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  • ISBN-10 ‏ : ‎ 1305256662
  • ISBN-13 ‏ : ‎ 978-1305256668
  • Author:  John E. McMurry

Renowned for its student-friendly writing style and fresh perspective, this fully updated Third Edition of John McMurry’s ORGANIC CHEMISTRY WITH BIOLOGICAL APPLICATIONS provides full coverage of the foundations of organic chemistry–enhanced by biological examples throughout. In addition, McMurry discusses the organic chemistry behind biological pathways. New problems, illustrations, and essays have been added. Media integration with OWL for Organic Chemistry, a customizable online learning system and assessment tool, reduces faculty workload, facilitates instruction, and helps students master concepts through tutorials, simulations, and algorithmically-generated homework questions.

 

Table of Content:

  1. Ch 1: Structure and Bonding
  2. 1-1: Atomic Structure: The Nucleus
  3. 1-2: Atomic Structure: Orbitals
  4. 1-3: Atomic Structure: Electron Configurations
  5. 1-4: Development of Chemical Bonding Theory
  6. 1-5: Describing Chemical Bonds: Valence Bond Theory
  7. 1-6: sp3 Hybrid Orbitals and the Structure of Methane
  8. 1-7: sp3 Hybrid Orbitals and the Structure of Ethane
  9. 1-8: sp2 Hybrid Orbitals and the Structure of Ethylene
  10. 1-9: sp Hybrid Orbitals and the Structure of Acetylene
  11. 1-10: Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
  12. 1-11: Describing Chemical Bonds: Molecular Orbital Theory
  13. 1-12: Drawing Chemical Structures
  14. Summary
  15. Ch 2: Polar Covalent Bonds; Acids and Bases
  16. 2-1: Polar Covalent Bonds: Electronegativity
  17. 2-2: Polar Covalent Bonds: Dipole Moments
  18. 2-3: Formal Charges
  19. 2-4: Resonance
  20. 2-5: Rules for Resonance Forms
  21. 2-6: Drawing Resonance Forms
  22. 2-7: Acids and Bases: The Bronsted-Lowry Definition
  23. 2-8: Acid and Base Strength
  24. 2-9: Predicting Acid-Base Reactions from pKa Values
  25. 2-10: Organic Acids and Organic Bases
  26. 2-11: Acids and Bases: The Lewis Definition
  27. 2-12: Noncovalent Interactions between Molecules
  28. Summary
  29. Ch 3: Organic Compounds: Alkanes and Their Stereochemistry
  30. 3-1: Functional Groups
  31. 3-2: Alkanes and Alkane Isomers
  32. 3-3: Alkyl Groups
  33. 3-4: Naming Alkanes
  34. 3-5: Properties of Alkanes
  35. 3-6: Conformations of Ethane
  36. 3-7: Conformations of Other Alkanes
  37. Summary
  38. Ch 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
  39. 4-1: Naming Cycloalkanes
  40. 4-2: Cis-Trans Isomerism in Cycloalkanes
  41. 4-3: Stability of Cycloalkanes: Ring Strain
  42. 4-4: Conformations of Cycloalkanes
  43. 4-5: Conformations of Cyclohexane
  44. 4-6: Axial and Equatorial Bonds in Cyclohexane
  45. 4-7: Conformations of Monosubstituted Cyclohexanes
  46. 4-8: Conformations of Disubstituted Cyclohexanes
  47. 4-9: Conformations of Polycyclic Molecules
  48. Summary
  49. Ch 5: Stereochemistry at Tetrahedral Centers
  50. 5-1: Enantiomers and the Tetrahedral Carbon
  51. 5-2: The Reason for Handedness in Molecules: Chirality
  52. 5-3: Optical Activity
  53. 5-4: Pasteur’s Discovery of Enantiomers
  54. 5-5: Sequence Rules for Specifying Configuration
  55. 5-6: Diastereomers
  56. 5-7: Meso Compounds
  57. 5-8: Racemic Mixtures and the Resolution of Enantiomers
  58. 5-9: A Review of Isomerism
  59. 5-10: Chirality at Nitrogen, Phosphorus, and Sulfur
  60. 5-11: Prochirality
  61. 5-12: Chirality in Nature and Chiral Environments
  62. Summary
  63. Ch 6: An Overview of Organic Reactions
  64. 6-1: Kinds of Organic Reactions
  65. 6-2: How Organic Reactions Occur: Mechanisms
  66. 6-3: Radical Reactions
  67. 6-4: Polar Reactions
  68. 6-5: An Example of a Polar Reaction: Addition of H2O to Ethylene
  69. 6-6: Using Curved Arrows in Polar Reaction Mechanisms
  70. 6-7: Describing a Reaction: Equilibria, Rates, and Energy Changes
  71. 6-8: Describing a Reaction: Bond Dissociation Energies
  72. 6-9: Describing a Reaction: Energy Diagrams and Transition States
  73. 6-10: Describing a Reaction: Intermediates
  74. 6-11: A Comparison between Biological Reactions and Laboratory Reactions
  75. Summary
  76. Ch 7: Alkenes and Alkynes
  77. 7-1: Calculating the Degree of Unsaturation
  78. 7-2: Naming Alkenes and Alkynes
  79. 7-3: Cis-Trans Isomerism in Alkenes
  80. 7-4: Alkene Stereochemistry and the E,Z Designation
  81. 7-5: Stability of Alkenes
  82. 7-6: Electrophilic Addition Reactions of Alkenes
  83. 7-7: Orientation of Electrophilic Addition: Markovnikov’s Rule
  84. 7-8: Carbocation Structure and Stability
  85. 7-9: The Hammond Postulate
  86. 7-10: Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
  87. Summary
  88. Ch 8: Reactions of Alkenes and Alkynes
  89. 8-1: Preparing Alkenes: A Preview of Elimination Reactions
  90. 8-2: Halogenation of Alkenes
  91. 8-3: Halohydrins from Alkenes
  92. 8-4: Hydration of Alkenes
  93. 8-5: Reduction of Alkenes: Hydrogenation
  94. 8-6: Oxidation of Alkenes: Epoxidation
  95. 8-7: Oxidation of Alkenes: Hydroxylation
  96. 8-8: Oxidation of Alkenes: Cleavage to Carbonyl Compounds
  97. 8-9: Addition of Carbenes to Alkenes: Cyclopropane Synthesis
  98. 8-10: Radical Additions to Alkenes: Chain-Growth Polymers
  99. 8-11: Biological Additions of Radicals to Alkenes
  100. 8-12: Conjugated Dienes
  101. 8-13: Reactions of Conjugated Dienes
  102. 8-14: The Diels-Alder Cycloaddition Reaction
  103. 8-15: Reactions of Alkynes
  104. Summary
  105. Ch 9: Aromatic Compounds
  106. 9-1: Naming Aromatic Compounds
  107. 9-2: Structure and Stability of Benzene
  108. 9-3: Aromaticity and the Huckel 4n + 2 Rule
  109. 9-4: Aromatic Ions and Aromatic Heterocycles
  110. 9-5: Polycyclic Aromatic Compounds
  111. 9-6: Reactions of Aromatic Compounds: Electrophilic Substitution
  112. 9-7: Alkylation and Acylation of Aromatic Rings: The Friedel-Crafts Reaction
  113. 9-8: Substituent Effects in Electrophilic Substitutions
  114. 9-9: Nucleophilic Aromatic Substitution
  115. 9-10: Oxidation and Reduction of Aromatic Compounds
  116. 9-11: An Introduction to Organic Synthesis: Polysubstituted Benzenes
  117. Summary
  118. Ch 10: Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectrosco
  119. 10-1: Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
  120. 10-2: Interpreting Mass Spectra
  121. 10-3: Mass Spectrometry of Some Common Functional Groups
  122. 10-4: Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
  123. 10-5: Spectroscopy and the Electromagnetic Spectrum
  124. 10-6: Infrared Spectroscopy
  125. 10-7: Interpreting Infrared Spectra
  126. 10-8: Infrared Spectra of Some Common Functional Groups
  127. 10-9: Ultraviolet Spectroscopy
  128. 10-10: Interpreting Ultraviolet Spectra: The Effect of Conjugation
  129. 10-11: Conjugation, Color, and the Chemistry of Vision
  130. Summary
  131. Ch 11: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
  132. 11-1: Nuclear Magnetic Resonance Spectroscopy
  133. 11-2: The Nature of NMR Absorptions
  134. 11-3: Chemical Shifts
  135. 11-4: 13C NMR Spectroscopy: Signal Averaging and FT-NMR
  136. 11-5: Characteristics of 13C NMR Spectroscopy
  137. 11-6: DEPT 13C NMR Spectroscopy
  138. 11-7: Uses of 13C NMR Spectroscopy
  139. 11-8: 1H NMR Spectroscopy and Proton Equivalence
  140. 11-9: Chemical Shifts in 1H NMR Spectroscopy
  141. 11-10: Integration of 1H NMR Absorptions: Proton Counting
  142. 11-11: Spin-Spin Splitting in 1H NMR Spectra
  143. 11-12: More Complex Spin-Spin Splitting Patterns
  144. 11-13: Uses of 1H NMR Spectroscopy
  145. Summary
  146. Ch 12: Organohalides: Nucleophilic Substitutions and Eliminations
  147. 12-1: Names and Structures of Alkyl Halides
  148. 12-2: Preparing Alkyl Halides from Alkenes: Allylic Bromination
  149. 12-3: Preparing Alkyl Halides from Alcohols
  150. 12-4: Reactions of Alkyl Halides: Grignard Reagents
  151. 12-5: Organometallic Coupling Reactions
  152. 12-6: Discovery of the Nucleophilic Substitution Reaction
  153. 12-7: The SN2 Reaction
  154. 12-8: Characteristics of the SN2 Reaction
  155. 12-9: The SN1 Reaction
  156. 12-10: Characteristics of the SN1 Reaction
  157. 12-11: Biological Substitution Reactions
  158. 12-12: Elimination Reactions: Zaitsev’s Rule
  159. 12-13: The E2 Reaction and the Deuterium Isotope Effect
  160. 12-14: The E1 and E1cB Reactions
  161. 12-15: Biological Elimination Reactions
  162. 12-16: A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
  163. Summary
  164. Ch 13: Alcohols, Phenols, and Thiols; Ethers and Sulfides
  165. 13-1: Naming Alcohols, Phenols, and Thiols
  166. 13-2: Properties of Alcohols, Phenols, and Thiols
  167. 13-3: Preparing Alcohols from Carbonyl Compounds
  168. 13-4: Reactions of Alcohols
  169. 13-5: Oxidation of Alcohols and Phenols
  170. 13-6: Protection of Alcohols
  171. 13-7: Preparation and Reactions of Thiols
  172. 13-8: Ethers and Sulfides
  173. 13-9: Preparing Ethers
  174. 13-10: Reactions of Ethers
  175. 13-11: Crown Ethers and Ionophores
  176. 13-12: Preparation and Reactions of Sulfides
  177. 13-13: Spectroscopy of Alcohols, Phenols, and Ethers
  178. Summary
  179. A Preview of Carbonyl Chemistry
  180. Ch 14: Aldehydes and Ketones: Nucleophilic Addition Reactions
  181. 14-1: Naming Aldehydes and Ketones
  182. 14-2: Preparing Aldehydes and Ketones
  183. 14-3: Oxidation of Aldehydes
  184. 14-4: Nucleophilic Addition Reactions of Aldehydes and Ketones
  185. 14-5: Nucleophilic Addition of H2O: Hydration
  186. 14-6: Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
  187. 14-7: Nucleophilic Addition of Amines: Imine and Enamine Formation
  188. 14-8: Nucleophilic Addition of Alcohols: Acetal Formation
  189. 14-9: Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
  190. 14-10: Biological Reductions
  191. 14-11: Conjugate Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones
  192. 14-12: Spectroscopy of Aldehydes and Ketones
  193. Summary
  194. Ch 15: Carboxylic Acids and Nitriles
  195. 15-1: Naming Carboxylic Acids and Nitriles
  196. 15-2: Structure and Properties of Carboxylic Acids
  197. 15-3: Biological Acids and the Henderson-Hasselbalch Equation
  198. 15-4: Substituent Effects on Acidity
  199. 15-5: Preparing Carboxylic Acids
  200. 15-6: Reactions of Carboxylic Acids: An Overview
  201. 15-7: Chemistry of Nitriles
  202. 15-8: Spectroscopy of Carboxylic Acids and Nitriles
  203. Summary
  204. Ch 16: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
  205. 16-1: Naming Carboxylic Acid Derivatives
  206. 16-2: Nucleophilic Acyl Substitution Reactions
  207. 16-3: Reactions of Carboxylic Acids
  208. 16-4: Reactions of Acid Halides
  209. 16-5: Reactions of Acid Anhydrides
  210. 16-6: Reactions of Esters
  211. 16-7: Reactions of Amides
  212. 16-8: Reactions of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
  213. 16-9: Polyamides and Polyesters: Step-Growth Polymers
  214. 16-10: Spectroscopy of Carboxylic Acid Derivatives
  215. Summary
  216. Ch 17: Carbonyl Alpha-Substitution and Condensation Reactions
  217. 17-1: Keto-Enol Tautomerism
  218. 17-2: Reactivity of Enols: a-Substitution Reactions
  219. 17-3: Alpha Bromination of Carboxylic Acids
  220. 17-4: Acidity of a Hydrogen Atoms: Enolate Ion Formation
  221. 17-5: Alkylation of Enolate Ions
  222. 17-6: Carbonyl Condensations: The Aldol Reaction
  223. 17-7: Dehydration of Aldol Products
  224. 17-8: Intramolecular Aldol Reactions
  225. 17-9: The Claisen Condensation Reaction
  226. 17-10: Intramolecular Claisen Condensations: The Dieckmann Cyclization
  227. 17-11: Conjugate Carbonyl Additions: The Michael Reaction
  228. 17-12: Carbonyl Condensations with Enamines: The Stork Reaction
  229. 17-13: Biological Carbonyl Condensation Reactions
  230. Summary
  231. Ch 18: Amines and Heterocycles
  232. 18-1: Naming Amines
  233. 18-2: Properties of Amines
  234. 18-3: Basicity of Amines
  235. 18-4: Basicity of Arylamines
  236. 18-5: Biological Amines and the Henderson-Hasselbalch Equation
  237. 18-6: Synthesis of Amines
  238. 18-7: Reactions of Amines
  239. 18-8: Heterocyclic Amines
  240. 18-9: Fused-Ring Heterocycles
  241. 18-10: Spectroscopy of Amines
  242. Summary
  243. Ch 19: Biomolecules: Amino Acids, Peptides, and Proteins
  244. 19-1: Structures of Amino Acids
  245. 19-2: Amino Acids and the Henderson-Hasselbalch Equation: Isoelectric Points
  246. 19-3: Synthesis of Amino Acids
  247. 19-4: Peptides and Proteins
  248. 19-5: Amino Acid Analysis of Peptides
  249. 19-6: Peptide Sequencing: The Edman Degradation
  250. 19-7: Peptide Synthesis
  251. 19-8: Protein Structure
  252. 19-9: Enzymes and Coenzymes
  253. 19-10: How Do Enzymes Work? Citrate Synthase
  254. Summary
  255. Ch 20: Amino Acid Metabolism
  256. 20-1: An Overview of Metabolism and Biochemical Energy
  257. 20-2: Catabolism of Amino Acids: Deamination
  258. 20-3: The Urea Cycle
  259. 20-4: Catabolism of Amino Acids: The Carbon Chains
  260. 20-5: Biosynthesis of Amino Acids
  261. Summary
  262. Ch 21: Biomolecules: Carbohydrates
  263. 21-1: Classifying Carbohydrates
  264. 21-2: Representing Carbohydrate Stereochemistry: Fischer Projections
  265. 21-3: D,L Sugars
  266. 21-4: Configurations of the Aldoses
  267. 21-5: Cyclic Structures of Monosaccharides: Anomers
  268. 21-6: Reactions of Monosaccharides
  269. 21-7: The Eight Essential Monosaccharides
  270. 21-8: Disaccharides
  271. 21-9: Polysaccharides and Their Synthesis
  272. 21-10: Some Other Important Carbohydrates
  273. Summary
  274. Ch 22: Carbohydrate Metabolism
  275. 22-1: Hydrolysis of Complex Carbohydrates
  276. 22-2: Catabolism of Glucose: Glycolysis
  277. 22-3: Conversion of Pyruvate to Acetyl CoA
  278. 22-4: The Citric Acid Cycle
  279. 22-5: Biosynthesis of Glucose: Gluconeogenesis
  280. Summary
  281. Ch 23: Biomolecules: Lipids and Their Metabolism
  282. 23-1: Waxes, Fats, and Oils
  283. 23-2: Soap
  284. 23-3: Phospholipids
  285. 23-4: Catabolism of Triacylglycerols: The Fate of Glycerol
  286. 23-5: Catabolism of Triacylglycerols: B-Oxidation
  287. 23-6: Biosynthesis of Fatty Acids
  288. 23-7: Prostaglandins and Other Eicosanoids
  289. 23-8: Terpenoids
  290. 23-9: Steroids
  291. 23-10: Biosynthesis of Steroids
  292. 23-11: Some Final Comments on Metabolism
  293. Summary
  294. Ch 24: Biomolecules: Nucleic Acids and Their Metabolism
  295. 24-1: Nucleotides and Nucleic Acids
  296. 24-2: Base Pairing in DNA: The Watson-Crick Model
  297. 24-3: Replication of DNA
  298. 24-4: Transcription of DNA
  299. 24-5: Translation of RNA: Protein Biosynthesis
  300. 24-6: DNA Sequencing
  301. 24-7: DNA Synthesis
  302. 24-8: The Polymerase Chain Reaction
  303. 24-9: Catabolism of Nucleotides
  304. 24-10: Biosynthesis of Nucleotides
  305. Summary
  306. Ch e25: Secondary Metabolites: An Introduction to Natural Products Chemistry
  307. 25-1: Classifying Natural Products
  308. 25-2: Biosynthesis of Pyridoxal Phosphate
  309. 25-3: Biosynthesis of Morphine
  310. 25-4: Biosynthesis of Erythromycin
  311. Summary
  312. Ch e26: Orbitals and Organic Chemistry: Pericyclic Reactions
  313. 26-1: Molecular Orbitals of Conjugated Pi Systems
  314. 26-2: Electrocyclic Reactions
  315. 26-3: Stereochemistry of Thermal Electrocyclic Reactions
  316. 26-4: Photochemical Electrocyclic Reactions
  317. 26-5: Cycloaddition Reactions
  318. 26-6: Stereochemistry of Cycloadditions
  319. 26-7: Sigmatropic Rearrangements
  320. 26-8: Some Examples of Sigmatropic Rearrangements
  321. 26-9: A Summary of Rules for Pericyclic Reactions
  322. Summary
  323. Ch e27: Synthetic Polymers
  324. 27-1: Chain-Growth Polymers
  325. 27-2: Stereochemistry of Polymerization: Ziegler-Natta Catalysts
  326. 27-3: Copolymers
  327. 27-4: Step-Growth Polymers
  328. 27-5: Olefin Metathesis Polymerization
  329. 27-6: Polymer Structure and Physical Properties
  330. Summary
  331. Appendix A: Nomenclature of Polyfunctional Organic Compounds
  332. Appendix B: Acidity Constants for Some Organic Compounds
  333. Appendix C: Glossary
  334. Appendix D: Answers to In-Text Problems
  335. Index

 

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