Chem 8A: Organic Chemistry - Brief Course

by Franz

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University of California, Davis
Subjects
Chemistry
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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. Quizzes and Agenda
  7. 1: Quizzes
  8. 1.1: Practice Final A
  9. 1.2: Practice Final A Key
  10. 1.3: Quiz 1A
  11. 1.4: Quiz 1A Key
  12. 1.5: Quiz 1B
  13. 1.6: Quiz 1B Key
  14. 1.7: Quiz 1C
  15. 1.8: Quiz 1C Key
  16. 1.9: Quiz 2A
  17. 1.10: Quiz 2A Key
  18. 1.11: Quiz 2B
  19. 1.12: Quiz 2B Key
  20. 1.13: Quiz 2C
  21. 1.14: Quiz 2C Key
  22. 1.15: Quiz 3A
  23. 1.16: Quiz 3A Key
  24. 1.16.1: How to answer an “Explain” Question
  25. 1.17: Quiz 3B
  26. 1.18: Quiz 3B Key
  27. 1.19: Quiz 3C
  28. 1.20: Quiz 3C Key
  29. 1.21: Quiz 4A
  30. 1.22: Quiz 4A Key
  31. 1.23: Quiz 4B
  32. 1.24: Quiz 4B Key
  33. 1.25: Quiz 5A
  34. 1.26: Quiz 5A Key
  35. 1.27: Quiz 5B
  36. 1.28: Quiz 5B Key
  37. 1.29: Quiz 6A
  38. 1.30: Quiz 6A Key
  39. 2: Agenda
  40. 1: Electronic Structure and Covalent Bonding
  41. 1.1: The Structure of an Atom
  42. 1.2: How Electrons in an Atom are Distributed
  43. 1.3: Ionic and Covalent Bonds
  44. 1.4: How the Structure of a Compound is Represented
  45. 1.5: Atomic Orbitals
  46. 1.6: How atoms form Covalent Bonds
  47. 1.7: How Single Bonds Are Formed in Organic Compounds
  48. 1.8: How a Double Bond is Formed- The Bonds in Ethene
  49. 1.9: How a Triple Bond is Formed- The Bonds in Ethyne
  50. 1.10: Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion
  51. 1.11: The Bonds in Water
  52. 1.12: The Bonds in Ammonia and in the Ammonium Ion
  53. 1.13: The Bond in a Hydrogen Halide
  54. 1.14: Summary- Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
  55. 1.15: The Dipole Moments of Molecules
  56. 1.16: An Introduction to Acids and Bases
  57. 1.17: pka and pH
  58. 1.18: 1.18 Organic Acids and Bases
  59. 1.19: How to Predict the Outcome of an Acid-Base Reaction
  60. 1.20: How to Determine the Position of Equilibrium
  61. 1.21: How the Structure of an Acid Affects its pka Value
  62. 1.22: How Substituents Affect the Strength of an Acid
  63. 1.23: An Introduction to Delocalized Electrons
  64. 1.24: A Summary of the Factors that Determine Acid Strength
  65. 1.25: How pH Affects the Structure of an Organic Compound
  66. 1.26: Buffer Solutions
  67. 1.27: Lewis Acids and Bases
  68. 2: Acids and Bases
  69. 2.1: An Introduction to Acids and Bases
  70. 2.2: pka and pH
  71. 2.3: Organic Acids and Bases
  72. 2.4: How to Predict the Outcome of an Acid-Base Reaction
  73. 2.5: How to Determine the Position of Equilibrium
  74. 2.6: How the Structure of an Acid Affects its pka Value
  75. 2.7: How pH Affects the Structure of an Organic Compound
  76. 2.8: Buffer Solutions
  77. 2.9: Lewis Acids and Bases
  78. 3: An Introduction to Organic Compounds- Nomenclature, Physical Properties, and Representation of Structure
  79. 3.1: How Alkyl Substituents Are Named
  80. 3.2: The Nomenclature of Alkanes
  81. 3.3: The Nomenclature of Cycloalkanes • Skeletal Structures
  82. 3.4: The Nomenclature of Alkyl Halides
  83. 3.5: The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
  84. 3.6: The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
  85. 3.7: Rotation Occurs About Carbon-Carbon Single Bonds
  86. 3.8: Some Cycloalkanes Have Angle Strain
  87. 3.9: Conformers of Cyclohexane
  88. 3.10: Conformers of Monosubstituted Cyclohexanes
  89. 3.11: Conformers of Disubstituted Cyclohexanes
  90. 3.12: Fused Cyclohexane Rings
  91. 4: Alkenes- Structure, Nomenclature, and an Introduction to Reactivity
  92. 4.1: Molecular Formulas and the Degree of Unsaturation
  93. 4.2: The Nomenclature of Alkenes
  94. 4.3: The Structures of Alkenes
  95. 4.4: Alkenes Can Have Cis and Trans Isomers
  96. 4.5: Naming Alkenes Using the E,Z System
  97. 4.6: How Alkenes React (Curved Arrows Show the Flow of Electrons)
  98. 4.7: A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction
  99. 5: The Reactions of Alkenes and Alkynes- An Introduction to Multistep Synthesis
  100. 5.1: The Addition of a Hydrogen Halide to an Alkene
  101. 5.2: Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
  102. 5.3: Electrophilic Addition Reactions Are Regioselective
  103. 5.4: The Addition of Water to an Alkene
  104. 5.5: The Addition of an Alcohol to an Alkene
  105. 5.6: The Nomenclature of Alkynes
  106. 5.7: The Structure of Alkynes
  107. 5.8: The Physical Properties of Unsaturated Hydrocarbons
  108. 5.9: The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne
  109. 5.10: The Addition of Hydrogen to Alkenes and Alkynes
  110. 5.11: A Hydrogen Bonded to an sp Carbon is “Acidic”
  111. 5.12: Synthesis Using Acetylide Ions
  112. 5.13: An Introduction to Multistep Synthesis
  113. 6: Isomers and Stereochemistry
  114. 6.1: Cis-Trans Isomers Result from Restricted Rotation
  115. 6.2: A Chiral Object Has a Nonsuperimposable Mirror Image
  116. 6.3: An Asymmetric Center Is a Cause of Chirality in a Molecule
  117. 6.4: Isomers with One Asymmetric Center
  118. 6.5: Asymmetric Centers and Stereocenters
  119. 6.6: How to Draw Enantiomers
  120. 6.7: Naming Enantiomers by the R,S System
  121. 6.8: Chiral Compounds Are Optically Active
  122. 6.9: How Specific Rotation is Measured
  123. 6.10: Enantiomeric Excess
  124. 6.11: Isomers with More than One Asymmetric Center
  125. 6.12: Meso Compounds Have Asymmetric Centers but Are Optically Inactive
  126. 6.13: How to Name Isomers with More than One Asymmetric Center
  127. 6.14: Reactions of Compounds that Contain an Asymmetric Center
  128. 6.15: Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations
  129. 6.16: How Enantiomers Can Be Separated
  130. 6.17: Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
  131. 6.18: Stereochemistry of Reactions- Regioselective, Stereoselective, and Stereospecific Reactions
  132. 6.19: The Stereochemistry of Electrophilic addition Reactions of Alkenes
  133. 6.20: The Stereochemistry of Enzyme-Catalyzed Reactions
  134. 6.21: Enantiomers Can Be Distinguished by Biological Molecules
  135. 7: Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa (Ultraviolet and Visible Spectroscopy)
  136. 7.1: Delocalized Electrons Explain Benzene’s Structure
  137. 7.2: The Bonding in Benzene
  138. 7.3: Resonance Contributors and the Resonance Hybrid
  139. 7.4: How to Draw Resonance Contributors
  140. 7.5: The Predicted Stabilities of Resonance Contributors
  141. 7.6: Delocalized Energy Is the Additional Stability Delocalized Electrons Give to a Compound
  142. 7.7: Examples That Show How Delocalized Electrons Affect Stability
  143. 7.8: A Molecular Orbital Description of Stability
  144. 7.9: How Delocalized Electrons Affect pKa Values
  145. 7.10: Delocalized Electrons Can Affect the Product of a Reaction
  146. 7.11: Thermodynamic Versus Kinetic Control of Reactions
  147. 7.12: The Diels-Adler Reaction Is a 1,4-Addition Reaction
  148. 8: Aromaticity- Reactions of Benzene and Substituted Benzenes
  149. 8.1: The Two Criteria for Aromaticity
  150. 8.2: Applying the Criteria for Aromaticity
  151. 8.3: Aromatic Heterocyclic Compounds
  152. 8.4: The Nomenclature of Monosubstituted Benzenes
  153. 8.5: How Benzene Reacts
  154. 8.6: The General Mechanism for Electrophilic Aromatic Substitution Reactions
  155. 8.7: Halogenation of Benzene
  156. 8.8: Nitration of Benzene
  157. 8.9: Sulfonation of Benzene
  158. 8.10: The Friedel-Crafts Acylation of Benzene
  159. 8.11: The Friedel-Crafts Alkylation of Benzene
  160. 8.12: The Nomenclature of Disubstituted and Polysubstituted Benzenes
  161. 8.13: The Effect of Substituents on Reactivity
  162. 8.14: The Effect of Substituents on Orientation
  163. 8.15: The Effect of Substituents on pKa
  164. 9: Substitution and Elimination Reactions of Alkyl Halides
  165. 9.1: How Alkyl Halides React
  166. 9.2: The Mechanism For an \(S_N2\) Reaction
  167. 9.3: Factors That Affect \(S_N2\) Reactions
  168. 9.4: The Mechanism for an \(S_N1\) Reaction
  169. 9.5: Factors That Affect \(S_N1\) Reactions
  170. 9.6: Comparing the \(S_N2\) and \(S_N1\) Reactions of Alkyl Halides
  171. 9.7: Elimination Reaction of Alkyl Halides
  172. 9.8: Products of Elimination Reactions
  173. 9.9: Comparing the E2 and E1 Reactions of Alkyl Halides
  174. 9.10: Does an Alkyl Halide Undergo SN2, E2 Reactions or SN1 Reactions?
  175. 9.11: Does an Alkyl Halide Undergo SN2
  176. 9.11.1: E2 Reactions or SN1
  177. 9.11.1.1: Does an Alkyl Halide Undergo SN2
  178. 9.12: Solvent Effects
  179. 9.13: Using Substitution Reactions to Synthesize Organic Compounds
  180. 9.14: Biological Methylating Reagents
  181. 10: The Chemistry of Nucleic Acids
  182. 10.1: Nucleosides and Nucleotides
  183. 10.2: Nucleic Acids Are Composed of Nucleotide Subunits
  184. 10.3: Why DNA Does Not Have A 2’- OH Group
  185. 10.4: The Biosynthesis of DNA is Called Replication
  186. 10.5: DNA and Heredity
  187. 10.6: The Biosynthesis of RNA is Called Transcription
  188. 10.7: There Are Three Kinds of RNA
  189. 10.8: The Biosynthesis of Proteins Is Called Translation
  190. 10.9: Why DNA Contains Thymine Instead of Uracil
  191. 10.10: How the Base Sequence of DNA Is Determined
  192. 10.11: The Polymerase Chain Reaction (PCR)
  193. 10.12: Genetic Engineering
  194. 11: The Organic Chemistry of Drugs- Discovery and Design
  195. 11.1: Naming Drugs
  196. 11.2: Lead Compounds
  197. 11.3: Molecular Modification
  198. 11.4: Random Screening
  199. 11.5: Serendipity in Drug Development
  200. 11.6: Receptors
  201. 11.7: Drug Resistance
  202. 11.8: Molecular Modeling
  203. 11.9: Antiviral Drugs
  204. 11.10: Economics of Drugs (Governmental Regulations)
  205. Back Matter
  206. Index
  207. Glossary
  208. Detailed Licensing