OIT: CHE 333 Organic Chemistry III

by Travis Lund

Read here Read at LibreTextsPDF
Publisher
Oregon Institute of Technology
Subjects
Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
Who can read
Tweens profiles and older, judged from its title and subjects

Contents

LibreTexts writes equations in TeX, and here they show as TeX; the PDF has them typeset.

  1. Review chapters
  2. 1: Introduction to Organic Structure and Bonding I
  3. 1.0: Prelude to Atoms, Electron Configurations, and Lewis Structures
  4. 1.1: Drawing Organic Structures
  5. 1.2: Functional groups and organic nomenclature
  6. 1.3: Structures of some important biomolecules
  7. 1.3.0: Introduction to Amino Acids and Proteins
  8. 1.3.1: Introduction to carbohydrate structure
  9. 1.3.2: Introduction to Lipid Structure
  10. 1.3.3: Introduction to nucleic acid (DNA and RNA) structure
  11. 1.4: Solutions to Chapter 1 Exercises
  12. 1.E: Problems for Chapter 1
  13. 1.0: Solutions to selected Chapter 1 problems
  14. 2: Introduction to Organic Structure and Bonding II
  15. 2.0: Prelude to Organic Structure and Bonding II
  16. 2.1: Valence Bond Theory
  17. 2.2: Molecular orbital theory- conjugation and aromaticity
  18. 2.3: Resonance
  19. 2.4: Non-covalent interactions
  20. 2.5: Physical properties of organic compounds
  21. 2.6: Solutions to Chapter 2 exercises
  22. 2.P: Problems for Chapter 2
  23. 1.0: Solutions to selected chapter 2 problems
  24. 3: Conformations and Stereochemistry
  25. 3.0: Prelude to Conformations and Stereochemistry
  26. 3.10: Stereochemistry in biology and medicine
  27. 3.11: Prochirality
  28. 3.12: Solutions to Chapter 3 exercises
  29. 3.1: Conformations of open-chain organic molecules
  30. 3.2: Conformations of cyclic organic molecules
  31. 3.3: Chirality and stereoisomers
  32. 3.4: Naming chiral centers- the R and S system
  33. 3.5: Optical Activity
  34. 3.6: Compounds with multiple chiral centers
  35. 3.7: Meso Compounds
  36. 3.8: Fischer and Haworth projections
  37. 3.9: Stereochemistry of alkenes
  38. 3.P: Problems for Chapter 3
  39. 4: Structure Determination I- UV-Vis and Infrared Spectroscopy, Mass Spectrometry
  40. 4.0: Prelude to Structure Determination I
  41. 4.1: Introduction to molecular spectroscopy
  42. 4.2: Mass Spectrometry
  43. 4.3: Infrared spectroscopy
  44. 4.4: Ultraviolet and visible spectroscopy
  45. 4.P: Problems for Chapter 4
  46. 5: Structure Determination II - Nuclear Magnetic Resonance Spectroscopy
  47. 5.0: Prelude to Structure Determination
  48. 5.1: The Origin of the NMR Signal
  49. 5.2: Chemical Equivalence
  50. 5.3: The 1H-NMR experiment
  51. 5.4: The Basis for Differences in Chemical Shift
  52. 5.5: Spin-Spin Coupling
  53. 5.6: 13C-NMR Spectroscopy
  54. 5.7: Solving Unknown Structures
  55. 5.8: Complex Coupling in Proton Spectra
  56. 5.9: Other Applications of NMR
  57. 5.E: Structure Determination (Exercises)
  58. 5.S: Structure Determination (Summary)
  59. 6: Overview of Organic Reactivity
  60. 6.0: Prelude to Organic Reactivity
  61. 6.1: A First Look at Some Organic Reaction Mechanism
  62. 6.2: A Quick Review of Thermodynamics and Kinetics
  63. 6.3: Catalysis
  64. 6.4: Comparing Biological Reactions to Laboratory Reactions
  65. 6.E: Overview of Organic Reactivity (Exercises)
  66. 6.S: Overview of Organic Reactivity (Summary)
  67. 7: Acid-base Reactions
  68. 7.0: Prelude to Acid-base Reactions
  69. 7.1: Overview of Acid-Base Reactions
  70. 7.2: The Acidity Constant
  71. 7.3: Structural Effects on Acidity and Basicity
  72. 7.4: Acid-base Properties of Phenols
  73. 7.5: Acid-base properties of nitrogen-containing functional groups
  74. 7.6: Carbon Acids
  75. 7.7: Polyprotic Acids
  76. 7.8: Effects of enzyme microenvironment on acidity and basicity
  77. 7.E: Acid-base Reactions (Exercises)
  78. 7.S: Acid-base Reactions (Summary)
  79. 8: Nucleophilic Substitution Reactions
  80. 8.0: Prelude to Nucleophilic Substitution Reactions
  81. 8.1: Two Mechanistic Models for Nucleophilic Substitution
  82. 8.2: Nucleophiles
  83. 8.3: Electrophiles
  84. 8.4: Leaving Groups
  85. 8.5: Regiochemistry of SN1 Reactions with Allylic Electrophiles
  86. 8.6: SN1 or SN2? Predicting the Mechanism
  87. 8.7: Biological Nucleophilic Substitution Reactions
  88. 8.8: Nucleophilic substitution in the Lab
  89. 8.E: Nucleophilic Substitution Reactions (Exercises)
  90. 8.S: Nucleophilic Substitution Reactions (Summary)
  91. 9: Phosphate Transfer Reactions
  92. 9.0: Prelude to Phosphate Transfer Reactions
  93. 9.1: Overview of Phosphate Groups
  94. 9.2: Phosphate Transfer Reactions - An Overview
  95. 9.3: ATP, The Principal Phosphate Group Donor
  96. 9.4: Phosphorylation of Alcohols
  97. 9.5: Phosphorylation of Carboxylates
  98. 9.6: Hydrolysis of Organic Phosphates
  99. 9.7: Phosphate Diesters in DNA and RNA
  100. 9.8: The Organic Chemistry of Genetic Engineering
  101. 9.9: NMR of phosphorylated compounds
  102. 9.E: Phosphate Transfer Reactions (Exercise)
  103. 9.S: Phosphate Transfer Reactions (Summary)
  104. 10: Nucleophilic Carbonyl Addition Reactions
  105. 10.0: Prelude to Nucleophilic Carbonyl Addition Reactions
  106. 10.1: Nucleophilic Additions to Aldehydes and Ketones - An Overview
  107. 10.2: Hemiacetals, Hemiketals, and Hydrates
  108. 10.3: Acetals and Ketals
  109. 10.4: N-glycosidic Bonds
  110. 10.5: Imines
  111. 10.6: A Look Ahead - Addition of Carbon and Hydride Nucleophiles to Carbonyls
  112. 10.E: Nucleophilic Carbonyl Addition Reactions (Exercises)
  113. 10.S: Nucleophilic Carbonyl Addition Reactions (Summary)
  114. 11: Nucleophilic Acyl Substitution Reactions
  115. 11.0: Prelude to Nucleophilic Acyl Substitution Reactions
  116. 11.10: A Look Ahead - Acyl Substitution Reactions with a Carbanion or Hydride Ion Nucleophile
  117. 11.1: Carboxylic Acid Derivatives
  118. 11.2: The Nucleophilic Acyl Substitution Mechanism
  119. 11.3: Acyl Phosphates
  120. 11.4: The Relative Reactivity of Carboxylic Acid Derivatives
  121. 11.5: Acyl Phosphates
  122. 11.6: Hydrolysis of Thioesters, Esters, and Amides
  123. 11.7: Protein Synthesis on the Ribosome
  124. 11.8: Nucleophilic Substitution at Activated Amides and Carbamides
  125. 11.9: Nucleophilic Acyl Substitution Reactions in the Laboratory
  126. 11.E: Nucleophilic Acyl Substitution Reactions (Exercises)
  127. 11.S: Nucleophilic Acyl Substitution Reactions (Summary)
  128. 12: Reactions at the α-Carbon, Part I
  129. 12.0: Prelude to Reactions at the α-carbon, part I
  130. 12.1: Review of Acidity at the α-Carbon
  131. 12.2: Isomerization at the α-Carbon
  132. 12.3: Aldol Addition
  133. 12.4: α-Carbon Reactions in the Synthesis Lab - Kinetic vs. Thermodynamic Alkylation Products
  134. 12.E: Reactions at the α-Carbon, Part I (Exercises)
  135. 12.S: Reactions at the α-Carbon, Part I (Summary)
  136. 13: Reactions at the α-Carbon, Part II
  137. 13.0: Prelude to Reactions at the α-Carbon, Part II
  138. 13.1: Decarboxylation
  139. 13.2: An Overview of Fatty Acid Metabolism
  140. 13.3: Claisen Condensation
  141. 13.4: Conjugate Addition and Elimination
  142. 13.5: Carboxylation
  143. 13.E: Reactions at the α-Carbon, Part II (Exercises)
  144. 13.S: Reactions at the α-Carbon, Part II (Summary)
  145. Interchapter: Retrosynthetic analysis and metabolic pathway prediction
  146. Pathway prediction practice problems
  147. 14: Electrophilic Reactions
  148. 14.0: Prelude to Electrophilic Reactions
  149. 14.1: Electrophilic Addition to Alkenes
  150. 14.2: Elimination by the E1 Mechanism
  151. 14.3: Electrophilic Isomerization
  152. 14.4: Electrophilic Substitution
  153. 14.5: Carbocation Rearrangements
  154. 14.6: Cycloaddition reactions
  155. 14.E: Electrophilic Reactions (Exercises)
  156. 14.S: Electrophilic Reactions (Summary)
  157. 15: Oxidation and Reduction Reactions
  158. 15.0: Prelude to Oxidation and Reduction Reactions
  159. 15.1: Oxidation and Reduction of Organic Compounds - An Overview
  160. 15.2: Oxidation and Reduction in the Context of Metabolism
  161. 15.3: Hydrogenation of Carbonyl and Imine Groups
  162. 15.4: Hydrogenation of alkenes and Dehydrogenation of Alkanes
  163. 15.5: Monitoring Hydrogenation and Dehydrogenation Reactions by UV Spectroscopy
  164. 15.6: Redox Reactions of Thiols and Disulfides
  165. 15.7: Flavin-Dependent Monooxygenase Reactions - Hydroxylation, Epoxidation, and the Baeyer-Villiger Oxidation
  166. 15.8: Hydrogen Peroxide is a Harmful - Reactive Oxygen Species
  167. 15.E: Oxidation and Reduction Reactions (Exercises)
  168. 15.S: Oxidation and Reduction Reactions (Summary)
  169. 16: Radical Reactions
  170. 16.0: Prelude to Radical Reactions
  171. 16.1: Overview of Single-Electron Reactions and Free Radicals
  172. 16.2: Radical Chain Reactions
  173. 16.3: Useful Polymers formed by Radical Chain Reactions
  174. 16.4: Destruction of the Ozone Layer by a Radical Chain Reaction
  175. 16.5: Oxidative Damage to cells, Vitamin C, and Scurvy
  176. 16.6: Flavin as a One-Electron Carrier
  177. 16.E: Radical Reactions (Exercises)
  178. 17: The Organic Chemistry of Vitamins
  179. 17.0: Prelude to the Organic Chemistry of Vitamins
  180. 17.1: Pyridoxal Phosphate (Vitamin B6)
  181. 17.2: Thiamine Diphosphate (Vitamin B1)
  182. 17.3: Thiamine Diphosphate, Lipoamide and the Pyruvate Dehydrogenase Reaction
  183. 17.4: Folate
  184. 17.E: The Oganic Chemistry of Vitamins (Exercises)
  185. 17.S: The Oganic Chemistry of Vitamins (Summary)
  186. Appendix I: Index of enzymatic reactions by pathway
  187. Amino acid biosynthesis
  188. Amino acid catabolism
  189. Citric Acid Cycle
  190. Fatty acid metabolism
  191. Glycolysis, Gluconeogenesis, Fermentation
  192. Isoprenoid biosynthesis
  193. Nucleoside biosynthesis
  194. Nucleotide catabolism
  195. Pentose Phosphate Pathway, Calvin Cycle
  196. Appendix II: Review of laboratory synthesis reactions
  197. Back Matter
  198. Index
  199. Glossary
  200. Detailed Licensing
  201. Front Matter
  202. TitlePage
  203. InfoPage
  204. Table of Contents
  205. Licensing