An International Thomson Publishing Company

Organic Chemistry Joseph M. Hornback University of Denver 5t Brooks/Cole Publishing Company I(T)P An International Thomson Publishing Company Pacific Grove 'Albany Belmont Bonn Boston Cincinnati Detroit Johannesburg London Madrid Melbourne Mexico City New York Paris Singapore Mjo Toronto Washington

Brief Contents JL A Simple Model for Chemical Bonds 1 /il Organic Compounds: A First Look 29 J) Orbitals and Bonding 59 Ah Proton Transfer: A Simple Reaction 105 J) Functional Groups and Nomenclature I 147 lu) Stereochemistry 183 II Nucleophilic Substitution Reactions 257 Elimination Reactions 309 j) Synthetic Uses of Substitution and Elimination Reactions 345 1(0) Additions to Carbon-Carbon Double and Triple Bonds 401 Functional Groups and Nomenclature II 461 Structure Determination by Spectroscopy I: Infrared and Nuclear Magnetic Resonance Spectroscopy 497

VÜi Brief Contents 13 Structure Determination by Spectroscopy II: Ultraviolet-Visible Spectroscopy and Mass Spectrometry 607 14 Additions to the Carbonyl Group 635 15 Substitutions at the Carbonyl Group 693 JLO Enolate and Other Carbon Nucleophiles 757 17 Benzene and Aromatic Compounds 807 1(0) Aromatic Substitution Reactions 837 19 The Chemistry of Radicals 903 2(0) Pericyclic Reactions 943 21 The Synthesis of Organic Compounds 7007 Industrial Organic Chemistry 1041 235 Synthetic Polymers 7069 24 Carbohydrates 7705 25 Amino Acids, Peptides, and Proteins 1145 26 Nucleotides and Nucleic Acids 77S7 27/ Other Natural Products 7279

Contents 1 A Simple Model for Chemical Bonds 1.1 Introduction 1 1.2 The Field of Organic Chemistry 1 Elaboration: The Death of the Vital Force Theory 1.3 Simple Atomic Structure 3 1.4 Ionic Bonding 4 1.5 Covalent Bonding 6 1.6 Lewis Structures 7 1.7 Covalent Ions 10 1.8 Formal Charges 12 1.9 Resonance 16 1.10 Polar Bonds 17 1.11 Shapes of Molecules 19 1.12 Dipole Moments 22 1.13 Summary 24 End-of-Chapter Problems 25 JL Organic Compounds: A First Look 29 2.1 Introduction 29 2.2 Common Bonding Situations 29 2.3 Bond Strengths and Bond Lengths 32 2.4 Structural Isomers 33 Elaboration: Life Based on Silicon? 34 2.5 Degree of Unsaturation 39 Elaboration: Enumerating Structural Isomers 43 ix '

Contents 2.6 Physical Properties and Molecular Structure 44 2.7 Melting Points, Boiling Points, and Solubilities 46 Elaboration: Melting Point of Cubane 47 Elaboration: Boiling Points of Fuels 48 Elaboration: A Chemical Handwarmer 49 2.8 Introduction to Functional Croups 50 2.9 Summary 53 End-of-Chapter Problems 53 3) Orbitals and Bonding 59 3.1 Introduction 59 3.2 Atomic Orbitals 59 Elaboration: Quantum Numbers 60 3.3 Molecular Orbitals 64 3.4 Single Bonds and sp 3 Hybridization 67 3.5 Double Bonds and sp 2 Hybridization 70 3.6 Triple Bonds and sp Hybridization 74 3.7 Resonance and MO Theory 77 3.8 Rules for Resonance Structures 80 3.9 Types of Resonance Interactions 84 Elaboration: Resonance Stabilization of theallyl Radical 88 Elaboration: Resonance and the Bond Lengths of Naphthalene 92 3.10 Molecular Orbital Energies 94 Elaboration: Reaction of Formaldehyde with Sodium 96 3.11 Summary 97 End-of-Chapter Problems 99 4 Proton Transfer: A Simple Reaction 105 4.1 Introduction 105 4.2 Definitions 105 4.3 The Acid-Base Equilibrium 109 Elaboration: Base Dissociation Constants 111 4.4 Rate of the Acid-Base Reaction 115 4.5 Effect of the Atom Bonded to the Hydrogen on Acidity 117

Contents 4.6 Inductive Effects 119 4.7 Hydrogen Bonding 122 4.8 Hybridization 123 Elaboration: Calcium Carbide 124 4.9 Resonance 125 4.10 Tables of Acids and Bases 131 4.11 Substitution Reactions 134 Elaboration: Acidic and Basic Functional Groups 136 Elaboration: TheAcidity of Solvents 138 Elaboration: Superacids 139 4.12 Summary 140 End-of-Chapter Problems 141 J) Functional Groups and Nomenclature I 147 5.1 Introduction 147 5.2 Alkanes 147 5.3 Common Nomenclature of Alkanes 150 Elaboration: Energy Content of Fuels 151 5.4 Systematic Nomenclature of Alkanes 153 5.5 Systematic Nomenclature of Cycloalkanes 161 5.6 Alkenes 162 5.7 Alkynes 165 5.8 Alkyl Halides 166 5.9 Alcohols 168 Elaboration: Chlorinated Organic Compounds and the Environment 169 Elaboration: Chlorofluorocarbons and the Ozone Hole 171 5.10 Ethers 173 5.11 Amines 175 5.12 Summary 178 End-of-Chapter Problems 178 (6) Stereochemistry 183 6.1 Introduction 183 6.2 Geometricai Isomers 184 6.3 Designating the Connguration of Geometricai Isomers 188 6.4 Conformations 192

6.5 Conformations of Cyclic Molecules 199 6.6 Conformations of Cyclohexane 203 6.7 Conformations of Other Rings 208 6.8 Conformations of Cyclohexanes with One Substituent 208 Elaboration: How Much Strain Is Too Much? 209 6.9 Conformations of Cyclohexanes with Two or More Substituents 214 6.10 Chiral Molecules 219 6.11 Recognizing Chiral Molecules 221 6.12 Designating Configuration of Enantiomers 223 6.13 Properties of Enantiomers 227 Elaboration: The D, L Methodfor Designating Absolute Configuration 230 6.14 Molecules with Multiple Chiral Centers 232 6.15 Stereoisomers and Cyclic Compounds 236 6.16 Resolution: Separating Enantiomers 238 6.17 Fischer Projections 239 Elaboration: History of the Development of an Understanding of Stereochemistry 242 6.18 Reactions That Produce Enantiomers 244 Elaboration: Thalidomide and Chiral Synthesis 245 Elaboration: Other Chiral Compounds 246 6.19 Summary 249 End-of-Chapter Problems 250 Nucleophilic Substitution Reactions 257 7.1 Introduction 257 7.2 The General Reaction 258 7.3 Reaction Mechanisms 258 7.4 Bimolecular Nucleophilic Substitution 259 7.5 Stereochemistry of the S N 2 Reaction 260 7.6 Effect of Substitutents on the Rate of the S N 2 Reaction 263 7.7 Unimolecular Nucleophilic Substitution 267 7.8 Stereochemistry of the S N 1 Reaction 271 7.9 Effects of Substituents on the Rate of the S N 1 Reaction 274 Elaboration: The Triphenylmethyl Carbocation 276 7.10 Leaving Groups 277 Elaboration: Experimental Evidencefor Inversion of Configuration in S N 2 Reactions 281

Contents xiii 7.11 Nucleophiles 282 7.12 Effect of Solvent 285 7.13 Competition Between S N 1 and S N 2 Reactions 288 Elaboration: Chemical Tests Involving S N 1 and S N 2 Reactions 291 7.14 Intramolecular Reactions 292 7.15 Competing Reactions 293 Elaboration: Carbocation Rearrangements in Superacids 297 7.16 Summary 299 End-of-Chapter Problems 300 o Elimination Reactions 309 8.1 Introduction 309 8.2 The General Reaction 309 8.3 Bimolecular Elimination 310 Elaboration: Investigating Mechanisms I: Kinetic Isotope Effects 311 Elaboration: DDT-Resistant Insects 312 8.4 Stereochemistry of the E2 Reaction 313 8.5 Direction of Elimination 318 Elaboration: Syn Eliminations 319 8.6 Unimolecular Elimination 326 Elaboration: Investigating Mechanisms II: The Competition Between the S N 1 and El Pathways 328 8.7 Regiochemistry and Stereochemistry of the El Reaction 329 Elaboration: The Elcb Mechanism 330 8.8 The Competition Between Elimination and Substitution 332 Elaboration: Biological Elimination Reactions 337 8.9 Summary 338 End-of-Chapter Problems 339 9 Synthetic Uses of Substitution and Elimination Reactions 345 9.1 Introduction 345 9.2 Substitution Reactions 345

xiv Contents 9.3 Preparation of Alcohols 346 9.4 Preparation of Ethers 349 Elaboration: Poisonous A Ikylating Agents 354 9.5 Preparation of Esters 356 9.6 Preparation of Alkyl Halides 357 9.7 Preparation of Amines 361 Elaboration: Biological Methylations 365 9.8 Preparation of Hydrocarbons 366 9.9 Formation of Carbon-Carbon Bonds 367 9.10 Phosphorus and Sulfur Nucleophiles 369 9.11 Ring Opening of Epoxides 370 Elaboration: Sulfur Nucleophiles in Biochemistry 370 9.12 Elimination Reactions 373 Elaboration: Uses of Epoxides in Industry 374 9.13 Elimination of Hydrogen Halides (Dehydrohalogenation) 375 9.14 Preparation of Alkynes 376 9.15 Dehydration 377 9.16 Eliminations to Form Carbon-Oxygen Double Bonds; Oxidation Reactions 380 9.17 The Strategy of Organic Synthesis 383 Elaboration: Environmental^ Friendly Chemistry (Green Chemistry) 384 Elaboration: Cancer Chemotherapy 388 9.18 Summary 389 End-of-Chapter Problems 394 11(0) Additions to Carbon-Carbon Double and Triple Bonds 401 10.1 Introduction 401 10.2 The General Mechanism 402 10.3 Addition of Hydrogen Halides 403 10.4 Addition of Halogens 409 Elaboration: Formation of Carbocations in Halogen Additions 413 10.5 Halohydrin Formation 415 10.6 Addition of Water (Hydration) 417 Elaboration: Industrial Addition Reactions 419 10.7 Oxymercuration-Reduction 420

Contents XV 10.8 Hydroboration-Oxidation 424 Elaboration: Chiral Boranes in Organic Synthesis 430 10.9 Addition of Carbenes 433 Elaboration: Singlet and Triplet Carbenes 436 10.10 Epoxidation 437 10.11 Hydroxylation 439 10.12 Ozonolysis 440 10.13 Catalytic Hydrogenation 443 10.14 Additions to Conjugated Dienes 446 Elaboration: Asymmetrie Hydrogenation 447 10.15 Summary 449 End-of-Chapter Problems 454 II Functional Groups and Nomenclature II 461 11.1 Introduction 461 11.2 Aromatic Hydrocarbons 461 Elaboration: Structure Proof by the Number of Isomers 465 11.3 Phenols 466 11.4 Aldehydes and Ketones 469 11.5 Carboxylic Acids 473 11.6 Derivatives of Carboxylic Acids 475 Elaboration: Fragrant Organic Compounds 483 11.7 Sulfur and Phosphorus Compounds 485 11.8 Nomenclature of Compounds with Several Functional Groups 488 Elaboration: Medicinal Uses of DMSO 488 11.9 Summary 491 End-of-Chapter Problems 492 12! Structure Determination by Spectroscopy I: Infrared and Nuclear Magnetic Resonance Spectroscopy 497 12.1 Introduction 497 12.2 Electromagnetic Radiation 498 12.3 Interaction of Electromagnetic Radiation with Molecules 499 12.4 The Electromagnetic Spectrum 501

12.5 Infrared Spectroscopy 503 12.6 Generalizations 505 12.7 The Hydrogen Region 506 12.8 The Triple Bond Region 514 Elaboration: Remote Sensing of Automobile Pollutants 516 12.9 The Double-Bond Region 518 12.10 The Fingerprint Region 520 12.11 Interpretation of IR Spectra 522 Elaboration: The Greenhouse Effect 537 12.12 Nuclear Magnetic Resonance Spectroscopy 538 12.13 Theory of ^-NMR 540 12.14 The Chemical Shift 541 12.15 Spin Coupling 551 12.16 Complex Coupling 556 12.17 Chemical Exchange 557 12.18 Deuterium 558 Elaboration: NMR Spectroscopy of Carbocations in Superacid 558 12.19 Interpretation of 'H-NMR Spectra 560 Elaboration: Magnetic Resonance Imaging 566 12.20 Carbon-13 Magnetic Resonance Spectroscopy 567 12.21 Solved Problems Employing IR and NMR Spectra 575 Elaboration: Use of NMR to Study Reactions 586 12.22 Summary 587 End-of-Chapter Problems 588 Structure Determination by Spectroscopy II: Ultraviolet-Visible Spectroscopy and Mass Spectrometry 601 13.1 Introduction 601 13.2 Ultraviolet-Visible Spectroscopy 601 13.3 Types of Electronic Transitions 604 13.4 UV-Visible Spectroscopy in Structure Determination 607 13.5 Mass Spectrometry 608 Elaboration: Ozone and Ultraviolet Radiation 609 13.6 Determining the Molecular Formula 610 13.7 Fragmentation of the Molecular Ion 616

* Contents xvii 13.8 Summary 626 Elaboration: Gas Chromatography and Mass Spectrometry 626 End-of-Chapter Problems 627 14 Additions to the Carbonyl Group 635 14.1 Introduction 635 14.2 General Mechanisms 636 14.3 Addition of Hydride; Reduction of Aldehydes and Ketones 638 14.4 Addition of Water 640 14.5 Addition of Hydrogen Cyanide 644 14.6 Preparation and Properties of Organometallic Nucleophiles 646 14.7 Addition of Organometallic Nucleophiles 649 14.8 Addition of Phosphorus Ylides; The Wittig Reaction 653 Elaboration: Synthesis of Vitamin A 657 14.9 Addition of Nitrogen Nucleophiles 659 Elaboration: Removal of Water 661 Elaboration: Methamphetamine 667 14.10 Addition of Alcohols 667 Elaboration: Imines in Living Organisms 668 14.11 Conjugate Additions 674 14.12 Summary 678 End-of-Chapter Problems 682 Spectroscopy Problems 691 15 Substitutions at the Carbonyl Group 693 15.1 Introduction 693 15.2 The General Mechanism 693 15.3 Preparation of Acyl Chlorides 699 15.4 Preparation of Anhydrides 701 15.5 Preparation of Esters 702 15.6 Preparation of Carboxylic Acids 705 Elaboration: The Preparation of Soap 708 Elaboration: Establishing the Mechanism of Saponification 710 15.7 Preparation of Amides 715

Elaboration: Reaction Conditions 716 15.8 Reaction with Hydride Nucleophiles 718 15.9 Reduction of Acid Derivatives to Aldehydes 722 15.10 Reactions with Organometallic Nucleophiles 724 15.11 Preparation of Ketones 726 15.12 Derivatives of Sulfur and Phosphorus Acids 728 Elaboration: Nerve Gases and Pesticides 730 Elaboration: ATP as an Energy Carrier 732 15.13 Summary 734 End-of-Chapter Problems 739 Problems Involving Spectroscopy 747 11(6 Enolate and Other Carbon Nucleophiles 751 16.1 Introduction 751 16.2 Enols and Enolate Anions 752 16.3 Alkylation of Enolate Anions 755 Elaboration: Isomerization of Sugars 756 16.4 Alkylation of More Stabilized Anions 759 16.5 The Aldol Condensation 765 Elaboration: The Reverse Aldol Reaction in Metabolism 772 16.6 Ester Condensations 772 Elaboration: A n Industrial A Idol Reaction 774 16.7 Enamines 779 16.8 Other Carbon Nucleophiles 780 16.9 Conjugate Additions 784 16.10 Synthesis 787 16.11 Summary 792 End-of-Chapter Problems 796 Problems Involving Spectroscopy 803 17 Benzene and Aromatic Compounds 807 17.1 Introduction 807 17.2 Benzene 807 17.3 Resonance Energy of Benzene 809 17.4 Molecular Orbital Model for Cyclic Conjugated Molecules 811 17.5 Cyclobutadiene 814 17.6 Hückel's Rule 816

Contents xix 17.7 Cyclooctatetraene 817 Elaboration: Isomeric Cyclooctatetraenes 818 17.8 Heterocyclic Aromatic Compounds 819 17.9 Polycyclic Aromatic Hydrocarbons 822 Elaboration: Carcinogenic Polycyclic Aromatic Hydrocarbons 823 Elaboration: Buckminsterfullerene, A New Form of Carbon 824 17.10 NMR and Aromaticity 824 17.11 Annulenes 827 17.12 Aromatic and Antiaromatic Ions 828 17.13 Summary 830 End-of-Chapter Problems 831 Problems Involving Spectroscopy 834 lo Aromatic Substitution Reactions 837 18.1 Introduction 837 18.2 Mechanism for Electrophilic Aromatic Substitution 837 18.3 Effect of Substitutents 840 18.4 Effect of Multiple Substituents 848 18.5 Nitration 849 18.6 Halogenation 852 18.7 Sulfonation 854 18.8 Friedel-Crafts Alkylation 855 Elaboration: Synthetic Detergents 859 18.9 Friedel-Crafts Acylation 860 Elaboration: Preparation of BHT and BHA 862 18.10 Electrophilic Substitutions of Polycyclic Aromatic Compounds 865 18.11 Nucleophilic Aromatic Substitution; Diazonium Ions 866 18.12 Nucleophilic Aromatic Substitution; Addition-Elimination 869 18.13 Nucleophilic Aromatic Substitution; Elimination-Addition 872 Elaboration: Experimental Evidencefor the Benzyne Mechanism 874 Elaboration: Herbicides, Disinfectants, Dioxin, and Agent Orange 875

18.14 18.15 18.16 Some Additional Useful Reactions 876 Synthesis of Aromatic Compounds 881 Summary 885 End-of-Chapter Problems 890 Problems Invoiving Spectroscopy 900 119 The Chemistry of Radicals 903 19.1 Introduction 903 19.2 Radicals 903 19.3 Stability of Radicals 904 19.4 Geometry of Carbon Radicals 906 19.5 Generation of Radicals 907 19.6 General Radical Reactions 909 Elaboration: The Triphenylmethyl Radical 911 19.7 Kolbe Electrolysis 912 19.8 Halogenation 913 19.9 Dehalogenation 920 19.10 Autoxidation 921 Elaboration: The Industrial Preparation of Phenol 922 Elaboration: Vitamin E and Lipid Autoxidation 924 19.11 Radical Additions to Alkenes 926 19.12 Reductions and Radical Anions 929 19.13 Summary 934 End-of-Chapter Problems 936 Problems Invoiving Spectroscopy 941 2(0) Pericyclic Reactions 20.1 Introduction 943 20.2 Pericyclic Reactions 943 20.3 MO Theory for Conjugated Molecules 20.4 Electrocyclic Reactions 951 20.5 Examples of Electrocyclic Reactions Elaboration: Dewar Benzene 957 20.6 Cycloaddition Reactions 961 20.7 The Diels-Alder Reaction 963 956 946 943 Elaboration: Diels-Alder Adducts as Pesticides 968 20.8 Other Cycloaddition Reactions 971 20.9 Sigmatropic Rearrangements 972 20.10 Examples of Sigmatropic Rearrangements 977

< Contents xxi Elaboration: Degenerate Rearrangements 979 Elaboration: Suprafacial and Antarafacial Reactions 982 Elaboration: Pericyclic Reactions and Vitamin D 983 20.11 Rearrangements to Electron Deficient Centers 986 20.12 Summary 989 End-of-Chapter Problems 991 Problems Involving Spectroscopy 998 211 The Synthesis of Organic Compounds 1001 21.1 Introduction 1001 21.2 Protective Groups for Alcohols 1001 21.3 Protective Groups for Aldehydes and Ketones 1006 21.4 Protective Groups for Carboxylic Acids 1006 21.5 Protective Groups for Amines 1008 21.6 Retrosynthetic Analysis 1010 Elaboration: Pheromones 1014 21.7 Examples of Syntheses 1016 21.8 Reactions That Form Carbon-Carbon Bonds 1019 21.9 Preparation of Functional Groups 1020 21.10 Summary 1035 End-of-Chapter Problems 1035 22 Industrial Organic Chemistry 1041 22.1 Introduction 1041 22.2 The Organic Chemical Industry 1041 22.3 Important Industrial Organic Chemicals 1042 22.4 Sources of Organic Chemicals 1043 22.5 Chemicals from Ethylene 1046 Elaboration: Carbonylation Reactions 1048 22.6 Chemicals from Propylene 1050 Elaboration: The Metathesis Reaction 1052 22.7 Chemicals from Benzene and Other Aromatic Compounds 1053 Elaboration: Industrial Electrophilic Aromatic Substitution Reactions 1056 Elaboration: Dioctyl Phthalate Plasticizer 1060 22.8 Chemicals from Butylene 1061 22.9 Chemicals from Other Sources 1063

xxii Contents 22.10 Summary 1064 End-of-Chapter Problems 1065 Problems Involving Spectroscopy 1068 23] Synthetic Polymers 1069 23.1 Introduction 1069 23.2 Radical Chain Polymerization 1069 23.3 Structures of Polymers 1073 23.4 Ionic Polymerization 1076 Elaboration: Super Glue 1076 23.5 Coordination Polymerization 1078 23.6 Physical Properties of Polymers 1079 23.7 Major Thermoplastic Addition Polymers 1081 Elaboration: Teflon 1082 23.8 Elastomers 1084 Elaboration: Charles Goodyear and Vulcanization 1085 23.9 Condensation Polymers 1087 23.10 Thermoset Polymers 1092 Elaboration: Polybenzimidazole 1092 23.11 Chemical Properties of Polymers 1095 Elaboration: Recycling Plastics 1097 23.12 Summary 1098 End-of-Chapter Problems 1099 24 Carbohydrates 1103 24.1 Introduction 1103 24.2 Structures of Carbohydrates 1103 24.3 Stereochemistry of Carbohydrates 1104 Elaboration: R and S Nomenclature Applied to Sugars 1106 24.4 Cyclization of Monosaccharides 1108 24.5 Reactions of Monosaccharides 1113 Elaboration: Determination of Anomer Configuration 1114 Elaboration: A rtificial Sweeteners 1117 24.6 Fischer's Structure Proof for Glucose 1124 Elaboration: Emil Fischer 1130

Contents 24.7 Disaccharides 1130 24.8 Polysaccharides 1132 24.9 Other Carbohydrate-Containing Compounds 1134 Elaboration: Blood Groups 1136 24.10 Summary 1137 End-of-Chapter Problems 1138 Problems Involving Spectroscopy 1143 Amino Acids, Peptides, and Proteins 1145 25.1 Introduction 1145 25.2 Amino Acids 1145 25.3 Acid-Base Chemistry of Amino Acids 1148 25.4 Chemical Reactions of Amino Acids 1152 25.5 Laboratory Synthesis of Amino Acids 1153 Elaboration: Asymmetrie Synthesis of Amino Acids 1157 25.6 Peptides and Proteins 1159 Elaboration: Biosynthesis of Amino Acids from a-ketoacids 1160 Elaboration: NMR Spectra of Amides 1164 25.7 Sequencing Peptides 1165 25.8 Laboratory Synthesis of Peptides 1170 Elaboration: Frederick Sanger and the Sequence of Insulin 1171 25.9 Protein Structure 1180 25.10 Enzymes 1180 25.11 Summary 1182 End-of-Chapter Problems 1184 26 Nucleotides and Nucleic Acids 1187 26.1 Introduction 1187 26.2 Nucleosides and Nucleotides 1187 26.3 Structure of DNA and RNA 1190 Elaboration: Tautomers of Guanine and Thymine 1193 26.4 Replication, Transcription, and Translation 1196 Elaboration: Base-Catalyzed Hydrolysis of RNA 1196 Elaboration: The Treatment of AIDS with AZT 1199 26.5 Sequencing DNA 1200

xxiv Contents 26.6 Laboratory Synthesis of DNA 1207 Elaboration: Automated DNA Sequencing 1207 Elaboration: DNA Fingerprinting 1208 26.7 Summary 1212 End-of-Chapter Problems 1212 27/ Other Natural Products 1219 27.1 Introduction 1219 27.2 Terpenes 1219 27.3 Monoterpenes 1221 27.4 Sesquiterpenes 1225 27.5 Larger Terpenes 1228 Elaboration: Conformations of Decalin 1228 27.6 Steroids 1233 Elaboration: Syntheses That Mimic Nature 1235 27.7 Synthesis of Steroids 1237 Elaboration: The Birth Control Pill 1239 27.8 Alkaloids 1241 27.9 Fats and Related Compounds 1243 Elaboration: Partialfy Hydrogenated Vegetable Oil 1245 27.10 Prostaglandins 1246 Elaboration: Laboratory Synthesis of Prostaglandins 1248 27.11 Summary 1248 End-of-Chapter Problems 1249 Problems Involving Spectroscopy 1256 Appendix: Answers to Selected In-Chapter Problems AI Glossary Index II Gl