Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018)

Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018) Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018) Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018) Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018) Preview Organic Chemistry Structure and Function by K. Peter C. Vollhardt (2018)

About the Authors K PETER C VOLLHARDT was born in Madrid, raised in Buenos Aires and Munich, studied at the University of Munich, received his Ph.D with Professor Peter Garratt at the University College, London, and was a postdoctoral fellow with Professor Bob Bergman (then) at the California Institute of Technology He moved to Berkeley in 1974 when he began his efforts toward the development of organocobalt reagents in organic synthesis, the preparation of theoretically interesting hydrocarbons, the assembly of novel transition metal arrays with potential in catalysis, and the discovery of a parking space Among other pleasant experiences, he was a Studienstiftler, Adolf Windaus medalist, Humboldt Senior Scientist, ACS Organometallic Awardee, Otto Bayer Prize Awardee, A C Cope Scholar, Japan Society for the Promotion of Science Prize Holder, and recipient of the Medal of the University Aix-Marseille and an Honorary Doctorate from The University of Rome Tor Vergata He is an editor of Synlett Among his more than 350 publications, he treasures especially this textbook in organic chemistry, translated into 13 languages Peter is married to Marie-José Sat, a French artist, and they have three children, Maïa (b 1982, Peter’s stepdaughter), whose splendid tattoo you can admire on p 1067, Paloma (b 1994), and Julien (b 1997) NEIL E SCHORE was born in Newark, New Jersey in 1948 His education took him through the public schools of the Bronx, New York, and Ridgefield, New Jersey, after which he completed a B.A with honors in chemistry at the University of Pennsylvania in 1969 Moving back to New York, he worked with the late Professor Nicholas J Turro at Columbia University, studying photochemical and photophysical processes of organic compounds for his Ph.D thesis He first met Peter Vollhardt when he and Peter were doing postdoctoral work in Professor Robert Bergman’s laboratory at Cal Tech in the 1970s Since joining the U.C Davis faculty in 1976, he has taught organic chemistry to some 20,000 nonchemistry majors, winning seven teaching awards, publishing over 100 papers in various areas related to organic chemistry, and refereeing several hundred local youth soccer games He has also pioneered Study Abroad programs in Taiwan and the U.K for chemistry students and is an Adjunct Professor in the Korea University International Summer Campus program Neil is married to Carrie Erickson, a microbiologist at the U.C Davis School of Veterinary Medicine They have two children, Michael (b 1981) and Stefanie (b 1983), both of whom carried out experiments for this book Grandson Roman (b 2016) is a bit too young for that as yet PETER VOLLHARDT University of California at Berkeley NEIL SCHORE University of California at Davis Vice President: Ben Roberts Program Manager: Beth Cole Development Editor: Randi Blatt Rossignol Marketing Manager: Maureen Rachford Marketing Assistant: Savannah DiMarco Director of Content: Kristen Ford Lead Content Developer: Lily Huang Assistant Editor: Allison Greco Director, Content Management Enhancement: Tracey Kuehn Managing Editor: Lisa Kinne Director of Design, Content Management: Diana Blume Photo Editor: Sheena Goldstein Photo Researcher: Lisa Passmore Design Director, Content Management: Diana Blume Media Project Manager: Daniel Comstock Senior Design Manager: Vicki Tomaselli Project Management and Composition: Aptara®, Inc Illustrations: Network Graphics; Precision Graphics Senior Workflow Supervisor: Susan Wein Cover Image: Jürgen Müller/imageBROKER/Alamy Library of Congress Control Number: 2017950317 ISBN-13: 978-1-319-18896-2 (EPUB) © 2018, 2014, 2011, 2007 by W H Freeman and Company All rights reserved W H Freeman and Company One New York Plaza Suite 4500 New York, NY 10004-1562 www.macmillanlearning.com Brief Contents PREFACE: A User’s Guide to ORGANIC CHEMISTRY: Structure and Function STRUCTURE AND BONDING IN ORGANIC MOLECULES STRUCTURE AND REACTIVITY Acids and Bases, Polar and Nonpolar Molecules REACTIONS OF ALKANES Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity CYCLOALKANES STEREOISOMERS PROPERTIES AND REACTIONS OF HALOALKANES Bimolecular Nucleophilic Substitution FURTHER REACTIONS OF HALOALKANES Unimolecular Substitution and Pathways of Elimination HYDROXY FUNCTIONAL GROUP: ALCOHOLS Properties, Preparation, and Strategy of Synthesis FURTHER REACTIONS OF ALCOHOLS AND THE CHEMISTRY OF ETHERS 10 USING NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY TO DEDUCE STRUCTURE 8-1 8-2 8-3 8-4 8-5 8-6 8-7 8-8 8-9 Naming the Alcohols Structural and Physical Properties of Alcohols Alcohols as Acids and Bases Synthesis of Alcohols by Nucleophilic Substitution Synthesis of Alcohols: Oxidation–Reduction Relation Between Alcohols and Carbonyl Compounds Real Life: Medicine 8-1 Oxidation and Reduction in the Body Real Life: Medicine 8-2 Don’t Drink and Drive: The Breath Analyzer Test Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis Organometallic Reagents in the Synthesis of Alcohols Keys to Success: An Introduction to Synthetic Strategy Real Life: Chemistry 8-3 What Magnesium Does Not Do, Copper Can: Alkylation of Organometallics Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems FURTHER REACTIONS OF ALCOHOLS AND THE CHEMISTRY OF ETHERS 9-1 9-2 9-3 9-4 9-5 9-6 9-7 9-8 Reactions of Alcohols with Base: Preparation of Alkoxides Reactions of Alcohols with Strong Acids: Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols Carbocation Rearrangements Esters from Alcohols and Haloalkane Synthesis Names and Physical Properties of Ethers Williamson Ether Synthesis Real Life: Nature 9-1 Chemiluminescence of 1,2Dioxacyclobutanes Synthesis of Ethers: Alcohols and Mineral Acids Reactions of Ethers Real Life: Medicine 9-2 Protecting Groups in the Synthesis of 9-9 9-10 9-11 9-12 10 Testosterone Reactions of Oxacyclopropanes Real Life: Chemistry 9-3 Hydrolytic Kinetic Resolution of Oxacyclopropanes Sulfur Analogs of Alcohols and Ethers Physiological Properties and Uses of Alcohols and Ethers Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems USING NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY TO DEDUCE STRUCTURE 10-1 10-2 10-3 10-4 10-5 10-6 10-7 10-8 10-9 Physical and Chemical Tests Defining Spectroscopy Hydrogen Nuclear Magnetic Resonance Real Life: Spectroscopy 10-1 Recording an NMR Spectrum Using NMR Spectra to Analyze Molecular Structure: The Proton Chemical Shift Tests for Chemical Equivalence Real Life: Medicine 10-2 Magnetic Resonance Imaging (MRI) in Medicine Integration of NMR Signals Spin–Spin Splitting: The Effect of Nonequivalent Neighboring Hydrogens Spin–Spin Splitting: Some Complications Real Life: Spectroscopy 10-3 The Nonequivalence of Diastereotopic Hydrogens Carbon-13 Nuclear Magnetic Resonance Real Life: Spectroscopy 10-4 How to Determine Atom Connectivity in NMR Real Life: Medicine 10-5 Structural Characterization of Natural and “Unnatural” Products: An Antioxidant from Grape Seeds and a Fake Drug in Herbal Medicines 10-10 11 Worked Examples: Integrating the Concepts Important Concepts Problems ALKENES: INFRARED SPECTROSCOPY AND MASS SPECTROMETRY 11-1 11-2 11-3 11-4 11-5 11-6 11-7 11-8 11-9 11-10 11-11 11-12 12 Naming the Alkenes Structure and Bonding in Ethene: The Pi Bond Physical Properties of Alkenes Nuclear Magnetic Resonance of Alkenes Real Life: Medicine 11-1 NMR of Complex Molecules: The Powerfully Regulating Prostaglandins Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds Preparation of Alkenes from Haloalkanes and Alkyl Sulfonates: Bimolecular Elimination Revisited Preparation of Alkenes by Dehydration of Alcohols Infrared Spectroscopy Measuring the Molecular Mass of Organic Compounds: Mass Spectrometry Real Life: Medicine 11-2 Detecting Performance-Enhancing Drugs Using Mass Spectrometry Fragmentation Patterns of Organic Molecules Degree of Unsaturation: Another Aid to Identifying Molecular Structure Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems REACTIONS OF ALKENES 12-1 12-2 12-3 12-4 12-5 12-6 12-7 12-8 12-9 12-10 12-11 12-12 12-13 12-14 12-15 12-16 12-17 12-18 13 Why Addition Reactions Proceed: Thermodynamic Feasibility Catalytic Hydrogenation Basic and Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control Electrophilic Addition of Halogens to Alkenes The Generality of Electrophilic Addition Oxymercuration–Demercuration: A Special Electrophilic Addition Real Life: Medicine 12-1 Juvenile Hormone Analogs in the Battle Against Insect-Borne Diseases Hydroboration–Oxidation: A Stereospecific Anti-Markovnikov Hydration Diazomethane, Carbenes, and Cyclopropane Synthesis Oxacyclopropane (Epoxide) Synthesis: Epoxidation by Peroxycarboxylic Acids Vicinal Syn Dihydroxylation with Osmium Tetroxide Real Life: Medicine 12-2 Synthesis of Antitumor Drugs: Sharpless Enantioselective Oxacyclopropanation (Epoxidation) and Dihydroxylation Oxidative Cleavage: Ozonolysis Radical Additions: Anti-Markovnikov Product Formation Dimerization, Oligomerization, and Polymerization of Alkenes Synthesis of Polymers Ethene: An Important Industrial Feedstock Alkenes in Nature: Insect Pheromones Real Life: Medicine 12-3 Alkene Metathesis Transposes the Termini of Two Alkenes: Construction of Rings Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems ALKYNES The Carbon–Carbon Triple Bond 13-1 13-2 13-3 13-4 13-5 13-6 13-7 13-8 13-9 13-10 13-11 13-12 14 Naming the Alkynes Properties and Bonding in the Alkynes Spectroscopy of the Alkynes Preparation of Alkynes by Double Elimination Preparation of Alkynes from Alkynyl Anions Reduction of Alkynes: The Relative Reactivity of the Two Pi Bonds Electrophilic Addition Reactions of Alkynes Anti-Markovnikov Additions to Triple Bonds Chemistry of Alkenyl Halides Real Life: Synthesis 13-1 Metal-Catalyzed Stille, Suzuki, and Sonogashira Coupling Reactions Ethyne as an Industrial Starting Material Alkynes in Nature and in Medicine Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems DELOCALIZED Pi SYSTEMS Investigation by Ultraviolet and Visible Spectroscopy 14-1 14-2 14-3 14-4 14-5 14-6 Overlap of Three Adjacent p Orbitals: Electron Delocalization in the 2-Propenyl (Allyl) System Radical Allylic Halogenation Nucleophilic Substitution of Allylic Halides: SN1 and SN2 Allylic Organometallic Reagents: Useful Three-Carbon Nucleophiles Two Neighboring Double Bonds: Conjugated Dienes Electrophilic Attack on Conjugated Dienes: Kinetic and Thermodynamic Control 14-7 14-8 14-9 14-10 14-11 14-12 Delocalization Among More than Two Pi Bonds: Extended Conjugation and Benzene A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition Real Life: Materials 14-1 Organic Polyenes Conduct Electricity Real Life: Sustainability 14-2 The Diels-Alder Reaction is “Green” Electrocyclic Reactions Polymerization of Conjugated Dienes: Rubber Electronic Spectra: Ultraviolet and Visible Spectroscopy Real Life: Spectroscopy 14-3 The Contributions of IR, MS, and UV to the Characterization of Viniferone Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems INTERLUDE A Summary of Organic Reaction Mechanisms 15 BENZENE AND AROMATICITY Electrophilic Aromatic Substitution 15-1 15-2 15-3 15-4 15-5 15-6 15-7 15-8 Naming the Benzenes Structure and Resonance Energy of Benzene: A First Look at Aromaticity Pi Molecular Orbitals of Benzene Spectral Characteristics of the Benzene Ring Real Life: Materials 15-1 Compounds Made of Pure Carbon: Graphite, Graphene, Diamond, and Fullerenes Polycyclic Aromatic Hydrocarbons Other Cyclic Polyenes: Hückel’s Rule Hückel’s Rule and Charged Molecules Synthesis of Benzene Derivatives: Electrophilic Aromatic 15-9 15-10 15-11 15-12 15-13 15-14 16 Substitution Halogenation of Benzene: The Need for a Catalyst Nitration and Sulfonation of Benzene Friedel-Crafts Alkylation Limitations of Friedel-Crafts Alkylations Friedel-Crafts Acylation Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems ELECTROPHILIC ATTACK ON DERIVATIVES OF BENZENE Substituents Control Regioselectivity 16-1 16-2 16-3 16-4 16-5 16-6 16-7 16-8 17 Activation or Deactivation by Substituents on a Benzene Ring Directing Electron-Donating Effects of Alkyl Groups Directing Effects of Substituents in Conjugation with the Benzene Ring Real Life: Materials 16-1 Explosive Nitroarenes: TNT and Picric Acid Electrophilic Attack on Disubstituted Benzenes Keys to Success: Synthetic Strategies Toward Substituted Benzenes Reactivity of Polycyclic Benzenoid Hydrocarbons Polycyclic Aromatic Hydrocarbons and Cancer Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems ALDEHYDES AND KETONES The Carbonyl Group 17-1 17-2 17-3 17-4 17-5 17-6 17-7 17-8 17-9 17-10 17-11 17-12 17-13 17-14 17-15 18 Naming the Aldehydes and Ketones Structure of the Carbonyl Group Spectroscopic Properties of Aldehydes and Ketones Preparation of Aldehydes and Ketones Reactivity of the Carbonyl Group: Mechanisms of Addition Addition of Water to Form Hydrates Addition of Alcohols to Form Hemiacetals and Acetals Acetals as Protecting Groups Nucleophilic Addition of Ammonia and Its Derivatives Real Life: Biochemistry 17-1 Imines Mediate the Biochemistry of Amino Acids Deoxygenation of the Carbonyl Group Addition of Hydrogen Cyanide to Give Cyanohydrins Addition of Phosphorus Ylides: The Wittig Reaction Oxidation by Peroxycarboxylic Acids: The Baeyer-Villiger Oxidation Oxidative Chemical Tests for Aldehydes Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems ENOLS, ENOLATES, AND THE ALDOL CONDENSATION α,β -Unsaturated Aldehydes and Ketones 18-1 18-2 18-3 18-4 18-5 Acidity of Aldehydes and Ketones: Enolate Ions Keto–Enol Equilibria Halogenation of Aldehydes and Ketones Alkylation of Aldehydes and Ketones Attack by Enolates on the Carbonyl Function: Aldol Condensation Real Life: Biology And Medicine 18-1 Stereoselective Aldol 18-6 18-7 18-8 18-9 18-10 18-11 18-12 19 19-1 19-2 19-3 19-4 19-5 19-6 19-7 19-8 19-9 19-10 19-11 19-12 19-13 Reactions in Nature and in the Laboratory: “Organocatalysis” Crossed Aldol Condensation Keys to Success: Competitive Reaction Pathways and the Intramolecular Aldol Condensation Real Life: Nature 18-2 Absorption of Photons by Unsaturated Aldehydes Enables Vision Properties of α,β -Unsaturated Aldehydes and Ketones Conjugate Additions to α,β -Unsaturated Aldehydes and Ketones 1,2- and 1,4-Additions of Organometallic Reagents Conjugate Additions of Enolate Ions: Michael Addition and Robinson Annulation Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems CARBOXYLIC ACIDS Naming the Carboxylic Acids Structural and Physical Properties of Carboxylic Acids Spectroscopy and Mass Spectrometry of Carboxylic Acids Acidic and Basic Character of Carboxylic Acids Carboxylic Acid Synthesis in Industry Methods for Introducing the Carboxy Functional Group Substitution at the Carboxy Carbon: The Addition–Elimination Mechanism Carboxylic Acid Derivatives: Acyl Halides and Anhydrides Carboxylic Acid Derivatives: Esters Carboxylic Acid Derivatives: Amides Reduction of Carboxylic Acids by Lithium Aluminum Hydride Bromination Next to the Carboxy Group: The Hell-VolhardZelinsky Reaction Biological Activity of Carboxylic Acids Real Life: Materials 19-1 Long-Chain Carboxylates and 19-14 20 20-1 20-2 20-3 20-4 20-5 20-6 20-7 20-8 20-9 21 Sulfonates Make Soaps and Detergents Real Life: Health 19-2 Artery-Clogging Trans Fatty Acids Phasing Out Real Life: Materials 19-3 Green Plastics, Fibers, and Energy from Biomass-Derived Hydroxyesters Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems CARBOXYLIC ACID DERIVATIVES Relative Reactivities, Structures, and Spectra of Carboxylic Acid Derivatives Chemistry of Acyl Halides Chemistry of Carboxylic Anhydrides Chemistry of Esters Esters in Nature: Waxes, Fats, Oils, and Lipids Real Life: Sustainability 20-1 Moving Away from Petroleum: Green Fuels from Vegetable Oil Amides: The Least Reactive Carboxylic Acid Derivatives Real Life: Medicine 20-2 Killing the Bugs that Kill the Drugs: Antibiotic Wars Amidates and Their Halogenation: The Hofmann Rearrangement Alkanenitriles: A Special Class of Carboxylic Acid Derivatives Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems AMINES AND THEIR DERIVATIVES Functional Groups Containing Nitrogen 21-1 21-2 21-3 21-4 21-5 21-6 21-7 21-8 21-9 21-10 21-11 22 Naming the Amines Real Life: Medicine 21-1 Physiologically Active Amines and Weight Control Structural and Physical Properties of Amines Spectroscopy of the Amine Group Acidity and Basicity of Amines Synthesis of Amines by Alkylation Synthesis of Amines by Reductive Amination Synthesis of Amines from Carboxylic Amides Reactions of Quaternary Ammonium Salts: Hofmann Elimination Mannich Reaction: Alkylation of Enols by Iminium Ions Nitrosation of Amines Real Life: Medicine 21-2 Sodium Nitrite as a Food Additive, N-Nitrosodialkanamines, and Cancer Real Life: Materials 21-3 Amines in Industry: Nylon, the “Miracle Fiber” Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems CHEMISTRY OF BENZENE SUBSTITUENTS Alkylbenzenes, Phenols, and Anilines 22-1 22-2 22-3 22-4 22-5 22-6 Reactivity at the Phenylmethyl (Benzyl) Carbon: Benzylic Resonance Stabilization Oxidations and Reductions of Substituted Benzenes Names and Properties of Phenols Real Life: Medicine 22-1 Two Phenols in the News: Bisphenol A and Resveratrol Preparation of Phenols: Nucleophilic Aromatic Substitution Alcohol Chemistry of Phenols Real Life: Medicine 22-2 Aspirin: The Miracle Drug Electrophilic Substitution of Phenols 22-7 22-8 22-9 22-10 22-11 22-12 23 An Electrocyclic Reaction of the Benzene Ring: The Claisen Rearrangement Oxidation of Phenols: Benzoquinones Real Life: Biology 22-3 Chemical Warfare in Nature: The Bombardier Beetle Oxidation-Reduction Processes in Nature Arenediazonium Salts Electrophilic Substitution with Arenediazonium Salts: Diazo Coupling Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems ESTER ENOLATES AND THE CLAISEN CONDENSATION Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents 23-1 23-2 23-3 23-4 23-5 β -Dicarbonyl Compounds: Claisen Condensations Real Life: Nature 23-1 Claisen Condensations Assemble Biological Molecules β -Dicarbonyl Compounds as Synthetic Intermediates β -Dicarbonyl Anion Chemistry: Michael Additions Acyl Anion Equivalents: Preparation of α -Hydroxyketones Real Life: Nature 23-2 Thiamine: A Natural, Metabolically Active Thiazolium Salt Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems 24 CARBOHYDRATES Polyfunctional Compounds in Nature 24-1 24-2 24-3 24-4 24-5 24-6 24-7 24-8 24-9 24-10 24-11 24-12 24-13 25 Names and Structures of Carbohydrates Conformations and Cyclic Forms of Sugars Anomers of Simple Sugars: Mutarotation of Glucose Polyfunctional Chemistry of Sugars: Oxidation to Carboxylic Acids Oxidative Cleavage of Sugars Reduction of Monosaccharides to Alditols Carbonyl Condensations with Amine Derivatives Ester and Ether Formation: Glycosides Step-by-Step Buildup and Degradation of Sugars Real Life: Nature 24-1 Biological Sugar Synthesis Relative Configurations of the Aldoses: An Exercise in Structure Determination Complex Sugars in Nature: Disaccharides Real Life: Food Chemistry 24-2 Manipulating Our Sweet Tooth Polysaccharides and Other Sugars in Nature Real Life: Medicine 24-3 Sialic Acid, “Bird Flu,” and Rational Drug Design Worked Example: Integrating the Concepts New Reactions Important Concepts Problems HETEROCYCLES Heteroatoms in Cyclic Organic Compounds 25-1 25-2 Naming the Heterocycles Nonaromatic Heterocycles Real Life: Medicine 25-1 Smoking, Nicotine, Cancer, and Medicinal Chemistry 25-3 25-4 25-5 25-6 25-7 25-8 25-9 26 Structures and Properties of Aromatic Heterocyclopentadienes Reactions of the Aromatic Heterocyclopentadienes Structure and Preparation of Pyridine: An Azabenzene Reactions of Pyridine Real Life: Biochemistry 25-2 Lessons from Redox-Active Pyridinium Salts in Nature: Nicotinamide Adenine Dinucleotide, Dihydropyridines, and Synthesis Quinoline and Isoquinoline: The Benzopyridines Real Life: Biology 25-3 Folic Acid, Vitamin D, Cholesterol, and the Color of Your Skin Alkaloids: Physiologically Potent Nitrogen Heterocycles in Nature Real Life: Nature 25-4 Nature is Not Always Green: Natural Pesticides Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems AMINO ACIDS, PEPTIDES, PROTEINS, AND NUCLEIC ACIDS Nitrogen-Containing Polymers in Nature 26-1 26-2 26-3 26-4 26-5 26-6 Structure and Properties of Amino Acids Real Life: Medicine 26-1 Arginine and Nitric Oxide in Biochemistry and Medicine Synthesis of Amino Acids: A Combination of Amine and Carboxylic Acid Chemistry Synthesis of Enantiomerically Pure Amino Acids Real Life: Chemistry 26-2 Enantioselective Synthesis of Optically Pure Amino Acids: Phase-Transfer Catalysis Peptides and Proteins: Amino Acid Oligomers and Polymers Determination of Primary Structure: Amino Acid Sequencing Synthesis of Polypeptides: A Challenge in the Application of Protecting Groups 26-7 26-8 26-9 26-10 26-11 26-12 Merrifield Solid-Phase Peptide Synthesis Polypeptides in Nature: Oxygen Transport by the Proteins Myoglobin and Hemoglobin Biosynthesis of Proteins: Nucleic Acids Real Life: Medicine 26-3 Synthetic Nucleic Acid Bases and Nucleosides in Medicine Protein Synthesis Through RNA DNA Sequencing and Synthesis: Cornerstones of Gene Technology Real Life: Forensics 26-4 DNA Fingerprinting Worked Examples: Integrating the Concepts New Reactions Important Concepts Problems Answers to Exercises Index ... Contents PREFACE: A User’s Guide to ORGANIC CHEMISTRY: Structure and Function STRUCTURE AND BONDING IN ORGANIC MOLECULES STRUCTURE AND REACTIVITY Acids and Bases, Polar and Nonpolar Molecules REACTIONS... User’s Guide to ORGANIC CHEMISTRY: Structure and Function STRUCTURE AND BONDING IN ORGANIC MOLECULES 1-1 1-2 1-3 1-4 1-5 1-6 1-7 1-8 1-9 1-10 The Scope of Organic Chemistry: An Overview Real Life:... 1976, he has taught organic chemistry to some 20,000 nonchemistry majors, winning seven teaching awards, publishing over 100 papers in various areas related to organic chemistry, and refereeing several