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Test Bank for Organic Chemistry 8th by Vollhardt

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Test Bank for Organic Chemistry 8th by Vollhardt

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Gain a deeper understanding of reactions, mechanisms, and synthetic analysis and their practical applications as Organic Chemistry breaks down topics using a sensible organization based on the concept that an organic molecule’s structure will determine its function.

 

Table of Content:

  1. Chapter 1 Structure and Bonding in Organic Molecules
  2. 1-1 The Scope of Organic Chemistry: An Overview
  3. Real Life: Nature 1-1 Urea: From Urine to Wöhler’s Synthesis to Industrial Fertilizer
  4. 1-2 Coulomb Forces: A Simplified View of Bonding
  5. 1-3 Ionic and Covalent Bonds: The Octet Rule
  6. 1-4 Electron-Dot Model of Bonding: Lewis Structures
  7. 1-5 Resonance Forms
  8. 1-6 Atomic Orbitals: A Quantum Mechanical Description of Electrons Around the Nucleus
  9. 1-7 Molecular Orbitals and Covalent Bonding
  10. 1-8 Hybrid Orbitals: Bonding in Complex Molecules
  11. 1-9 Structures and Formulas of Organic Molecules
  12. 1-10 A General Strategy for Solving Problems in Organic Chemistry
  13. Worked Examples: Integrating the Concepts
  14. Chapter 1 Review
  15. Chapter 2 Structure and Reactivity
  16. Acids and Bases, Polar and Nonpolar Molecules
  17. 2-1 Kinetics and Thermodynamics of Simple Chemical Processes
  18. 2-2 Keys to Success: Using Curved “Electron-Pushing” Arrows to Describe Chemical Reactions
  19. 2-3 Acids and Bases
  20. Real Life: Medicine 2-1 Stomach Acid, Peptic Ulcers, Pharmacology, and Organic Chemistry
  21. 2-4 Functional Groups: Centers of Reactivity
  22. 2-5 Straight-Chain and Branched Alkanes
  23. 2-6 Naming the Alkanes
  24. 2-7 Structural and Physical Properties of Alkanes
  25. Real Life: Nature 2-2 “Sexual Swindle” by Means of Chemical Mimicry
  26. 2-8 Rotation about Single Bonds: Conformations
  27. 2-9 Rotation in Substituted Ethanes
  28. 2-10 Worked Examples: Integrating the Concepts
  29. Chapter 2 Review
  30. Chapter 3 Reactions of Alkanes
  31. Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity
  32. 3-1 Strength of Alkane Bonds: Radicals
  33. 3-2 Structure of Alkyl Radicals: Hyperconjugation
  34. 3-3 Conversion of Petroleum: Pyrolysis
  35. Real Life: Sustainability 3-1 Sustainability and the Needs of the 21st Century: “Green” Chemistry
  36. 3-4 Chlorination of Methane: The Radical Chain Mechanism
  37. 3-5 Other Radical Halogenations of Methane
  38. 3-6 Keys to Success: Using the “Known” Mechanism as a Model for the “Unknown”
  39. 3-7 Chlorination of Higher Alkanes: Relative Reactivity and Selectivity
  40. 3-8 Selectivity in Radical Halogenation with Fluorine and Bromine
  41. 3-9 Synthetic Radical Halogenation
  42. Real Life: Medicine 3-2 Chlorination, Chloral, and DDT: The Quest to Eradicate Malaria
  43. 3-10 Synthetic Chlorine Compounds and the Stratospheric Ozone Layer
  44. 3-11 Combustion and the Relative Stabilities of Alkanes
  45. 3-12 Worked Examples: Integrating the Concepts
  46. Chapter 3 Review
  47. Chapter 4 Cycloalkanes
  48. 4-1 Names and Physical Properties of Cycloalkanes
  49. 4-2 Ring Strain and the Structure of Cycloalkanes
  50. 4-3 Cyclohexane: A Strain-Free Cycloalkane
  51. 4-4 Substituted Cyclohexanes
  52. 4-5 Larger Cycloalkanes
  53. 4-6 Polycyclic Alkanes
  54. 4-7 Carbocyclic Products in Nature
  55. Real Life: Materials 4-1 Cyclohexane, Adamantane, and Diamandoids: Diamond “Molecules”
  56. Real Life: Medicine 4-2 Cholesterol: How Is It Bad and How Bad Is It?
  57. Real Life: Medicine 4-3 Controlling Fertility: From “the Pill” to RU-486 to Male Contraceptives
  58. 4-8 Worked Examples: Integrating the Concepts
  59. Chapter 4 Review
  60. Chapter 5 Stereoisomers
  61. 5-1 Chiral Molecules
  62. Real Life: Nature 5-1 Chiral Substances in Nature
  63. 5-2 Optical Activity
  64. 5-3 Absolute Configuration: R,S Sequence Rules
  65. 5-4 Fischer Projections
  66. 5-5 Molecules Incorporating Several Stereocenters: Diastereomers
  67. Real Life: Nature 5-2 Stereoisomers of Tartaric Acid
  68. 5-6 Meso Compounds
  69. 5-7 Stereochemistry in Chemical Reactions
  70. Real Life: Medicine 5-3 Chiral Drugs—Racemic or Enantiomerically Pure?
  71. Real Life: Medicine 5-4 Why Is Nature “Handed”?
  72. 5-8 Resolution: Separation of Enantiomers
  73. 5-9 Worked Examples: Integrating the Concepts
  74. Chapter 5 Review
  75. Chapter 6 Properties and Reactions of Haloalkanes
  76. Bimolecular Nucleophilic Substitution
  77. 6-1 Physical Properties of Haloalkanes
  78. Real Life: Medicine 6-1 Fluorinated Pharmaceuticals
  79. 6-2 Nucleophilic Substitution
  80. 6-3 Reaction Mechanisms Involving Polar Functional Groups: Using “Electron-Pushing” Arrows
  81. 6-4 A Closer Look at the Nucleophilic Substitution Mechanism: Kinetics
  82. 6-5 Frontside or Backside Attack? Stereochemistry of the SN2 Reaction
  83. 6-6 Consequences of Inversion in SN2 Reactions
  84. 6-7 Structure and SN2 Reactivity: The Leaving Group
  85. 6-8 Structure and SN2 Reactivity: The Nucleophile
  86. 6-9 Keys to Success: Choosing Among Multiple Mechanistic Pathways
  87. 6-10 Structure and SN2 Reactivity: The Substrate
  88. 6-11 The SN2 Reaction at a Glance
  89. 6-12 Worked Examples: Integrating the Concepts
  90. Chapter 6 Review
  91. Chapter 7 Further Reactions of Haloalkanes
  92. Unimolecular Substitution and Pathways of Elimination
  93. 7-1 Solvolysis of Tertiary and Secondary Haloalkanes
  94. 7-2 Unimolecular Nucleophilic Substitution
  95. 7-3 Stereochemical Consequences of SN1 Reactions
  96. 7-4 Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular Substitution
  97. 7-5 Effect of the Alkyl Group on the SN1 Reaction: Carbocation Stability
  98. Real Life: Medicine 7-1 Unusually Stereoselective SN1 Displacement in Anticancer Drug Synthesis
  99. 7-6 Unimolecular Elimination: E1
  100. 7-7 Bimolecular Elimination: E2
  101. 7-8 Keys to Success: Substitution versus Elimination—Structure Determines Function
  102. 7-9 Summary of Reactivity of Haloalkanes
  103. 7-10 Worked Examples: Integrating the Concepts
  104. Chapter 7 Review
  105. Chapter 8 Hydroxy Functional Group: Alcohols
  106. Properties, Preparation, and Strategy of Synthesis
  107. 8-1 Naming the Alcohols
  108. 8-2 Structural and Physical Properties of Alcohols
  109. 8-3 Alcohols as Acids and Bases
  110. 8-4 Synthesis of Alcohols by Nucleophilic Substitution
  111. 8-5 Synthesis of Alcohols: Oxidation–Reduction Relation Between Alcohols and Carbonyl Compounds
  112. Real Life: Medicine 8-1 Oxidation and Reduction in the Body
  113. Real Life: Medicine 8-2 Don’t Drink and Drive: The Breath Analyzer Test
  114. 8-6 Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis
  115. 8-7 Organometallic Reagents in the Synthesis of Alcohols
  116. 8-8 Keys to Success: An Introduction to Synthetic Strategy
  117. Real Life: Chemistry 8-3 What Magnesium Does Not Do, Copper Can: Alkylation of Organometallics
  118. 8-9 Worked Examples: Integrating the Concepts
  119. Chapter 8 Review
  120. Chapter 9 Further Reactions of Alcohols and the Chemistry of Ethers
  121. 9-1 Reactions of Alcohols with Base: Preparation of Alkoxides
  122. 9-2 Reactions of Alcohols with Strong Acids: Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols
  123. 9-3 Carbocation Rearrangements
  124. 9-4 Esters from Alcohols and Haloalkane Synthesis
  125. 9-5 Names and Physical Properties of Ethers
  126. 9-6 Williamson Ether Synthesis
  127. Real Life: Nature 9-1 Chemiluminescence of 1,2-Dioxacyclobutanes
  128. 9-7 Synthesis of Ethers: Alcohols and Mineral Acids
  129. 9-8 Reactions of Ethers
  130. Real Life: Medicine 9-2 Protecting Groups in the Synthesis of Testosterone
  131. 9-9 Reactions of Oxacyclopropanes
  132. Real Life: Chemistry 9-3 Hydrolytic Kinetic Resolution of Oxacyclopropanes
  133. 9-10 Sulfur Analogs of Alcohols and Ethers
  134. 9-11 Physiological Properties and Uses of Alcohols and Ethers
  135. 9-12 Worked Examples: Integrating the Concepts
  136. Chapter 9 Review
  137. Chapter 10 Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure
  138. 10-1 Physical and Chemical Tests
  139. 10-2 Defining Spectroscopy
  140. 10-3 Hydrogen Nuclear Magnetic Resonance
  141. Real Life: Spectroscopy 10-1 Recording an NMR Spectrum
  142. 10-4 Using NMR Spectra to Analyze Molecular Structure: The Proton Chemical Shift
  143. 10-5 Tests for Chemical Equivalence
  144. Real Life: Medicine 10-2 Magnetic Resonance Imaging (MRI) in Medicine
  145. 10-6 Integration of NMR Signals
  146. 10-7 Spin–Spin Splitting: The Effect of Nonequivalent Neighboring Hydrogens
  147. 10-8 Spin–Spin Splitting: Some Complications
  148. Real Life: Spectroscopy 10-3 The Nonequivalence of Diastereotopic Hydrogens
  149. 10-9 Carbon-13 Nuclear Magnetic Resonance
  150. Real Life: Spectroscopy 10-4 How to Determine Atom Connectivity in NMR
  151. Real Life: Medicine 10-5 Structural Characterization of Natural and “Unnatural” Products: An Antioxidant from Grape Seeds and a Fake Drug in Herbal Medicines
  152. 10-10 Worked Examples: Integrating the Concepts
  153. Chapter 10 Review
  154. Chapter 11 Alkenes: Infrared Spectroscopy and Mass Spectrometry
  155. 11-1 Naming the Alkenes
  156. 11-2 Structure and Bonding in Ethene: The Pi Bond
  157. 11-3 Physical Properties of Alkenes
  158. 11-4 Nuclear Magnetic Resonance of Alkenes
  159. Real Life: Medicine 11-1 NMR of Complex Molecules: The Powerfully Regulating Prostaglandins
  160. 11-5 Catalytic Hydrogenation of Alkenes: Relative Stability of Double Bonds
  161. 11-6 Preparation of Alkenes from Haloalkanes and Alkyl Sulfonates: Bimolecular Elimination Revisited
  162. 11-7 Preparation of Alkenes by Dehydration of Alcohols
  163. 11-8 Infrared Spectroscopy
  164. 11-9 Measuring the Molecular Mass of Organic Compounds: Mass Spectrometry
  165. Real Life: Medicine 11-2 Detecting Performance-Enhancing Drugs Using Mass Spectrometry
  166. 11-10 Fragmentation Patterns of Organic Molecules
  167. 11-11 Degree of Unsaturation: Another Aid to Identifying Molecular Structure
  168. 11-12 Worked Examples: Integrating the Concepts
  169. Chapter 11 Review
  170. Chapter 12 Reactions of Alkenes
  171. 12-1 Why Addition Reactions Proceed: Thermodynamic Feasibility
  172. 12-2 Catalytic Hydrogenation
  173. 12-3 Basic and Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides
  174. 12-4 Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control
  175. 12-5 Electrophilic Addition of Halogens to Alkenes
  176. 12-6 The Generality of Electrophilic Addition
  177. 12-7 Oxymercuration–Demercuration: A Special Electrophilic Addition
  178. Real Life: Medicine 12-1 Juvenile Hormone Analogs in the Battle Against Insect-Borne Diseases
  179. 12-8 Hydroboration–Oxidation: A Stereospecific Anti-Markovnikov Hydration
  180. 12-9 Diazomethane, Carbenes, and Cyclopropane Synthesis
  181. 12-10 Oxacyclopropane (Epoxide) Synthesis: Epoxidation by Peroxycarboxylic Acids
  182. 12-11 Vicinal Syn Dihydroxylation with Osmium Tetroxide
  183. Real Life: Medicine 12-2 Synthesis of Antitumor Drugs: Sharpless Enantioselective Oxacyclopropanation (Epoxidation) and Dihydroxylation
  184. 12-12 Oxidative Cleavage: Ozonolysis
  185. 12-13 Radical Additions: Anti-Markovnikov Product Formation
  186. 12-14 Dimerization, Oligomerization, and Polymerization of Alkenes
  187. 12-15 Synthesis of Polymers
  188. 12-16 Ethene: An Important Industrial Feedstock
  189. 12-17 Alkenes in Nature: Insect Pheromones
  190. Real Life: Medicine 12-3 Alkene Metathesis Transposes the Termini of Two Alkenes: Construction of Rings
  191. 12-18 Worked Examples: Integrating the Concepts
  192. Chapter 12 Review
  193. Chapter 13 Alkynes
  194. The Carbon–Carbon Triple Bond
  195. 13-1 Naming the Alkynes
  196. 13-2 Properties and Bonding in the Alkynes
  197. 13-3 Spectroscopy of the Alkynes
  198. 13-4 Preparation of Alkynes by Double Elimination
  199. 13-5 Preparation of Alkynes from Alkynyl Anions
  200. 13-6 Reduction of Alkynes: The Relative Reactivity of the Two Pi Bonds
  201. 13-7 Electrophilic Addition Reactions of Alkynes
  202. 13-8 Anti-Markovnikov Additions to Triple Bonds
  203. 13-9 Chemistry of Alkenyl Halides
  204. Real Life: Synthesis 13-1 Metal-Catalyzed Stille, Suzuki, and Sonogashira Coupling Reactions
  205. 13-10 Ethyne as an Industrial Starting Material
  206. 13-11 Alkynes in Nature and in Medicine
  207. 13-12 Worked Examples: Integrating the Concepts
  208. Chapter 13 Review
  209. Chapter 14 Delocalized Pi Systems
  210. Investigation by Ultraviolet and Visible Spectroscopy
  211. 14-1 Overlap of Three Adjacent p Orbitals: Electron Delocalization in the 2-Propenyl (Allyl) System
  212. 14-2 Radical Allylic Halogenation
  213. 14-3 Nucleophilic Substitution of Allylic Halides: SN1 and SN2
  214. 14-4 Allylic Organometallic Reagents: Useful Three-Carbon Nucleophiles
  215. 14-5 Two Neighboring Double Bonds: Conjugated Dienes
  216. 14-6 Electrophilic Attack on Conjugated Dienes: Kinetic and Thermodynamic Control
  217. 14-7 Delocalization Among More than Two Pi Bonds: Extended Conjugation and Benzene
  218. 14-8 A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition
  219. Real Life: Materials 14-1 Organic Polyenes Conduct Electricity
  220. Real Life: Sustainability 14-2 The Diels-Alder Reaction is “Green”
  221. 14-9 Electrocyclic Reactions
  222. 14-10 Polymerization of Conjugated Dienes: Rubber
  223. 14-11 Electronic Spectra: Ultraviolet and Visible Spectroscopy
  224. Real Life: Spectroscopy 14-3 The Contributions of IR, MS, and UV to the Characterization of Viniferone
  225. 14-12 Worked Examples: Integrating the Concepts
  226. Chapter 14 Review
  227. Chapter 15 Benzene and Aromaticity
  228. Electrophilic Aromatic Substitution
  229. 15-1 Naming the Benzenes
  230. 15-2 Structure and Resonance Energy of Benzene: A First Look at Aromaticity
  231. 15-3 Pi Molecular Orbitals of Benzene
  232. 15-4 Spectral Characteristics of the Benzene Ring
  233. Real Life: Materials 15-1 Compounds Made of Pure Carbon: Graphite, Graphene, Diamond, and Fullerenes
  234. 15-5 Polycyclic Aromatic Hydrocarbons
  235. 15-6 Other Cyclic Polyenes: Hückel’s Rule
  236. 15-7 Hückel’s Rule and Charged Molecules
  237. 15-8 Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution
  238. 15-9 Halogenation of Benzene: The Need for a Catalyst
  239. 15-10 Nitration and Sulfonation of Benzene
  240. 15-11 Friedel-Crafts Alkylation
  241. 15-12 Limitations of Friedel-Crafts Alkylations
  242. 15-13 Friedel-Crafts Acylation
  243. 15-14 Worked Examples: Integrating the Concepts
  244. Chapter 15 Review
  245. Chapter 16 Electrophilic Attack on Derivatives of Benzene
  246. Substituents Control Regioselectivity
  247. 16-1 Activation or Deactivation by Substituents on a Benzene Ring
  248. 16-2 Directing Electron-Donating Effects of Alkyl Groups
  249. 16-3 Directing Effects of Substituents in Conjugation with the Benzene Ring
  250. Real Life: Materials 16-1 Explosive Nitroarenes: TNT and Picric Acid
  251. 16-4 Electrophilic Attack on Disubstituted Benzenes
  252. 16-5 Keys to Success: Synthetic Strategies Toward Substituted Benzenes
  253. 16-6 Reactivity of Polycyclic Benzenoid Hydrocarbons
  254. 16-7 Polycyclic Aromatic Hydrocarbons and Cancer
  255. 16-8 Worked Examples: Integrating the Concepts
  256. Chapter 16 Review
  257. Chapter 17 Aldehydes and Ketones
  258. The Carbonyl Group
  259. 17-1 Naming the Aldehydes and Ketones
  260. 17-2 Structure of the Carbonyl Group
  261. 17-3 Spectroscopic Properties of Aldehydes and Ketones
  262. 17-4 Preparation of Aldehydes and Ketones
  263. 17-5 Reactivity of the Carbonyl Group: Mechanisms of Addition
  264. 17-6 Addition of Water to Form Hydrates
  265. 17-7 Addition of Alcohols to Form Hemiacetals and Acetals
  266. 17-8 Acetals as Protecting Groups
  267. 17-9 Nucleophilic Addition of Ammonia and Its Derivatives
  268. Real Life: Biochemistry 17-1 Imines Mediate the Biochemistry of Amino Acids
  269. 17-10 Deoxygenation of the Carbonyl Group
  270. 17-11 Addition of Hydrogen Cyanide to Give Cyanohydrins
  271. 17-12 Addition of Phosphorus Ylides: The Wittig Reaction
  272. 17-13 Oxidation by Peroxycarboxylic Acids: The Baeyer-Villiger Oxidation
  273. 17-14 Oxidative Chemical Tests for Aldehydes
  274. 17-15 Worked Examples: Integrating the Concepts
  275. Chapter 17 Review
  276. Chapter 18 Enols, Enolates, and the Aldol Condensation
  277. α,β-Unsaturated Aldehydes and Ketones
  278. 18-1 Acidity of Aldehydes and Ketones: Enolate Ions
  279. 18-2 Keto–Enol Equilibria
  280. 18-3 Halogenation of Aldehydes and Ketones
  281. 18-4 Alkylation of Aldehydes and Ketones
  282. 18-5 Attack by Enolates on the Carbonyl Function: Aldol Condensation
  283. Real Life: Biology And Medicine 18-1 Stereoselective Aldol Reactions in Nature and in the Laboratory: “Organocatalysis”
  284. 18-6 Crossed Aldol Condensation
  285. 18-7 Keys to Success: Competitive Reaction Pathways and the Intramolecular Aldol Condensation
  286. Real Life: Nature 18-2 Absorption of Photons by Unsaturated Aldehydes Enables Vision
  287. 18-8 Properties of α,β-Unsaturated Aldehydes and Ketones
  288. 18-9 Conjugate Additions to α,β-Unsaturated Aldehydes and Ketones
  289. 18-10 1,2- and 1,4-Additions of Organometallic Reagents
  290. 18-11 Conjugate Additions of Enolate Ions: Michael Addition and Robinson Annulation
  291. 18-12 Worked Examples: Integrating the Concepts
  292. Chapter 18 Review
  293. Chapter 19 Carboxylic Acids
  294. 19-1 Naming the Carboxylic Acids
  295. 19-2 Structural and Physical Properties of Carboxylic Acids
  296. 19-3 Spectroscopy and Mass Spectrometry of Carboxylic Acids
  297. 19-4 Acidic and Basic Character of Carboxylic Acids
  298. 19-5 Carboxylic Acid Synthesis in Industry
  299. 19-6 Methods for Introducing the Carboxy Functional Group
  300. 19-7 Substitution at the Carboxy Carbon: The Addition–Elimination Mechanism
  301. 19-8 Carboxylic Acid Derivatives: Acyl Halides and Anhydrides
  302. 19-9 Carboxylic Acid Derivatives: Esters
  303. 19-10 Carboxylic Acid Derivatives: Amides
  304. 19-11 Reduction of Carboxylic Acids by Lithium Aluminum Hydride
  305. 19-12 Bromination Next to the Carboxy Group: The Hell-Volhard-Zelinsky Reaction
  306. 19-13 Biological Activity of Carboxylic Acids
  307. Real Life: Materials 19-1 Long-Chain Carboxylates and Sulfonates Make Soaps and Detergents
  308. Real Life: Health 19-2 Artery-Clogging Trans Fatty Acids Phasing Out
  309. Real Life: Materials 19-3 Green Plastics, Fibers, and Energy from Biomass-Derived Hydroxyesters
  310. 19-14 Worked Examples: Integrating the Concepts
  311. Chapter 19 Review
  312. Chapter 20 Carboxylic Acid Derivatives
  313. 20-1 Relative Reactivities, Structures, and Spectra of Carboxylic Acid Derivatives
  314. 20-2 Chemistry of Acyl Halides
  315. 20-3 Chemistry of Carboxylic Anhydrides
  316. 20-4 Chemistry of Esters
  317. 20-5 Esters in Nature: Waxes, Fats, Oils, and Lipids
  318. Real Life: Sustainability 20-1 Moving Away from Petroleum: Green Fuels from Vegetable Oil
  319. 20-6 Amides: The Least Reactive Carboxylic Acid Derivatives
  320. Real Life: Medicine 20-2 Killing the Bugs that Kill the Drugs: Antibiotic Wars
  321. 20-7 Amidates and Their Halogenation: The Hofmann Rearrangement
  322. 20-8 Alkanenitriles: A Special Class of Carboxylic Acid Derivatives
  323. 20-9 Worked Examples: Integrating the Concepts
  324. Chapter 20 Review
  325. Chapter 21 Amines and Their Derivatives
  326. Functional Groups Containing Nitrogen
  327. 21-1 Naming the Amines
  328. Real Life: Medicine 21-1 Physiologically Active Amines and Weight Control
  329. 21-2 Structural and Physical Properties of Amines
  330. 21-3 Spectroscopy of the Amine Group
  331. 21-4 Acidity and Basicity of Amines
  332. 21-5 Synthesis of Amines by Alkylation
  333. 21-6 Synthesis of Amines by Reductive Amination
  334. 21-7 Synthesis of Amines from Carboxylic Amides
  335. 21-8 Reactions of Quaternary Ammonium Salts: Hofmann Elimination
  336. 21-9 Mannich Reaction: Alkylation of Enols by Iminium Ions
  337. 21-10 Nitrosation of Amines
  338. Real Life: Medicine 21-2 Sodium Nitrite as a Food Additive, N-Nitrosodialkanamines, and Cancer
  339. Real Life: Materials 21-3 Amines in Industry: Nylon, the “Miracle Fiber”
  340. 21-11 Worked Examples: Integrating the Concepts
  341. Chapter 21 Review
  342. Chapter 22 Chemistry of Benzene Substituents
  343. Alkylbenzenes, Phenols, and Anilines
  344. 22-1 Reactivity at the Phenylmethyl (Benzyl) Carbon: Benzylic Resonance Stabilization
  345. 22-2 Oxidations and Reductions of Substituted Benzenes
  346. 22-3 Names and Properties of Phenols
  347. Real Life: Medicine 22-1 Two Phenols in the News: Bisphenol A and Resveratrol
  348. 22-4 Preparation of Phenols: Nucleophilic Aromatic Substitution
  349. 22-5 Alcohol Chemistry of Phenols
  350. Real Life: Medicine 22-2 Aspirin: The Miracle Drug
  351. 22-6 Electrophilic Substitution of Phenols
  352. 22-7 An Electrocyclic Reaction of the Benzene Ring: The Claisen Rearrangement
  353. 22-8 Oxidation of Phenols: Benzoquinones
  354. Real Life: Biology 22-3 Chemical Warfare in Nature: The Bombardier Beetle
  355. 22-9 Oxidation-Reduction Processes in Nature
  356. 22-10 Arenediazonium Salts
  357. 22-11 Electrophilic Substitution with Arenediazonium Salts: Diazo Coupling
  358. 22-12 Worked Examples: Integrating the Concepts
  359. Chapter 22 Review
  360. Chapter 23 Ester Enolates and the Claisen Condensation
  361. Synthesis of β-Dicarbonyl Compounds; Acyl Anion Equivalents
  362. 23-1 β-Dicarbonyl Compounds: Claisen Condensations
  363. Real Life: Nature 23-1 Claisen Condensations Assemble Biological Molecules
  364. 23-2 β-Dicarbonyl Compounds as Synthetic Intermediates
  365. 23-3 β-Dicarbonyl Anion Chemistry: Michael Additions
  366. 23-4 Acyl Anion Equivalents: Preparation of [H9251]-Hydroxyketones
  367. Real Life: Nature 23-2 Thiamine: A Natural, Metabolically Active Thiazolium Salt
  368. 23-5 Worked Examples: Integrating the Concepts
  369. Chapter 23 Review
  370. Chapter 24 Carbohydrates
  371. Polyfunctional Compounds in Nature
  372. 24-1 Names and Structures of Carbohydrates
  373. 24-2 Conformations and Cyclic Forms of Sugars
  374. 24-3 Anomers of Simple Sugars: Mutarotation of Glucose
  375. 24-4 Polyfunctional Chemistry of Sugars: Oxidation to Carboxylic Acids
  376. 24-5 Oxidative Cleavage of Sugars
  377. 24-6 Reduction of Monosaccharides to Alditols
  378. 24-7 Carbonyl Condensations with Amine Derivatives
  379. 24-8 Ester and Ether Formation: Glycosides
  380. 24-9 Step-by-Step Buildup and Degradation of Sugars
  381. Real Life: Nature 24-1 Biological Sugar Synthesis
  382. 24-10 Relative Configurations of the Aldoses: An Exercise in Structure Determination
  383. 24-11 Complex Sugars in Nature: Disaccharides
  384. Real Life: Food Chemistry 24-2 Manipulating Our Sweet Tooth
  385. 24-12 Polysaccharides and Other Sugars in Nature
  386. Real Life: Medicine 24-3 Sialic Acid, “Bird Flu,” and Rational Drug Design
  387. 24-13 Worked Example: Integrating the Concepts
  388. Chapter 24 Review
  389. Chapter 25 Heterocycles
  390. Heteroatoms in Cyclic Organic Compounds
  391. 25-1 Naming the Heterocycles
  392. 25-2 Nonaromatic Heterocycles
  393. Real Life: Medicine 25-1 Smoking, Nicotine, Cancer, and Medicinal Chemistry
  394. 25-3 Structures and Properties of Aromatic Heterocyclopentadienes
  395. 25-4 Reactions of the Aromatic Heterocyclopentadienes
  396. 25-5 Structure and Preparation of Pyridine: An Azabenzene
  397. 25-6 Reactions of Pyridine
  398. Real Life: Biochemistry 25-2 Lessons from Redox-Active Pyridinium Salts in Nature: Nicotinamide Adenine Dinucleotide, Dihydropyridines, and Synthesis
  399. 25-7 Quinoline and Isoquinoline: The Benzopyridines
  400. Real Life: Biology 25-3 Folic Acid, Vitamin D, Cholesterol, and the Color of Your Skin
  401. 25-8 Alkaloids: Physiologically Potent Nitrogen Heterocycles in Nature
  402. Real Life: Nature 25-4 Nature is Not Always Green: Natural Pesticides
  403. 25-9 Worked Examples: Integrating the Concepts
  404. Chapter 25 Review
  405. Chapter 26 Amino Acids, Peptides, Proteins, and Nucleic Acids
  406. Nitrogen-Containing Polymers in Nature
  407. 26-1 Structure and Properties of Amino Acids
  408. Real Life: Medicine 26-1 Arginine and Nitric Oxide in Biochemistry and Medicine
  409. 26-2 Synthesis of Amino Acids: A Combination of Amine and Carboxylic Acid Chemistry
  410. 26-3 Synthesis of Enantiomerically Pure Amino Acids
  411. Real Life: Chemistry 26-2 Enantioselective Synthesis of Optically Pure Amino Acids: Phase-Transfer Catalysis
  412. 26-4 Peptides and Proteins: Amino Acid Oligomers and Polymers
  413. 26-5 Determination of Primary Structure: Amino Acid Sequencing
  414. 26-6 Synthesis of Polypeptides: A Challenge in the Application of Protecting Groups
  415. 26-7 Merrifield Solid-Phase Peptide Synthesis
  416. 26-8 Polypeptides in Nature: Oxygen Transport by the Proteins Myoglobin and Hemoglobin
  417. 26-9 Biosynthesis of Proteins: Nucleic Acids
  418. Real Life: Medicine 26-3 Synthetic Nucleic Acid Bases and Nucleosides in Medicine
  419. 26-10 Protein Synthesis Through RNA
  420. 26-11 DNA Sequencing and Synthesis: Cornerstones of Gene Technology
  421. Real Life: Forensics 26-4 DNA Fingerprinting
  422. 26-12 Worked Examples: Integrating the Concepts
  423. Chapter 26 Review
  424. Back Matter
  425. Footnotes
  426. Answers to Exercises
  427. Index
  428. A
  429. B
  430. C
  431. D
  432. E
  433. F
  434. G
  435. H
  436. I
  437. J
  438. K
  439. L
  440. M
  441. N
  442. O
  443. P
  444. Q
  445. R
  446. S
  447. T
  448. U
  449. V
  450. W
  451. X
  452. Y
  453. Z
  454. Study Notes
  455. Inside Back Cover
  456. Back Cover

 

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