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Athabasca University Chemistry 350 Organic Chemistry I

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Athabasca University Chemistry 350 Organic Chemistry I

CHEM 350 deals with the chemistry of carbon compounds through a study of the characteristic reactions of the common functional groups. 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. The course also includes an introduction to the use of spectroscopy in the analysis of organic compounds.

Chemistry
Author
Dietmar Kennepohl
Publisher
Athabasca University
Source
LibreTexts
License
CC BY-NC-SA
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 214 sections
  1. 01: Structure and Bonding
  2. 1.00: Introduction
  3. 1.01: Atomic Structure- The Nucleus
  4. 1.02: Atomic Structure- Orbitals
  5. 1.03: Atomic Structure- Electron Configurations
  6. 1.04: Development of Chemical Bonding Theory
  7. 1.05: The Nature of Chemical Bonds- Valence Bond Theory
  8. 1.06: sp Hybrid Orbitals and the Structure of Methane
  9. 1.07: sp Hybrid Orbitals and the Structure of Ethane
  10. 1.08: sp Hybrid Orbitals and the Structure of Ethylene
  11. 1.09: sp Hybrid Orbitals and the Structure of Acetylene
  12. 1.10: Hybridization of Nitrogen Oxygen Phosphorus and Sulfur
  13. 1.11: The Nature of Chemical Bonds- Molecular Orbital Theory
  14. 1.12: Drawing Chemical Structures
  15. 1.S: Structure and Bonding (Summary)
  16. 02: Polar Covalent Bonds Acids and Bases
  17. 2.00: Prelude
  18. 2.01: Polar Covalent Bonds- Electronegativity
  19. 2.02: Polar Covalent Bonds- Dipole Moments
  20. 2.03: Formal Charges
  21. 2.04: Resonance
  22. 2.05: Rules for Resonance Forms
  23. 2.06: Drawing Resonance Forms
  24. 2.07: Acids and Bases- The Brnsted-Lowry Definition
  25. 2.08: Acid and Base Strength
  26. 2.09: Predicting Acid-Base Reactions from pKa Values
  27. 2.10: Organic Acids and Organic Bases
  28. 2.11: Acids and Bases- The Lewis Definition
  29. 2.12: Noncovalent Interactions Between Molecules
  30. 2.13: Molecular Models
  31. 2.S: Polar Covalent Bonds Acids and Bases (Summary)
  32. 03: Organic Compounds- Alkanes and Their Stereochemistry
  33. 3.00: Prelude
  34. 3.01: Functional Groups
  35. 3.02: Alkanes and Alkane Isomers
  36. 3.03: Alkyl Groups
  37. 3.04: Naming Alkanes
  38. 3.05: Properties of Alkanes
  39. 3.06: Conformations of Ethane
  40. 3.07: Conformations of Other Alkanes
  41. 3.08: Gasoline- A Deeper Look
  42. 3.S: Organic Compounds- Alkanes and Their Stereochemistry (Summary)
  43. 04: Organic Compounds- Cycloalkanes and their Stereochemistry
  44. 4.00: Prelude
  45. 4.01: Naming Cycloalkanes
  46. 4.02: Cis-Trans Isomerism in Cycloalkanes
  47. 4.03: Stability of Cycloalkanes - Ring Strain
  48. 4.04: Conformations of Cycloalkanes
  49. 4.05: Conformations of Cyclohexane
  50. 4.06: Axial and Equatiorial Bonds in Cyclohexane
  51. 4.07: Conformations of Monosubstituted Cyclohexanes
  52. 4.08: Conformations of Disubstituted Cyclohexanes
  53. 4.09: Conformations of Polycyclic Molecules
  54. 4.S: Organic Compounds- Cycloalkanes and their Stereochemistry (Summary)
  55. 05: Stereochemistry at Tetrahedral Centres
  56. 5.00: Prelude
  57. 5.01: Enantiomers and the Tetrahedral Carbon
  58. 5.02: The Reason for Handedness in Molecules- Chirality
  59. 5.03: Optical Activity
  60. 5.04: Pasteur's Discovery of Enantiomers
  61. 5.05: Sequence Rules for Specifying Configuration
  62. 5.06: Diastereomers
  63. 5.07: Meso Compounds
  64. 5.08: Racemic Mixtures and the Resolution of Enantiomers
  65. 5.09: A Review of Isomerism
  66. 5.10: Chirality at Nitrogen Phosphorus and Sulfur
  67. 5.11: Prochirality
  68. 5.12: Chirality in Nature and Chiral Environments
  69. 5.S: Stereochemistry at Tetrahedral Centers (Summary)
  70. 06: An Overview of Organic Reactions
  71. 6.00: Prelude
  72. 6.01: Kinds of Organic Reactions
  73. 6.02: How Organic Reactions Occur- Mechanisms
  74. 6.03: Radical Reactions
  75. 6.04: Polar Reactions
  76. 6.05: An Example of a Polar Reaction- Addition of HBr to Ethylene
  77. 6.06: Using Curved Arrows in Polar Reaction Mechanisms
  78. 6.07: Describing a Reaction- Equilibria Rates and Energy Changes
  79. 6.08: Describing a Reaction- Bond Dissociation Energies
  80. 6.09: Describing a Reaction- Energy Diagrams and Transition States
  81. 6.10: Describing a Reaction - Intermediates
  82. 6.11: A Comparison between Biological Reactions and Laboratory Reactions
  83. 6.S: An Overview of Organic Reactions (Summary)
  84. 07: Alkenes- Structure and Reactivity
  85. 7.00: Introduction
  86. 7.01: Industrial Preparation and Use of Alkenes
  87. 7.02: Calculating Degree of Unsaturation
  88. 7.03: Naming Alkenes
  89. 7.04: Cis-Trans Isomerism in Alkenes
  90. 7.05: Sequence Rules- The EZ Designation
  91. 7.06: Stability of Alkenes
  92. 7.07: Electrophilic Addition Reactions of Alkenes
  93. 7.08: Orientation of Electrophilic Additions- Markovnikov's Rule
  94. 7.09: Carbocation Structure and Stability
  95. 7.10: The Hammond Postulate
  96. 7.11: Evidence for the Mechanism of Electrophilic Additions- Carbocation Rearrangements
  97. 7.S: Alkenes - Structure and Reactivity (Summary)
  98. 08: Alkenes- Reactions and Synthesis
  99. 8.00: Prelude
  100. 8.01: Preparation of Alkenes- A Preview of Elimination Reactions
  101. 8.02: Halogenation of Alkenes- Addition of X
  102. 8.03: Halohydrins from Alkenes- Addition of HOX
  103. 8.04: Hydration of Alkenes- Addition of HO by Oxymercuration
  104. 8.05: Hydration of Alkenes- Addition of HO by Hydroboration
  105. 8.06: Reduction of Alkenes- Hydrogenation
  106. 8.07: Oxidation of Alkenes- Epoxidation and Hydroxylation
  107. 8.08: Oxidation of Alkenes- Cleavage to Carbonyl Compounds
  108. 8.09: Addition of Carbenes to Alkenes- Cyclopropane Synthesis
  109. 8.10: Radical Additions to Alkenes - Chain-Growth Polymers
  110. 8.11: Biological Additions of Radicals to Alkenes
  111. 8.12: Stereochemistry of Reactions- Addition of HO to an Achiral Alkene
  112. 8.13: Stereochemistry of Reactions- Addition of HO to a Chiral Alkene
  113. 8.S: Alkenes - Reactions and Synthesis (Summary)
  114. 09: Alkynes- An Introduction to Organic Synthesis
  115. 9.00: Prelude
  116. 9.01: Naming Alkynes
  117. 9.02: Preparation of Alkynes- Elimination Reactions of Dihalides
  118. 9.03: Reactions of Alkynes- Addition of HX and (X 2)
  119. 9.04: Hydration of Alkynes
  120. 9.05: Reduction of Alkynes
  121. 9.06: Oxidative Cleavage of Alkynes
  122. 9.07: Alkyne Acidity- Formation of Acetylide Anions
  123. 9.08: Alkylation of Acetylide Anions
  124. 9.09: An Introduction to Organic Synthesis
  125. 9.S: Alkynes - An Introduction to Organic Synthesis (Summary)
  126. 10: Organohalides
  127. 10.00: Introduction
  128. 10.01: Names and Properties of Alkyl Halides
  129. 10.02: Preparing Alkyl Halides from Alkanes- Radical Halogenation
  130. 10.03: Preparing Alkyl Halides from Alkenes- Allylic Bromination
  131. 10.04: Stability of the Allyl Radical- Resonance Revisited
  132. 10.05: Preparing Alkyl Halides from Alcohols
  133. 10.06: Reactions of Alkyl Halides- Grignard Reagents
  134. 10.07: Organometallic Coupling Reactions
  135. 10.08: Oxidation and Reduction in Organic Chemistry
  136. 10.S: Organohalides (Summary)
  137. 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  138. 11.00: Introduction
  139. 11.01: The Discovery of Nucleophilic Substitution Reactions
  140. 11.02: The SN2 Reaction
  141. 11.03: Characteristics of the SN2 Reaction
  142. 11.04: The SN1 Reaction
  143. 11.05: Characteristics of the SN1 Reaction
  144. 11.06: Biological Substitution Reactions
  145. 11.07: Elimination Reactions- Zaitsev's Rule
  146. 11.08: The E2 Reaction and the Deuterium Isotope Effect
  147. 11.09: The E2 Reaction and Cyclohexane Conformation
  148. 11.10: The E1 and E1cB Reactions
  149. 11.11: Biological Elimination Reactions
  150. 11.12: A Summary of Reactivity- SN1 SN2 E1 E1cB and E2
  151. 11.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
  152. 12: Structure Determination- Mass Spectrometry and Infrared Spectroscopy
  153. 12.00: Introduction
  154. 12.01: Mass Spectrometry of Small Molecules- Magnetic-Sector Instruments
  155. 12.02: Interpreting Mass Spectra
  156. 12.03: Mass Spectrometry of Some Common Functional Groups
  157. 12.04: Mass Spectrometry in Biological- Time-of-flight (TOF) Instruments
  158. 12.05: Spectroscopy and the Electromagnetic Spectrum
  159. 12.06: Infrared Spectroscopy
  160. 12.07: Interpreting Infrared Spectra
  161. 12.08: Infrared Spectra of Some Common Functional Groups
  162. 12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
  163. 13: Structure Determination- Nuclear Magnetic Resonance Spectroscopy
  164. 13.00: Prelude
  165. 13.01: Nuclear Magnetic Resonance Spectroscopy
  166. 13.02: The Nature of NMR Absorptions
  167. 13.03: Chemical Shifts
  168. 13.04: C NMR Spectroscopy- Signal Averaging and FT-NMR
  169. 13.05: Characteristics of C NMR Spectroscopy
  170. 13.06: DEPT C NMR Spectroscopy
  171. 13.07: Uses of C NMR Spectroscopy
  172. 13.08: H NMR Spectroscopy and Proton Equivalence
  173. 13.09: Chemical Shifts in H NMR Spectroscopy
  174. 13.10: Integration of H NMR Absorptions- Proton Counting
  175. 13.11: Spin-Spin Splitting in H NMR Spectra
  176. 13.12: More Complex Spin-Spin Splitting Patterns
  177. 13.13: Uses of H NMR Spectroscopy
  178. 13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
  179. 14: Conjugated Compounds and Ultraviolet Spectroscopy
  180. 14.00: Introduction
  181. 14.01: Stability of Conjugated Dienes- Molecular Orbital Theory
  182. 14.02: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  183. 14.03: Kinetic vs. Thermodynamic Control of Reactions
  184. 14.04: The Diels-Alder Cycloaddition Reaction
  185. 14.05: Characteristics of the Diels-Alder Reaction
  186. 14.06: Diene Polymers- Natural and Synthetic Rubbers
  187. 14.07: Structure Determination in Conjugated Systems- Ultraviolet Spectroscopy
  188. 14.08: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  189. 14.09: Conjugation Color and the Chemistry of Vision
  190. 14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
  191. 15: Benzene and Aromaticity
  192. 15.00: Introduction
  193. 15.01: Sources and Names of Aromatic Compounds
  194. 15.02: Structure and Stability of Benzene
  195. 15.03: Aromaticity and the Huckel 4n 2 Rule
  196. 15.04: Aromatic Ions
  197. 15.05: Aromatic Heterocycles- Pyridine and Pyrrole
  198. 15.06: Polycyclic Aromatic Compounds
  199. 15.07: Spectroscopy of Aromatic Compounds
  200. 15.S: Benzene and Aromaticity (Summary)
  201. 16: Chemistry of Benzene- Electrophilic Aromatic Substitution
  202. 16.00: Introduction
  203. 16.01: Electrophilic Aromatic Substitution Reactions- Bromination
  204. 16.02: Other Aromatic Substitutions
  205. 16.03: Alkylation and Acylation of Aromatic Rings- The Friedel-Crafts Reaction
  206. 16.04: Substituent Effects in Substituted Aromatic Rings
  207. 16.05: An Explanation of Substituent Effects
  208. 16.06: Trisubstituted Benzenes- Additivity of Effects
  209. 16.07: Nucleophilic Aromatic Substitution
  210. 16.08: Benzyne
  211. 16.09: Oxidation of Aromatic Compounds
  212. 16.10: Reduction of Aromatic Compounds
  213. 16.11: Synthesis of Polysubstituted Benzenes
  214. 16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)