>20.18 Lipids 568</p> <p>20.19 Properties and Reactions of Waxes 569</p> <p>20.20 Properties and Reactions of Triglycerides 569</p> <p>20.21 Properties and Reactions of Phospholipids 572</p> <p>20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes 572</p> <p>End of Chapter Problems 573</p> <p>Index 577</p>

<p><b>Allan D. Headley, PhD,</b> is a Professor of Chemistry at Texas A&M University, Commerce, where he teaches various undergraduate and graduate courses in organic chemistry.

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