CHEM 232 - Organic Chemistry II

by Sol Parajon Puenzo

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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.

Description from LibreTexts.

Publisher
Cañada College
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

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  1. Front Matter
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. Licensing
  6. 1: Conjugated Compounds and Ultraviolet Spectroscopy
  7. 1.0: Introduction
  8. 1.1: Stability of Conjugated Dienes- Molecular Orbital Theory
  9. 1.2: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  10. 1.3: Kinetic vs. Thermodynamic Control of Reactions
  11. 1.4: The Diels-Alder Cycloaddition Reaction
  12. 1.5: Characteristics of the Diels-Alder Reaction
  13. 1.6: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
  14. 1.7: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  15. 1.8: Conjugation, Color, and the Chemistry of Vision
  16. 1.9: Additional Problems
  17. 1.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
  18. 2: Benzene and Aromaticity
  19. 2.0: Introduction
  20. 2.1: Naming Aromatic Compounds
  21. 2.2: Acidity of Phenols
  22. 2.3: Basicity of Arylamines
  23. 2.4: Structure and Stability of Benzene
  24. 2.5: Aromaticity and the Hückel 4n + 2 Rule
  25. 2.6: Aromatic Ions
  26. 2.7: Aromatic Heterocycles
  27. 2.8: Polycyclic Aromatic Compounds
  28. 2.9: Reactions at the Benzylic Position
  29. 2.10: Spectroscopy of Aromatic Compounds
  30. 2.11: Additional Problems
  31. 2.S: Benzene and Aromaticity (Summary)
  32. 3: Chemistry of Benzene - Reactions of Aromatic Compounds
  33. 3.0: Introduction
  34. 3.1: Electrophilic Aromatic Substitution Reactions - Bromination
  35. 3.2: Other Aromatic Substitutions
  36. 3.3: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
  37. 3.4: Substituent Effects in the Reactivity of Aromatic Rings
  38. 3.5: The Direction of the Reaction
  39. 3.6: Trisubstituted Benzenes - Additivity of Effects
  40. 3.7: Nucleophilic Aromatic Substitution
  41. 3.8: Benzyne
  42. 3.9: Reduction of Aromatic Compounds
  43. 3.10: Synthesis of Polysubstituted Benzenes
  44. 3.11: Reactions of Arylamines
  45. 3.12: Additional Problems
  46. 3.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
  47. 4: Ethers and Epoxides; Thiols and Sulfides
  48. 4.0: Introduction
  49. 4.1: Names and Properties of Ethers
  50. 4.2: Preparing Ethers
  51. 4.3: Reactions of Ethers - Acidic Cleavage
  52. 4.4: Reactions of Ethers - Claisen Rearrangement
  53. 4.5: Cyclic Ethers - Epoxides
  54. 4.6: Reactions of Epoxides - Ring-opening
  55. 4.7: Crown Ethers
  56. 4.8: Thiols and Sulfides
  57. 4.9: Spectroscopy of Ethers and Epoxides
  58. 4.10: Interchapter - A Preview of Carbonyl Chemistry
  59. 4.11: Additional Problems
  60. 4.S: Ethers and Epoxides; Thiols and Sulfides (Summary)
  61. 5: Aldehydes and Ketones - Nucleophilic Addition Reactions
  62. 5.0: Chapter Objectives and Preview of Carbonyl Chemistry
  63. 5.1: Naming Aldehydes and Ketones
  64. 5.2: Preparing Aldehydes and Ketones
  65. 5.3: Oxidation of Aldehydes and Ketones
  66. 5.4: Nucleophilic Addition Reactions of Aldehydes and Ketones
  67. 5.5: Nucleophilic Addition of Hydride - Alcohol Formation
  68. 5.6: Nucleophilic Addition via Organometallic Reactions - Alcohol Formation
  69. 5.7: Nucleophilic Addition of HCN - Cyanohydrin Formation
  70. 5.8: Nucleophilic Addition of Phosphorus Ylides - The Wittig Reaction
  71. 5.9: Nucleophilic Addition of Water- Hydration
  72. 5.10: Nucleophilic Addition of Alcohols - Acetal Formation
  73. 5.11: Nucleophilic Addition of Amines - Imine and Enamine Formation
  74. 5.12: Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction
  75. 5.13: Biological Reductions
  76. 5.14: Conjugate Nucleophilic Addition to α, β-unsaturated Aldehydes and Ketones
  77. 5.15: Spectroscopy of Aldehydes and Ketones
  78. 5.16: Additional Problems
  79. 5.S: Aldehydes and Ketones (Summary)
  80. 6: Carboxylic Acids and Nitriles
  81. 6.0: Chapter Objectives and Introduction to Carboxylic Acids
  82. 6.1: Naming Carboxylic Acids and Nitriles
  83. 6.2: Structure and Properties of Carboxylic Acids
  84. 6.3: Substituent Effects on Acidity
  85. 6.4: Preparing Carboxylic Acids
  86. 6.5: Reactions of Carboxylic Acids - An Overview
  87. 6.6: Chemistry of Nitriles
  88. 6.7: Spectroscopy of Carboxylic Acids and Nitriles
  89. 6.8: Additional Problems
  90. 6.S: Carboxylic Acids and Nitriles (Summary)
  91. 7: Carboxylic Acid Derivatives - Nucleophilic Acyl Substitution Reactions
  92. 7.0: Chapter Objectives and Introduction to Carboxylic Acid Derivatives
  93. 7.1: Naming Carboxylic Acid Derivatives
  94. 7.2: Nucleophilic Acyl Substitution Reactions
  95. 7.3: Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
  96. 7.4: Chemistry of Acid Halides
  97. 7.5: Chemistry of Acid Anhydrides
  98. 7.6: Chemistry of Esters
  99. 7.7: Chemistry of Amides
  100. 7.8: Chemistry of Thioesters and Acyl Phosphates - Biological Carboxylic Acid Derivatives
  101. 7.9: Polyamides and Polyesters - Step-Growth Polymers
  102. 7.10: Spectroscopy of Carboxylic Acid Derivatives
  103. 7.11: Additional Problems
  104. 7.S: Carboxylic Acid Derivatives (Summary)
  105. 8: Carbonyl Alpha-Substitution Reactions
  106. 8.0: Chapter Objectives and Introduction to Carbonyl Alpha-Substitution Reactions
  107. 8.1: Keto-Enol Tautomerism
  108. 8.2: Reactivity of Enols- The Mechanism of Alpha-Substitution Reactions
  109. 8.3: Alpha Halogenation of Aldehydes and Ketones
  110. 8.4: Alpha Bromination of Carboxylic Acids
  111. 8.5: Acidity of Alpha Hydrogen Atoms- Enolate Ion Formation
  112. 8.6: Reactivity of Enolate Ions
  113. 8.7: Alkylation of Enolate Ions
  114. 8.8: Additional Problems
  115. 8.S: Carbonyl Alpha-Substitution Reactions (Summary)
  116. 9: Carbonyl Condensation Reactions
  117. 9.0: Chapter Objectives
  118. 9.1: Carbonyl Condensations - The Aldol Reaction
  119. 9.2: Carbonyl Condensations versus Alpha Substitutions
  120. 9.3: Aldol Condensation - Dehydration of Aldol Products
  121. 9.4: Using Aldol Reactions in Synthesis
  122. 9.5: Mixed Aldol Reactions
  123. 9.6: Intramolecular Aldol Reactions
  124. 9.7: The Claisen Condensation Reaction
  125. 9.8: Mixed Claisen Condensations
  126. 9.9: Intramolecular Claisen Condensations - The Dieckmann Cyclization
  127. 9.10: Conjugate Carbonyl Additions - The Michael Reaction
  128. 9.11: Carbonyl Condensations with Enamines - The Stork Reaction
  129. 9.12: The Robinson Annulation Reaction
  130. 9.13: Some Biological Carbonyl Condensation Reactions
  131. 9.14: Additional Problems
  132. 9.S: Carbonyl Condensation Reactions (Summary)
  133. 10: Amines and Heterocycles
  134. 10.0: Introduction
  135. 10.1: Naming Amines
  136. 10.2: Structure and Properties of Amines
  137. 10.3: Basicity of Amines
  138. 10.4: Biological Amines and the Henderson-Hasselbalch Equation
  139. 10.5: Synthesis of Amines
  140. 10.6: Reactions of Amines
  141. 10.7: Heterocyclic Amines
  142. 10.8: Spectroscopy of Amines
  143. 10.9: Drugs and the Mind
  144. 10.10: Additional Problems
  145. 10.S: Amines and Heterocycles (Summary)
  146. 11: Biomolecules - Carbohydrates
  147. 11.0: Introduction
  148. 11.1: Classification of Carbohydrates
  149. 11.2: Depicting Carbohydrate Stereochemistry - Fischer Projections
  150. 11.3: D, L Sugars
  151. 11.4: Configurations of Aldoses
  152. 11.5: Cyclic Structures of Monosaccharides - Anomers
  153. 11.6: Reactions of Monosaccharides
  154. 11.7: The Eight Essential Monosaccharides + Fructose
  155. 11.8: Disaccharides
  156. 11.9: Polysaccharides and Their Synthesis
  157. 11.10: Other Important Carbohydrates
  158. 11.11: Cell-Surface Carbohydrates and Influenza Viruses
  159. 11.12: Additional Problems
  160. 11.S: Biomolecules- Carbohydrates (Summary)
  161. 12: Biomolecules - Amino Acids, Peptides, and Proteins
  162. 12.0: Introduction
  163. 12.1: Structures of Amino Acids
  164. 12.2: Amino Acids and Isoelectric Points
  165. 12.3: Synthesis of Amino Acids
  166. 12.4: Peptides and Proteins
  167. 12.5: Peptide Synthesis- Solution-Phase
  168. 12.6: Automated Peptide Synthesis - Solid-Phase Technique
  169. 12.7: Protein Structure
  170. 12.8: Protein Misfolding and Denaturation
  171. 12.9: Enzymes and Coenzymes
  172. 12.10: Regulation of Enzyme Activity
  173. 12.11: How do Enzymes Work? Citrate Synthase
  174. 12.12: Additional Problems
  175. 12.S: Biomolecules - Amino Acids (Summary)
  176. 13: Biomolecules - Nucleic Acids
  177. 13.0: Why This Chapter?
  178. 13.1: Nucleotides and Nucleic Acids
  179. 13.2: Base Pairing in DNA - The Watson-Crick Model
  180. 13.3: Transcription of DNA
  181. 13.4: Translation of RNA - Protein Biosynthesis
  182. 13.5: Drugs and Infectious Diseases
  183. 13.6: Chemicals Against Cancer
  184. 13.7: Chemistry Matters—DNA Fingerprinting
  185. 13.8: Additional Problems
  186. 13.S: Biomolecules - Nucleic Acids (Summary)
  187. 14: Biomolecules - Lipids
  188. 14.0: Introduction to Lipids
  189. 14.1: Waxes, Fats, and Oils
  190. 14.2: Soap
  191. 14.3: Phospholipids
  192. 14.4: Prostaglandins and Other Eicosanoids
  193. 14.5: Terpenoids
  194. 14.6: Steroids
  195. 14.7: Hormones - The Regulators
  196. 14.8: Biosynthesis of Steroids
  197. 14.9: Additional Problems
  198. 14.S: Biomolecules - Lipids (Summary)
  199. 15: Orbitals and Organic Chemistry - Pericyclic Reactions
  200. 15.0: Chapter Overview
  201. 15.1: Molecular Orbitals of Conjugated Pi Systems
  202. 15.2: Electrocyclic Reactions
  203. 15.3: Stereochemistry of Thermal Electrocyclic Reactions
  204. 15.4: Photochemical Electrocyclic Reactions
  205. 15.5: Cycloaddition Reactions
  206. 15.6: Stereochemistry of Cycloadditions
  207. 15.7: Sigmatropic Rearrangements
  208. 15.8: Some Examples of Sigmatropic Rearrangements
  209. 15.9: Additional Problems
  210. 15.S: A Summary of Rules for Pericyclic Reactions
  211. 16: Synthetic Polymers
  212. 16.0: Chapter Objectives
  213. 16.1: Chain-Growth Polymers
  214. 16.2: Stereochemistry of Polymerization - Ziegler-Natta Catalysts
  215. 16.3: Copolymers
  216. 16.4: Step-Growth Polymers
  217. 16.5: Olefin Metathesis Polymerization
  218. 16.6: Polymer Structure and Physical Properties
  219. 16.7: Additional Problems
  220. 16.S: Synthetic Polymers (Summary)
  221. Back Matter
  222. Index
  223. 1.0: Index
  224. Glossary
  225. 1.0: Appendix C - Glossary
  226. Detailed Licensing
  227. 1.0: Detailed Licensing
  228. Appendix C - Nomenclature of Polyfunctional Organic Compounds
  229. Appendix A - Periodic Table
  230. Appendix B - Acidity Constants for Some Organic Compounds