Organic Chemistry

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.

Autorentext

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.

Inhalt
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 AcidBase 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 AcidBase 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 AcidBases 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 (Halogena...