Organic Chemistry

by Ege, Seyhan N.

• ISBN13: 9780618318094
• ISBN10: 0618318097
• Edition: 5th
• Format: Hardcover
• Copyright: 2003-07-01
• Publisher: Cengage Learning

Summary

This text\'s clear explanations and descriptions of the mechanisms of chemical reactions teach students how to apply principles in order to predict the outcomes of reactions. The Fifth Edition offers a strengthened focus on biological applications that renders the text more accessible to the majority of organic chemistry students and more consistent with the interdisciplinary nature of scientific research. "One Small Step" features apply familiar concepts to new reagents and reactions, encouraging students to analyze material rather than memorize the outcome to each new reaction. "Visualizing the Reaction" features help students recognize important reactions by demonstrating the complete mechanisms for each type of reaction. The "Problem-Solving Skills" sections offer students a systematic approach to solving organic chemistry problems, allowing them to reason their way to a solution. HM ClassPrep with HM Testing version V.6.1 CD-ROM includes lecture outlines and line art from the textbook in PowerPoint, the Computerized Test Bank and the Word files of the Test Bank in a new, easy-to-use interface with complete cross-platform flexibility, electronic versions of materials from the Instructor\'s Resource Manual, and a transition guide that directs instructors through this new edition.

Table of Contents

Contents Note: Each chapter begins with "A Look Ahead" and concludes with a Summary and Additional Problems. 1. An Introduction to Structure and Bonding in Organic Compounds 1.1. How to Study Organic Chemistry 1.2. Ionic and Covalent Compounds 1.3. Ionic Bonding 1.4. Covalent Bonding 1.5. Multiple Bonds 1.6. Resonance 1.7. Isomers 1.8. Shapes of Covalent Molecules 1.9. The Polarity of Covalent Molecules 1.10. Nonbonding Interactions Between Molecules 2. Covalent Bonding and Chemical Reactivity 2.1. Introduction 2.2. Atomic Orbitals 2.3. Overlap of Atomic Orbitals. The Formation of Molecular Orbitals 2.4. Hybrid Orbitals 2.5. The Orbital Picture for Compounds Containing Trigonal Planar Carbon Atoms 2.6. The Orbital Picture for Linear Molecules 2.7. Covalent Bond Lengths and Their Relation to Orbital Hybridization 2.8. Covalent Bond Strengths 2.9. Effects of Bonding on Chemical Reactivity 2.10. The Structure of Benzene 2.11. Electronic Transitions between Bonding and Antibonding Molecular Orbitals 3. Reactions of Organic Compounds as Acids and Bases 3.1. Bronsted and Lewis Acids and Bases 3.2. Reactions of Organic Compounds as Bases 3.3. The Use of Curved Arrows in Writing Mechanisms 3.4. Carbon, Nitrogen, Oxygen, Sulfur, and Halogen Acids 3.5. Equilibria in Acid-Base Reactions 3.6. The Effects of Structural Changes on Acidity 3.7. Amines 4. Reaction Pathways 4.1. Introduction. Electrophiles and Nucleophiles 4.2. The Reaction of Chloromethane with Hydroxide Ion 4.3. Addition of Hydrogen Bromide to Propene 4.4. Chemical Transformations 5. Alkanes and Cycloalkanes 5.1. Isomerism and Physical Properties 5.2. Methane 5.3. Ethane 5.4. Nuclear Magnetic Resonance as a Tool for the Study of Molecular Structures 5.5. Propane 5.6. Butanes 5.7. A Closer Look at Equivalence of Groups and Atoms in Molecular Structures 5.8. Conformation 5.9. Line Structures for Organic Compounds 5.10. Nomenclature 5.11. Cycloalkanes 5.12. The Chemical Properties of Alkanes 6. Stereochemistry 6.1. Enantiomers 6.2. Chirality 6.3. Stereocenters 6.4. Plane-Polarized Light and Optical Activity 6.5. The Formation of Stereoisomers in Chemical Reactions. Racemic Mixtures 6.6. The Discovery of Molecular Dissymmetry 6.7. Configuration. Representation and Nomenclature of Stereoisomers 6.8. Diastereomers 6.9. Stereoisomerism in Cyclic Compounds 6.10. Stereoisomerism in Alkenes 6.11. The Resolution of a Racemic Mixture 7. Nucleophilic Substitution and Elimination Reactions 7.1. Synthesis. Nucleophilic Substitution Reactions in Chemical Transformations 7.2. The Art of Solving Problems 7.3. Substitution Reactions 7.4. Nucleophilicity 7.5. Solvent Effects 7.6. Leaving Groups 7.7. Elimination Reactions 8. Alkenes 8.1. Structure and Isomerism of Alkenes 8.2. Nomenclature of Alkenes 8.3. Relative Stabilities of Alkenes 8.4. Electrophilic Addition of Acids to Alkenes 8.5. Rearrangements of Carbocations 8.6. Addition of Diborane to Alkenes 8.7. Addition of Hydrogen to Alkenes. Catalytic Hydrogenation Reactions 8.8. Addition of Bromine to Alkenes 8.9. Reactions of Alkenes with Oxygen Electrophiles 9. Alkynes 9.1. Structure and Isomerism of Alkynes 9.2. Nomenclature of Alkynes 9.3. Alkynes as Acids 9.4. Electrophilic Addition Reactions of Alkynes 9.5. Reduction of Alkynes 9.6. Planning Syntheses 10. The Chemistry of Aromatic Compounds. Electrophilic Aromatic Substitution 10.1. Aromaticity 10.2. Kekuleacute; Structures and Nomenclature for Aromatic Compounds 10.3. C60. Buckminsterfullerene 10.4. Electrophilic Aromatic Substitution Reactions 10.5. Aromatic Substitution Reactions with Carbocations as Electrophiles 10.6. Polychlorinated Aromatic Hydrocarbons 11. Nuclear Magnetic Resonance Spectroscopy 11.1. The Experimental Observations 11.2. The Electromagnetic Spectrum and Absorption Spectroscopy 11.3. The Origin of Nuclear Magnetic Resonance Spectra 11.4. Chemical Shift 11.5. Spin-Spin Coupling 11.6. Medical Applications of Nuclear Magnetic Resonance 12. Ultraviolet-Visible and Infrared Spectroscopy. Mass Spectrometry 12.1. Ultraviolet Spectroscopy 12.2. Infrared Spectroscopy 12.3. Mass Spectrometry 13. Alcohols, Diols, and Ethers 13.1. Structure and Nomenclature of Alcohols and Ethers 13.2. Preparation of Alcohols 13.3. Converting Alcohols to Alkyl Halides 13.4. Reactions of Alkoxide Anions 13.5. Ring-Opening Reactions of Oxiranes 13.6. The Biologic Reactivity of Oxiranes. Arene Oxides 13.7. Oxidation Reactions of Alcohols 14. Aldehydes and Ketones. Addition Reactions at Electrophilic Carbon Atoms 14.1. Introduction to Carbonyl Compounds 14.2. Nomenclature of Carbonyl Compounds 14.3. Preparation of Aldehydes and Ketones 14.4. Addition of the Nucleophile Hydride Ion. Reduction of Aldehydes and Ketones to Alcohols 14.5. Addition of the Nucleophile Cyanide Ion to the Carbonyl Group. Cyanohydrin Formation 14.6. Addition of Other Carbon Nucleophiles to the Carbonyl Group 14.7. Reactions of Aldehydes and Ketones with Alcohols. The Formation of Acetals and Ketals 14.8. Biologic Hemiacetals and Acetals. Carbohydrates 14.9. Addition Reactions of Nucleophiles Related to Ammonia 14.10. Reduction of Carbonyl Groups to Methylene Groups 15. Carboxylic Acids and Their Derivatives. Acyl-Transfer Reactions 15.1. Properties of the Functional Groups in Carboxylic Acids and Their Derivatives 15.2. Nomenclature of Carboxylic Acids and Their Derivatives 15.3. Preparation of Carboxylic Acids 15.4. Converting Carboxylic Acids to Acid Chlorides and Acid Anhydrides 15.5. Hydrolysis Reactions. Acylation of Water 15.6. Esterification. Acylation of Alcohols 15.7. Formation of Amides. Acylation of Ammonia and Amines 15.8. Acyl-Transfer Reactions in Biologic Systems 15.9. Lipids, Fats, Oils, and Waxes 15.10. Surface-Active Compounds. Soaps 16. Structural Effects in Acidity and Basicity Revisited. Enolization 16.1. Resonance and Inductive Effects in Acidity and Basicity. A Review in the Context of Aromatic Compounds 16.2. Acidity and Basicity in Polyfunctional Compounds 16.3. Carbon Acids 16.4. Enolization 16.5. Enols and Enolates as Intermediates in the Exchange of Protons in Carbon Acids 16.6. The Biologic Importance of Enolization Reactions 17. Enols and Enolate Anions as Nucleophiles. Alkylation and Condensation Reactions 17.1. Reactions of Enols and Enolates with Halogens as Electrophiles 17.2. Reactions of Enolate Anions with Alkyl Halides as Electrophiles 17.3. Reaction of Stabilized Enolate Anions with Alkyl Halides as Electrophiles 17.4. Condensation Reactions. Reactions of Enolate Anions with Carbonyl Compounds 17.5. Reactions of Nucleophiles with alpha,beta-Unsaturated Carbonyl Compounds as Electrophiles 17.6. Biologic Pathways. A Review of Reaction Mechanisms 18. Polyenes 18.1. Isolated, Skipped, Conjugated, and Cumulative Multiple Bonds 18.2. 1,3-Butadiene 18.3. 1,2- and 1,4-Addition of Electrophiles to Conjugated Systems 18.4. The Diels-Alder Reaction 18.5. Biologically Interesting Alkenes and polyenes 19. Free Radicals 19.1. Free-Radical Reactions of Alkanes 19.2. Free-Radical Substitution of Allylic Hydrogen Atoms 19.3. Free-Radical Halogenation Reactions at the Benzylic Position 19.4. The Triphenylmethyl Radical, a Stable Free radical 19.5. Free-Radical Addition Reactions of Alkenes 19.6. Free-Radical Oxidations with Molecular Oxygen 19.7. Oxidation of Phenols 20. The Chemistry of Ami