CHEM 231: Organic Chemistry I Textbook

by Sol Parajon Puenzo

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This text is designed for CHEM 231 Organic Chemistry I, the first semester of a one-year organic chemistry sequence. Topics include the chemistry of hydrocarbons with emphasis on structure and reactivity of alkanes, alkenes, alkynes, alkyl halides, and conjugated systems. Mechanisms, stereochemistry and spectroscopy are an integral part of the course.

Description from LibreTexts.

Publisher
Cañada College
Subjects
Chemistry
Licence
CC BY-SA 4.0, as LibreTexts states it
Who can read
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: Why This Chapter?
  8. 1.1: Atomic Structure - The Nucleus
  9. 1.2: Atomic Structure - Orbitals
  10. 1.3: Atomic Structure - Electron Configurations
  11. 1.4: Describing Chemical Bonds - Valence Bond Theory
  12. 1.5: Development of Chemical Bonding Theory
  13. 1.6: The Shapes of Molecules
  14. 1.7: Describing Chemical Bonds - Molecular Orbital Theory
  15. 1.8: sp³ Hybrid Orbitals and the Structure of Methane
  16. 1.9: sp³ Hybrid Orbitals and the Structure of Ethane
  17. 1.10: sp² Hybrid Orbitals and the Structure of Ethylene
  18. 1.11: sp Hybrid Orbitals and the Structure of Acetylene
  19. 1.12: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  20. 1.13: Drawing Chemical Structures
  21. 1.14: Chemistry Matters—Organic Foods- Risk versus Benefit
  22. 1.A: Structure and Bonding (Summary)
  23. 1.B: Additional Problems
  24. 2: Polar Covalent Bonds; Acids and Bases
  25. 2.0: Why This Chapter?
  26. 2.1: Polar Covalent Bonds - Electronegativity
  27. 2.2: Polar Covalent Bonds - Dipole Moments
  28. 2.3: Intermolecular Forces
  29. 2.4: Physical Properties of Organic Compounds
  30. 2.5: Formal Charges
  31. 2.6: Resonance
  32. 2.7: Drawing Resonance Forms
  33. 2.8: Acids and Bases - The Brønsted-Lowry Definition
  34. 2.9: Acid and Base Strength
  35. 2.10: Organic Acids and Organic Bases
  36. 2.11: Structural Effects on Acidity and Basicity
  37. 2.12: Acids and Bases - The Lewis Definition
  38. 2.13: Chemistry Matters—Alkaloids- From Cocaine to Dental Anesthetics
  39. 2.A: Polar Covalent Bonds; Acids and Bases (Summary)
  40. 2.B: Additional Problems
  41. 3: Organic Compounds- Functional Groups and Nomenclature
  42. 3.0: Why This Chapter?
  43. 3.1: Functional Groups
  44. 3.2: Alkanes and Alkane Isomers
  45. 3.3: Alkyl Groups
  46. 3.4: Naming Alkanes
  47. 3.5: Naming Cycloalkanes
  48. 3.6: Naming Alkenes
  49. 3.7: Naming Alkynes
  50. 3.8: Names of Alkyl Halides
  51. 3.9: Naming Alcohols
  52. 3.10: Chemistry Matters—Gasoline
  53. 3.A: Functional Groups and Nomenclature (Summary)
  54. 3.B: Additional Problems
  55. 4: Organic Compounds - Conformation of Alkanes and Cycloalkanes
  56. 4.0: Why This Chapter?
  57. 4.1: Conformations of Ethane
  58. 4.2: Conformations of Other Alkanes
  59. 4.3: Cis-Trans Isomerism in Cycloalkanes
  60. 4.4: Stability of Cycloalkanes - Ring Strain
  61. 4.5: Conformations of Cycloalkanes
  62. 4.6: Conformations of Cyclohexane
  63. 4.7: Axial and Equatorial Bonds in Cyclohexane
  64. 4.8: Conformations of Monosubstituted Cyclohexanes
  65. 4.9: Conformations of Disubstituted Cyclohexanes
  66. 4.10: Conformations of Polycyclic Molecules
  67. 4.11: Chemistry Matters—Molecular Mechanics
  68. 4.A: Conformation of Alkanes and Cycloalkanes (Summary)
  69. 4.B: Additional Problems
  70. 5: Stereochemistry at Tetrahedral Centers
  71. 5.0: Why This Chapter?
  72. 5.1: Enantiomers and the Tetrahedral Carbon
  73. 5.2: The Reason for Handedness in Molecules - Chirality
  74. 5.3: Optical Activity
  75. 5.4: Pasteur's Discovery of Enantiomers
  76. 5.5: Sequence Rules for Specifying Configuration
  77. 5.6: Diastereomers
  78. 5.7: Meso Compounds
  79. 5.8: Racemic Mixtures and the Resolution of Enantiomers
  80. 5.9: A Review of Isomerism
  81. 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
  82. 5.11: Prochirality
  83. 5.12: Chirality in Nature and Chiral Environments
  84. 5.13: Chemistry Matters—Chiral Drugs
  85. 5.A: Stereochemistry at Tetrahedral Centers (Summary)
  86. 5.B: Additional Problems
  87. 6: An Overview of Organic Reactions
  88. 6.0: Why This Chapter?
  89. 6.1: Kinds of Organic Reactions
  90. 6.2: How Organic Reactions Occur - Mechanisms
  91. 6.3: Radical Reactions
  92. 6.4: Polar Reactions
  93. 6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene
  94. 6.6: Using Curved Arrows in Polar Reaction Mechanisms
  95. 6.7: Describing a Reaction - Equilibria, Rates, and Energy Changes
  96. 6.8: Describing a Reaction - Bond Dissociation Energies
  97. 6.9: Describing a Reaction - Energy Diagrams and Transition States
  98. 6.10: Describing a Reaction- Intermediates
  99. 6.11: A Comparison between Biological Reactions and Laboratory Reactions
  100. 6.12: Chemistry Matters—Where Do Drugs Come From?
  101. 6.A: An Overview of Organic Reactions (Summary)
  102. 6.B: Additional Problems
  103. 7: Alkenes- Structure and Reactivity
  104. 7.0: Why This Chapter?
  105. 7.1: Industrial Preparation and Use of Alkenes
  106. 7.2: Calculating Degree of Unsaturation
  107. 7.3: Cis-Trans Isomerism in Alkenes
  108. 7.4: Alkene Stereochemistry and the E,Z Designation
  109. 7.5: Stability of Alkenes
  110. 7.6: Electrophilic Addition Reactions of Alkenes
  111. 7.7: Orientation of Electrophilic Additions - Markovnikov's Rule
  112. 7.8: Carbocation Structure and Stability
  113. 7.9: The Hammond Postulate
  114. 7.10: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
  115. 7.11: Chemistry Matters—Bioprospecting- Hunting for Natural Products
  116. 7.A: Alkenes - Structure and Reactivity (Summary)
  117. 7.B: Additional Problems
  118. 8: Alkenes- Reactions and Synthesis
  119. 8.0: Why This Chapter?
  120. 8.1: Preparation of Alkenes - A Preview of Elimination Reactions
  121. 8.2: Halogenation of Alkenes - Addition of X₂
  122. 8.3: Halohydrins from Alkenes - Addition of HO-X
  123. 8.4: Hydration of Alkenes- Acid-Catalyzed Hydration
  124. 8.5: Stereochemistry of Reactions
  125. 8.6: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  126. 8.7: Hydration of Alkenes - Addition of H₂O by Hydroboration
  127. 8.8: Reduction of Alkenes - Hydrogenation
  128. 8.9: Oxidation of Alkenes - Epoxidation and Hydroxylation
  129. 8.10: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  130. 8.11: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  131. 8.12: Radical Additions to Alkenes - Chain-Growth Polymers
  132. 8.13: Biological Additions of Radicals to Alkenes
  133. 8.14: Chemistry Matters—Terpenes- Naturally Occurring Alkenes
  134. 8.A: Alkenes - Reactions and Synthesis (Summary)
  135. 8.B: Additional Problems
  136. 9: Alkynes - An Introduction to Organic Synthesis
  137. 9.0: Why This Chapter?
  138. 9.1: Preparation of Alkynes - Elimination Reactions of Dihalides
  139. 9.2: Reactions of Alkynes - Addition of HX and X₂
  140. 9.3: Hydration of Alkynes
  141. 9.4: Reduction and Oxidation of Alkynes
  142. 9.5: Alkyne Acidity - Formation of Acetylide Anions
  143. 9.6: Alkylation of Acetylide Anions
  144. 9.7: An Introduction to Organic Synthesis
  145. 9.8: Chemistry Matters—The Art of Organic Synthesis
  146. 9.A: Alkynes - An Introduction to Organic Synthesis (Summary)
  147. 9.B: Additional Problems
  148. 10: Organohalides
  149. 10.0: Why This Chapter?
  150. 10.1: Names and Properties of Alkyl Halides
  151. 10.2: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  152. 10.3: Radical Hydrobromination of Alkenes - HBr with peroxides
  153. 10.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  154. 10.5: Stability of the Allyl Radical - Resonance Revisited
  155. 10.6: Preparing Alkyl Halides from Alcohols
  156. 10.7: Reactions of Alkyl Halides - Grignard Reagents
  157. 10.8: Organometallic Coupling Reactions
  158. 10.9: Oxidation and Reduction in Organic Chemistry
  159. 10.10: Chemistry Matters—Naturally Occurring Organohalides
  160. 10.A: Organohalides (Summary)
  161. 10.B: Additional Problems
  162. 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  163. 11.0: Why This Chapter?
  164. 11.1: The Discovery of Nucleophilic Substitution Reactions
  165. 11.2: The SN2 Reaction
  166. 11.3: Characteristics of the SN2 Reaction
  167. 11.4: The SN1 Reaction
  168. 11.5: Characteristics of the SN1 Reaction
  169. 11.6: Predicting SN1 vs. SN2 mechanisms
  170. 11.7: Elimination Reactions- Zaitsev's Rule
  171. 11.8: The E2 Reaction and Mechanism
  172. 11.9: The E2 Reaction and Cyclohexane Conformation
  173. 11.10: The E1 and E1cB Reactions
  174. 11.11: Biological Reactions
  175. 11.12: Deciding between SN1, SN2, E1, and E2
  176. 11.13: Chemistry Matters—Green Chemistry
  177. 11.A: Nucleophilic Substitutions and Eliminations Reactions (Summary)
  178. 11.B: Additional Problems
  179. 12: Alcohols
  180. 12.0: Why This Chapter?
  181. 12.1: Properties of Alcohols and Phenols
  182. 12.2: Preparation of Alcohols- A Review
  183. 12.3: Alcohols from Carbonyl Compounds- Reduction
  184. 12.4: Alcohols from Carbonyl Compounds - Grignard Reagents
  185. 12.5: Reactions of Alcohols
  186. 12.6: Oxidation of Alcohols
  187. 12.7: Protection of Alcohols
  188. 12.8: Chemistry Matters—Ethanol- Chemical, Drug, and Poison
  189. 12.A: Alcohols (Summary)
  190. 12.B: Additional Problems
  191. 13: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
  192. 13.0: Why This Chapter?
  193. 13.1: Spectroscopy and the Electromagnetic Spectrum
  194. 13.2: Infrared Spectroscopy
  195. 13.3: Interpreting Infrared Spectra
  196. 13.4: Infrared Spectra of Some Common Functional Groups
  197. 13.5: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
  198. 13.6: Interpreting Mass Spectra
  199. 13.7: Mass Spectroscopy and Natural Abundances of Isotopes
  200. 13.8: Mass Spectrometry of Some Common Functional Groups
  201. 13.9: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
  202. 13.10: Chemistry Matters—X-Ray Crystallography
  203. 13.A: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
  204. 13.B: Additional Problems
  205. 14: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
  206. 14.0: Why This Chapter?
  207. 14.1: Nuclear Magnetic Resonance Spectroscopy
  208. 14.2: Acquiring a NMR Spectrum
  209. 14.3: The Shielding Effect
  210. 14.4: Proton Equivalence
  211. 14.5: Chemical Shifts in ¹H NMR Spectroscopy
  212. 14.6: ¹H NMR Signal Integration and Splitting
  213. 14.7: More Complex Spin-Spin Splitting Patterns
  214. 14.8: Uses of ¹H NMR Spectroscopy
  215. 14.9: Characteristics of ¹³C NMR Spectroscopy
  216. 14.10: DEPT ¹³C NMR Spectroscopy
  217. 14.11: H-NMR and C-NMR of Alcohols and Phenols
  218. 14.12: Uses of ¹³C NMR Spectroscopy
  219. 14.13: Constructing Partial Structures
  220. 14.14: Combined Spectra for Structure Elucidation
  221. 14.15: Chemistry Matters—Magnetic Resonance Imaging (MRI)
  222. 14.A: Structure Determination - NMR Spectroscopy (Summary)
  223. 14.B: Additional Problems
  224. Back Matter
  225. Index
  226. 15.7: Detailed Licensing
  227. Glossary