Synopses & Reviews
Written for the short course?where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Sixth Edition, continues to provide an effective, clear, and readable introduction to the beauty and logic of organic chemistry. McMurry presents only those subjects needed for a brief course while maintaining the important pedagogical tools commonly found in larger books. With clear explanations, thought-provoking examples, and an innovative vertical format for explaining reaction mechanisms, FUNDAMENTALS takes a modern approach: primary organization is by functional group, beginning with the simple (alkanes) and progressing to the more complex. Within the primary organization, there is also an emphasis on explaining the fundamental mechanistic similarities of reactions. Through this approach, memorization is minimized and understanding is maximized. The sixth edition brings in new content that applies organic chemistry to students, for example all of the chapter openers have been changed and incorporate a model and photograph of an application of organic chemistry such as Taxol from the pacific yew tree. The book introduces a running application in the Interlude boxes and in the problems relating agricultural chemicals intended to unify the subject further for students. All of the problems have been reorganized by topic to make easier to assign and review. New problem categories have been added. The new problem categories are "In the Field with Agrochemicals" and "In the Medicine Cabinet" to reinforce the focus on applications.
Synopsis
Written for the short course-where content must be thorough, but to-the-point, FUNDAMENTALS OF ORGANIC CHEMISTRY, Fifth Edition provides an effective, clear, and readable introduction to the beauty and logic of organic chemistry. McMurry presents only those subjects needed for a brief course while maintaining the important pedagogical tools commonly found in larger books. With clear explanations, thought-provoking examples, and an innovative vertical format for explaining reaction mechanisms, FUNDAMENTALS takes a modern approach: primary organization is by functional group, beginning with the simple (alkanes) and progressing to the more complex. Within the primary organization, there is also an emphasis on explaining the fundamental mechanistic similarities of reactions. Through this approach, memorization is minimized and understanding is maximized. This new edition represents a major revision. The text has been revised at the sentence level to further improve clarity and readability; many new examples and topics of biological relevance have been added; and many new features have been introduced.
About the Author
John E. McMurry received his B.A. from Harvard University and his Ph.D. at Columbia University. He is a Fellow of the American Association for the Advancement of Science, and an Alfred P. Sloan Research Foundation Fellow. He has received several awards, which include the National Institutes of Health Career Development Award, the Alexander von Humboldt Senior Scientist Award, and the Max Planck Research Award. In addition to ORGANIC CHEMISTRY, he is also the author or coauthor of ORGANIC CHEMISTRY: A BIOLOGICAL APPROACH, FUNDAMENTALS OF ORGANIC CHEMISTRY, THE ORGANIC CHEMISTRY OF BIOLOGICAL PATHWAYS.A new co-author, Eric Simanek of Texas A&M University, has expertise in both biochemistry and organic chemistry. Dr. Simanek received his B.S. Chemistry from the University of Illinois at Urbana-Champaign, and his M.S. and Ph.D. in chemistry from Harvard University, where his advisor was George M. Whitesides. He was most recently featured in the Journal of Chemical Education's October edition with an article on dendrimers. Dendrimers are polymers named for trees that show snowflake-like perfection. In 2000, Eric's group introduced dendrimers based on melamine. These architectures are unique in a variety of ways and subsequent reports from his group have addressed synthetic aspects of these architectures. He is also involved in improving science education the state of Texas.
Table of Contents
1. STRUCTURE AND BONDING; ACIDS AND BASES. Atomic Structure. Electron Configuration of Atoms. Development of Chemical Bonding Theory. The Nature of Chemical Bonds. Forming Covalent Bonds: Valence Bond Theory. Hybridization: sp3 Orbitals and the Structure of Methane. Hybridization: sp3 Orbitals and the Structure of Ethane. Hybridization: sp2 Orbitals and the Structure of Ethylene. Hybridization: sp Orbitals and the Structure of Acetylene. Polar Covalent Bonds: Electronegativity. Acids and Bases: The Brønsted-Lowry Definition. Acids and Bases: The Lewis Definition. Interlude--Chemicals, Toxicity, and Risk. Summary and Key Words. Visualizing Chemistry. Additional Problems. 2. THE NATURE OF ORGANIC COMPOUNDS: ALKANES. Functional Groups. Alkanes and Alkyl Groups: Isomers. Naming Branched-Chain Alkanes. Properties of Alkanes. Conformations of Ethane. Drawing Chemical Structures. Cycloalkanes. Cis-Trans Isomerism in Cycloalkanes. Conformations of Some Common Cycloalkanes. Axial and Equatorial Bonds in Cyclohexane. Conformational Mobility of Cyclohexane. Interlude - Gasoline. Summary and Key Words. Visualizing CHEMISTRY. ADDITIONAL PROBLEMS. 3. THE NATURE OF ORGANIC REACTIONS: ALKENES. Naming Alkenes. Electronic Structure of Alkenes. Cis-Trans Isomers of Alkenes. Sequence Rules: The E,Z Designation. Kinds of Organic Reactions. How Reactions Occur: Mechanisms. The Mechanism of an Organic Reaction: Addition of HCl to Ethylene. Describing a Reaction: Reaction Energy Diagrams and Transition States. Describing a Reaction: Intermediates. Interlude - Terpenes: Naturally Occurring Alkenes. Summary and Key Words. Visualizing Chemistry. Additional Problems. 4. REACTIONS OF ALKENES AND ALKYNES. Addition of HX to Alkenes: Hydrohalogenation. Orientation of Alkene Addition Reactions: Markovnikov's Rule. Carbocation Structure and Stability. Addition of H2O to Alkenes: Hydration. Addition of X2 to Alkenes: Halogenation. Addition of H2 to Alkenes: Hydrogenation. Oxidation of Alkenes: Hydroxylation and Cleavage. Biological Addition Reactions of Alkenes. Addition of Radicals to Alkenes: Polymers. Conjugated Dienes. Stability of Allylic Carbocations: Resonance. Drawing and Interpreting Resonance Forms. Alkynes and Their Reactions. Interlude - Natural Rubber. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 5. AROMATIC COMPOUNDS. Structure of Benzene: The Kekule Proposal. Structure of Benzene: The Resonance Proposal. Naming Aromatic Compounds. Electrophilic Aromatic Substitution Reactions: Bromination. Other Electrophilic Aromatic Substitution Reactions. The Friedel-Crafts Alkylation and Acylation Reactions. Substituent Effects in Electrophilic Aromatic Substitution. An Explanation of Substituent Effects. Oxidation and Reduction of Aromatic Compounds. Polycyclic Aromatic Hydrocarbons. Organic Synthesis. Interlude - Aspirin, NSAID's, and COX-2 Inhibitors. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 6. STEREOCHEMISTRY. Stereochemistry and the Tetrahedral Carbon. The Reason for Handedness in Molecules: Chirality. Optical Activity. Specific Rotation. Pasteur's Discovery of Enantiomers. Sequence Rules for Specifying Configuration. Diastereomers. Meso Compounds. Molecules with More Than Two Stereocenters. Racemic Mixtures and the Resolution of Enantiomers. Physical Properties of Stereoisomers. A Brief Review of Isomerism. Chirality in Nature. Interlude - Chiral Drugs. Summary and Key Words. Additional Problems. 7. ALKYL HALIDES. Naming Alkyl Halides. Preparing Alkyl Halides. Reactions of Alkyl Halides: Grignard Reagents. Nucleophilic Substitution Reactions. The SN2 Reaction. The SN1 Reaction. Eliminations: The E2 Reaction. Eliminations: The E1 Reaction. A Summary of Reactivity: SN1, SN2, E1, E2. Substitution Reactions in Living Organisms. Interlude - Naturally Occurring Organohalogen Compounds. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 8. ALCOHOLS, PHENOLS, AND ETHERS. Naming Alcohols, Phenols, and Ethers. Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding. Properties of Alcohols and Phenols: Acidity. Synthesis of Alcohols. Reactions of Alcohols. Synthesis and Reactions of Phenols. Synthesis and Reactions of Ethers. Cyclic Ethers: Epoxides. Thiols and Sulfides. Interlude - Ethanol as Chemical, Drug, and Poison. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 9. ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION REACTIONS. The Nature of Carbonyl Compounds. Naming Aldehydes and Ketones. Synthesis of Aldehydes and Ketones. Oxidation of Aldehydes. Nucleophilic Addition Reactions of Aldehydes and Ketones: Reduction. Nucleophilic Addition of Water: Hydration. Nucleophilic Addition of Alcohols: Acetal Formation. Nucleophilic Addition of Amines: Imine Formation. Nucleophilic Addition of Grignard Reagents: Alcohol Formation. Conjugate Nucleophilic Addition Reactions. Some Biological Nucleophilic Addition Reactions. Interlude -Carbonyl Compounds for Insect Control. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 10. CARBOXYLIC ACIDS AND DERIVATIVES. Naming Carboxylic Acids and Derivatives. Occurrence and Properties of Carboxylic Acids. Synthesis of Carboxylic Acids. Nucleophilic Acyl Substitution Reactions. Reactions of Carboxylic Acids. Chemistry of Acid Halides. Chemistry of Acid Anhydrides. Chemistry of Esters. Chemistry of Amides. Chemistry of Nitriles. Polymers from Carbonyl Compounds: Nylons and Polyesters. Interlude - Vitamin C. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 11. CARBONYL ALPHA-SUBSTITUTION REACTIONS AND CONDENSATION REACTIONS. Keto-Enol Tautomerism. Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions. Alpha Halogenation of Aldehydes and Ketones. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation. Reactivity of Enolate Ions. Alkylation of Enolate Ions. Carbonyl Condensation Reactions. Condensations of Aldehydes and Ketones: The Aldol Reaction. Dehydration of Aldol Products: Synthesis of Enones. Condensations of Esters: The Claisen Condensation Reaction. Biological Carbonyl Reactions. Interlude - Lactam Antibiotics. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. 12. AMINES. Naming Amines. Structure and Properties of Amines. Basicity of Amines. Synthesis of Amines. Reactions of Amines. Heterocyclic Amines. Alkaloids: Naturally Occurring Amines. Interlude - Opium and Opiates. Summary and Key Words. Summary of Reactions. Visualizing Chemistry.Additional Problems. 13. STRUCTURE DETERMINATION. Infrared Spectroscopy and The Electromagnetic Spectrum. Infrared Spectroscopy of Organic Molecules. Ultraviolet Spectroscopy. Interpreting Ultraviolet Spectra: The Effect of Conjugation. Nuclear Magnetic Resonance Spectroscopy. The Nature of NMR Absorptions. Chemical Shifts. Chemical Shifts in 1H NMR Spectra. Integration of 1H NMR Spectra: Proton Counting. Spin-Spin Splitting in 1H NMR Spectra. Uses of 1H NMR Spectra. 13C NMR Spectroscopy. Interlude - Magnetic Resonance Imaging (MRI). Summary and Key Words. Visualizing Chemistry. Additional Problems. 14. BIOMOLECULES: CARBOHYDRATES. Classification of Carbohydrates. Configurations of Monosaccharides: Fischer Projections. D,L Sugars. Configurations of Aldoses. Cyclic Structures of Monosaccharides: Hemiacetal Formation. Monosaccharide Anomers: Mutarotation. Reactions of Monosaccharides. Disaccharides. Polysaccharides. Other Important Carbohydrates. Cell-Surface Carbohydrates and Carbohydrate Vaccines. Interlude - Sweetness. Summary and Key Words. Visualizing Chemistry. Additional Problems. 15. BIOMOLECULES: AMINO ACIDS, PEPTIDES, AND PROTEINS. Structures of Amino Acids. Isoelectric Points. Peptides and Proteins. Covalent Bonding in Peptides. Peptide Structure Determination: Amino Acid Analysis. Peptide Sequencing: The Edman Degradation. Peptide Synthesis. Classification of Proteins. Protein Structure. Enzymes. How Do Enzymes Work? Citrate Synthase. Interlude - Protein and Nutrition. Summary and Key Words. Visualizing Chemistry. Additional Problems. 16. BIOMOLECULES: LIPIDS AND NUCLEIC ACIDS. Lipids. Fats and Oils. Soaps. Phospholipids. Steroids. Nucleic Acids and Nucleotides. Structure of DNA. Base Pairing in DNA: The Watson-Crick Model. Nucleic Acids and Heredity. Replication of DNA. Structure and Synthesis of RNA: Transcription. RNA and Protein Biosynthesis: Translation. Sequencing DNA. The Polymerase Chain Reaction. Interlude - DNA Fingerprinting. Summary and Key Words. Visualizing Chemistry. Additional Problems. 17. THE ORGANIC CHEMISTRY OF METABOLIC PATHWAYS. An Overview of Metabolism and Biochemical Energy. Catabolism of Fats: Oxidation Pathway. Catabolism of Carbohydrates: Glycolysis. The Citric Acid Cycle. Catabolism of Proteins: Transamination. The Organic Chemistry of Metabolic Pathways: A Summary. Interlude - Basal Metabolism. Summary and Key Words. Visualizing Chemistry. Additional Problems. Appendix: Nomenclature of Polyfunctional Organic Compounds. Index.