SCC: Chem 420 - Organic Chemistry I

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This text is designed to introduce students to the study of basic concepts of organic chemistry. Lecture topics include chemistry of alkanes, cycloalkanes, alkenes, alkyl halides, alcohols, and ether with emphasis on stereochemistry, reaction mechanisms, and spectroscopy. Laboratory work includes basic techniques of separation and identification. Students will be introduced to a variety of modern instrumentation (GC, HPLC, FT-IR, GC-MS) in the laboratory.

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Subjects
Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
Who can read
Teens 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: Introduction and Review
  7. 1.1: The Origins of Organic Chemistry
  8. 1.2: Principles of Atomic Structure (Review)
  9. 1.3: Electronic Structure (Review)
  10. 1.4: Electron Configurations
  11. 1.5: Octet Rule - Ionic and Covalent Bonding (Review)
  12. 1.6: Lewis Structures
  13. 1.7: Common Bonding Patterns for Organic Chemistry
  14. 1.8: Structural Formulas - Lewis, Kekule, Bond-line, Condensed,
  15. 1.9: Electronegativity and Bond Polarity (Review)
  16. 1.10: Resonance
  17. 1.11: Arrhenius Acids and Bases (Review)
  18. 1.12: Brønsted-Lowry Acids and Bases (Review)
  19. 1.13: Lewis Acids and Bases
  20. 1.14: Distinguishing between pH and pKa
  21. 1.15: Predicting Relative Acidity
  22. 1.16: Molecular Formulas and Empirical Formulas (Review)
  23. 1.17: Additional Exercises
  24. 1.18: Solutions to Additional Exercises
  25. 2: Structure and Properties of Organic Molecules
  26. 2.1: Pearls of Wisdom
  27. 2.2: Molecular Orbital (MO) Theory (Review)
  28. 2.3: Hybridization and Molecular Shapes (Review)
  29. 2.4: 2.4 Conjugated Pi Bond Systems
  30. 2.5: Lone Pair Electrons and Bonding Theories
  31. 2.6: Bond Rotation
  32. 2.7: Isomerism Introduction
  33. 2.8: Hydrocarbons
  34. 2.9: Organic Functional Groups
  35. 2.10: Intermolecular Forces (IMFs) - Review
  36. 2.11: Intermolecular Forces
  37. 2.12: Intermolecular Forces
  38. 2.13: Additional Practice Problems
  39. 2.14: Organic Functional Groups- H-bond donors
  40. 2.15: Additional Exercises
  41. 2.16: 2.15 Solutions to Additional Exercises
  42. 3: Functional Groups and Nomenclature
  43. 3.1: Generic (Abbreviated) Structures (aka R Groups)
  44. 3.2: Overview of the IUPAC Naming Strategy
  45. 3.3: Alkanes
  46. 3.4: Cycloalkanes
  47. 3.5: Haloalkane - Classification and Nomenclature
  48. 3.6: Alkenes
  49. 3.7: Alkynes
  50. 3.8: 3.8 Alcohols - Classification and Nomenclature
  51. 3.9: Ethers, Epoxides and Sulfides
  52. 3.10: Benzene and its Derivatives
  53. 3.11: Aldehydes and Ketones
  54. 3.12: 3.12 Amines - Classification and Nomenclature
  55. 3.13: Carboxylic Acids
  56. 3.14: The Carboxylic Acid Derivatives
  57. 3.15: Additional Exercises
  58. 3.16: Solutions to Additional Exercises
  59. 3.17: Appendix - IUPAC Nomenclature Rules
  60. 4: Structure and Stereochemistry of Alkanes
  61. 4.1: Hydrocarbon Functional Groups
  62. 4.2: Physical Properties of Alkanes
  63. 4.3: Structure and Conformations of Alkanes
  64. 4.4: Conformations of Butane
  65. 4.5: Conformations of Higher Alkanes
  66. 4.6: Cycloalkanes and Ring Strain
  67. 4.7: Cyclohexane Conformations
  68. 4.8: Conformations of Monosubstituted Cyclohexanes
  69. 4.9: Cis-trans Isomerism in Cycloalkanes
  70. 4.10: Conformations of Disubstituted Cyclohexanes
  71. 4.11: Joined Rings
  72. 4.12: Uses and Sources of Alkanes
  73. 4.13: Reactions of Alkanes - a Brief Overview
  74. 4.14: Additional Exercises
  75. 4.15: Solutions to Additional Exercises
  76. 5: An Introduction to Organic Reactions using Free Radical Halogenation of Alkanes
  77. 5.1: Types of Organic Reactions
  78. 5.2: 5.2 Reaction Mechanism Notation and Symbols
  79. 5.3: the Dance of the Nucleophile and Electrophile
  80. 5.4: Describing a Reaction - Equilibrium and Free Energy Changes
  81. 5.5: Homolytic Cleavage and Bond Dissociation Energies
  82. 5.6: Reaction Energy Diagrams and Transition States
  83. 5.7: 5.7 Reactive Intermediates - Carbocations
  84. 5.8: 5.8 Reactive Intermediates - Radicals
  85. 5.9: Reactive Intermediates- Carbanions and Carbon Acids
  86. 5.10: The Free-Radical Halogenation of Alkanes
  87. 5.11: Reactivity and Selectivity
  88. 5.12: A Comparison between Biological Reactions and Laboratory Reactions
  89. 5.13: Additional Exercises
  90. 5.14: Solutions to Additional Exercises
  91. 6: Stereochemistry at Tetrahedral Centers
  92. 6.1: Chirality
  93. 6.2: Fischer Projections to communicate Chirality
  94. 6.3: Absolute Configuration and the (R) and (S) System
  95. 6.4: Diastereomers - more than one chiral center
  96. 6.5: Meso Compounds
  97. 6.6: Isomerism Summary Diagram
  98. 6.7: Optical Activity and Racemic Mixtures
  99. 6.8: 6.8 Resolution (Separation) of Enantiomers
  100. 6.9: Stereochemistry of Molecules with Three or More Asymmetric Carbons
  101. 6.10: Absolute and Relative Configuration - the distinction
  102. 6.11: Chirality at Nitrogen, Phosphorus, and Sulfur
  103. 6.12: Biochemistry of Enantiomers
  104. 6.13: 6.13 The Discovery of Enantiomers
  105. 6.14: Additional Exercises
  106. 6.15: Solutions to Additional Exercises
  107. 7: Alkyl Halides- Nucleophilic Substitution and Elimination
  108. 7.1: 7.1 Alkyl Halides - Structure and Physical Properties
  109. 7.2: Common Uses of Alkyl Halides
  110. 7.3: Preparation of Alkyl Halides
  111. 7.4: Reactions of Alkyl Halides- Substitution and Elimination
  112. 7.5: The Sₙ2 Reaction
  113. 7.6: Characteristics of the Sₙ2 Reaction
  114. 7.7: Stereochemistry of the SN2 Reaction
  115. 7.8: The Sₙ1 Reaction
  116. 7.9: Characteristics of the Sₙ1 Reaction
  117. 7.10: Rearrangements of the Carbocation and Sₙ1 Reactions
  118. 7.11: The Hammond Postulate and Transition States
  119. 7.12: Comparison of SN1 and SN2 Reactions
  120. 7.13: Characteristics of the E2 Reaction
  121. 7.14: Zaitsev's Rule
  122. 7.15: Characteristics of the E1 Reaction
  123. 7.16: E2 Regiochemistry and Cyclohexane Conformations
  124. 7.17: The E2 Reaction and the Deuterium Isotope Effect
  125. 7.18: Comparison of E1 and E2 Reactions
  126. 7.19: Comparing Substitution and Elimination Reactions
  127. 7.20: Biological Substitution Reactions
  128. 7.21: Biological Elimination Reactions
  129. 7.22: Additional Exercises
  130. 7.23: Solutions to Additional Exercises
  131. 8: Structure and Synthesis of Alkenes
  132. 8.1: Alkene Structure
  133. 8.2: Physical Properties and Important Common Names
  134. 8.3: The Alkene Double Bond and Stereoisomerism
  135. 8.4: Degrees of Unsaturation
  136. 8.5: The E
  137. 8.5.1: Z System (when cis
  138. 8.5.1.1: The E/Z System (when cis/trans does not work)
  139. 8.6: Stability of Alkenes
  140. 8.7: Alkene Synthesis by Elimination of Alkyl Halides
  141. 8.8: Alkene Synthesis by Dehydration of Alcohols
  142. 8.9: Uses
  143. 8.10: Additional Exercises
  144. 8.11: Solutions to Additional Exercises
  145. 9: Reactions of Alkenes
  146. 9.1: Electrophilic Addition Reactions (EARs)
  147. 9.2: Addition of Hydrogen Halides to Symmetrical Alkenes
  148. 9.3: Alkene Asymmetry and Markovnikov's Rule
  149. 9.4: Hydration- Acid Catalyzed Addition of Water
  150. 9.5: Hydration- Oxymercuration-Demercuration
  151. 9.6: Hydration- Hydroboration-Oxidation
  152. 9.7: Stereochemistry of Reactions - Hydration of Achiral Alkenes
  153. 9.8: Stereochemistry of Reactions - Hydration of Chiral Alkenes
  154. 9.9: Addition of Halogens
  155. 9.10: Formation of Halohydrins
  156. 9.11: Reduction of Alkenes - Catalytic Hydrogenation
  157. 9.12: Oxidation of Alkenes - Epoxidation
  158. 9.13: Dihydroxylation of Alkenes
  159. 9.14: Opening of Epoxides - Acidic versus Basic Conditions
  160. 9.15: Oxidative Cleavage of Alkenes
  161. 9.16: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  162. 9.17: Radical Chain-Growth Polymerization
  163. 9.18: 9.18 Biological Additions of Radicals to Alkenes
  164. 9.19: Additional Exercises
  165. 9.20: Solutions to Additional Exercises
  166. 10: Alkynes
  167. 10.1: Structure and Physical Properties
  168. 10.2: Synthesis of Alkynes - Elimination Reactions of Dihalides
  169. 10.3: Reactions of Alkynes - Addition of HX and X₂
  170. 10.4: Hydration of Alkynes for Markovnikov Products
  171. 10.5: Hydration of Alkynes for Anti-Markovnikov Products
  172. 10.6: 10.6 Reduction of Alkynes
  173. 10.7: Oxidation of Alkynes
  174. 10.8: Acidity of Terminal Alkynes
  175. 10.9: Synthesis of Larger Alkynes from Acetylides
  176. 10.10: An Introduction to Multiple Step Synthesis
  177. 10.11: Additional Exercises
  178. 10.12: Solutions to Additional Exercises
  179. Back Matter
  180. Index
  181. Glossary
  182. Detailed Licensing