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Organic Chemistry: Concepts and Applications

Organic Chemistry: Concepts and Applications

Authors
Publisher John Wiley and Sons Ltd
Year 25/11/2019
Pages 624
Version paperback
Readership level Professional and scholarly
ISBN 9781119504580
Categories Chemistry
$152.67 (with VAT)
571.00 PLN / €125.67 / £111.65
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Book description

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.

Organic Chemistry: Concepts and Applications

Table of contents

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 ?Amino Acids 547


20.11 Reactions of ?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

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