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CHEM 232 - Organic Chemistry II

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CHEM 232 - Organic Chemistry II

This text is designed for CHEM 232 Organic Chemistry II at Cañada College, the second semester of a one-year organic chemistry sequence. It introduces the chemistry of aromatic compounds, aldehydes, ketones, carboxylic acids, carbohydrates, lipids, amino acids, and proteins, with emphasis on synthesis and reaction mechanisms.

Chemistry
Author
Sol Parajon Puenzo
Publisher
Cañada College
Source
LibreTexts
License
CC BY-NC-SA
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 203 sections
  1. 01: Conjugated Compounds and Ultraviolet Spectroscopy
  2. 1.01: Introduction
  3. 1.02: Stability of Conjugated Dienes- Molecular Orbital Theory
  4. 1.03: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  5. 1.04: Kinetic vs. Thermodynamic Control of Reactions
  6. 1.05: The Diels-Alder Cycloaddition Reaction
  7. 1.06: Characteristics of the Diels-Alder Reaction
  8. 1.07: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
  9. 1.08: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  10. 1.09: Conjugation Color and the Chemistry of Vision
  11. 1.10: Additional Problems
  12. 1.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
  13. 02: Benzene and Aromaticity
  14. 2.01: Introduction
  15. 2.02: Naming Aromatic Compounds
  16. 2.03: Structure and Stability of Benzene
  17. 2.04: Aromaticity and the Huckel 4n 2 Rule
  18. 2.05: Aromatic Ions
  19. 2.06: Aromatic Heterocycles
  20. 2.07: Polycyclic Aromatic Compounds
  21. 2.08: Reactions at the Benzylic Position
  22. 2.09: Spectroscopy of Aromatic Compounds
  23. 2.10: Additional Problems
  24. 2.S: Benzene and Aromaticity (Summary)
  25. 03: Chemistry of Benzene - Reactions of Aromatic Compounds
  26. 3.01: Introduction
  27. 3.02: Electrophilic Aromatic Substitution Reactions - Bromination
  28. 3.03: Other Aromatic Substitutions
  29. 3.04: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
  30. 3.05: Substituent Effects in the Reactivity of Aromatic Rings
  31. 3.06: The Direction of the Reaction
  32. 3.07: Trisubstituted Benzenes - Additivity of Effects
  33. 3.08: Nucleophilic Aromatic Substitution
  34. 3.09: Benzyne
  35. 3.10: Reduction of Aromatic Compounds
  36. 3.11: Synthesis of Polysubstituted Benzenes
  37. 3.12: Additional Problems
  38. 3.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
  39. 04: Ethers and Epoxides Thiols and Sulfides
  40. 4.01: Introduction
  41. 4.02: Names and Properties of Ethers
  42. 4.03: Preparing Ethers
  43. 4.04: Reactions of Ethers - Acidic Cleavage
  44. 4.05: Reactions of Ethers - Claisen Rearrangement
  45. 4.06: Cyclic Ethers - Epoxides
  46. 4.07: Reactions of Epoxides - Ring-opening
  47. 4.08: Crown Ethers
  48. 4.09: Thiols and Sulfides
  49. 4.10: Spectroscopy of Ethers and Epoxides
  50. 4.11: Interchapter - A Preview of Carbonyl Chemistry
  51. 4.12: Additional Problems
  52. 4.S: Ethers and Epoxides Thiols and Sulfides (Summary)
  53. 05: Aldehydes and Ketones- Nucleophilic Addition Reactions
  54. 5.01: Chapter Objectives and Preview of Carbonyl Chemistry
  55. 5.02: Naming Aldehydes and Ketones
  56. 5.03: Preparing Aldehydes and Ketones
  57. 5.04: Oxidation of Aldehydes and Ketones
  58. 5.05: Nucleophilic Addition Reactions of Aldehydes and Ketones
  59. 5.06: Nucleophilic Addition of Hydride - Alcohol Formation
  60. 5.07: Nucleophilic Addition via Organometallic Reactions - Alcohol Formation
  61. 5.08: Nucleophilic Addition of HCN - Cyanohydrin Formation
  62. 5.09: Nucleophilic Addition of Phosphorus Ylides - The Wittig Reaction
  63. 5.10: Nucleophilic Addition of Water- Hydration
  64. 5.11: Nucleophilic Addition of Alcohols - Acetal Formation
  65. 5.12: Nucleophilic Addition of Amines - Imine and Enamine Formation
  66. 5.13: Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction
  67. 5.14: Biological Reductions
  68. 5.15: Conjugate Nucleophilic Addition to -unsaturated Aldehydes and Ketones
  69. 5.16: Spectroscopy of Aldehydes and Ketones
  70. 5.17: Additional Problems
  71. 5.S: Aldehydes and Ketones (Summary)
  72. 06: Carboxylic Acids and Nitriles
  73. 6.01: Chapter Objectives and Introduction to Carboxylic Acids
  74. 6.02: Naming Carboxylic Acids and Nitriles
  75. 6.03: Structure and Properties of Carboxylic Acids
  76. 6.04: Substituent Effects on Acidity
  77. 6.05: Preparing Carboxylic Acids
  78. 6.06: Reactions of Carboxylic Acids - An Overview
  79. 6.07: Chemistry of Nitriles
  80. 6.08: Spectroscopy of Carboxylic Acids and Nitriles
  81. 6.09: Additional Problems
  82. 6.S: Carboxylic Acids and Nitriles (Summary)
  83. 07: Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions
  84. 7.01: Chapter Objectives and Introduction to Carboxylic Acid Derivatives
  85. 7.02: Naming Carboxylic Acid Derivatives
  86. 7.03: Nucleophilic Acyl Substitution Reactions
  87. 7.04: Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
  88. 7.05: Chemistry of Acid Halides
  89. 7.06: Chemistry of Acid Anhydrides
  90. 7.07: Chemistry of Esters
  91. 7.08: Chemistry of Amides
  92. 7.09: Chemistry of Thioesters and Acyl Phosphates - Biological Carboxylic Acid Derivatives
  93. 7.10: Polyamides and Polyesters - Step-Growth Polymers
  94. 7.11: Spectroscopy of Carboxylic Acid Derivatives
  95. 7.12: Additional Problems
  96. 7.S: Carboxylic Acid Derivatives (Summary)
  97. 08: Carbonyl Alpha-Substitution Reactions
  98. 8.01: Chapter Objectives and Introduction to Carbonyl Alpha-Substitution Reactions
  99. 8.02: Keto-Enol Tautomerism
  100. 8.03: Reactivity of Enols- The Mechanism of Alpha-Substitution Reactions
  101. 8.04: Alpha Halogenation of Aldehydes and Ketones
  102. 8.05: Alpha Bromination of Carboxylic Acids
  103. 8.06: Acidity of Alpha Hydrogen Atoms- Enolate Ion Formation
  104. 8.07: Reactivity of Enolate Ions
  105. 8.08: Alkylation of Enolate Ions
  106. 8.09: Additional Problems
  107. 8.S: Carbonyl Alpha-Substitution Reactions (Summary)
  108. 09: Carbonyl Condensation Reactions
  109. 9.01: Chapter Objectives
  110. 9.02: Carbonyl Condensations - The Aldol Reaction
  111. 9.03: Carbonyl Condensations versus Alpha Substitutions
  112. 9.04: Aldol Condensation - Dehydration of Aldol Products
  113. 9.05: Using Aldol Reactions in Synthesis
  114. 9.06: Mixed Aldol Reactions
  115. 9.07: Intramolecular Aldol Reactions
  116. 9.08: The Claisen Condensation Reaction
  117. 9.09: Mixed Claisen Condensations
  118. 9.10: Intramolecular Claisen Condensations - The Dieckmann Cyclization
  119. 9.11: Conjugate Carbonyl Additions - The Michael Reaction
  120. 9.12: Carbonyl Condensations with Enamines - The Stork Reaction
  121. 9.13: The Robinson Annulation Reaction
  122. 9.14: Some Biological Carbonyl Condensation Reactions
  123. 9.15: Additional Problems
  124. 9.S: Carbonyl Condensation Reactions (Summary)
  125. 10: Amines and Heterocycles
  126. 10.01: Introduction
  127. 10.02: Naming Amines
  128. 10.03: Structure and Properties of Amines
  129. 10.04: Basicity of Amines
  130. 10.05: Basicity of Arylamines
  131. 10.06: Biological Amines and the Henderson-Hasselbalch Equation
  132. 10.07: Synthesis of Amines
  133. 10.08: Reactions of Amines
  134. 10.09: Reactions of Arylamines
  135. 10.10: Heterocyclic Amines
  136. 10.11: Spectroscopy of Amines
  137. 10.12: Additional Problems
  138. 10.S: Amines and Heterocycles (Summary)
  139. 11: Biomolecules- Carbohydrates
  140. 11.01: Introduction
  141. 11.02: Classification of Carbohydrates
  142. 11.03: Depicting Carbohydrate Stereochemistry - Fischer Projections
  143. 11.04: D L Sugars
  144. 11.05: Configurations of Aldoses
  145. 11.06: Cyclic Structures of Monosaccharides - Anomers
  146. 11.07: Reactions of Monosaccharides
  147. 11.08: The Eight Essential Monosaccharides Fructose
  148. 11.09: Disaccharides
  149. 11.10: Polysaccharides and Their Synthesis
  150. 11.11: Other Important Carbohydrates
  151. 11.12: Cell-Surface Carbohydrates and Influenza Viruses
  152. 11.13: Nucleotides and Nucleic Acids
  153. 11.14: Base Pairing in DNA - The Watson-Crick Model
  154. 11.15: Additional Problems
  155. 11.S: Biomolecules- Carbohydrates (Summary)
  156. 12: Biomolecules- Amino Acids Peptides and Proteins
  157. 12.01: Introduction
  158. 12.02: Structures of Amino Acids
  159. 12.03: Amino Acids and Isoelectric Points
  160. 12.04: Synthesis of Amino Acids
  161. 12.05: Peptides and Proteins
  162. 12.06: Peptide Synthesis- Solution-Phase
  163. 12.07: Automated Peptide Synthesis - Solid-Phase Technique
  164. 12.08: Protein Structure
  165. 12.09: Protein Misfolding and Denaturation
  166. 12.10: Enzymes and Coenzymes
  167. 12.11: Regulation of Enzyme Activity
  168. 12.12: How do Enzymes Work Citrate Synthase
  169. 12.13: Summary of Reactions
  170. 12.14: Additional Problems
  171. 13: Biomolecules - Lipids
  172. 13.01: Introduction to Lipids
  173. 13.02: Waxes Fats and Oils
  174. 13.03: Soap
  175. 13.04: Phospholipids
  176. 13.05: Prostaglandins and Other Eicosanoids
  177. 13.06: Terpenoids
  178. 13.07: Steroids
  179. 13.08: Biosynthesis of Steroids
  180. 13.09: Additional Problems
  181. 13.S: Biomolecules - Lipids (Summary)
  182. 14: Orbitals and Organic Chemistry - Pericyclic Reactions
  183. 14.01: Chapter Overview
  184. 14.02: Molecular Orbitals of Conjugated Pi Systems
  185. 14.03: Electrocyclic Reactions
  186. 14.04: Stereochemistry of Thermal Electrocyclic Reactions
  187. 14.05: Photochemical Electrocyclic Reactions
  188. 14.06: Cycloaddition Reactions
  189. 14.07: Stereochemistry of Cycloadditions
  190. 14.08: Sigmatropic Rearrangements
  191. 14.09: Some Examples of Sigmatropic Rearrangements
  192. 14.10: A Summary of Rules for Pericyclic Reactions
  193. 14.11: Additional Problems
  194. 15: Synthetic Polymers
  195. 15.01: Chapter Objectives
  196. 15.02: Chain-Growth Polymers
  197. 15.03: Stereochemistry of Polymerization - Ziegler-Natta Catalysts
  198. 15.04: Copolymers
  199. 15.05: Step-Growth Polymers
  200. 15.06: Olefin Metathesis Polymerization
  201. 15.07: Polymer Structure and Physical Properties
  202. 15.08: Summary
  203. 15.09: Additional Problems