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أخوانى فى الله أحضرت لكم كتاب Organic Chemistry Sixth Edition Janice Gorzynski Smith University of Hawai'i at Manoa
![كتاب Organic Chemistry O_c_e_10](https://i.servimg.com/u/f61/15/36/74/14/o_c_e_10.jpg) و المحتوى كما يلي :
Page v Contents Preface ?xix Acknowledgments ?xxv Prologue ?1 What Is Organic Chemistry? ?1 Some Representative Molecules ?2 Marine Natural Products ?4 buttchi 3 Sha Life/ Shutterstock Structure and Bonding ?7 The Periodic Table ?8 Bonding ?10 Lewis Structures ?12 Isomers ?17 Exceptions to the Octet Rule ?18 Resonance ?18 Determining Molecular Shape ?24 Drawing Organic Structures Page vi Hybridization ?35 Ethane, Ethylene, and Acetylene ?38 Bond Length and Bond Strength ?43 Electronegativity and Bond Polarity ?44 Polarity of Molecules ?46 Oxybenzone—A Representative Organic Molecule ?47 Chapter 1 Review ?49 Key Concepts ?49 Key Skills ?50 Problems ?52 Comstock/PunchStock Acids and Bases ?59 Br?nsted–Lowry Acids and Bases ?60 Reactions of Br?nsted–Lowry Acids and Bases ?61 Acid Strength and pKa ?64 Predicting the Outcome of Acid–Base Reactions ?64 Factors That Determine Acid Strength ?68 Common Acids and Bases ?78 Aspirin ?79 Lewis Acids and Bases ?80 Chapter 2 Review ?83 Key Concepts ?83 Key Skills ?84 Problems Introduction to Organic Molecules and Functional Groups ?93 Functional Groups ?94 An Overview of Functional Groups ?95 Intermolecular Forces ?102 Physical Properties ?105 Application: Vitamins ?112 Application: Soap ?114 Application: The Cell Membrane ?115 Functional Groups and Reactivity ?118 Biomolecules ?119 Chapter 3 Review ?121 Key Concepts ?121 Key Skills ?123 Problems ?124 Narongsak Nagadhana/Shutterstock Alkanes ?131 Alkanes—An Introduction Cycloalkanes ?134 An Introduction to Nomenclature ?135 Naming Alkanes ?136 Naming Cycloalkanes ?141 Common Names ?143 Natural Occurrence of Alkanes ?144 Properties of Alkanes ?145 Conformations of Acyclic Alkanes—Ethane ?146 Conformations of Butane ?149 An Introduction to Cycloalkanes ?153 Cyclohexane ?154 Substituted Cycloalkanes ?157 Oxidation of Alkanes ?163 Lipids—Part 1 ?166 Chapter 4 Review ?168 Key Concepts ?168 Key Skills ?170 Problems ?172 George Ostertag/ Alamy Stock Photo Stereochemistry ?179 Starch and Cellulose ?180 The Two Major Classes of Isomers ?182 Looking Glass Chemistry—Chiral and Achiral Molecules ?183 Stereogenic Centers ?186 Stereogenic Centers in Cyclic Compounds ?189 Labeling Stereogenic Centers with R or S ?192 Disastereomers ?197 Meso Compounds R and S Assignments in Compounds with Two or Page vii More Stereogenic Centers ?201 Disubstituted Cycloalkanes ?202 Isomers—A Summary ?203 Physical Properties of Stereoisomers ?204 Chemical Properties of Enantiomers ?209 Chapter 5 Review ?211 Key Concepts ?211 Key Skills ?213 Problems ?215 Ninikas/Getty Images Understanding Organic Reactions ?222 Writing Equations for Organic Reactions ?223 Kinds of Organic Reactions ?224 Bond Breaking and Bond Making ?226 Bond Dissociation Energy ?230 Thermodynamics ?234 Enthalpy and Entropy ?236 Energy Diagrams ?238 Energy Diagram for a Two-Step Reaction Mechanism ?240 Kinetics ?242 Catalysts ?245 Enzymes ?246 Chapter 6 Review ?247 Key Concepts ?247 Key Equations ?248 Key Skills ?248 Problems Page viii Source: Claire Fackler, CINMS/NOAA Alkyl Halides and Nucleophilic Substitution ?256 Introduction to Alkyl Halides ?257 Nomenclature ?258 Properties of Alkyl Halides ?259 Interesting Alkyl Halides ?260 The Polar Carbon–Halogen Bond ?262 General Features of Nucleophilic Substitution ?263 The Leaving Group ?264 The Nucleophile ?266 Possible Mechanisms for Nucleophilic Substitution ?270 Two Mechanisms for Nucleophilic Substitution ?271 The SN2 Mechanism ?272 The SN1 Mechanism ?277 Carbocation Stability ?282 The Hammond Postulate ?283 When Is the Mechanism SN1 or SN2? ?286 Biological Nucleophilic Substitution ?292 Vinyl Halides and Aryl Halides ?295 Organic Synthesis ?295 Chapter 7 Review ?297 Key Concepts ?297 Key Skills ?299 Key Mechanism Concepts ?300 Problems Forest & Kim Starr Alkyl Halides and Elimination Reactions ?308 General Features of Elimination ?309 Alkenes—The Products of Elimination Reactions ?310 The Mechanisms of Elimination ?314 The E2 Mechanism ?314 The Zaitsev Rule ?318 The E1 Mechanism ?320 SN1 and E1 Reactions ?323 Stereochemistry of the E2 Reaction ?324 When Is the Mechanism E1 or E2? ?328 E2 Reactions and Alkyne Synthesis ?328 When Is the Reaction SN1, SN2, E1, or E2? ?330 Chapter 8 Review ?334 Key Concepts ?334 Key Skills ?335 Key Mechanism Concepts ?337 Problems ?338 Daniel C. Smith 9.18 Page ix Alcohols, Ethers, and Related Compounds ?345 Introduction ?346 Structure and Bonding ?347 Nomenclature ?348 Properties of Alcohols, Ethers, and Epoxides ?351 Interesting Alcohols, Ethers, and Epoxides ?352 Preparation of Alcohols, Ethers, and Epoxides ?355 General Features—Reactions of Alcohols, Ethers, and Epoxides ?357 Dehydration of Alcohols to Alkenes ?359 Carbocation Rearrangements ?362 Dehydration Using POCl3 and Pyridine ?364 Conversion of Alcohols to Alkyl Halides with HX ?365 Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3 Tosylate—Another Good Leaving Group ?372 Reaction of Ethers with Strong Acid ?375 Thiols and Sulfides ?376 Reactions of Epoxides ?379 Application: Epoxides, Leukotrienes, and Asthma ?384 Application: Benzo[a]pyrene, Epoxides, and Cancer ? Chapter 9 Review ?386 Key Concepts ?386 Key Reactions ?386 Key Skills ?388 Key Mechanism Concepts in Reactions of Alcohols ?390 Problems Adam Gault/Getty Images Alkenes and Addition Reactions ?397 Introduction ?398 Calculating Degrees of Unsaturation ?399 Nomenclature ?401 Properties of Alkenes ?405 Interesting Alkenes ?406 Lipids—Part 2 ?407 Preparation of Alkenes ?409 Introduction to Addition Reactions ?410 Hydrohalogenation—Electrophilic Addition of HX ?411 Markovnikov's Rule ?413 Stereochemistry of Electrophilic Addition of HX ?415 Hydration—Electrophilic Addition of Water ?417 Halogenation—Addition of Halogen ?418 Stereochemistry of Halogenation ?419 Halohydrin Formation ?421 Hydroboration–Oxidation ?424 Keeping Track of Reactions ?428 Alkenes in Organic Synthesis ?430 Chapter 10 Review ?432 Key Concepts ?432 Key Reactions ?433 Key Skills ?433 Key Mechanism Concepts ?434 Problems ?435 McGraw-Hill Education/ Chris Kerrigan, photographer Alkynes and Synthesis Page x Introduction ?442 Nomenclature ?443 Properties of Alkynes ?444 Interesting Alkynes ?445 Preparation of Alkynes ?446 Introduction to Alkyne Reactions ?447 Addition of Hydrogen Halides ?449 Addition of Halogen ?451 Addition of Water ?451 Hydroboration–Oxidation ?454 Reaction of Acetylide Anions ?456 Synthesis ?460 Chapter 11 Review ?463 Key Reactions ?463 Key Skills ?463 Problems ?465 Amarita/Shutterstock Oxidation and Reduction ?472 Introduction ?473 Reducing Agents ?474 Reduction of Alkenes ?475 Application: Hydrogenation of Oils ?478 Reduction of Alkynes ?480 The Reduction of Polar C–X ? Bonds ?483 Oxidizing Agents ?484 Epoxidation ?485 Dihydroxylation Spectroscopy A Oxidative Cleavage of Alkenes ?491 Oxidative Cleavage of Alkynes ?493 Oxidation of Alcohols ?494 Green Chemistry ?497 Biological Oxidation ?498 Sharpless Epoxidation ?499 Chapter 12 Review ?502 Key Concepts ?502 Key Reactions ?502 Key Skills ?504 Problems ?505 atomazul/123RF Mass Spectrometry ?512 Mass Spectrometry and the Molecular Ion ?513 Alkyl Halides and the M + 2 Peak ?518 Fragmentation ?520 Fragmentation Patterns of Some Common Functional Groups ?523 Other Types of Mass Spectrometry ?525 Chapter Review ?528 Key Concepts ?528 Key Skills ?528 Problems ?529Spectroscopy B Spectroscopy C Page xi T.Daly/Alamy Stock Photo Infrared Spectroscopy ?534 Electromagnetic Radiation ?535 The General Features of Infrared Spectroscopy ?537 IR Absorptions ?539 Infrared Spectra of Common Functional Groups ?546 IR and Structure Determination ?554 Chapter Review ?556 Key Concepts ?556 Key Skills ?557 Problems ?558 Daniel C. Smith Nuclear Magnetic Resonance Spectroscopy ?562 An Introduction to NMR Spectroscopy ?563 1H NMR: Number of Signals ?566 1H NMR: Position of Signals ?571 The Chemical Shifts of Protons on sp2 and sp Hybridized Carbons ?575 1H NMR: Intensity of Signals 1H NMR: Spin–Spin Splitting ?578 More-Complex Examples of Splitting ?582 Spin–Spin Splitting in Alkenes ?585 Other Facts About 1H NMR Spectroscopy ?587 Using 1H NMR to Identify an Unknown ?590 13C NMR Spectroscopy ?593 Magnetic Resonance Imaging (MRI) ?597 Chapter Review ?598 Key Concepts ?598 Key Skills ?598 Problems ?602 jeep2499/Shutterstock Radical Reactions ?611 Introduction ?612 General Features of Radical Reactions ?613 Halogenation of Alkanes ?615 The Mechanism of Halogenation ?616 Chlorination of Other Alkanes ?619 Chlorination Versus Bromination ?619 Halogenation as a Tool in Organic Synthesis ?622 The Stereochemistry of Halogenation Reactions ?623 Application: The Ozone Layer and CFCs ?625 Radical Halogenation at an Allylic Carbon ?627 Application: Oxidation of Unsaturated Lipids ?630 Application: Antioxidants ?631 Radical Addition Reactions to Double Bonds ?632 Polymers and Polymerization Page xii Chapter 13 Review ?638 Key Concepts ?638 Key Reactions ?638 Key Skills ?639 Problems ?641 John Foxx/Getty Images Conjugation, Resonance, and Dienes ?648 Conjugation ?649 Resonance and Allylic Carbocations ?651 Common Examples of Resonance ?653 The Resonance Hybrid ?654 Electron Delocalization, Hybridization, and Geometry ?656 Conjugated Dienes ?657 Interesting Dienes and Polyenes ?659 The Carbon–Carbon ? Bond Length in Buta-1,3-diene ?660 Stability of Conjugated Dienes ?660 Electrophilic Addition: 1,2- Versus 1,4-Addition ?661 Kinetic Versus Thermodynamic Products ?663 The Diels–Alder Reaction ?666 Specific Rules Governing the Diels–Alder Reaction ?668 Other Facts About the Diels–Alder Reaction ?672 Conjugated Dienes and Ultraviolet Light ?675 Chapter 14 Review ?678 Key Concepts ?678 Key Reactions ?679 Key Skills ?679 Problems Daniel C. Smith Benzene and Aromatic Compounds ?689 Background ?690 The Structure of Benzene ?691 Nomenclature of Benzene Derivatives ?693 Spectroscopic Properties ?695 Interesting Aromatic Compounds ?696 Benzene's Unusual Stability ?697 The Criteria for Aromaticity—Hückel's Rule ?699 Examples of Aromatic Compounds ?701 What Is the Basis of Hückel's Rule? ?708 The Inscribed Polygon Method for Predicting Aromaticity ? Buckminsterfullerene—Is It Aromatic? ?713 Chapter 15 Review ?715 Key Concepts ?715 Key Skills ?715 Problems ?717 Jill Braaten Reactions of Aromatic Compounds Page xiii Electrophilic Aromatic Substitution ?726 The General Mechanism ?727 Halogenation ?728 Nitration and Sulfonation ?730 Friedel–Crafts Alkylation and Friedel–Crafts Acylation ?732 Substituted Benzenes ?739 Electrophilic Aromatic Substitution of Substituted Benzenes ?742 Why Substituents Activate or Deactivate a Benzene Ring ?746 Orientation Effects in Substituted Benzenes ?747 Limitations on Electrophilic Substitution Reactions with Substituted Benzenes ?750 Disubstituted Benzenes ?752 Synthesis of Benzene Derivatives ?754 Nucleophilic Aromatic Substitution ?755 Halogenation of Alkyl Benzenes ?759 Oxidation and Reduction of Substituted Benzenes ?761 Multistep Synthesis ?765 Chapter 16 Review ?767 Key Concepts ?767 Key Reactions ?768 Key Skills ?769 Key Mechanism Concepts ?771 Problems ?772 AS Food studio/Shutterstock Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction ?780 Introduction General Reactions of Carbonyl Compounds ?782 A Preview of Oxidation and Reduction ?785 Reduction of Aldehydes and Ketones ?787 The Stereochemistry of Carbonyl Reduction ?789 Enantioselective Carbonyl Reductions ?790 Reduction of Carboxylic Acids and Their Derivatives ?793 Oxidation of Aldehydes ?798 Organometallic Reagents ?799 Reaction of Organometallic Reagents with Aldehydes and Ketones ?802 Retrosynthetic Analysis of Grignard Products ?805 Protecting Groups ?807 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives ?810 Reaction of Organometallic Reagents with Other Compounds ?,?-Unsaturated Carbonyl Compounds ?815 Summary—The Reactions of Organometallic Reagents ?818 Synthesis ?818 Chapter 17 Review ?821 Key Reactions ?821 Key Skills ?823 Key Mechanism Concepts ?825 Problems ?825 iStock/Getty Images Aldehydes and Ketones—Nucleophilic Addition ? Introduction Page xiv Nomenclature ?835 Properties of Aldehydes and Ketones ?839 Interesting Aldehydes and Ketones ?841 Preparation of Aldehydes and Ketones ?842 Reactions of Aldehydes and Ketones—General Considerations ?843 Nucleophilic Addition of H? and R?—A Review ?846 Nucleophilic Addition of ?CN ?848 The Wittig Reaction ?850 Addition of 1° Amines ?855 Addition of 2° Amines ?858 Addition of H2O—Hydration ?861 Addition of Alcohols—Acetal Formation ?863 Acetals as Protecting Groups ?867 Cyclic Hemiacetals ?868 An Introduction to Carbohydrates ?871 Chapter 18 Review ?872 Key Concepts ?872 Key Reactions ?873 Key Skills ?874 Problems ?876 Sarka Babicka/Getty Images Carboxylic Acids and Nitriles ?885 Structure and Bonding ?886 Nomenclature ?887 Physical and Spectroscopic Properties ?890 Interesting Carboxylic Acids and Nitriles ?892 Aspirin, Arachidonic Acid, and Prostaglandins Page xv Preparation of Carboxylic Acids ?894 Carboxylic Acids—Strong Organic Br?nsted–Lowry Acids ? 895 Inductive Effects in Aliphatic Carboxylic Acids ?899 Substituted Benzoic Acids ?901 Extraction ?904 Amino Acids ?907 Nitriles ?911 Chapter 19 Review ?915 Key Concepts ?915 Key Reactions ?916 Key Skills ?916 Problems ?918 LIKIT SUPASAI/Shutterstock Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution ?926 Introduction ?927 Structure and Bonding ?929 Nomenclature ?930 Physical and Spectroscopic Properties ?934 Interesting Esters and Amides ?936 Introduction to Nucleophilic Acyl Substitution ?938 Reactions of Acid Chlorides ?941 Reactions of Anhydrides ?943 Reactions of Carboxylic Acids ?945 Reactions of Esters ?950 Application: Lipid Hydrolysis ?952 Reactions of Amides Application: The Mechanism of Action of ?-Lactam Antibiotics ?956 Summary of Nucleophilic Acyl Substitution Reactions ?957 Natural and Synthetic Fibers ?958 Biological Acylation Reactions ?960 Chapter 20 Review ?962 Key Concepts ?962 Key Reactions ?962 Key Skills ?964 Problems ?964 surachetkhamsuk/ iStock/Getty Images Substitution Reactions of Carbonyl Compounds at the ? Carbon ?973 Introduction ?974 Enols ?975 Enolates ?977 Enolates of Unsymmmetrical Carbonyl Compounds ?982 Racemization at the ? Carbon ?984 A Preview of Reactions at the ? Carbon ?985 Halogenation at the ? Carbon ?986 Direct Enolate Alkylation ?990 Malonic Ester Synthesis ?993 Acetoacetic Ester Synthesis ?998 Chapter 21 Review ?1001 Key Reactions ?1001 Key Skills ?1002 Problems Page xvi Jill Braaten Carbonyl Condensation Reactions ?1011 The Aldol Reaction ?1012 Crossed Aldol Reactions ?1016 Directed Aldol Reactions ?1020 Intramolecular Aldol Reactions ?1022 The Claisen Reaction ?1025 The Crossed Claisen and Related Reactions ?1027 The Dieckmann Reaction ?1029 The Michael Reaction ?1030 The Robinson Annulation ?1032 Chapter 22 Review ?1036 Key Reactions ?1036 Key Skills ?1037 Problems ?1038 Daniel C. Smith Amines ?1047 Introduction ?1048 Structure and Bonding ?1048 Nomenclature Physical and Spectroscopic Properties ?1052 Interesting and Useful Amines ?1054 Preparation of Amines ?1057 Reactions of Amines—General Features ?1064 Amines as Bases ?1064 Relative Basicity of Amines and Other Compounds ?1066 Amines as Nucleophiles ?1072 Hofmann Elimination ?1074 Reactions of Amines with Nitrous Acid ?1077 Substitution Reactions of Aryl Diazonium Salts ?1079 Coupling Reactions of Aryl Diazonium Salts ?1084 Application: Synthetic Dyes and Sulfa Drugs ?1085 Chapter 23 Review ?1088 Key Concepts ?1088 Key Reactions ?1089 Key Skills ?1091 Problems ?1093 DEA/M. Giovanoli/Getty Images Carbon–Carbon Bond-Forming Reactions in Organic Synthesis ?1102 Coupling Reactions of Organocuprate Reagents ?1103 Suzuki Reaction ?1105 Heck Reaction ?1110 Carbenes and Cyclopropane Synthesis ?1112 Simmons–Smith Reaction ?1115 Metathesis ?1116 Chapter 24 Review ?1121 Key Reactions Page xvii Key Skills ?1122 Problems ?1123 Nature Picture Library/Alamy Stock Photo Pericyclic Reactions ?1131 Types of Pericyclic Reactions ?1132 Molecular Orbitals ?1133 Electrocyclic Reactions ?1136 Cycloaddition Reactions ?1142 Sigmatropic Rearrangements ?1146 Summary of Rules for Pericyclic Reactions ?1152 Chapter 25 Review ?1153 Key Concepts ?1153 Key Reactions ?1153 Key Skills ?1154 Problems ?1155 MaraZe/Shutterstock Carbohydrates ?1162 Introduction ?1163 Monosaccharides ?1164 The Family of D-Aldoses The Family of D-Ketoses ?1171 Physical Properties of Monosaccharides ?1172 The Cyclic Forms of Monosaccharides ?1172 Glycosides ?1180 Reactions of Monosaccharides at the OH Groups ?1183 Reactions at the Carbonyl Group—Oxidation and Reduction ? 1184 Reactions at the Carbonyl Group—Adding or Removing One Carbon Atom ?1187 Disaccharides ?1191 Polysaccharides ?1193 Other Important Sugars and Their Derivatives ?1196 Chapter 26 Review ?1201 Key Reactions ?1201 Key Skills ?1203 Problems ?1206 Daniel C. Smith Amino Acids and Proteins ?1212 Amino Acids ?1213 Synthesis of Amino Acids ?1217 Separation of Amino Acids ?1220 Enantioselective Synthesis of Amino Acids ?1223 Peptides ?1225 Peptide Sequencing ?1229 Peptide Synthesis ?1232 Automated Peptide Synthesis ?1237 Protein Structure ?1239 Important Proteins Page xviii Chapter 27 Review ?1248 Key Reactions ?1248 Key Skills ?1250 Problems ?1253 stuar/Shutterstock Synthetic Polymers ?1259 Introduction ?1260 Chain-Growth Polymers—Addition Polymers ?1261 Anionic Polymerization of Epoxides ?1268 Ziegler–Natta Catalysts and Polymer Stereochemistry ?1269 Natural and Synthetic Rubbers ?1270 Step-Growth Polymers—Condensation Polymers ?1272 Polymer Structure and Properties ?1276 Green Polymer Synthesis ?1278 Polymer Recycling and Disposal ?1281 Chapter 28 Review ?1284 Key Concepts ?1284 Key Reactions ?1284 Key Skills ?1285 Problems ?1285 Iconotec/Glowimages Appendix A Appendix B Appendix C Appendix D Appendix E Appendix F Appendix G Appendix H Appendix I Appendix J Lipids 1292 (Available Online) Introduction ?1293 Waxes ?1294 Triacylglycerols ?1295 Phospholipids ?1299 Fat-Soluble Vitamins ?1302 Eicosanoids ?1303 Terpenes ?1306 Steroids ?1312 Chapter 29 Review ?1317 Key Concepts ?1317 Key Reactions ?1318 Key Skills ?1319 Problems ?1319 Periodic Table of the Elements ?A Common Abbreviations, Arrows, and Symbols ?A-1 pKa Values for Selected Compounds ?A-3 Nomenclature ?A-5 Bond Dissociation Energies for Some Common Bonds [A–B ? A· + ·B] ?A-9 Reactions That Form Carbon–Carbon Bonds ?A-10 Characteristic IR Absorption Frequencies ?A-11 Characteristic NMR Absorptions ?A-12 General Types of Organic Reactions ?A-14 How to Synthesize Particular Functional Groups ?A-16 Glossary ?G Index
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