Athabasca University Chemistry 360 Organic Chemistry II

by Dietmar Kennepohl

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CHEM 360 deals with the chemistry of carbon compounds through a study of the characteristic reactions of the common functional groups. The chemistry of alcohols, ethers, aldehydes and ketones, carboxylic acids and their derivatives, carbohydrates, and amines are discussed. Particular emphasis is placed on the study of reaction mechanisms, in an attempt to show similarities between apparently unrelated reactions. The importance of stereochemistry is stressed throughout the course.

Description from LibreTexts.

Publisher
Athabasca University
Subjects
Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
Who can read
Teens 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. Chapter 17: Alcohols and Phenols
  7. 17.0 Introduction
  8. 17.1 Naming Alcohols and Phenols
  9. 17.2 Properties of Alcohols and Phenols
  10. 17.3 Preparation of Alcohols: A Review
  11. 17.4 Alcohols from Carbonyl Compounds: Reduction
  12. 17.5 Alcohols from Reaction of Carbonyl Compounds - Grignard Reagents
  13. 17.6 Reactions of Alcohols
  14. 17.7 Oxidation of Alcohols
  15. 17.8 Protection of Alcohols
  16. 17.9 Phenols and Their Uses
  17. 17.10 Reactions of Phenols
  18. 17.11 Spectroscopy of Alcohols and Phenols
  19. 17.S: Alcohols and Phenols (Summary)
  20. Chapter 18: Ethers and Epoxides; Thiols and Sulfides
  21. 18.0 Introduction
  22. 18.1 Names and Properties of Ethers
  23. 18.2 Synthesis of Ethers
  24. 18.3 Reactions of Ethers: Acidic Cleavage
  25. 18.4 Reactions of Ethers - Claisen Rearrangement
  26. 18.5 Cyclic Ethers: Epoxides
  27. 18.6 Reactions of Epoxides: Ring-opening
  28. 18.7 Crown Ethers
  29. 18.8 Thiols and Sulfides
  30. 18.9 Spectroscopy of Ethers
  31. Chapter 18 - Affix: A Preview of Carbonyl Compounds
  32. 18.S: Ethers and Epoxides; Thiols and Sulfides (Summary)
  33. Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
  34. Chapter Objectives
  35. 19.1 Naming Aldehydes and Ketones
  36. 19.2 Preparing Aldehydes and Ketones
  37. 19.3 Oxidation of Aldehydes and Ketones
  38. 19.4 Nucleophilic Addition Reactions of Aldehydes and Ketones
  39. 19.5 Nucleophilic Addition of Water: Hydration
  40. 19.6 Nucleophilic Addition of HCN: Cyanohydrin Formation
  41. 19.7 Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation
  42. 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation
  43. 19.9 Nucleophilic Addition of Hydrazin - The Wolff-Kishner Reaction
  44. 19.10 Nucleophilic Addition of Alcohols: Acetal Formation
  45. 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
  46. 19.12 Biological Reductions
  47. 19.13 Conjugate Nucleophilic Addition to alpha, beta-unsaturated Aldehydes and Ketones
  48. 19.14 Spectroscopy of Aldehydes and Ketones
  49. 19.S: Aldehydes and Ketones (Summary)
  50. Chapter 20: Carboxylic Acids and Nitriles
  51. Chapter Objectives
  52. 20.0 Introduction
  53. 20.1 Naming Carboxylic Acids and Nitriles
  54. 20.2 Structure and Properties of Carboxylic Acids
  55. 20.3 Biological Acids and the Henderson-Hasselbalch Equation
  56. 20.4 Substituent Effects on Acidity
  57. 20.5 Preparing Carboxylic Acids
  58. 20.6 Reactions of Carboxylic Acids: An Overview
  59. 20.7 Chemistry of Nitriles
  60. 20.8 Spectroscopy of Carboxylic Acids and Nitriles
  61. 20.S: Carboxylic Acids and Nitriles (Summary)
  62. 20: Carboxylic Acids and Nitriles
  63. Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
  64. Chapter Objectives
  65. 21.0 Introduction
  66. 21.1 Naming Carboxylic Acid Derivatives
  67. 21.2 Nucleophilic Acyl Substitution Reactions
  68. 21.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
  69. 21.4 Chemistry of Acid Halides
  70. 21.5 Chemistry of Acid Anhydrides
  71. 21.6 Chemistry of Esters
  72. 21.7 Chemistry of Amides
  73. 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
  74. 21.9 Polyamides and Polyesters: Step-Growth Polymers
  75. 21.10 Spectroscopy of Carboxylic Acid Derivatives
  76. 21.S: Carboxylic Acid Derivatives (Summary)
  77. Chapter 22: Carbonyl Alpha-Substitution Reactions
  78. Chapter Objectives
  79. 22.0 Introduction
  80. 22.1 Keto-Enol Tautomerism
  81. 22.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
  82. 22.3 Alpha Halogenation of Aldehydes and Ketones
  83. 22.4 Alpha Bromination of Carboxylic Acids
  84. 22.5 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
  85. 22.6 Reactivity of Enolate Ions
  86. 22.7 Alkylation of Enolate Ions
  87. 22.S: Carbonyl Alpha-Substitution Reactions (Summary)
  88. Chapter 23: Carbonyl Condensation Reactions
  89. Chapter Objectives
  90. 23.1 Carbonyl Condensations - The Aldol Reaction
  91. 23.2 Carbonyl Condensations versus Alpha Substitutions
  92. 23.3 Dehydration of Aldol Products - Synthesis of Enones
  93. 23.4 Using Aldol Reactions in Synthesis
  94. 23.5 Mixed Aldol Reactions
  95. 23.6 Intramolecular Aldol Reactions
  96. 23.7 The Claisen Condensation Reaction
  97. 23.8 Mixed Claisen Condensations
  98. 23.9 Intramolecular Claisen Condensations - The Dieckmann Cyclization
  99. 23.10 Conjugate Carbonyl Additions - The Michael Reaction
  100. 23.11 Carbonyl Condensations with Enamines - The Stork Reaction
  101. 23.12 The Robinson Annulation Reaction
  102. 23.13 Some Biological Carbonyl Condensation Reactions
  103. 23.S: Carbonyl Condensation Reactions (Summary)
  104. Chapter 24: Amines and Heterocycles
  105. Chapter Objectives
  106. 24.1 Naming Amines
  107. 24.2 Structure and Properties of Amines
  108. 24.3 Basicity of Amines
  109. 24.4 Basicity of Arylamines
  110. 24.5 Biological Amines and the Henderson-Hasselbalch Equation
  111. 24.6 Synthesis of Amines
  112. 24.7 Reactions of Amines
  113. 24.8 Reactions of Arylamines
  114. 24.9 Heterocyclic Amines
  115. 24.10 Spectroscopy of Amines
  116. 24.S: Amines and Heterocycles (Summary)
  117. Chapter 25: Biomolecules: Carbohydrates
  118. Chapter Objectives
  119. 25.0 Introduction
  120. 25.1 Classification of Carbohydrates
  121. 25.2 Depicting Carbohydrate Stereochemistry: Fischer Projections
  122. 25.3 D, L Sugars
  123. 25.4 Configurations of Aldoses
  124. 25.5 Cyclic Structures of Monosaccharides: Anomers
  125. 25.6 Reactions of Monosaccharides
  126. 25.7 The Eight Essential Monosaccharides
  127. 25.8 Disaccharides
  128. 25.9 Polysaccharides and Their Synthesis
  129. 25.10 Other Important Carbohydrates
  130. 25.11 Cell-Surface Carbohydrates and Influenza Viruses
  131. 25.S: Biomolecules- Carbohydrates (Summary)
  132. Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
  133. Chapter Objectives
  134. 26.0 Introduction
  135. 26.1 Structures of Amino Acids
  136. 26.2 Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
  137. 26.3 Synthesis of Amino Acids
  138. 26.4 Peptides and Proteins
  139. 26.5 Amino Acid Analysis of Peptides
  140. 26.6 Peptide Sequencing: The Edman Degradation
  141. 26.7 Peptide Synthesis
  142. 26.8 Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
  143. 26.9 Protein Structure
  144. 26.10 Enzymes and Coenzymes
  145. 26.11 How do Enzymes Work? Citrate Synthase
  146. Chapter 27: Biomolecules - Lipids
  147. Chapter Objectives
  148. 27.0 Introduction to Lipids
  149. 27.1 Waxes, Fats, and Oils
  150. 27.2 Soap
  151. 27.3 Phospholipids
  152. 27.4 Prostaglandins and Other Eicosanoids
  153. 27.5 Terpenoids
  154. 27.6 Steroids
  155. 27.7 Biosynthesis of Steroids
  156. Chapter 28: Biomolecules - Nucleic Acids
  157. Chapter Objectives
  158. 28.1 Nucleotides and Nucleic Acids
  159. 28.2 Base Pairing in DNA: The Watson-Crick Model
  160. 28.3 Replication of DNA
  161. 28.4 Transcription of DNA
  162. 28.5 Translation of RNA: Protein Biosynthesis
  163. 28.6 DNA Sequencing
  164. 28.7 DNA Synthesis
  165. 28.8 The Polymerase Chain Reaction
  166. Back Matter
  167. Index
  168. Glossary
  169. Detailed Licensing