John Wiley & Sons Organic Chemistry Cover This textbook provides an in-depth study of organic compounds and is intended for a two-semester sop.. Product #: 978-1-119-50458-0 Regular price: $120.56 $120.56 In Stock

Organic Chemistry

Concepts and Applications

Headley, Allan D.

Cover

1. Edition January 2020
624 Pages, Softcover
Wiley & Sons Ltd

ISBN: 978-1-119-50458-0
John Wiley & Sons

Short Description

This textbook provides an in-depth study of organic compounds and is intended for a two-semester sophomore organic chemistry course, primarily for students in science or pre-professional programs. Whereas most textbooks categorize content by functional groups and encourage a memorization approach, this book divides information into reaction types. This better bridges the gap between general and organic chemistry and helps students better understand the material.

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Provides an in-depth study of organic compounds that bridges the gap between general and organic chemistry

Organic Chemistry: Concepts and Applications presents a comprehensive review of organic compounds that is appropriate for a two-semester sophomore organic chemistry course. The text covers the fundamental concepts needed to understand organic chemistry and clearly shows how to apply the concepts of organic chemistry to problem-solving. In addition, the book highlights the relevance of organic chemistry to the environment, industry, and biological and medical sciences. The author includes multiple-choice questions similar to aptitude exams for professional schools, including the Medical College Admissions Test (MCAT) and Dental Aptitude Test (DAT) to help in the preparation for these important exams.

Rather than categorize content information by functional groups, which often stresses memorization, this textbook instead divides the information into reaction types. This approach bridges the gap between general and organic chemistry and helps students develop a better understanding of the material. A manual of possible solutions for chapter problems for instructors and students is available in the supplementary websites. This important book:

* Provides an in-depth study of organic compounds with division by reaction types that bridges the gap between general and organic chemistry

* Covers the concepts needed to understand organic chemistry and teaches how to apply them for problem-solving

* Puts a focus on the relevance of organic chemistry to the environment, industry, and biological and medical sciences

* Includes multiple choice questions similar to aptitude exams for professional schools

Written for students of organic chemistry, Organic Chemistry: Concepts and Applications is the comprehensive text that presents the material in clear terms and shows how to apply the concepts to problem solving.

Preface xvii

About the Campanion Website xxiii

1 Bonding and Structure of Organic Compounds 1

1.1 Introduction 1

1.2 Electronic Structure of Atoms 4

1.3 Chemical Bonds 9

1.4 Chemical Formulas 18

1.5 The Covalent Bond 20

1.6 Bonding- Concept Summary and Applications 28

1.7 Intermolecular Attractions 29

1.8 Intermolecular Molecular Interactions - Concept Summary and Applications 31

End of Chapter Problems 34

2 Carbon Functional Groups and Organic Nomenclature 39

2.1 Introduction 39

2.2 Functional Groups 39

2.3 Saturated Hydrocarbons 41

2.4 Organic Nomenclature 45

2.5 Structure and Nomenclature of Alkanes 45

2.6 Unsaturated Hydrocarbons 54

2.7 Structure and Nomenclature of Alkenes 56

2.8 Structure and Nomenclature of Substituted Benzenes 58

2.9 Structure and Nomenclature of Alkynes 60

End of Chapter Problems 61

3 Heteroatomic Functional Groups and Organic Nomenclature 63

3.1 Properties and Structure of Alcohols, Phenols, and Thiols 63

3.2 Nomenclature of Alcohols 66

3.3 Nomenclature of Thiols 68

3.4 Structure and Properties of Aldehydes and Ketones 69

3.5 Nomenclature of Aldehydes 70

3.6 Nomenclature of Ketones 71

3.7 Structure and Properties of Carboxylic Acids 73

3.8 Nomenclature of Carboxylic Acids 75

3.9 Structure and Properties of Esters 78

3.10 Structure and Properties of Acid Chlorides 82

3.11 Structure and Properties of Anhydrides 83

3.12 Structure and Properties of Amines 84

3.13 Structure and Properties of Amides 88

3.14 Structure and Properties of Nitriles 90

3.15 Structure and Properties of Ethers 91

3.16 An Overview of Spectroscopy and the Relationship to Functional Groups 94

4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities 103

4.1 Introduction 103

4.2 Structural Isomers 103

4.3 Conformational Isomers of Alkanes 104

4.4 Conformational Isomers of Cycloalkanes 108

4.5 Geometric Isomers 114

4.6 Stability of Alkanes 119

4.7 Stability of Alkenes 121

4.8 Stability of Alkynes 122

End of Chapter Problems 123

5 Stereochemistry 125

5.1 Introduction 125

5.2 Chiral Stereoisomers 126

5.3 Significance of Chirality 129

5.4 Nomenclature of the Absolute Configuration of Chiral Molecules 131

5.5 Properties of Stereogenic Compounds 133

5.6 Compounds with More Than One Stereogenic Carbon 134

5.7 Resolution of Enantiomers 137

End of Chapter Problems 140

6 An Overview of the Reactions of Organic Chemistry 145

6.1 Introduction 145

6.2 Acid-Base Reactions 145

6.3 Addition Reactions 149

6.4 Reduction Reactions 150

6.5 Oxidation Reactions 153

6.6 Elimination Reactions 154

6.7 Substitution Reactions 156

6.8 Pericyclic Reactions 158

6.9 Catalytic Coupling Reactions 158

End of Chapter Problems 159

7 Acid-Base Reactions in Organic Chemistry 165

7.1 Introduction 165

7.2 Lewis Acids and Bases 165

7.3 Relative Strengths of Acids and Conjugate Bases 166

7.4 Predicting the Relative Strengths of Acids and Bases 169

7.5 Factors That Affect Acid and Base Strengths 170

7.6 Applications of Acid-Bases Reactions in Organic Chemistry 176

End of Chapter Problems 180

8 Addition Reactions Involving Alkenes and Alkynes 183

8.1 Introduction 183

8.2 The Mechanism for Addition Reactions Involving Alkenes 183

8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes) 185

8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes) 196

8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation) 198

8.6 Addition of Water to Alkenes (Hydration of Alkenes) 199

8.7 Addition of Carbenes to Alkenes 207

8.8 The Mechanism for Addition Reactions Involving Alkynes 209

8.9 Applications of Addition Reactions to Synthesis 213

End of Chapter Problems 214

9 Addition Reactions Involving Carbonyls and Nitriles 223

9.1 Introduction 223

9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds 223

9.3 Addition of HCN to Carbonyl Compounds 224

9.4 Addition of Water to Carbonyl Compounds 226

9.5 Addition of Alcohols to Carbonyl Compounds 230

9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction) 235

9.7 Addition of Enolates to Carbonyl Compounds 237

9.8 Addition of Amines to Carbonyl Compounds 240

9.9 Mechanism for Addition Reactions Involving Imines 241

9.10 Mechanism for Addition Reactions Involving Nitriles 242

9.11 Applications of Addition Reactions to Synthesis 244

End of Chapter Problems 246

10 Reduction Reactions in Organic Chemistry 251

10.1 Introduction 251

10.2 Reducing Agents of Organic Chemistry 252

10.3 Reduction of C=O and C=S Containing Compounds 255

10.4 Reduction of Imines 263

10.5 Reduction of Oxiranes 266

10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes 268

End of Chapter Problems 272

11 Oxidation Reactions in Organic Chemistry 275

11.1 Introduction 275

11.2 Oxidation 275

11.3 Oxidation of Alcohols and Aldehydes 279

11.4 Oxidation of Alkenes Without Bond Cleavage 288

11.5 Oxidation of Alkenes with Bond Cleavage 293

11.6 Applications of Oxidation Reactions of Alkenes 296

11.7 Oxidation of Alkynes 299

11.8 Oxidation of Aromatic Compounds 300

11.9 Autooxidation of Ethers and Alkenes 301

11.10 Applications of Oxidation Reactions to Synthesis 302

End of Chapter Problems 304

12 Elimination Reactions of Organic Chemistry 309

12.1 Introduction 309

12.2 Mechanisms of Elimination Reactions 309

12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation) 316

12.4 Elimination of Water (Dehydration) 319

12.5 Applications of Elimination Reactions to Synthesis 323

End of Chapter Problems 326

13 Spectroscopy Revisited, A More Detailed Examination 331

13.1 Introduction 331

13.2 The Electromagnetic Spectrum 331

13.3 UV-Vis Spectroscopy and Conjugated Systems 334

13.4 Infrared Spectroscopy 337

13.5 Mass Spectrometry 343

13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy 346

End of Chapter Problems 367

14 Free Radical Substitution Reactions Involving Alkanes 369

14.1 Introduction 369

14.2 Types of Alkanes and Alkyl Halides 371

14.3 Chlorination of Alkanes 376

14.4 Bromination of Alkanes 380

14.5 Applications of Free Radical Substitution Reactions 386

14.6 Free Radical Inhibitors 388

14.7 Environmental Impact of Organohalides and Free Radicals 389

End of Chapter Problems 391

15 Nucleophilic Substitution Reactions at sp³ Carbons 393

15.1 Introduction 393

15.2 The Electrophile 393

15.3 The Leaving Group 394

15.4 The Nucleophile 397

15.5 Nucleophilic Substitution Reactions 397

15.6 Bimolecular Substitution Reaction Mechanism (SN2 Mechanism) 400

15.7 Unimolecular Substitution Reaction Mechanism (SN1 Mechanism) 406

15.8 Applications of Nucleophilic Substitution Reactions - Synthesis 414

End of Chapter Problems 420

16 Nucleophilic Substitution Reactions at Acyl Carbons 425

16.1 Introduction 425

16.2 Mechanism for Acyl Substitution 426

16.3 Substitution Reactions Involving Acid Chlorides 428

16.4 Substitution Reactions Involving Anhydrides 436

16.5 Substitution Reactions Involving Esters 442

16.6 Substitution Reactions Involving Amides 451

16.7 Substitution Reactions Involving Carboxylic Acids 454

16.8 Substitution Reactions Involving Oxalyl Chloride 458

16.9 Substitution Reactions Involving Sulfur Containing Compounds 458

16.10 Applications of Acyl Substitution Reactions 460

End of Chapter Problems 462

17 Aromaticity and Aromatic Substitution Reactions 467

17.1 Introduction 467

17.2 Structure and Properties of Benzene 468

17.3 Nomenclature of Substituted Benzene 470

17.4 Stability of Benzene 473

17.5 Characteristics of Aromatic Compounds 475

17.6 Electrophilic Aromatic Substitution Reactions of Benzene 478

17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene 484

17.8 Applications- Synthesis of Substituted Benzene Compounds 491

17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds 494

17.10 Electrophilic Substitution Reactions of Pyrrole 496

17.11 Electrophilic Substitution Reactions of Pyridine 497

17.12 Nucleophilic Aromatic Substitution 499

End of Chapter Problems 504

18 Conjugated Systems and Pericyclic Reactions 511

18.1 Conjugated Systems 511

18.2 Pericyclic Reactions 513

End of Chapter Problems 522

19 Catalytic Carbon-Carbon Coupling Reactions 525

19.1 Introduction 525

19.2 Reactions of Transition Metal Complexes 525

19.3 Palladium- Catalyzed Coupling Reactions 528

End of Chapter Problems 535

20 Synthetic Polymers and Biopolymers 537

20.1 Introduction 537

20.2 Cationic Polymerization of Alkenes 537

20.3 Anionic Polymerization of Alkenes 540

20.4 Free Radical Polymerization of Alkenes 540

20.5 Copolymerization of Alkenes 542

20.6 Properties of Polymers 543

20.7 Biopolymers 544

20.8 Amino Acids, Monomers of Peptides and Proteins 545

20.9 Acid-Base Properties of Amino Acids 547

20.10 Synthesis of alpha-Amino Acids 547

20.11 Reactions of alpha-Amino Acids 550

20.12 Primary Structure and Properties of Peptides 556

20.13 Secondary Structure of Proteins 558

20.14 Monosaccharides, Monomers of Carbohydrates 559

20.15 Reactions of Monosaccharides 560

20.16 Disaccharides and Polysaccharides 566

20.17 N-Glycosides and Amino Sugars 567

20.18 Lipids 568

20.19 Properties and Reactions of Waxes 569

20.20 Properties and Reactions of Triglycerides 569

20.21 Properties and Reactions of Phospholipids 572

20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes 572

End of Chapter Problems 573

Index 577
Allan D. Headley, PhD, is a Professor of Chemistry at Texas A&M University, Commerce, where he teaches various undergraduate and graduate courses in organic chemistry.