ISBN13:978-1439049716 ISBN10: 1439049718 This edition has also been released as: ISBN13: 978-1439050378 ISBN10: 1439050376
Summary: 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 for
mat 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.
Summary: 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. ...show less
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.
View Table of Contents
Preface xvi A Note for Students xxi 1 Structure and Bonding; Acids and Bases 1 1.1 Atomic Structure 3 1.2 Electron Configuration of Atoms 5 1.3 Development of Chemical Bonding Theory 6 1.4 The Nature of Chemical Bonds 7 1.5 Forming Covalent Bonds: Valence Bond Theory 10 1.6 Hybridization: sp[superscript 3] Orbitals and the Structure of Methane 11 1.7 Hybridization: sp[superscript 3] Orbitals and the Structure of Ethane 12 1.8 Hybridization: sp[subscript 2] Orbitals and the Structure of Ethylene 13 1.9 Hybridization: sp Orbitals and the Structure of Acetylene 16 1.10 Polar Covalent Bonds: Electronegativity 17 1.11 Acids and Bases: The Bronsted--Lowry Definition 20 1.12 Acids and Bases: The Lewis Definition 24 2 The Nature of Organic Compounds: Alkanes 34 2.1 Functional Groups 35 2.2 Alkanes and Alkyl Groups: Isomers 41 2.3 Naming Branched-Chain Alkanes 46 2.4 Properties of Alkanes 49 2.5 Conformations of Ethane 50 2.6 Drawing Chemical Structures 53 2.7 Cycloalkanes 54 2.8 Cis--Trans Isomerism in Cycloalkanes 55 2.9 Conformations of Some Cycloalkanes 57 2.10 Axial and Equatorial Bonds in Cyclohexane 60 2.11 Conformational Mobility of Cyclohexane 61 3 The Nature of Organic Reactions: Alkenes 74 3.1 Naming Alkenes 75 3.2 Electronic Structure of Alkenes 78 3.3 Cis--Trans Isomers of Alkenes 79 3.4 Sequence Rules: The E,Z Designation 81 3.5 Kinds of Organic Reactions 84 3.6 How Reactions Occur: Mechanisms 86 3.7 The Mechanism of an Organic Reaction: Addition of HCl to Ethylene 89 3.8 Describing a Reaction: Reaction Energy Diagrams and Transition States 92 3.9 Describing a Reaction: Intermediates 94 4 Reactions of Alkenes and Alkynes 105 4.1 Addition of HX to Alkenes: Hydrohalogenation 106 4.2 Orientation of Alkene Addition Reactions: Markovnikov's Rule 106 4.3 Carbocation Structure and Stability 109 4.4 Addition of H[subscript 2]O to Alkenes: Hydration 111 4.5 Addition of X[subscript 2] to Alkenes: Halogenation 113 4.6 Addition of H[subscript 2] to Alkenes: Hydrogenation 115 4.7 Oxidation of Alkenes: Hydroxylation and Cleavage 116 4.8 Biological Addition Reactions of Alkenes 118 4.9 Addition of Radicals to Alkenes: Polymers 119 4.10 Conjugated Dienes 122 4.11 Stability of Allylic Carbocations: Resonance 124 4.12 Drawing and Interpreting Resonance Forms 126 4.13 Alkynes and Their Reactions 128 5 Aromatic Compounds 143 5.1 Structure of Benzene: The Kekule Proposal 144 5.2 Structure of Benzene: The Resonance Proposal 145 5.3 Naming Aromatic Compounds 146 5.4 Electrophilic Aromatic Substitution Reactions: Bromination 149 5.5 Other Electrophilic Aromatic Substitution Reactions 153 5.6 The Friedel--Crafts Alkylation and Acylation Reactions 154 5.7 Substituent Effects in Electrophilic Aromatic Substitution 156 5.8 An Explanation of Substituent Effects 158 5.9 Oxidation and Reduction of Aromatic Compounds 162 5.10 Polycyclic Aromatic Hydrocarbons 163 5.11 Organic Synthesis 164 6 Stereochemistry 177 6.1 Stereochemistry and the Tetrahedral Carbon 178 6.2 The Reason for Handedness in Molecules: Chirality 180 6.3 Optical Activity 183 6.4 Specific Rotation 184 6.5 Pasteur's Discovery of Enantiomers 186 6.6 Sequence Rules for Specifying Configuration 187 6.7 Diastereomers 191 6.8 Meso Compounds 193 6.9 Molecules with More Than Two Stereocenters 195 6.10 Racemic Mixtures and the Resolution of Enantiomers 196 6.11 Physical Properties of Stereoisomers 199 6.12 A Brief Review of Isomerism 199 6.13 Chirality in Nature 201 7 Alkyl Halides 211 7.1 Naming Alkyl Halides 212 7.2 Preparing Alkyl Halides 213 7.3 Reactions of Alkyl Halides: Grignard Reagents 215 7.4 Nucleophilic Substitution Reactions 217 7.5 The S[subscript N]2 Reaction 220 7.6 The S[subscript N]1 Reaction 224 7.7 Eliminations: The E2 Reaction 228 7.8 Eliminations: The E1 Reaction 230 7.9 A Summary of Reactivity: S[subscript N]1, S[subscript N]2, E1, E2 232 7.10 Substitution Reactions in Living Organisms 233 8 Alcohols, Phenols, and Ethers 243 8.1 Naming Alcohols, Phenols, and Ethers 244 8.2 Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding 246 8.3 Properties of Alcohols and Phenols: Acidity 248 8.4 Synthesis of Alcohols 250 8.5 Reactions of Alcohols 253 8.6 Synthesis and Reactions of Phenols 258 8.7 Synthesis and Reactions of Ethers 261 8.8 Cyclic Ethers: Epoxides 262 8.9 Thiols and Sulfides 264 9 Aldehydes and Ketones: Nucleophilic Addition Reactions 276 9.1 The Nature of Carbonyl Compounds 277 9.2 Naming Aldehydes and Ketones 279 9.3 Synthesis of Aldehydes and Ketones 281 9.4 Oxidation of Aldehydes 282 9.5 Nucleophilic Addition Reactions of Aldehydes and Ketones: Reduction 283 9.6 Nucleophilic Addition of Water: Hydration 285 9.7 Nucleophilic Addition of Alcohols: Acetal Formation 288 9.8 Nucleophilic Addition of Amines: Imine Formation 290 9.9 Nucleophilic Addition of Grignard Reagents: Alcohol Formation 291 9.10 Conjugate Nucleophilic Addition Reactions 294 9.11 Some Biological Nucleophilic Addition Reactions 295 10 Carboxylic Acids and Derivatives 305 10.1 Naming Carboxylic Acids and Derivatives 306 10.2 Occurrence and Properties of Carboxylic Acids 310 10.3 Synthesis of Carboxylic Acids 313 10.4 Nucleophilic Acyl Substitution Reactions 314 10.5 Reactions of Carboxylic Acids 317 10.6 Chemistry of Acid Halides 320 10.7 Chemistry of Acid Anhydrides 322 10.8 Chemistry of Esters 324 10.9 Chemistry of Amides 329 10.10 Chemistry of Nitriles 331 10.11 Polymers from Carbonyl Compounds: Nylons and Polyesters 334 11 Carbonyl Alpha-Substitution Reactions and Condensation Reactions 347 11.1 Keto--Enol Tautomerism 348 11.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions 352 11.3 Alpha Halogenation of Aldehydes and Ketones 353 11.4 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation 355 11.5 Reactivity of Enolate Ions 358 11.6 Alkylation of Enolate Ions 359 11.7 Carbonyl Condensation Reactions 362 11.8 Condensations of Aldehydes and Ketones: The Aldol Reaction 362 11.9 Dehydration of Aldol Products: Synthesis of Enones 364 11.10 Condensations of Esters: The Claisen Condensation Reaction 366 11.11 Biological Carbonyl Reactions 368 12 Amines 379 12.1 Naming Amines 380 12.2 Structure and Properties of Amines 383 12.3 Basicity of Amines 383 12.4 Synthesis of Amines 386 12.5 Reactions of Amines 392 12.6 Heterocyclic Amines 393 12.7 Alkaloids: Naturally Occurring Amines 397 13 Structure Determination 406 13.1 Infrared Spectroscopy and the Electromagnetic Spectrum 407 13.2 Infrared Spectroscopy of Organic Molecules 410 13.3 Ultraviolet Spectroscopy 415 13.4 Interpreting Ultraviolet Spectra: The Effect of Conjugation 416 13.5 Nuclear Magnetic Resonance Spectroscopy 418 13.6 The Nature of NMR Absorptions 419 13.7 Chemical Shifts 422 13.8 Chemical Shifts in [superscript 1]H NMR Spectra 423 13.9 Integration of [superscript 1]H NMR Spectra: Proton Counting 425 13.10 Spin--Spin Splitting in [superscript 1]H NMR Spectra 426 13.11 Uses of [superscript 1]H NMR Spectra 430 13.12 [superscript 13]C NMR Spectroscopy 430 14 Biomolecules: Carbohydrates 441 14.1 Classification of Carbohydrates 442 14.2 Configurations of Monosaccharides: Fischer Projections 444 14.3 D,L Sugars 446 14.4 Configurations of Aldoses 448 14.5 Cyclic Structures of Monosaccharides: Hemiacetal Formation 450 14.6 Monosaccharide Anomers: Mutarotation 452 14.7 Reactions of Monosaccharides 454 14.9 Polysaccharides 460 14.10 Other Important Carbohydrates 463 14.11 Cell-Surface Carbohydrates and Carbohydrate Vaccines 463 15 Biomolecules: Amino Acids, Peptides, and Proteins 472 15.1 Structures of Amino Acids 473 15.2 Isoelectric Points 478 15.3 Peptides and Proteins 481 15.4 Covalent Bonding in Peptides 482 15.5 Peptide Structure Determination: Amino Acid Analysis 484 15.6 Peptide Sequencing: The Edman Degradation 484 15.7 Peptide Synthesis 487 15.8 Classification of Proteins 490 15.9 Protein Structure 491 15.10 Enzymes 494 15.11 How Do Enzymes Work? Citrate Synthase 497 16 Biomolecules: Lipids and Nucleic Acids 507 16.1 Lipids 508 16.2 Fats and Oils 508 16.3 Soaps 511 16.4 Phospholipids 513 16.5 Steroids 515 16.6 Nucleic Acids and Nucleotides 517 16.7 Structure of DNA 520 16.8 Base Pairing in DNA: The Watson--Crick Model 521 16.9 Nucleic Acids and Heredity 524 16.10 Replication of DNA 524 16.11 Structure and Synthesis of RNA: Transcription 526 16.12 RNA and Protein Biosynthesis: Translation 527 16.13 Sequencing DNA 530 16.14 The Polymerase Chain Reaction 532 17 The Organic Chemistry of Metabolic Pathways 540 17.1 An Overview of Metabolism and Biochemical Energy 541 17.2 Catabolism of Fats: [beta]-Oxidation Pathway 544 17.3 Catabolism of Carbohydrates: Glycolysis 549 17.4 The Citric Acid Cycle 554 17.5 Catabolism of Proteins: Transamination 557 17.6 The Organic Chemistry of Metabolic Pathways: A Summary 559 Appendixes A Nomenclature of Polyfunctional Organic Compounds 1 B Glossary 8 C Answers to Selected In-Chapter Problems 18 Index 1
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