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  • ISBN-10 ‏ : ‎ 1305580354
  • ISBN-13 ‏ : ‎ 978-1305580350
  • Author: William H. Brown; Brent L. Iverson

Master course concepts and improve problem-solving skills with ORGANIC CHEMISTRY, 8th Edition. This student-friendly text focuses on how to skills, and includes examples, problems, and end-of-chapter comprehensive study guides to help you prepare for exams. To help you understand reaction mechanisms, the authors offset them in a stepwise fashion and emphasize similarities between related mechanisms using just four different characteristics: breaking a bond, making a new bond, adding a proton, and taking a proton away. Thoroughly updated, the book offers numerous biological examples for premed students, unique roadmap problems, a wide range of in-text learning tools, and new author-created videos to help you excel.

Table Of Contents:

  1. Chapter 1: Covalent Bonding and Shapes of Molecules
  2. 1.1 Electronic Structure of Atoms
  3. 1.2 Lewis Model of Bonding
  4. 1.3 Functional Groups
  5. 1.4 Bond Angles and Shapes of Molecules
  6. 1.5 Polar and Nonpolar Molecules
  7. 1.6 Quantum or Wave Mechanics
  8. 1.7 A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding
  9. 1.8 Resonance
  10. 1.9 Molecular Orbitals for Delocalized Systems
  11. 1.10 Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes
  12. Study Guide
  13. Problems
  14. Things You Should Know I : General Conclusions from Quantum Mechanics
  15. Chapter 2: Alkanes and Cycloalkanes
  16. 2.1 The Structure of Alkanes
  17. 2.2 Constitutional Isomerism in Alkanes
  18. 2.3 Nomenclature of Alkanes and the IUPAC System
  19. 2.4 Cycloalkanes
  20. 2.5 Conformations of Alkanes and Cycloalkanes
  21. 2.6 Cis,Trans Isomerism in Cycloalkanes and Bicycloalkanes
  22. 2.7 Physical Properties of Alkanes and Cycloalkanes
  23. 2.8 Reactions of Alkanes
  24. 2.9 Sources and Importance of Alkanes
  25. Study Guide
  26. Problems
  27. Chapter 3: Stereoisomerism and Chirality
  28. 3.1 Chirality – The Handedness of Molecules
  29. 3.2 Stereoisomerism
  30. 3.3 Naming Chiral Centers – The R,S System
  31. 3.4 Acyclic Molecules with Two or More Stereocenters
  32. 3.5 Cyclic Molecules with Two or More Chiral Centers
  33. 3.6 Tying All the Terminology Together
  34. 3.7 Optical Activity – How Chirality Is Detected in the Laboratory
  35. 3.8 The Significance of Chirality in the Biological World
  36. 3.9 Separation of Enantiomers – Resolution
  37. Study Guide
  38. Problems
  39. Chapter 4: Acids and Bases
  40. 4.1 Arrhenius Acids and Bases
  41. 4.2 Bronsted-Lowry Acids and Bases
  42. 4.3 Acid Dissociation Constants, pKa, and the Relative Strengths of Acids and Bases
  43. 4.4 The Position of Equilibrium in Acid-Base Reactions
  44. 4.5 Thermochemistry and Mechanisms of Acid-Base Reactions
  45. 4.6 Molecular Structure and Acidity
  46. 4.7 Lewis Acids and Bases
  47. Study Guide
  48. Problems
  49. Chapter 5: Alkenes: Bonding, Nomenclature, and Properties
  50. 5.1 Structure of Alkenes
  51. 5.2 Nomenclature of Alkenes
  52. 5.3 Physical Properties of Alkenes
  53. 5.4 Naturally Occurring Alkenes – Terpene Hydrocarbons
  54. Study Guide
  55. Problems
  56. Things You Should Know II: Nucleophiles and Electrophiles
  57. Things You Should Know III: Reaction Mechanisms
  58. Chapter 6: Reactions of Alkenes
  59. 6.1 Reactions of Alkenes – An Overview
  60. 6.2 Organic Reactions Involving Reactive Intermediates
  61. 6.3 Electrophilic Additions
  62. 6.4 Hydroboration-Oxidation
  63. 6.5 Oxidation
  64. 6.6 Reduction
  65. 6.7 Molecules Containing Chiral Centersas Reactants or Products
  66. Study Guide
  67. Problems
  68. Chapter 7: Alkynes
  69. 7.1 Structure of Alkynes
  70. 7.2 Nomenclature of Alkynes
  71. 7.3 Physical Properties of Alkynes
  72. 7.4 Acidity of 1-Alkynes
  73. 7.5 Preparation of Alkynes
  74. 7.6 Electrophilic Addition to Alkynes
  75. 7.7 Hydration of Alkynes to Aldehydes and Ketones
  76. 7.8 Reduction of Alkynes
  77. 7.9 Organic Synthesis
  78. Problems
  79. Study Guide
  80. Chapter 8: Haloalkanes, Halogenation, and Radical Reactions
  81. 8.1 Structure
  82. 8.2 Nomenclature
  83. 8.3 Physical Properties of Haloalkanes
  84. 8.4 Preparation of Haloalkanes by Halogenation of Alkanes
  85. 8.5 Mechanism of Halogenation of Alkanes
  86. 8.6 Allylic Halogenation
  87. 8.7 Radical Autoxidation
  88. 8.8 Radical Addition of HBr to Alkenes
  89. Study Guide
  90. Problems
  91. Things You Should Know IV: Common Mistakes in Arrow Pushing
  92. Chapter 9: Nucleophilic Substitution and B-Elimination
  93. 9.1 Nucleophilic Substitution in Haloalkanes
  94. 9.2 Mechanisms of Nucleophilic Aliphatic Substitution
  95. 9.3 Experimental Evidence for SN1 and SN2 Mechanisms
  96. 9.4 Analysis of Several Nucleophilic Substitution Reactions
  97. 9.5 B-Elimination
  98. 9.6 Mechanisms of B-Elimination
  99. 9.7 Experimental Evidence for E1 and E2 Mechanisms
  100. 9.8 Substitution versus Elimination
  101. 9.9 Analysis of Several Competitions between Substitutions and Eliminations
  102. 9.10 Neighboring Group Participation
  103. Study Guide
  104. Problems
  105. Chapter 10: Alcohols
  106. 10.1 Structure and Nomenclature of Alcohols
  107. 10.2 Physical Properties of Alcohols
  108. 10.3 Acidity and Basicity of Alcohols
  109. 10.4 Reaction of Alcohols with Active Metals
  110. 10.5 Conversion of Alcohols to Haloalkanes and Sulfonates
  111. 10.6 Acid-Catalyzed Dehydration of Alcohols
  112. 10.7 The Pinacol Rearrangement
  113. 10.8 Oxidation of Alcohols
  114. 10.9 Thiols
  115. Study Guide
  116. Problems
  117. Chapter 11: Ethers, Epoxides, and Sulfides
  118. 11.1 Structure of Ethers
  119. 11.2 Nomenclature of Ethers
  120. 11.3 Physical Properties of Ethers
  121. 11.4 Preparation of Ethers
  122. 11.5 Reactions of Ethers
  123. 11.6 Silyl Ethers as Protecting Groups
  124. 11.7 Epoxides: Structure and Nomenclature
  125. 11.8 Synthesis of Epoxides
  126. 11.9 Reactions of Epoxides
  127. 11.10 Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis
  128. 11.11 Crown Ethers
  129. 11.12 Sulfides
  130. Study Guide
  131. Problems
  132. Chapter 12: Infrared Spectroscopy
  133. 12.1 Electromagnetic Radiation
  134. 12.2 Molecular Spectroscopy
  135. 12.3 Infrared Spectroscopy
  136. 12.4 Interpreting Infrared Spectra
  137. 12.5 Solving Infrared Spectral Problems
  138. Study Guide
  139. Problems
  140. Chapter 13: Nuclear Magnetic Resonance Spectroscopy
  141. 13.1 Nuclear Spin States
  142. 13.2 Orientation of Nuclear Spins in an Applied Magnetic Field
  143. 13.3 Nuclear Magnetic “Resonance”
  144. 13.4 An NMR Spectrometer
  145. 13.5 Equivalent Hydrogens
  146. 13.6 Signal Areas
  147. 13.7 Chemical Shift
  148. 13.8 Signal Splitting and the (n + 1) Rule
  149. 13.9 The Origins of Signal Splitting
  150. 13.10 Stereochemistry and Topicity
  151. 13.11 13C-NMR
  152. 13.12 Interpretation of NMR Spectra
  153. Study Guide
  154. Problems
  155. Chapter 14: Mass Spectrometry
  156. 14.1 A Mass Spectrometer
  157. 14.2 Features of a Mass Spectrum
  158. 14.3 Interpreting Mass Spectra
  159. 14.4 Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications
  160. Study Guide
  161. Problems
  162. Chapter 15: An Introduction to Organometallic Compounds
  163. 15.1 Organomagnesium and Organolithium Compounds
  164. 15.2 Lithium Diorganocopper (Gilman) Reagents
  165. 15.3 Carbenes and Carbenoids
  166. Study Guide
  167. Problems
  168. Chapter 16: Aldehydes and Ketones
  169. 16.1 Structure and Bonding
  170. 16.2 Nomenclature
  171. 16.3 Physical Properties
  172. 16.4 Reactions
  173. 16.5 Addition of Carbon Nucleophiles
  174. 16.6 The Wittig Reaction
  175. 16.7 Addition of Oxygen Nucleophiles
  176. 16.8 Addition of Nitrogen Nucleophiles
  177. 16.9 Keto-Enol Tautomerism
  178. 16.10 Oxidation
  179. 16.11 Reduction
  180. 16.12 Reactions at an a-Carbon
  181. Study Guide
  182. Problems
  183. Chapter 17: Carboxylic Acids
  184. 17.1 Structure
  185. 17.2 Nomenclature
  186. 17.3 Physical Properties
  187. 17.4 Acidity
  188. 17.5 Preparation of Carboxylic Acids
  189. 17.6 Reduction
  190. 17.7 Esterification
  191. 17.8 Conversion to Acid Chlorides
  192. 17.9 Decarboxylation
  193. Study Guide
  194. Problems
  195. Things You Should Know V: Carboxylic Acid Derivative Reaction Mechanisms
  196. Chapter 18: Functional Derivatives of Carboxylic Acids
  197. 18.1 Structure and Nomenclature
  198. 18.2 Acidity of Amides, Imides, and Sulfonamides
  199. 18.3 Characteristic Reactions
  200. 18.4 Reaction with Water: Hydrolysis
  201. 18.5 Reaction with Alcohols
  202. 18.6 Reactions with Ammonia and Amines
  203. 18.7 Reaction of Acid Chlorides with Salts of Carboxylic Acids
  204. 18.8 Interconversion of Functional Derivatives
  205. 18.9 Reactions with Organometallic Compounds
  206. 18.10 Reduction
  207. Study Guide
  208. Problems
  209. Chapter 19: Enolate Anions and Enamines
  210. 19.1 Formation and Reactions of Enolate Anions: An Overview
  211. 19.2 Aldol Reaction
  212. 19.3 Claisen and Dieckmann Condensations
  213. 19.4 Claisen and Aldol Condensations in the Biological World
  214. 19.5 Enamines
  215. 19.6 Acetoacetic Ester Synthesis
  216. 19.7 Malonic Ester Synthesis
  217. 19.8 Conjugate Addition to a,B-Unsaturated Carbonyl Compounds
  218. 19.9 Crossed Enolate Reactions Using LDA
  219. Study Guide
  220. Problems
  221. Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions
  222. 20.1 Stability of Conjugated Dienes
  223. 20.2 Electrophilic Addition to Conjugated Dienes
  224. 20.3 UV-Visible Spectroscopy
  225. 20.4 Pericyclic Reaction Theory
  226. 20.5 The Diels-Alder Reaction
  227. 20.6 Sigmatropic Shifts
  228. Study Guide
  229. Problems
  230. Chapter 21: Benzene and the Concept of Aromaticity
  231. 21.1 The Structure of Benzene
  232. 21.2 The Concept of Aromaticity
  233. 21.3 Nomenclature
  234. 21.4 Phenols
  235. 21.5 Reactions at a Benzylic Position
  236. Study Guide
  237. Problems
  238. Chapter 22: Reactions of Benzene and Its Derivatives
  239. 22.1 Electrophilic Aromatic Substitution
  240. 22.2 Disubstitution and Polysubstitution
  241. 22.3 Nucleophilic Aromatic Substitution
  242. Study Guide
  243. Problems
  244. Chapter 23: Amines
  245. 23.1 Structure and Classification
  246. 23.2 Nomenclature
  247. 23.3 Chirality of Amines and Quaternary Ammonium Ions
  248. 23.4 Physical Properties
  249. 23.5 Basicity
  250. 23.6 Reactions with Acids
  251. 23.7 Preparation
  252. 23.8 Reaction with Nitrous Acid
  253. 23.9 Hofmann Elimination
  254. 23.10 Cope Elimination
  255. Study Guide
  256. Problems
  257. Chapter 24: Catalytic Carbon-Carbon Bond Formation
  258. 24.1 Carbon-Carbon Bond-Forming Reactions from Earlier Chapters
  259. 24.2 Organometallic Compounds and Catalysis
  260. 24.3 The Heck Reaction
  261. 24.4 Catalytic Allylic Alkylation
  262. 24.5 Palladium-Catalyzed Cross-Coupling Reactions
  263. 24.6 Alkene Metathesis
  264. Study Guide
  265. Problems
  266. Chapter 25: Carbohydrates
  267. 25.1 Monosaccharides
  268. 25.2 The Cyclic Structure of Monosaccharides
  269. 25.3 Reactions of Monosaccharides
  270. 25.4 Disaccharides and Oligosaccharides
  271. 25.5 Polysaccharides
  272. 25.6 Glucosaminoglycans
  273. Study Guide
  274. Problems
  275. Chapter 26: Lipids
  276. 26.1 Triglycerides
  277. 26.2 Soaps and Detergents
  278. 26.3 Prostaglandins
  279. 26.4 Steroids
  280. 26.5 Phospholipids
  281. 26.6 Fat-Soluble Vitamins
  282. Study Guide
  283. Problems
  284. Chapter 27: Amino Acids and Proteins
  285. 27.1 Amino Acids
  286. 27.2 Acid-Base Properties of Amino Acids
  287. 27.3 Polypeptides and Proteins
  288. 27.4 Primary Structure of Polypeptides and Proteins
  289. 27.5 Synthesis of Polypeptides
  290. 27.6 Three-Dimensional Shapes of Polypeptides and Proteins
  291. Study Guide
  292. Problems
  293. Chapter 28: Nucleic Acids
  294. 28.1 Nucleosides and Nucleotides
  295. 28.2 The Structure of DNA
  296. 28.3 Ribonucleic Acids
  297. 28.4 The Genetic Code
  298. 28.5 Sequencing Nucleic Acids
  299. Study Guide
  300. Problems
  301. Chapter 29: Organic Polymer Chemistry
  302. 29.1 The Architecture of Polymers
  303. 29.2 Polymer Notation and Nomenclature
  304. 29.3 Molecular Weights of Polymers
  305. 29.4 Polymer Morphology – Crystalline versus Amorphous Materials
  306. 29.5 Step-Growth Polymerizations
  307. 29.6 Chain-Growth Polymerizations
  308. Study Guide
  309. Problems
  310. Appendix 1: Thermodynamics and the Equilibrium Constant
  311. Appendix 2: Major Classes of Organic Acids
  312. Appendix 3: Bond Dissociation Enthalpies
  313. Appendix 4: Characteristic 1H-NMR Chemical Shifts
  314. Appendix 5: Characteristic 13C-NMR Chemical Shifts
  315. Appendix 6: Characteristic Infrared Absorption Frequencies
  316. Appendix 7: Electrostatic Potential Maps
  317. Appendix 8: Summary of Stereochemical Terms
  318. Appendix 9: Summary of the Rules of Nomenclature
  319. Appendix 10: Organic Chemistry Reaction Roadmaps
  320. Glossary
  321. Index

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