CHE 267 - Organic Chemistry I

by Layne Morsch

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CHE 267 is the first semester of university-level organic chemistry. Study of organic structure, reactions and mechanisms. Includes relationship of structure to function.

Description from LibreTexts.

Publisher
University of Illinois Springfield
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. Readings
  2. Chapters
  3. Front Matter
  4. TitlePage
  5. InfoPage
  6. Table of Contents
  7. Licensing
  8. Chapter 1: Structure and Bonding
  9. 1.1: The Periodic Table
  10. 1.2: Bonding
  11. 1.3: Lewis Structures
  12. 1.4: Lewis Structures Exceptions
  13. 1.5: Resonance
  14. 1.6: Determining Molecular Shape
  15. 1.7: Drawing Organic Structures
  16. 1.8: Hybridization
  17. 1.9: Hybridization Examples
  18. 1.10 Bond Length and Bond Strength
  19. 1.11: Electronegativity and Bond Polarity
  20. 1.12: Polarity of Molecules
  21. Chapter 2: Introduction to Organic Molecules and Functional Groups
  22. 2.1: An Overview of Functional Groups
  23. 2.2: Intermolecular Forces
  24. 2.3: Physical Properties
  25. 2.4: Application: Vitamins
  26. 2.5: Application of Solubility: Soap
  27. 2.6: Application: The Cell Membrane
  28. 2.7: Functional Groups and Reactivity
  29. 2.8: Biomolecules
  30. Chapter 3: Alkanes
  31. 3.1: Alkanes—An Introduction
  32. 3.2: Cycloalkanes
  33. 3.3: An Introduction to Nomenclature
  34. 3.4: Naming Alkanes
  35. 3.5: Naming Cycloalkanes
  36. 3.6: Common Names of Alkanes
  37. 3.7: Physical Properties of Alkanes
  38. 3.8: Conformations of Ethane
  39. 3.9: Conformations of Butane
  40. 3.10: An Introduction to Cycloalkanes
  41. 3.11: Cyclohexane
  42. 3.12: Substituted Cycloalkanes
  43. 3.13: Lipids—Part 1
  44. Chapter 4: Stereochemistry
  45. 4.1: The Two Major Classes of Isomers
  46. 4.2: Chiral and Achiral Molecules
  47. 4.3: Stereogenic Centers
  48. 4.4: Labeling Stereogenic Centers with R or S
  49. 4.5: Diastereomers
  50. 4.6: Fischer Projections and Meso Compounds
  51. 4.7: R and S Assignments in Compounds with Two or More Stereogenic Centers
  52. 4.8: Disubstituted Cycloalkanes
  53. 4.9: Isomers—A Summary
  54. 4.10: Physical Properties of Stereoisomers
  55. 4.11: Chemical Properties of Enantiomers
  56. Chapter 5: Acids and Bases
  57. 5.1: Brønsted–Lowry Acids and Bases
  58. 5.2: Acid Strength and pKa
  59. 5.3: Predicting the Outcome of Acid–Base Reactions
  60. 5.4: Factors That Determine Acid Strength
  61. 5.5: Common Acids and Bases
  62. 5.6: Lewis Acids and Bases
  63. Chapter 6: Understanding Organic Reactions
  64. 6.1: Writing Equations for Organic Reactions
  65. 6.2: Kinds of Organic Reactions
  66. 6.3: Drawing Organic Mechanisms
  67. 6.4: Thermodynamics
  68. 6.5: Enthalpy and Entropy
  69. 6.6: Reaction Coordinate Diagrams
  70. 6.7: Reaction Coordinate Diagram for a Two-Step Reaction Mechanism
  71. 6.8: Kinetics
  72. 6.9: Catalysts
  73. 6.10: Enzymes
  74. 6 extra: Bond Dissociation Energy
  75. Chapter 7: Alkyl Halides and Nucleophilic Substitution
  76. 7.1: Introduction to Alkyl Halides
  77. 7.2: Nomenclature of Alkyl Halides
  78. 7.3: Physical Properties of Alkyl Halides
  79. 7.4: Interesting Alkyl Halides
  80. 7.5: The Polar Carbon–Halogen Bond
  81. 7.6: General Features of Nucleophilic Substitution
  82. 7.7: The Leaving Group
  83. 7.8: The Nucleophile
  84. 7.9: Two Mechanisms for Nucleophilic Substitution
  85. 7.10: The SN2 Mechanism
  86. 7.11: Application: Useful SN2 Reactions
  87. 7.12: The SN1 Mechanism
  88. 7.13: Carbocation Stability
  89. 7.14: The Hammond Postulate
  90. 7.15: When Is the Mechanism SN1 or SN2?
  91. 7.16: Vinyl Halides and Aryl Halides
  92. 7.17: Introduction to Organic Synthesis
  93. Chapter 8: Alkyl Halides and Elimination Reactions
  94. 8.1: General Features of Elimination
  95. 8.3: The Mechanisms of Elimination
  96. 8.4: The E2 Mechanism
  97. 8.5: The Zaitsev Rule
  98. 8.6: The E1 Mechanism
  99. 8.7: SN1 and E1 Reactions
  100. 8.8: Stereochemistry of the E2 Reaction
  101. 8.9: E2 Reactions and Alkyne Synthesis
  102. 8.2: Alkenes—The Products of Elimination Reactions
  103. 8.10: When Is the Reaction SN1, SN2, E1, or E2?
  104. Chapter 9: Alcohols, Ethers, and Epoxides
  105. 9.1: Introduction to Alcohols, Ethers and Epoxides
  106. 9.2: Structure and Bonding of Alcohols, Ethers and Epoxides
  107. 9.3: Nomenclature of Alcohols, Ethers and Epoxides
  108. 9.4: Physical Properties of Alcohols, Ethers and Epoxides
  109. 9.5: Interesting Alcohols, Ethers, and Epoxides
  110. 9.6: Preparation of Alcohols, Ethers, and Epoxides
  111. 9.7: General Features—Reactions of Alcohols, Ethers, and Epoxides
  112. 9.8: Dehydration of Alcohols to Alkenes
  113. 9.9: Carbocation Rearrangements
  114. 9.10: Dehydration Using POCl3 and Pyridine
  115. 9.11: Conversion of Alcohols to Alkyl Halides with HX
  116. 9.12: Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3
  117. 9.13: Tosylate—Another Good Leaving Group
  118. 9.14: Reaction of Ethers with Strong Acid
  119. 9.15: Reactions of Epoxides
  120. 9.16: Application: Epoxides, Leukotrienes, and Asthma
  121. Chapter 10: Alkenes
  122. 10.1: Introduction to Alkenes
  123. 10.2: Calculating Degrees of Unsaturation
  124. 10.3: Nomenclature of Alkenes
  125. 10.4: Physical Properties of Alkenes
  126. 10.5: Preparation of Alkenes
  127. 10.6: Introduction to Addition Reactions
  128. 10.7: Hydrohalogenation—Electrophilic Addition of HX
  129. 10.8: Markovnikov’s Rule
  130. 10.9: Stereochemistry of Electrophilic Addition of HX
  131. 10.10: Hydration—Electrophilic Addition of Water
  132. 10.11: Halogenation—Addition of Halogen
  133. 10.12: Stereochemistry of Halogenation
  134. 10.13: Hydroboration–Oxidation
  135. 10.14: Interesting Alkenes
  136. 10.15: Lipids—Part 2
  137. 10.16: Keeping Track of Reactions
  138. Chapter 11: Alkynes
  139. 11.1: Introduction to Alkynes
  140. 11.2: Nomenclature of Alkynes
  141. 11.3: Physical Properties of Alkynes
  142. 11.4: Interesting Alkynes
  143. 11.5: Preparation of Alkynes
  144. 11.6: Introduction to Alkyne Reactions
  145. 11.7: Addition of Hydrogen Halides to Alkynes
  146. 11.8: Addition of Halogen to Alkynes
  147. 11.9: Addition of Water to Alkynes
  148. 11.10: Hydroboration–Oxidation of Alkynes
  149. 11.11: Reaction of Acetylide Anions
  150. 11.12: Synthesis
  151. Chapter 12: Oxidation and Reduction
  152. 12.1: Introduction to Redox
  153. 12.2: Reducing Agents
  154. 12.3: Reduction of Alkenes
  155. 12.4: Application: Hydrogenation of Oils
  156. 12.5: Reduction of Alkynes
  157. 12.6: The Reduction of Polar C–X σ Bonds
  158. 12.7: Oxidizing Agents
  159. 12.8: Epoxidation
  160. 12.9: Dihydroxylation
  161. 12.10: Oxidative Cleavage of Alkenes
  162. 12.11: Oxidative Cleavage of Alkynes
  163. 12.12: Oxidation of Alcohols
  164. Chapter 13: Benzene and Aromatic Compounds
  165. 13.1 Background of Aromaticity
  166. 13.2 The Structure of Benzene
  167. 13.3 Nomenclature of Benzene Derivatives
  168. 13.4 Spectroscopic Properties of Aromatic Compounds
  169. 13.5 Interesting Aromatic Compounds
  170. 13.6 Benzene’s Unusual Stability
  171. 13.7 The Criteria for Aromaticity—Hückel’s Rule
  172. 13.8 Examples of Aromatic Compounds
  173. 13.9 What Is the Basis of Hückel’s Rule?
  174. 13.10 The Inscribed Polygon Method for Predicting Aromaticity
  175. Chapter 20: Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
  176. 20.1: Introduction
  177. 20.2: General Reactions of Carbonyl Compounds
  178. 20.3: A Preview of Oxidation and Reduction
  179. 20.4: Reduction of Aldehydes and Ketones
  180. 20.5: The Stereochemistry of Carbonyl Reduction
  181. 20.6: Enantioselective Carbonyl Reductions
  182. 20.7: Reduction of Carboxylic Acids and Their Derivatives
  183. 20.8: Oxidation of Aldehydes
  184. 20.9: Organometallic Reagents
  185. 20.10: Reaction of Organometallic Reagents with Aldehydes and Ketones
  186. 20.11: Retrosynthetic Analysis of Grignard Products
  187. 20.12: Protecting Groups
  188. 20.13: Reaction of Organometallic Reagents with Carboxylic Acid Derivatives
  189. 20.14: Reaction of Organometallic Reagents with Other Compounds
  190. 20.17: Synthesis
  191. 20.15: α,β-Unsaturated Carbonyl Compounds
  192. 20.16: Summary—The Reactions of Organometallic Reagents
  193. Chapter 21: Aldehydes and Ketones—Nucleophilic Addition
  194. 21.1: Introduction
  195. 21.2: Nomenclature of Aldehydes and Ketones
  196. 21.3: Physical Properties
  197. 21.4: Spectroscopic Properties
  198. 21.5: Interesting Aldehydes and Ketones
  199. 21.6: Preparation of Aldehydes and Ketones
  200. 21.10: The Wittig Reaction
  201. 21.15: Acetals as Protecting Groups
  202. 21.16: Cyclic Hemiacetals
  203. 21.17: An Introduction to Carbohydrates
  204. 21.7: Reactions of Aldehydes and Ketones—General Considerations
  205. 21.8: Nucleophilic Addition of H– and R–—A Review
  206. 21.9: Nucleophilic Addition of –CN
  207. 21.11: Addition of 1° Amines
  208. 21.12: Addition of 2° Amines
  209. 21.13: Addition of H2O—Hydration
  210. 21.14: Addition of Alcohols—Acetal Formation
  211. Back Matter
  212. Index
  213. Detailed Licensing
  214. 00: Front Matter
  215. Table of Contents