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CHE 267 - Organic Chemistry I

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CHE 267 - Organic Chemistry I

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

Chemistry
Author
Layne Morsch
Publisher
University of Illinois Springfield
Source
LibreTexts
License
CC BY-NC-SA
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 205 sections
  1. Chapters
  2. Chapter 01: Structure and Bonding
  3. 1.01: The Periodic Table
  4. 1.02: Bonding
  5. 1.03: Lewis Structures
  6. 1.04: Lewis Structures Continued
  7. 1.05: Resonance
  8. 1.06: Determining Molecular Shape
  9. 1.07: Drawing Organic Structures
  10. 1.08: Hybridization
  11. 1.09: Hybridization Examples
  12. 1.10 Bond Length and Bond Strength
  13. 1.11: Electronegativity and Bond Polarity
  14. 1.12: Polarity of Molecules
  15. Chapter 02: Acids and Bases
  16. 5.1: BrnstedLowry Acids and Bases
  17. 5.2: Acid Strength and pKa
  18. 5.3: Predicting the Outcome of AcidBase Reactions
  19. 5.4: Factors That Determine Acid Strength
  20. 5.5: Common Acids and Bases
  21. 5.6: Lewis Acids and Bases
  22. Chapter 02: Introduction to Organic Molecules and Functional Groups
  23. 2.1: An Overview of Functional Groups
  24. 2.2: Intermolecular Forces
  25. 2.3: Physical Properties
  26. 2.4: Application: Vitamins
  27. 2.5: Application of Solubility: Soap
  28. 2.6: Application: The Cell Membrane
  29. 2.7: Functional Groups and Reactivity
  30. 2.8: Biomolecules
  31. Chapter 04: Alkanes
  32. 3.01 Alkanes-An Introduction
  33. 3.02: Cycloalkanes
  34. 3.03: An Introduction to Nomenclature
  35. 3.04: Naming Alkanes
  36. 3.05: Naming Cycloalkanes
  37. 3.06: Common Names
  38. 3.07: Physical Properties of Alkanes
  39. 3.08: Conformations of Acyclic AlkanesEthane
  40. 3.09: Conformations of Butane
  41. 3.10: An Introduction to Cycloalkanes
  42. 3.11: Cyclohexane
  43. 3.12: Substituted Cycloalkanes
  44. 313: LipidsPart 1
  45. Chapter 05: Stereochemistry
  46. 4.01: The Two Major Classes of Isomers
  47. 4.02: Looking Glass ChemistryChiral and Achiral Molecules
  48. 4.03: Stereogenic Centers
  49. 4.04: Labeling Stereogenic Centers with R or S
  50. 4.05: Diastereomers
  51. 4.06: Fischer Projections and Meso Compounds
  52. 4.07: R and S Assignments in Compounds with Two or More Stereogenic Centers
  53. 4.08: Disubstituted Cycloalkanes
  54. 4.09: IsomersA Summary
  55. 4.10: Physical Properties of Stereoisomers
  56. 4.11: Chemical Properties of Enantiomers
  57. Chapter 06: Understanding Organic Reactions
  58. 6.01: Writing Equations for Organic Reactions
  59. 6.02: Kinds of Organic Reactions
  60. 6.03: Drawing Organic Mechanisms
  61. 6.05: Thermodynamics
  62. 6.06: Enthalpy and Entropy
  63. 6.07: Energy Diagrams
  64. 6.08: Energy Diagram for a Two-Step Reaction Mechanism
  65. 6.08: Kinetics
  66. 6.09: Catalysts
  67. 6.10: Enzymes
  68. 6.99: Bond Dissociation Energy
  69. Chapter 07: Alkyl Halides and Nucleophilic Substitution
  70. 7.01: Introduction to Alkyl Halides
  71. 7.02: Nomenclature
  72. 7.03: Physical Properties
  73. 7.04: Interesting Alkyl Halides
  74. 7.05: The Polar CarbonHalogen Bond
  75. 7.06: General Features of Nucleophilic Substitution
  76. 7.07: The Leaving Group
  77. 7.08: The Nucleophile
  78. 7.09: Two Mechanisms for Nucleophilic Substitution
  79. 7.10: The SN2 Mechanism
  80. 7.11: Application: Useful SN2 Reactions
  81. 7.12: The SN1 Mechanism
  82. 7.13: Carbocation Stability
  83. 7.14: The Hammond Postulate
  84. 7.15: When Is the Mechanism SN1 or SN2
  85. 7.16: Vinyl Halides and Aryl Halides
  86. 7.17: Introduction to Organic Synthesis
  87. Chapter 08: Alkyl Halides and Elimination Reactions
  88. 8.01: General Features of Elimination
  89. 8.03: The Mechanisms of Elimination
  90. 8.04: The E2 Mechanism
  91. 8.05: The Zaitsev Rule
  92. 8.06: The E1 Mechanism
  93. 8.07: SN1 and E1 Reactions
  94. 8.08: Stereochemistry of the E2 Reaction
  95. 8.09: E2 Reactions and Alkyne Synthesis
  96. 802: AlkenesThe Products of Elimination Reactions
  97. 810: When Is the Reaction SN1 SN2 E1 or E2
  98. Chapter 09: Alcohols Ethers and Epoxides
  99. 9.01: Introduction
  100. 9.02: Structure and Bonding
  101. 9.03: Nomenclature
  102. 9.04: Physical Properties
  103. 9.05: Interesting Alcohols Ethers and Epoxides
  104. 9.06: Preparation of Alcohols Ethers and Epoxides
  105. 9.07: General FeaturesReactions of Alcohols Ethers and Epoxides
  106. 9.08: Dehydration of Alcohols to Alkenes
  107. 9.09: Carbocation Rearrangements
  108. 9.10: Dehydration Using (POCl 3) and Pyridine
  109. 9.11: Conversion of Alcohols to Alkyl Halides with HX
  110. 9.12: Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3
  111. 9.13: TosylateAnother Good Leaving Group
  112. 9.14: Reaction of Ethers with Strong Acid
  113. 9.15: Reactions of Epoxides
  114. 9.16: Application: Epoxides Leukotrienes and Asthma
  115. Chapter 10: Alkenes
  116. 10.01: Introduction
  117. 10.02: Calculating Degrees of Unsaturation
  118. 10.03: Nomenclature
  119. 10.04: Physical Properties
  120. 10.05: Preparation of Alkenes
  121. 10.06: Introduction to Addition Reactions
  122. 10.07: HydrohalogenationElectrophilic Addition of HX
  123. 10.08: Markovnikovs Rule
  124. 10.09: Stereochemistry of Electrophilic Addition of HX
  125. 10.10: HydrationElectrophilic Addition of Water
  126. 10.11: HalogenationAddition of Halogen
  127. 10.12: Stereochemistry of Halogenation
  128. 10.13: HydroborationOxidation
  129. 10.14: Interesting Alkenes
  130. 10.15: Lipids—Part 2
  131. 10.16: Keeping Track of Reactions
  132. Chapter 11: Alkynes
  133. 11.01: Introduction
  134. 11.02: Nomenclature
  135. 11.03: Physical Properties
  136. 11.04: Interesting Alkynes
  137. 11.05: Preparation of Alkynes
  138. 11.06: Introduction to Alkyne Reactions
  139. 11.07: Addition of Hydrogen Halides
  140. 11.08: Addition of Halogen
  141. 11.09: Addition of Water
  142. 11.10: HydroborationOxidation of Alkynes
  143. 11.11: Reaction of Acetylide Anions
  144. 11.12: Synthesis
  145. Chapter 12: Oxidation and Reduction
  146. 12.01: Introduction
  147. 12.02: Reducing Agents
  148. 12.03: Reduction of Alkenes
  149. 12.04: Application: Hydrogenation of Oils
  150. 12.05: Reduction of Alkynes
  151. 12.06: The Reduction of Polar CX Bonds
  152. 12.07: Oxidizing Agents
  153. 12.08: Epoxidation
  154. 12.09: Dihydroxylation
  155. 12.10: Oxidative Cleavage of Alkenes
  156. 12.11: Oxidative Cleavage of Alkynes
  157. 12.12: Oxidation of Alcohols
  158. Chapter 13: Benzene and Aromatic Compounds
  159. 13.01 Background of Aromaticity
  160. 13.02 The Structure of Benzene
  161. 13.03 Nomenclature of Benzene Derivatives
  162. 13.04 Spectroscopic Properties
  163. 13.05 Interesting Aromatic Compounds
  164. 13.06 Benzenes Unusual Stability
  165. 13.07 The Criteria for AromaticityHuckels Rule
  166. 13.08 Examples of Aromatic Compounds
  167. 13.09 What Is the Basis of Huckels Rule
  168. 13.10 The Inscribed Polygon Method for Predicting Aromaticity
  169. Chapter 20: Introduction to Carbonyl Chemistry Organometallic Reagents Oxidation and Reduction
  170. 20.01: Introduction
  171. 20.02: General Reactions of Carbonyl Compounds
  172. 20.03: A Preview of Oxidation and Reduction
  173. 20.04: Reduction of Aldehydes and Ketones
  174. 20.05: The Stereochemistry of Carbonyl Reduction
  175. 20.06: Enantioselective Carbonyl Reductions
  176. 20.07: Reduction of Carboxylic Acids and Their Derivatives
  177. 20.08: Oxidation of Aldehydes
  178. 20.09: Organometallic Reagents
  179. 20.10: Reaction of Organometallic Reagents with Aldehydes and Ketones
  180. 20.11: Retrosynthetic Analysis of Grignard Products
  181. 20.12: Protecting Groups
  182. 20.13: Reaction of Organometallic Reagents with Carboxylic Acid Derivatives
  183. 20.14: Reaction of Organometallic Reagents with Other Compounds
  184. 20.17: Synthesis
  185. 2015: ,-Unsaturated Carbonyl Compounds
  186. 2016: SummaryThe Reactions of Organometallic Reagents
  187. Chapter 21: Aldehydes and KetonesNucleophilic Addition
  188. 21.01: Introduction
  189. 21.02: Nomenclature
  190. 21.03: Physical Properties
  191. 21.04: Spectroscopic Properties
  192. 21.05: Interesting Aldehydes and Ketones
  193. 21.06: Preparation of Aldehydes and Ketones
  194. 21.10: The Wittig Reaction
  195. 21.15: Acetals as Protecting Groups
  196. 21.16: Cyclic Hemiacetals
  197. 21.17: An Introduction to Carbohydrates
  198. 2107: Reactions of Aldehydes and KetonesGeneral Considerations
  199. 2108: Nucleophilic Addition of H and RA Review
  200. 2109: Nucleophilic Addition of CN
  201. 2111: Addition of 1 Amines
  202. 2112: Addition of 2 Amines
  203. 2113: Addition of H2OHydration
  204. 2114: Addition of AlcoholsAcetal Formation
  205. Readings