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SCC: Chem 420 - Organic Chemistry I

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SCC: Chem 420 - Organic Chemistry I

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.

Chemistry
Publisher
LibreTexts
Source
LibreTexts
License
CC BY-NC-SA
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 173 sections
  1. 01: Introduction and Review
  2. 1.01: The Origins of Organic Chemistry
  3. 1.02: Principles of Atomic Structure (Review)
  4. 1.03: Electronic Structure (Review)
  5. 1.04: Electron Configurations
  6. 1.05: Octet Rule - Ionic and Covalent Bonding (Review)
  7. 1.06: Lewis Structures
  8. 1.07: Common Bonding Patterns for Organic Chemistry
  9. 1.08: Structural Formulas - Lewis Kekule Bond-line Condensed
  10. 1.09: Electronegativity and Bond Polarity (Review)
  11. 1.10: Resonance
  12. 1.11: Arrhenius Acids and Bases (Review)
  13. 1.12: Brnsted-Lowry Acids and Bases (Review)
  14. 1.13: Lewis Acids and Bases
  15. 1.14: Distinguishing between pH and pKa
  16. 1.15: Predicting Relative Acidity
  17. 1.16: Molecular Formulas and Empirical Formulas (Review)
  18. 1.17: Additional Exercises
  19. 1.18: Solutions to Additional Exercises
  20. 02: Structure and Properties of Organic Molecules
  21. 2.01: Pearls of Wisdom
  22. 2.02: Molecular Orbital (MO) Theory (Review)
  23. 2.03: Hybridization and Molecular Shapes (Review)
  24. 2.04: 2.4 Conjugated Pi Bond Systems
  25. 2.05: Lone Pair Electrons and Bonding Theories
  26. 2.06: Bond Rotation
  27. 2.07: Isomerism Introduction
  28. 2.08: Hydrocarbons
  29. 2.09: Organic Functional Groups
  30. 2.10: Intermolecular Forces (IMFs) - Review
  31. 2.11: Intermolecular Forces
  32. 2.12: Intermolecular Forces
  33. 2.13: Additional Practice Problems
  34. 2.14: Organic Functional Groups- H-bond donors
  35. 2.15: Additional Exercises
  36. 2.16: 2.15 Solutions to Additional Exercises
  37. 03: Functional Groups and Nomenclature
  38. 3.01: Generic (Abbreviated) Structures (aka R Groups)
  39. 3.02: Overview of the IUPAC Naming Strategy
  40. 3.03: Alkanes
  41. 3.04: Cycloalkanes
  42. 3.05: Haloalkane - Classification and Nomenclature
  43. 3.06: Alkenes
  44. 3.07: Alkynes
  45. 3.08: 3.8 Alcohols - Classification and Nomenclature
  46. 3.09: Ethers Epoxides and Sulfides
  47. 3.10: Benzene and its Derivatives
  48. 3.11: Aldehydes and Ketones
  49. 3.12: 3.12 Amines - Classification and Nomenclature
  50. 3.13: Carboxylic Acids
  51. 3.14: The Carboxylic Acid Derivatives
  52. 3.15: Additional Exercises
  53. 3.16: Solutions to Additional Exercises
  54. 3.17: Appendix - IUPAC Nomenclature Rules
  55. 04: Structure and Stereochemistry of Alkanes
  56. 4.01: Hydrocarbon Functional Groups
  57. 4.02: Physical Properties of Alkanes
  58. 4.03: Structure and Conformations of Alkanes
  59. 4.04: Conformations of Butane
  60. 4.05: Conformations of Higher Alkanes
  61. 4.06: Cycloalkanes and Ring Strain
  62. 4.07: Cyclohexane Conformations
  63. 4.08: Conformations of Monosubstituted Cyclohexanes
  64. 4.09: Cis-trans Isomerism in Cycloalkanes
  65. 4.10: Conformations of Disubstituted Cyclohexanes
  66. 4.11: Joined Rings
  67. 4.12: Uses and Sources of Alkanes
  68. 4.13: Reactions of Alkanes - a Brief Overview
  69. 4.14: Additional Exercises
  70. 4.15: Solutions to Additional Exercises
  71. 05: An Introduction to Organic Reactions using Free Radical Halogenation of Alkanes
  72. 5.01: Types of Organic Reactions
  73. 5.02: 5.2 Reaction Mechanism Notation and Symbols
  74. 5.03: the Dance of the Nucleophile and Electrophile
  75. 5.04: Describing a Reaction - Equilibrium and Free Energy Changes
  76. 5.05: Homolytic Cleavage and Bond Dissociation Energies
  77. 5.06: Reaction Energy Diagrams and Transition States
  78. 5.07: 5.7 Reactive Intermediates - Carbocations
  79. 5.08: 5.8 Reactive Intermediates - Radicals
  80. 5.09: Reactive Intermediates- Carbanions and Carbon Acids
  81. 5.10: The Free-Radical Halogenation of Alkanes
  82. 5.11: Reactivity and Selectivity
  83. 5.12: A Comparison between Biological Reactions and Laboratory Reactions
  84. 5.13: Additional Exercises
  85. 5.14: Solutions to Additional Exercises
  86. 06: Stereochemistry at Tetrahedral Centers
  87. 6.01: Chirality
  88. 6.02: Fischer Projections to communicate Chirality
  89. 6.03: Absolute Configuration and the (R) and (S) System
  90. 6.04: Diastereomers - more than one chiral center
  91. 6.05: Meso Compounds
  92. 6.06: Isomerism Summary Diagram
  93. 6.07: Optical Activity and Racemic Mixtures
  94. 6.08: 6.8 Resolution (Separation) of Enantiomers
  95. 6.09: Stereochemistry of Molecules with Three or More Asymmetric Carbons
  96. 6.10: Absolute and Relative Configuration - the distinction
  97. 6.11: Chirality at Nitrogen Phosphorus and Sulfur
  98. 6.12: Biochemistry of Enantiomers
  99. 6.13: 6.13 The Discovery of Enantiomers
  100. 6.14: Additional Exercises
  101. 6.15: Solutions to Additional Exercises
  102. 07: Alkyl Halides- Nucleophilic Substitution and Elimination
  103. 7.01: 7.1 Alkyl Halides - Structure and Physical Properties
  104. 7.02: Common Uses of Alkyl Halides
  105. 7.03: Preparation of Alkyl Halides
  106. 7.04: Reactions of Alkyl Halides- Substitution and Elimination
  107. 7.05: The S2 Reaction
  108. 7.06: Characteristics of the S2 Reaction
  109. 7.07: Stereochemistry of the SN2 Reaction
  110. 7.08: The S1 Reaction
  111. 7.09: Characteristics of the S1 Reaction
  112. 7.10: Rearrangements of the Carbocation and S1 Reactions
  113. 7.11: The Hammond Postulate and Transition States
  114. 7.12: Comparison of SN1 and SN2 Reactions
  115. 7.13: Characteristics of the E2 Reaction
  116. 7.14: Zaitsev's Rule
  117. 7.15: Characteristics of the E1 Reaction
  118. 7.16: E2 Regiochemistry and Cyclohexane Conformations
  119. 7.17: The E2 Reaction and the Deuterium Isotope Effect
  120. 7.18: Comparison of E1 and E2 Reactions
  121. 7.19: Comparing Substitution and Elimination Reactions
  122. 7.20: Biological Substitution Reactions
  123. 7.21: Biological Elimination Reactions
  124. 7.22: Additional Exercises
  125. 7.23: Solutions to Additional Exercises
  126. 08: Structure and Synthesis of Alkenes
  127. 8.01: Alkene Structure
  128. 8.02: Physical Properties and Important Common Names
  129. 8.03: The Alkene Double Bond and Stereoisomerism
  130. 8.04: Degrees of Unsaturation
  131. 8.05: The E
  132. 8.5.01: Z System (when cis
  133. 8.5.1.01: The E Z System (when cis trans does not work)
  134. 8.06: Stability of Alkenes
  135. 8.07: Alkene Synthesis by Elimination of Alkyl Halides
  136. 8.08: Alkene Synthesis by Dehydration of Alcohols
  137. 8.09: Uses
  138. 8.10: Additional Exercises
  139. 8.11: Solutions to Additional Exercises
  140. 09: Reactions of Alkenes
  141. 9.01: Electrophilic Addition Reactions (EARs)
  142. 9.02: Addition of Hydrogen Halides to Symmetrical Alkenes
  143. 9.03: Alkene Asymmetry and Markovnikov's Rule
  144. 9.04: Hydration- Acid Catalyzed Addition of Water
  145. 9.05: Hydration- Oxymercuration-Demercuration
  146. 9.06: Hydration- Hydroboration-Oxidation
  147. 9.07: Stereochemistry of Reactions - Hydration of Achiral Alkenes
  148. 9.08: Stereochemistry of Reactions - Hydration of Chiral Alkenes
  149. 9.09: Addition of Halogens
  150. 9.10: Formation of Halohydrins
  151. 9.11: Reduction of Alkenes - Catalytic Hydrogenation
  152. 9.12: Oxidation of Alkenes - Epoxidation
  153. 9.13: Dihydroxylation of Alkenes
  154. 9.14: Opening of Epoxides - Acidic versus Basic Conditions
  155. 9.15: Oxidative Cleavage of Alkenes
  156. 9.16: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  157. 9.17: Radical Chain-Growth Polymerization
  158. 9.18: 9.18 Biological Additions of Radicals to Alkenes
  159. 9.19: Additional Exercises
  160. 9.20: Solutions to Additional Exercises
  161. 10: Alkynes
  162. 10.01: Structure and Physical Properties
  163. 10.02: Synthesis of Alkynes - Elimination Reactions of Dihalides
  164. 10.03: Reactions of Alkynes - Addition of HX and X
  165. 10.04: Hydration of Alkynes for Markovnikov Products
  166. 10.05: Hydration of Alkynes for Anti-Markovnikov Products
  167. 10.06: 10.6 Reduction of Alkynes
  168. 10.07: Oxidation of Alkynes
  169. 10.08: Acidity of Terminal Alkynes
  170. 10.09: Synthesis of Larger Alkynes from Acetylides
  171. 10.10: An Introduction to Multiple Step Synthesis
  172. 10.11: Additional Exercises
  173. 10.12: Solutions to Additional Exercises