Athabasca University Chemistry 350 Organic Chemistry I

by Dietmar Kennepohl

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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.

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Publisher
Athabasca University
Subjects
Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
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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: Structure and Bonding
  7. 1.0: Introduction
  8. 1.1: Atomic Structure- The Nucleus
  9. 1.2: Atomic Structure- Orbitals
  10. 1.3: Atomic Structure- Electron Configurations
  11. 1.4: Development of Chemical Bonding Theory
  12. 1.5: The Nature of Chemical Bonds- Valence Bond Theory
  13. 1.6: sp³ Hybrid Orbitals and the Structure of Methane
  14. 1.7: sp³ Hybrid Orbitals and the Structure of Ethane
  15. 1.8: sp² Hybrid Orbitals and the Structure of Ethylene
  16. 1.9: sp Hybrid Orbitals and the Structure of Acetylene
  17. 1.10: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  18. 1.11: The Nature of Chemical Bonds- Molecular Orbital Theory
  19. 1.12: Drawing Chemical Structures
  20. 1.S: Structure and Bonding (Summary)
  21. 2: Polar Covalent Bonds; Acids and Bases
  22. 2.0: Prelude
  23. 2.1: Polar Covalent Bonds- Electronegativity
  24. 2.2: Polar Covalent Bonds- Dipole Moments
  25. 2.3: Formal Charges
  26. 2.4: Resonance
  27. 2.5: Rules for Resonance Forms
  28. 2.6: Drawing Resonance Forms
  29. 2.7: Acids and Bases- The Brønsted-Lowry Definition
  30. 2.8: Acid and Base Strength
  31. 2.9: Predicting Acid-Base Reactions from pKa Values
  32. 2.10: Organic Acids and Organic Bases
  33. 2.11: Acids and Bases- The Lewis Definition
  34. 2.12: Noncovalent Interactions Between Molecules
  35. 2.13: Molecular Models
  36. 2.S: Polar Covalent Bonds; Acids and Bases (Summary)
  37. 3: Organic Compounds- Alkanes and Their Stereochemistry
  38. 3.0: Prelude
  39. 3.1: Functional Groups
  40. 3.2: Alkanes and Alkane Isomers
  41. 3.3: Alkyl Groups
  42. 3.4: Naming Alkanes
  43. 3.5: Properties of Alkanes
  44. 3.6: Conformations of Ethane
  45. 3.7: Conformations of Other Alkanes
  46. 3.8: Gasoline- A Deeper Look
  47. 3.S: Organic Compounds- Alkanes and Their Stereochemistry (Summary)
  48. 4: Organic Compounds- Cycloalkanes and their Stereochemistry
  49. 4.0: Prelude
  50. 4.1: Naming Cycloalkanes
  51. 4.2: Cis-Trans Isomerism in Cycloalkanes
  52. 4.3: Stability of Cycloalkanes - Ring Strain
  53. 4.4: Conformations of Cycloalkanes
  54. 4.5: Conformations of Cyclohexane
  55. 4.6: Axial and Equatiorial Bonds in Cyclohexane
  56. 4.7: Conformations of Monosubstituted Cyclohexanes
  57. 4.8: Conformations of Disubstituted Cyclohexanes
  58. 4.9: Conformations of Polycyclic Molecules
  59. 4.S: Organic Compounds- Cycloalkanes and their Stereochemistry (Summary)
  60. 5: Stereochemistry at Tetrahedral Centres
  61. 5.0: Prelude
  62. 5.1: Enantiomers and the Tetrahedral Carbon
  63. 5.2: The Reason for Handedness in Molecules- Chirality
  64. 5.3: Optical Activity
  65. 5.4: Pasteur's Discovery of Enantiomers
  66. 5.5: Sequence Rules for Specifying Configuration
  67. 5.6: Diastereomers
  68. 5.7: Meso Compounds
  69. 5.8: Racemic Mixtures and the Resolution of Enantiomers
  70. 5.9: A Review of Isomerism
  71. 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
  72. 5.11: Prochirality
  73. 5.12: Chirality in Nature and Chiral Environments
  74. 5.S: Stereochemistry at Tetrahedral Centers (Summary)
  75. 6: An Overview of Organic Reactions
  76. 6.0: Prelude
  77. 6.1: Kinds of Organic Reactions
  78. 6.2: How Organic Reactions Occur - Mechanisms
  79. 6.3: Radical Reactions
  80. 6.4: Polar Reactions
  81. 6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene
  82. 6.6: Using Curved Arrows in Polar Reaction Mechanisms
  83. 6.7: Describing a Reaction - Equilibria, Rates, and Energy Changes
  84. 6.8: Describing a Reaction - Bond Dissociation Energies
  85. 6.9: Describing a Reaction - Energy Diagrams and Transition States
  86. 6.10: Describing a Reaction - Intermediates
  87. 6.11: A Comparison between Biological Reactions and Laboratory Reactions
  88. 6.S: An Overview of Organic Reactions (Summary)
  89. 7: Alkenes- Structure and Reactivity
  90. 7.0: Introduction
  91. 7.1: Industrial Preparation and Use of Alkenes
  92. 7.2: Calculating Degree of Unsaturation
  93. 7.3: Naming Alkenes
  94. 7.4: Cis-Trans Isomerism in Alkenes
  95. 7.5: Sequence Rules - The E,Z Designation
  96. 7.6: Stability of Alkenes
  97. 7.7: Electrophilic Addition Reactions of Alkenes
  98. 7.8: Orientation of Electrophilic Additions - Markovnikov's Rule
  99. 7.9: Carbocation Structure and Stability
  100. 7.10: The Hammond Postulate
  101. 7.11: Evidence for the Mechanism of Electrophilic Additions- Carbocation Rearrangements
  102. 7.S: Alkenes - Structure and Reactivity (Summary)
  103. 8: Alkenes- Reactions and Synthesis
  104. 8.0: Prelude
  105. 8.1: Preparation of Alkenes- A Preview of Elimination Reactions
  106. 8.2: Halogenation of Alkenes - Addition of X₂
  107. 8.3: Halohydrins from Alkenes - Addition of HOX
  108. 8.4: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  109. 8.5: Hydration of Alkenes - Addition of H₂O by Hydroboration
  110. 8.6: Reduction of Alkenes - Hydrogenation
  111. 8.7: Oxidation of Alkenes - Epoxidation and Hydroxylation
  112. 8.8: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  113. 8.9: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  114. 8.10: Radical Additions to Alkenes - Chain-Growth Polymers
  115. 8.11: Biological Additions of Radicals to Alkenes
  116. 8.12: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene
  117. 8.13: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene
  118. 8.S: Alkenes - Reactions and Synthesis (Summary)
  119. 9: Alkynes- An Introduction to Organic Synthesis
  120. 9.0: Prelude
  121. 9.1: Naming Alkynes
  122. 9.2: Preparation of Alkynes - Elimination Reactions of Dihalides
  123. 9.3: Reactions of Alkynes - Addition of HX and X₂
  124. 9.4: Hydration of Alkynes
  125. 9.5: Reduction of Alkynes
  126. 9.6: Oxidative Cleavage of Alkynes
  127. 9.7: Alkyne Acidity - Formation of Acetylide Anions
  128. 9.8: Alkylation of Acetylide Anions
  129. 9.9: An Introduction to Organic Synthesis
  130. 9.S: Alkynes - An Introduction to Organic Synthesis (Summary)
  131. 10: Organohalides
  132. 10.0: Introduction
  133. 10.1: Names and Properties of Alkyl Halides
  134. 10.2: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  135. 10.3: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  136. 10.4: Stability of the Allyl Radical - Resonance Revisited
  137. 10.5: Preparing Alkyl Halides from Alcohols
  138. 10.6: Reactions of Alkyl Halides - Grignard Reagents
  139. 10.7: Organometallic Coupling Reactions
  140. 10.8: Oxidation and Reduction in Organic Chemistry
  141. 10.S: Organohalides (Summary)
  142. 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  143. 11.0: Introduction
  144. 11.1: The Discovery of Nucleophilic Substitution Reactions
  145. 11.2: The SN2 Reaction
  146. 11.3: Characteristics of the SN2 Reaction
  147. 11.4: The SN1 Reaction
  148. 11.5: Characteristics of the SN1 Reaction
  149. 11.6: Biological Substitution Reactions
  150. 11.7: Elimination Reactions - Zaitsev's Rule
  151. 11.8: The E2 Reaction and the Deuterium Isotope Effect
  152. 11.9: The E2 Reaction and Cyclohexane Conformation
  153. 11.10: The E1 and E1cB Reactions
  154. 11.11: Biological Elimination Reactions
  155. 11.12: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
  156. 11.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
  157. 12: Structure Determination- Mass Spectrometry and Infrared Spectroscopy
  158. 12.0: Introduction
  159. 12.1: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
  160. 12.2: Interpreting Mass Spectra
  161. 12.3: Mass Spectrometry of Some Common Functional Groups
  162. 12.4: Mass Spectrometry in Biological- Time-of-flight (TOF) Instruments
  163. 12.5: Spectroscopy and the Electromagnetic Spectrum
  164. 12.6: Infrared Spectroscopy
  165. 12.7: Interpreting Infrared Spectra
  166. 12.8: Infrared Spectra of Some Common Functional Groups
  167. 12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
  168. 13: Structure Determination- Nuclear Magnetic Resonance Spectroscopy
  169. 13.0: Prelude
  170. 13.1: Nuclear Magnetic Resonance Spectroscopy
  171. 13.2: The Nature of NMR Absorptions
  172. 13.3: Chemical Shifts
  173. 13.4: ¹³C NMR Spectroscopy- Signal Averaging and FT-NMR
  174. 13.5: Characteristics of ¹³C NMR Spectroscopy
  175. 13.6: DEPT ¹³C NMR Spectroscopy
  176. 13.7: Uses of ¹³C NMR Spectroscopy
  177. 13.8: ¹H NMR Spectroscopy and Proton Equivalence
  178. 13.9: Chemical Shifts in ¹H NMR Spectroscopy
  179. 13.10: Integration of ¹H NMR Absorptions- Proton Counting
  180. 13.11: Spin-Spin Splitting in ¹H NMR Spectra
  181. 13.12: More Complex Spin-Spin Splitting Patterns
  182. 13.13: Uses of ¹H NMR Spectroscopy
  183. 13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
  184. 14: Conjugated Compounds and Ultraviolet Spectroscopy
  185. 14.0: Introduction
  186. 14.1: Stability of Conjugated Dienes- Molecular Orbital Theory
  187. 14.2: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  188. 14.3: Kinetic vs. Thermodynamic Control of Reactions
  189. 14.4: The Diels-Alder Cycloaddition Reaction
  190. 14.5: Characteristics of the Diels-Alder Reaction
  191. 14.6: Diene Polymers- Natural and Synthetic Rubbers
  192. 14.7: Structure Determination in Conjugated Systems- Ultraviolet Spectroscopy
  193. 14.8: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  194. 14.9: Conjugation, Color, and the Chemistry of Vision
  195. 14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
  196. 15: Benzene and Aromaticity
  197. 15.0: Introduction
  198. 15.1: Sources and Names of Aromatic Compounds
  199. 15.2: Structure and Stability of Benzene
  200. 15.3: Aromaticity and the Huckel 4n + 2 Rule
  201. 15.4: Aromatic Ions
  202. 15.5: Aromatic Heterocycles- Pyridine and Pyrrole
  203. 15.6: Polycyclic Aromatic Compounds
  204. 15.7: Spectroscopy of Aromatic Compounds
  205. 15.S: Benzene and Aromaticity (Summary)
  206. 16: Chemistry of Benzene- Electrophilic Aromatic Substitution
  207. 16.0: Introduction
  208. 16.1: Electrophilic Aromatic Substitution Reactions- Bromination
  209. 16.2: Other Aromatic Substitutions
  210. 16.3: Alkylation and Acylation of Aromatic Rings- The Friedel-Crafts Reaction
  211. 16.4: Substituent Effects in Substituted Aromatic Rings
  212. 16.5: An Explanation of Substituent Effects
  213. 16.6: Trisubstituted Benzenes- Additivity of Effects
  214. 16.7: Nucleophilic Aromatic Substitution
  215. 16.8: Benzyne
  216. 16.9: Oxidation of Aromatic Compounds
  217. 16.10: Reduction of Aromatic Compounds
  218. 16.11: Synthesis of Polysubstituted Benzenes
  219. 16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
  220. Back Matter
  221. Index
  222. Glossary
  223. Detailed Licensing