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OIT: CHE 333 Organic Chemistry III

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OIT: CHE 333 Organic Chemistry III

Chemistry
Author
Travis Lund
Publisher
Oregon Institute of Technology
Source
LibreTexts
License
CC BY-NC-SA
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 196 sections
  1. 13: Reactions at the -Carbon Part II
  2. 13.0: Prelude to Reactions at the -Carbon Part II
  3. 13.1: Decarboxylation
  4. 13.2: An Overview of Fatty Acid Metabolism
  5. 13.3: Claisen Condensation
  6. 13.4: Conjugate Addition and Elimination
  7. 13.5: Carboxylation
  8. 13.E: Reactions at the -Carbon Part II (Exercises)
  9. 13.S: Reactions at the -Carbon Part II (Summary)
  10. 14: Electrophilic Reactions
  11. 8.2: Pericyclic reactions
  12. 14.0: Prelude to Electrophilic Reactions
  13. 14.1: Electrophilic Addition to Alkenes
  14. 14.2: Elimination by the E1 Mechanism
  15. 14.3: Electrophilic Isomerization
  16. 14.4: Electrophilic Substitution
  17. 14.5: Carbocation Rearrangements
  18. 14.E: Electrophilic Reactions (Exercises)
  19. 14.S: Electrophilic Reactions (Summary)
  20. 15: Oxidation and Reduction Reactions
  21. 15.0: Prelude to Oxidation and Reduction Reactions
  22. 15.1: Oxidation and Reduction of Organic Compounds - An Overview
  23. 15.2: Oxidation and Reduction in the Context of Metabolism
  24. 15.3: Hydrogenation of Carbonyl and Imine Groups
  25. 15.4: Hydrogenation of alkenes and Dehydrogenation of Alkanes
  26. 15.5: Monitoring Hydrogenation and Dehydrogenation Reactions by UV Spectroscopy
  27. 15.6: Redox Reactions of Thiols and Disulfides
  28. 15.7: Flavin-Dependent Monooxygenase Reactions - Hydroxylation Epoxidation and the Baeyer-Villiger Oxidation
  29. 15.8: Hydrogen Peroxide is a Harmful - Reactive Oxygen Species
  30. 15.E: Oxidation and Reduction Reactions (Exercises)
  31. 15.S: Oxidation and Reduction Reactions (Summary)
  32. 16: Radical Reactions
  33. 16.0: Prelude to Radical Reactions
  34. 16.1: Overview of Single-Electron Reactions and Free Radicals
  35. 16.2: Radical Chain Reactions
  36. 16.3: Useful Polymers formed by Radical Chain Reactions
  37. 16.4: Destruction of the Ozone Layer by a Radical Chain Reaction
  38. 16.5: Oxidative Damage to cells Vitamin C and Scurvy
  39. 16.6: Flavin as a One-Electron Carrier
  40. 16.E: Radical Reactions (Exercises)
  41. 17: The Organic Chemistry of Vitamins
  42. 17.0: Prelude to the Organic Chemistry of Vitamins
  43. 17.1: Pyridoxal Phosphate (Vitamin B6)
  44. 17.2: Thiamine Diphosphate (Vitamin B1)
  45. 17.3: Thiamine Diphosphate Lipoamide and the Pyruvate Dehydrogenase Reaction
  46. 17.4: Folate
  47. 17.E: The Oganic Chemistry of Vitamins (Exercises)
  48. 17.S: The Oganic Chemistry of Vitamins (Summary)
  49. Appendix I: Index of enzymatic reactions by pathway
  50. Amino acid biosynthesis
  51. Amino acid catabolism
  52. Citric Acid Cycle
  53. Fatty acid metabolism
  54. Glycolysis Gluconeogenesis Fermentation
  55. Isoprenoid biosynthesis
  56. Nucleoside biosynthesis
  57. Nucleotide catabolism
  58. Pentose Phosphate Pathway Calvin Cycle
  59. Appendix II: Review of laboratory synthesis reactions
  60. Interchapter: Retrosynthetic analysis and metabolic pathway prediction
  61. Pathway prediction practice problems
  62. New Page
  63. 1: Introduction to Organic Structure and Bonding I
  64. 1.0: Prelude to Atoms Electron Configurations and Lewis Structures
  65. 1.1: Drawing Organic Structures
  66. 1.2: Functional groups and organic nomenclature
  67. 1.3: Structures of some important biomolecules
  68. 1.3.0: Introduction to Amino Acids and Proteins
  69. 1.3.1: Introduction to carbohydrate structure
  70. 1.3.2: Introduction to Lipid Structure
  71. 1.3.3: Introduction to nucleic acid (DNA and RNA) structure
  72. 1.4: Solutions to Chapter 1 Exercises
  73. 1.E: Problems for Chapter 1
  74. 1.0: Solutions to selected Chapter 1 problems
  75. 2: Introduction to Organic Structure and Bonding II
  76. 2.0: Prelude to Organic Structure and Bonding II
  77. 2.1: Valence Bond Theory
  78. 2.2: Molecular orbital theory- conjugation and aromaticity
  79. 2.3: Resonance
  80. 2.4: Non-covalent interactions
  81. 2.5: Physical properties of organic compounds
  82. 2.6: Solutions to Chapter 2 exercises
  83. 2.P: Problems for Chapter 2
  84. 1.0: Solutions to selected chapter 2 problems
  85. 3: Conformations and Stereochemistry
  86. 3.0: Prelude to Conformations and Stereochemistry
  87. 3.1: Conformations of open-chain organic molecules
  88. 3.2: Conformations of cyclic organic molecules
  89. 3.3: Chirality and stereoisomers
  90. 3.4: Naming chiral centers- the R and S system
  91. 3.5: Optical Activity
  92. 3.6: Compounds with multiple chiral centers
  93. 3.7: Meso Compounds
  94. 3.8: Fischer and Haworth projections
  95. 3.9: Stereochemistry of alkenes
  96. 3.10: Stereochemistry in biology and medicine
  97. 3.11: Prochirality
  98. 3.12: Solutions to Chapter 3 exercises
  99. 3.P: Problems for Chapter 3
  100. 4: Structure Determination I- UV-Vis and Infrared Spectroscopy Mass Spectrometry
  101. 4.0: Prelude to Structure Determination I
  102. 4.1: Introduction to molecular spectroscopy
  103. 4.2: Mass Spectrometry
  104. 4.3: Infrared spectroscopy
  105. 4.4: Ultraviolet and visible spectroscopy
  106. 4.P: Problems for Chapter 4
  107. 5: Structure Determination II - Nuclear Magnetic Resonance Spectroscopy
  108. 5.0: Prelude to Structure Determination
  109. 5.1: The Origin of the NMR Signal
  110. 5.2: Chemical Equivalence
  111. 5.3: The 1H-NMR experiment
  112. 5.4: The Basis for Differences in Chemical Shift
  113. 5.5: Spin-Spin Coupling
  114. 5.6: 13C-NMR Spectroscopy
  115. 5.7: Solving Unknown Structures
  116. 5.8: Complex Coupling in Proton Spectra
  117. 5.9: Other Applications of NMR
  118. 5.E: Structure Determination (Exercises)
  119. 5.S: Structure Determination (Summary)
  120. 6: Overview of Organic Reactivity
  121. 6.0: Prelude to Organic Reactivity
  122. 6.1: A First Look at Some Organic Reaction Mechanism
  123. 6.2: A Quick Review of Thermodynamics and Kinetics
  124. 6.3: Catalysis
  125. 6.4: Comparing Biological Reactions to Laboratory Reactions
  126. 6.E: Overview of Organic Reactivity (Exercises)
  127. 6.S: Overview of Organic Reactivity (Summary)
  128. 7: Acid-base Reactions
  129. 7.0: Prelude to Acid-base Reactions
  130. 7.1: Overview of Acid-Base Reactions
  131. 7.2: The Acidity Constant
  132. 7.3: Structural Effects on Acidity and Basicity
  133. 7.4: Acid-base Properties of Phenols
  134. 7.5: Acid-base properties of nitrogen-containing functional groups
  135. 7.6: Carbon Acids
  136. 7.7: Polyprotic Acids
  137. 7.8: Effects of enzyme microenvironment on acidity and basicity
  138. 7.E: Acid-base Reactions (Exercises)
  139. 7.S: Acid-base Reactions (Summary)
  140. 8: Nucleophilic Substitution Reactions
  141. 8.0: Prelude to Nucleophilic Substitution Reactions
  142. 8.1: Two Mechanistic Models for Nucleophilic Substitution
  143. 8.2: Nucleophiles
  144. 8.3: Electrophiles
  145. 8.4: Leaving Groups
  146. 8.5: Regiochemistry of SN1 Reactions with Allylic Electrophiles
  147. 8.6: SN1 or SN2 Predicting the Mechanism
  148. 8.7: Biological Nucleophilic Substitution Reactions
  149. 8.8: Nucleophilic substitution in the Lab
  150. 8.E: Nucleophilic Substitution Reactions (Exercises)
  151. 8.S: Nucleophilic Substitution Reactions (Summary)
  152. 9: Phosphate Transfer Reactions
  153. 9.0: Prelude to Phosphate Transfer Reactions
  154. 9.1: Overview of Phosphate Groups
  155. 9.2: Phosphate Transfer Reactions - An Overview
  156. 9.3: ATP The Principal Phosphate Group Donor
  157. 9.4: Phosphorylation of Alcohols
  158. 9.5: Phosphorylation of Carboxylates
  159. 9.6: Hydrolysis of Organic Phosphates
  160. 9.7: Phosphate Diesters in DNA and RNA
  161. 9.8: The Organic Chemistry of Genetic Engineering
  162. 9.9: NMR of phosphorylated compounds
  163. 9.E: Phosphate Transfer Reactions (Exercise)
  164. 9.S: Phosphate Transfer Reactions (Summary)
  165. 10: Nucleophilic Carbonyl Addition Reactions
  166. 10.0: Prelude to Nucleophilic Carbonyl Addition Reactions
  167. 10.1: Nucleophilic Additions to Aldehydes and Ketones - An Overview
  168. 10.2: Hemiacetals Hemiketals and Hydrates
  169. 10.3: Acetals and Ketals
  170. 10.4: N-glycosidic Bonds
  171. 10.5: Imines
  172. 10.6: A Look Ahead - Addition of Carbon and Hydride Nucleophiles to Carbonyls
  173. 10.E: Nucleophilic Carbonyl Addition Reactions (Exercises)
  174. 10.S: Nucleophilic Carbonyl Addition Reactions (Summary)
  175. 11: Nucleophilic Acyl Substitution Reactions
  176. 11.0: Prelude to Nucleophilic Acyl Substitution Reactions
  177. 11.1: Carboxylic Acid Derivatives
  178. 11.2: The Nucleophilic Acyl Substitution Mechanism
  179. 11.3: Acyl Phosphates
  180. 11.4: The Relative Reactivity of Carboxylic Acid Derivatives
  181. 11.5: Acyl Phosphates
  182. 11.6: Hydrolysis of Thioesters Esters and Amides
  183. 11.7: Protein Synthesis on the Ribosome
  184. 11.8: Nucleophilic Substitution at Activated Amides and Carbamides
  185. 11.9: Nucleophilic Acyl Substitution Reactions in the Laboratory
  186. 11.10: A Look Ahead - Acyl Substitution Reactions with a Carbanion or Hydride Ion Nucleophile
  187. 11.E: Nucleophilic Acyl Substitution Reactions (Exercises)
  188. 11.S: Nucleophilic Acyl Substitution Reactions (Summary)
  189. 12: Reactions at the -Carbon Part I
  190. 12.0: Prelude to Reactions at the -carbon part I
  191. 12.1: Review of Acidity at the -Carbon
  192. 12.2: Isomerization at the -Carbon
  193. 12.3: Aldol Addition
  194. 12.4: -Carbon Reactions in the Synthesis Lab - Kinetic vs. Thermodynamic Alkylation Products
  195. 12.E: Reactions at the -Carbon Part I (Exercises)
  196. 12.S: Reactions at the -Carbon Part I (Summary)