Organic Chemistry / Edition 6

by John E. McMurry

Overview

Master organic chemistry with the help of this proven best-seller! John McMurry's ORGANIC CHEMISTRY is consistently praised as the most clearly written book available for the course. In John McMurry's words: "I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words." Through his lucid writing and ability to show the beauty and logic of organic chemistry,

Product Details

ISBN-13:	9780534409340
Publisher:	Brooks/Cole
Publication date:	04/01/2003
Edition description:	Study Guide
Product dimensions:	8.34(w) x 10.70(h) x 1.89(d)

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.

Table of Contents

PREFACE. A NOTE FOR STUDENTS. HOW TO USE SPARTANVIEW AND INTERPRET MOLECULAR MODELING DATA. 1. STRUCTURE AND BONDING. Atomic Structure. Atomic Structure: Orbitals. Atomic Structure: Electron Configurations. Development of Chemical Bonding Theory. Covalent Bonds. Valence Bond Theory and Molecular Orbital Theory. Hybridization: sp3 Orbitals and the Structure of Methane. The Structure of Ethane. Hybridization: sp2 Orbitals and the Structure of Ethylene. Hybridization: sp Orbitals and the Structure of Acetylene. Hybridization of Other Atoms: Nitrogen and Oxygen. Chemistry@Work: Chemical Toxicity and Risk. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 2. POLAR BONDS AND THEIR CONSEQUENCES. Polar Covalent Bonds and Electronegativity. Polar Covalent Bonds and Dipole Moment. Formal Charges. Resonance. Rules for Resonance Forms. A Useful Technique for Drawing Resonance Forms. Acids and Bases: The Brønsted-Lowry Definition. Acid and Base Strength. Predicting Acid-Base Reactions from pK[sub a] Values. Organic Acids and Organic Bases. Acids and Bases: The Lewis Definition. Drawing Chemical Structures. Molecular Models. Chemistry@Work: Alkaloids: Naturally Occurring Bases. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 3. ORGANIC COMPOUNDS: ALKANES AND CYCLOALKANES. Functional Groups. Alkanes and Alkane Isomers. Alkyl Groups. Naming Alkanes. Properties of Alkanes. Cycloalkanes. Naming Cycloalkanes. Cis-Trans Isomerism in Cycloalkanes. Chemistry@Work: Gasoline from Petroleum. Summary and Key Words.Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 4. STEREOCHEMISTRY OF ALKANES AND CYCLOALKANES. Conformations of Ethane. Conformations of Propane. Conformations of Butane. Conformation and Stability of Cycloalkanes: The Baeyer Strain Theory. Heats of Combustion of Cycloalkanes. The Nature of Ring Strain. Cyclopropane: An Orbital View. Conformations of Cyclobutane and Cyclopentane. Conformations of Cyclohexane . Axial and Equatorial Bonds in Cyclohexane. Conformational Mobility of Cyclohexane. Conformations of Monosubstituted Cyclohexanes. Conformational Analysis of Disubstituted Cyclohexanes. Boat Cyclohexane. Conformations of Polycyclic Molecules. Chemistry@Work: Molecular Mechanics. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 5. AN OVERVIEW OF ORGANIC REACTIONS. Kinds of Organic Reactions. How Organic Reactions Occur: Mechanisms. Radical Reactions and How They Occur. Polar Reactions and How They Occur. An Example of a Polar Reaction: Addition of HBr to Ethylene. Using Curved Arrows in Polar Reaction Mechanisms. Describing a Reaction: Equilibria, Rates, and Energy Changes. Describing a Reaction: Bond Dissociation Energies. Describing a Reaction: Energy Diagrams and Transition States. Describing a Reaction: Intermediates. Chemistry@Work: Explosives. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 6. ALKENES: STRUCTURE AND REACTIVITY. Industrial Preparation and Use of Alkenes. Calculating a Molecule's Degree of Unsaturation. Naming Alkenes. Electronic Structure of Alkenes. Cis-Trans Isomerism in Alkenes. Sequence Rules: the E,Z Designation. Alkene Stability. Electrophilic Addition of HX to Alkenes. Orientation of Electrophilic Addition: Markovnikov's Rule. Carbocation Structure and Stability. The Hammond Postulate. Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements. Chemistry@Work: Carrots, Alkenes, and the Chemistry of Vision. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 7. ALKENES: REACTIONS AND SYNTHESIS. Preparation of Alkenes: A Preview of Elimination Reactions. Addition of Halogens to Alkenes. Halohydrin Formation. Addition of Water to Alkenes: Oxymercuration. Addition of Water to Alkenes: Hydroboration. Addition of Carbenes to Alkenes: Cyclopropane Synthesis. Reduction of Alkenes: Hydrogenation. Oxidation of Alkenes: Hydroxylation and Cleavage. Biological Alkene Addition Reactions. Addition of Radicals to Alkenes: Polymers. Chemistry@Work: Rubber. Summary and Key Words. Working Problems. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 8. ALKYNES; AN INTRODUCTION TO ORGANIC SYNTHESIS. Electronic Structure of Alkynes. Naming Alkynes. Preparation of Alkynes: Elimination Reactions of Dihalides. Reactions of Alkynes: Addition of HX and X2. Hydration of Alkynes. Reduction of Alkynes. Oxidative Cleavage of Alkynes. Alkyne Acidity: Formation of Acetylide Anions. Alkylation of Acetylide Anions. An Introduction to Organic Synthesis. Chemistry@Work: The Art of Organic Synthesis. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 9. STEREOCHEMISTRY. Enantiomers and the Tetrahedral Carbon. The Reason for Handedness in Molecules: Chirality. Optical Activity. Specific Rotation. Pasteur's Discovery of Enantiomers. Sequence Rules for Specification of Configuration. Diastereomers. Meso Compounds. Molecules with More than Two Chirality Centers. Racemic Mixtures and Their Resolution. Physical Properties of Stereoisomers. A Brief Review of Isomerism. Fischer Projections. Assigning R,S Configuration to Fischer Projections. Stereochemistry of Reactions: Addition of HBr to Alkenes. Stereochemistry of Reactions: Addition of Br2 to Alkenes. Stereochemistry of Reactions: Addition of HBr to a Chiral Alkene. Chirality at Atoms Other Than Carbon. Chirality in Nature. Chemistry@Work: Chiral Drugs. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 10. ALKYL HALIDES. Naming Alkyl Halides. Structure of Alkyl Halides. Preparation of Alkyl Halides. Radical Halogenation of Alkanes. Allylic Bromination of Alkenes. Stability of the Allyl Radical: Resonance Revisited. Preparing Alkyl Halides from Alcohols. Reactions of Alkyl Halides: Grignard Reagents. Organometallic Coupling Reactions. Oxidation and Reduction in Organic Chemistry. Chemistry@Work: Naturally Occurring Organohalides. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 11. REACTIONS OF ALKYL HALIDES: NUCLEOPHILIC SUBSTITUTIONS AND ELIMINATIONS. The Discovery of the Walden Inversion. Stereochemistry of Nucleophilic Substitution. Kinetics of Nucleophilic Substitution. The SN2 Reaction. Characteristics of the SN2 Reaction. The SN1 Reaction. Kinetics of the SN1 Reaction. Stereochemistry of the SN1 Reaction. Characteristics of the SN1 Reaction. Elimination Reactions of Alkyl Halides: Zaitsev's Rule. The E2 Reaction. Elimination Reactions and Cyclohexane Conformation . The Deuterium Isotope Effect. The E1 Reaction. Summary of Reactivity: SN1, SN2, E1, E2. Substitution Reactions in Synthesis. Chemistry@Work: Biological Substitution Reactions. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 12. STRUCTURE DETERMINATION: MASS SPECTROMETRY AND INFRARED SPECTROSCOPY. Mass Spectrometry. Interpreting Mass Spectra. Interpreting Mass-Spectral Fragmentation Patterns. Mass-Spectral Behavior of Some Common Functional Groups. Spectroscopy and the Electromagnetic Spectrum. Infrared Spectroscopy of Organic Molecules. Interpreting Infrared Spectra. Infrared Spectra of Hydrocarbons. Infrared Spectra of Some Common Functional Groups. Chemistry@Work: Chromatography: Purifying Organic Compounds. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 13. STRUCTURE DETERMINATION: NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY. Nuclear Magnetic Resonance Spectroscopy. The Nature of NMR Absorptions. Chemical Shifts. 13C NMR Spectroscopy: Signal Averaging and FT-NMR. Characteristics of 13C NMR Spectroscopy. DEPT 13C NMR Spectroscopy. Uses of 13C NMR Spectroscopy. 1H NMR Spectroscopy and Proton Equivalence. Chemical Shifts in 1H NMR Spectroscopy. Integration of 1H NMR Absorptions: Proton Counting. Spin-Spin Splitting in 1H NMR Spectra. More Complex Spin-Spin Splitting Patterns. Uses of 1H NMR Spectroscopy. Chemistry@Work: Magnetic Resonance Imaging (MRI). Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 14. CONJUGATED DIENES AND ULTRAVIOLET SPECTROSCOPY. Preparation of Conjugated Dienes. Stability of Conjugated Dienes. Molecular Orbital Description of 1,3-Butadiene. Bond Lengths in 1,3-Butadiene. Electrophilic Additions to Conjugated Dienes: Allylic Carbocations. Kinetic versus Thermodynamic Control of Reactions. Diene Polymers: Natural and Synthetic Rubbers. The Diels-Alder Cycloaddition Reaction. Characteristics of the Diels-Alder Reaction. Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy. Ultraviolet Spectrum of 1,3-Butadiene. Interpreting Ultraviolet Spectra: The Effect of Conjugation. Colored Organic Compounds. Chemistry@Work: Resists for Integrated Circuits. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 15. BENZENE AND AROMATICITY. Sources of Aromatic Hydrocarbons. Naming Aromatic Compounds. Structure and Stability of Benzene. Molecular Orbital Description of Benzene. Aromaticity and the Hückel 4n + 2 Rule. Aromatic Ions. Pyridine and Pyrrole: Two Aromatic Heterocycles. Why 4n + 2?. Naphthalene: A Polycyclic Aromatic Compound. Spectroscopy of Aromatic Compounds. Chemistry@Work: Aspirin and Other Aromatic NSAID's. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 16. CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION. Bromination of Aromatic Rings. Other Aromatic Substitutions. Alkylation of Aromatic Rings: The Friedel-Crafts Reaction. Acylation of Aromatic Rings. Substituent Effects in Substituted Aromatic Rings. An Explanation of Substituent Effects. Trisubstituted Benzenes: Additivity of Effects. Nucleophilic Aromatic Substitution. Benzyne. Oxidation of Aromatic Compounds. Reduction of Aromatic Compounds. Synthesis of Trisubstituted Benzenes. Chemistry@Work: Combinatorial Chemistry. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. A BRIEF REVIEW OF ORGANIC REACTIONS. I. A Summary of the Kinds of Organic Reactions. II. A Summary of Organic Reaction Mechanisms. Problems. 17. ALCOHOLS AND PHENOLS. Naming Alcohols and Phenols. Properties of Alcohols and Phenols: Hydrogen Bonding. Properties of Alcohols and Phenols: Acidity and Basicity. Preparation of Alcohols: A Review. Alcohols from Reduction of Carbonyl Compounds. Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents. Some Reactions of Alcohols. Oxidation of Alcohols. Protection of Alcohols. Preparation and Uses of Phenols. Reactions of Phenols. Spectroscopy of Alcohols and Phenols. Chemistry@Work: Ethanol: Chemical, Drug, and Poison. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 18. ETHERS AND EPOXIDES; THIOLS AND SULFIDES. Naming Ethers. Structure, Properties, and Sources of Ethers. The Williamson Ether Synthesis. Alkoxymercuration of Alkenes. Reactions of Ethers: Acidic Cleavage. Reactions of Ethers: Claisen Rearrangement. Cyclic Ethers: Epoxides. Ring-Opening Reactions of Epoxides. Crown Ethers. Spectroscopy of Ethers. Thiols and Sulfides. Chemistry@Work: Epoxy Resins and Adhesives. Summary and Key Words. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. A PREVIEW OF CARBONYL COMPOUNDS. I. Kinds of Carbonyl Compounds. II. Nature of the Carbonyl Group. III. General Reactions of Carbonyl Compounds. IV. Summary. 19. ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION REACTIONS. Naming Aldehydes and Ketones. Preparation of Aldehydes and Ketones. Oxidation of Aldehydes and Ketones. Nucleophilic Addition Reactions of Aldehydes and Ketones. Relative Reactivity of Aldehydes and Ketones. Nucleophilic Addition of H2O: Hydration. Nucleophilic Addition of HCN: Cyanohydrin Formation. Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation. Nucleophilic Addition of Amines: Imine and Enamine Formation. Nucleophilic Addition of Hydrazine: The Wolff-Kishner reaction. Nucleophilic Addition of Alcohols: Acetal Formation. Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction. The Cannizzaro Reaction. Conjugate Nucleophilic Addition to Alpha,Beta-Unsaturated Aldehydes and Ketones. Some Biological Nucleophilic Addition Reactions. Spectroscopy of Aldehydes and Ketones. Chemistry@Work: Enantioselective Synthesis. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 20. CARBOXYLIC ACIDS. Naming Carboxylic Acids. Structure and Physical Properties of Carboxylic Acids. Dissociation of Carboxylic Acids. Substituent Effects on Acidity. Substituent Effects in Substituted Benzoic Acids. Preparation of Carboxylic Acids. Reactions of Carboxylic Acids: An Overview. Reduction of Carboxylic Acids. Spectroscopy of Carboxylic Acids. Chemistry@Work: Vitamin C. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 21. CARBOXYLIC ACID DERIVATIVES AND NUCLEOPHILIC ACYL SUBSTITUTION REACTIONS. Naming Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Reactions. Nucleophilic Acyl Substitution Reactions of Carboxylic Acids. Chemistry of Acid Halides. Chemistry of Acid Anhydrides. Chemistry of Esters. Chemistry of Amides. Chemistry of Nitriles. Thiol Esters: Biological Carboxylic Acid Derivatives. Polyamides and Polyesters: Step-Growth Polymers. Spectroscopy of Carboxylic Acid Derivatives and Nitriles. Chemistry@Work Beta-Lactam Antibiotics. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 22. CARBONYL ALPHA-SUBSTITUTION REACTIONS. Keto-Enol Tautomerism. Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions. Alpha Halogenation of Aldehydes and Ketones. Alpha Bromination of Carboxylic Acids: The Hell-Volhard-Zelinskii Reaction. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation. Reactivity of Enolate Ions. Halogenation of Enolate Ions: The Haloform Reaction. Alkylation of Enolate Ions. Chemistry@Work: Unusual Elements in Organic Chemistry. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 23. CARBONYL CONDENSATION REACTIONS. Mechanism of Carbonyl Condensation Reactions. Condensations of Aldehydes and Ketones: The Aldol Reaction. Carbonyl Condensation Reactions versus Alpha-Substitution Reactions. Dehydration of Aldol Products: Synthesis of Enones. Using Aldol Reactions in Synthesis. Mixed Aldol Reactions. Intramolecular Aldol Reactions. The Claisen Condensation Reaction. Mixed Claisen Condensations. Intramolecular Claisen Condensations: The Dieckmann Cyclization. The Michael Reaction. The Stork Enamine Reaction. Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation Reaction. Biological Carbonyl Condensation Reactions. Chemistry@Work: A Prologue to Metabolism. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 24. AMINES. Naming Amines. Structure and Bonding in Amines. Properties and Sources of Amines. Basicity of Amines. Basicity of Substituted Arylamines. Synthesis of Amines. Reactions of Amines. Reactions of Arylamines. Tetraalkylammonium Salts as Phase-Transfer Catalysts. Spectroscopy of Amines. Chemistry@Work: Morphine Alkaloids. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 25. BIOMOLECULES: CARBOHYDRATES. Classification of Carbohydrates. Configurations of Monosaccharides: Fischer Projections. D,L Sugars. Configurations of the Aldoses. Cyclic Structures of Monosaccharides: Hemiacetal Formation. Monosaccharide Anomers: Mutarotation. Reactions of Monosaccharides. Stereochemistry of Glucose: The Fischer Proof. Disaccharides. Polysaccharides and Their Synthesis. Other Important Carbohydrates. Cell-Surface Carbohydrates and Carbohydrate Vaccines. Chemistry@Work: Sweetness. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 26. BIOMOLECULES: AMINO ACIDS, PEPTIDES, AND PROTEINS. Structures of Amino Acids. Isoelectric Points. Synthesis of Alpha-Amino Acids. Resolution of R,S Amino Acids. Peptides and Proteins. Covalent Bonding in Peptides. Structure Determination of Peptides: Amino Acid Analysis. Sequencing of Peptides: The Edman Degradation. Sequencing of Peptides: C-Terminal Residue Determination. Synthesis of Peptides. Automated Peptide Synthesis: The Merrifield Solid-Phase Technique. Classification of Proteins. Protein Structure. Enzymes. How Do Enzymes Work? Citrate Synthase. Protein Denaturation. Chemistry@Work: Protein and Nutrition. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 27. BIOMOLECULES: LIPIDS. Waxes, Fats, and Oils. Soap. Phospholipids. Prostaglandins. Terpenes. Biosynthesis of Terpenes. Steroids. Stereochemistry of Steroids. Steroid Biosynthesis. Chemistry@Work: Cholesterol and Heart Disease. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 28. BIOMOLECULES: HETEROCYCLES AND NUCLEIC ACIDS. Five-Membered Unsaturated Heterocycles. Structures of Pyrrole, Furan, and Thiophene. Electrophilic Substitution Reactions of Pyrrole, Furan, and Thiophene. Pyridine, a Six-Membered Heterocycle. Electrophilic Substitution of Pyridine. Nucleophilic Substitution of Pyridine. Fused-Ring Heterocycles. Nucleic Acids and Nucleotides. Structure of Nucleic Acids. 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. DNA Sequencing. DNA Synthesis. The Polymerase Chain Reaction. Chemistry@Work: DNA Fingerprinting. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 29. THE ORGANIC CHEMISTRY OF METABOLIC PATHWAYS. An Overview of Metabolism and Biochemical Energy. Catabolism of Fats: Beta-Oxidation. Catabolism of Carbohydrates: Glycolysis. The Conversion of Pyruvate to Acetyl CoA. The Citric Acid Cycle. Catabolism of Proteins: Transamination. Anabolism of Fatty Acids. Anabolism of Carbohydrates: Gluconeogenesis. Some Conclusions About Biological Chemistry. Chemistry@Work: Basal Metabolism. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 30. ORBITALS AND ORGANIC CHEMISTRY: PERICYCLIC REACTIONS. Molecular Orbitals of Conjugated Pi Systems. Molecular Orbitals and Pericyclic Reactions. Electrocyclic Reactions. Stereochemistry of Thermal Electrocyclic Reactions. Photochemical Electrocyclic Reactions. Cycloaddition Reactions. Stereochemistry of Cycloadditions. Sigmatropic Rearrangements. Some Examples of Sigmatropic Rearrangements. A Summary of Rules for Pericyclic Reactions. Chemistry@Work: Vitamin D, the Sunshine Vitamin. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. 31. SYNTHETIC POLYMERS. Chain-Growth Polymers. Stereochemistry of Polymerization: Ziegler-Natta Catalysts. Copolymers. Step-Growth Polymers. Polymer Structure and Physical Properties. Chemistry@Work: Biodegradable Polymers. Summary and Key Words. Summary of Reactions. Visualizing Chemistry. Additional Problems. A Look Ahead. Molecular Modeling. APPENDIXES. A. Nomenclature of Polyfunctional Organic Compounds. B. Acidity Constants for Some Organic Compounds. C. How To Use SpartanBuild. D. Glossary. E. Answers to Selected In-Text Problems. INDEX.

Editorial Reviews

The textbook uses a dual organization that blends the traditional functional-group approach with a mechanistic approach. The primary organization is by functional group, beginning with the simple alkenes and progressing to the more complex carbonyl group and biomolecules. The updated fifth edition adds sections on acid-base strength, organic acids and bases, and curved-arrow formalism. Annotation c. Book News, Inc., Portland, OR (booknews.com)

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