Chemistry, Organic I

by Divan Fard

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This textbook is the result of a massive collaborative effort that leverages the Libre Texts project—a global initiative that has grown into the world’s most comprehensive open-access Textbook library. This specific remix was curated and edited by an organic chemist and graduate of the University of Pennsylvania. Reflecting 45 years of graduate and undergraduate teaching experience, this volume establishes the essential foundations of molecular structure, stereochemistry, and reaction mechanisms

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Publisher
Shasta College
Subjects
Chemistry
Licence
CC BY 4.0, as LibreTexts states it
Who can read
Tweens profiles and older, judged from its title and subjects

Contents

LibreTexts writes equations in TeX, and here they show as TeX; the PDF has them typeset.

  1. 1: Introduction
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. 1.4: Licensing
  6. 2: Structure and Bonding
  7. 2.1: Why This Chapter?
  8. 2.2: Atomic Structure - The Nucleus
  9. 2.3: Atomic Structure - Orbitals
  10. 2.4: Atomic Structure - Electron Configurations
  11. 2.5: Development of Chemical Bonding Theory
  12. 2.6: Describing Chemical Bonds - Valence Bond Theory
  13. 2.7: sp³ Hybrid Orbitals and the Structure of Methane
  14. 2.8: sp³ Hybrid Orbitals and the Structure of Ethane
  15. 2.9: sp² Hybrid Orbitals and the Structure of Ethylene
  16. 2.10: sp Hybrid Orbitals and the Structure of Acetylene
  17. 2.11: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  18. 2.12: Describing Chemical Bonds - Molecular Orbital Theory
  19. 2.13: Drawing Chemical Structures
  20. 2.14: Chemistry Matters—Organic Foods- Risk versus Benefit
  21. 2.15: Key Terms
  22. 2.16: Summary
  23. 2.17: Additional Problems
  24. 3: Polar Covalent Bonds; Acids and Bases
  25. 3.1: Why This Chapter?
  26. 3.2: Polar Covalent Bonds - Electronegativity
  27. 3.3: Polar Covalent Bonds - Dipole Moments
  28. 3.4: Formal Charges
  29. 3.5: Resonance
  30. 3.6: Rules for Resonance Forms
  31. 3.7: Drawing Resonance Forms
  32. 3.8: Acids and Bases - The Brønsted-Lowry Definition
  33. 3.9: Acid and Base Strength
  34. 3.10: Predicting Acid-Base Reactions from pKa Values
  35. 3.11: Organic Acids and Organic Bases
  36. 3.12: Acids and Bases - The Lewis Definition
  37. 3.13: Noncovalent Interactions Between Molecules
  38. 3.14: Chemistry Matters—Alkaloids- From Cocaine to Dental Anesthetics
  39. 3.15: Key Terms
  40. 3.16: Summary
  41. 3.17: Additional Problems
  42. 4: Organic Compounds- Alkanes and Their Stereochemistry
  43. 4.1: Why This Chapter?
  44. 4.2: Functional Groups
  45. 4.3: Alkanes and Alkane Isomers
  46. 4.4: Alkyl Groups
  47. 4.5: Naming Alkanes
  48. 4.6: Properties of Alkanes
  49. 4.7: Conformations of Ethane
  50. 4.8: Conformations of Other Alkanes
  51. 4.9: Chemistry Matters—Gasoline
  52. 4.10: Key Terms
  53. 4.11: Summary
  54. 4.12: Additional Problems
  55. 5: Organic Compounds - Cycloalkanes and their Stereochemistry
  56. 5.1: Why This Chapter?
  57. 5.2: Naming Cycloalkanes
  58. 5.3: Cis-Trans Isomerism in Cycloalkanes
  59. 5.4: Stability of Cycloalkanes - Ring Strain
  60. 5.5: Conformations of Cycloalkanes
  61. 5.6: Conformations of Cyclohexane
  62. 5.7: Axial and Equatorial Bonds in Cyclohexane
  63. 5.8: Conformations of Monosubstituted Cyclohexanes
  64. 5.9: Conformations of Disubstituted Cyclohexanes
  65. 5.10: Conformations of Polycyclic Molecules
  66. 5.11: Chemistry Matters—Molecular Mechanics
  67. 5.12: Key Terms
  68. 5.13: Summary
  69. 5.14: Additional Problems
  70. 6: Stereochemistry at Tetrahedral Centers
  71. 6.1: Why This Chapter?
  72. 6.2: Enantiomers and the Tetrahedral Carbon
  73. 6.3: The Reason for Handedness in Molecules - Chirality
  74. 6.4: Optical Activity
  75. 6.5: Pasteur's Discovery of Enantiomers
  76. 6.6: Sequence Rules for Specifying Configuration
  77. 6.7: Diastereomers
  78. 6.8: Meso Compounds
  79. 6.9: Racemic Mixtures and the Resolution of Enantiomers
  80. 6.10: A Review of Isomerism
  81. 6.11: Chirality at Nitrogen, Phosphorus, and Sulfur
  82. 6.12: Prochirality
  83. 6.13: Chirality in Nature and Chiral Environments
  84. 6.14: Chemistry Matters—Chiral Drugs
  85. 6.15: Key Terms
  86. 6.16: Summary
  87. 6.17: Additional Problems
  88. 7: An Overview of Organic Reactions
  89. 7.1: Why This Chapter?
  90. 7.2: Kinds of Organic Reactions
  91. 7.3: How Organic Reactions Occur - Mechanisms
  92. 7.4: Polar Reactions
  93. 7.5: An Example of a Polar Reaction - Addition of HBr to Ethylene
  94. 7.6: Using Curved Arrows in Polar Reaction Mechanisms
  95. 7.7: Radical Reactions
  96. 7.8: Describing a Reaction - Equilibria, Rates, and Energy Changes
  97. 7.9: Describing a Reaction - Bond Dissociation Energies
  98. 7.10: Describing a Reaction - Energy Diagrams and Transition States
  99. 7.11: Describing a Reaction- Intermediates
  100. 7.12: A Comparison between Biological Reactions and Laboratory Reactions
  101. 7.13: Chemistry Matters—Where Do Drugs Come From?
  102. 7.14: Key Terms
  103. 7.15: Summary
  104. 7.16: Additional Problems
  105. 8: Alkenes - Structure and Reactivity
  106. 8.1: Why This Chapter?
  107. 8.2: Industrial Preparation and Use of Alkenes
  108. 8.3: Calculating Degree of Unsaturation
  109. 8.4: Naming Alkenes
  110. 8.5: Cis-Trans Isomerism in Alkenes
  111. 8.6: Alkene Stereochemistry and the E,Z Designation
  112. 8.7: Stability of Alkenes
  113. 8.8: Electrophilic Addition Reactions of Alkenes
  114. 8.9: Orientation of Electrophilic Additions - Markovnikov's Rule
  115. 8.10: Carbocation Structure and Stability
  116. 8.11: The Hammond Postulate
  117. 8.12: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
  118. 8.13: Chemistry Matters - Bioprospecting - Hunting for Natural Products
  119. 8.14: Key Terms
  120. 8.15: Summary
  121. 8.16: Additional Problems
  122. 9: Alkenes - Reactions and Synthesis
  123. 9.1: Why This Chapter?
  124. 9.2: Preparation of Alkenes - A Preview of Elimination Reactions
  125. 9.3: Halogenation of Alkenes - Addition of X₂
  126. 9.4: Halohydrins from Alkenes - Addition of HO-X
  127. 9.5: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  128. 9.6: Hydration of Alkenes - Addition of H₂O by Hydroboration
  129. 9.7: Reduction of Alkenes - Hydrogenation
  130. 9.8: Oxidation of Alkenes - Epoxidation and Hydroxylation
  131. 9.9: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  132. 9.10: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  133. 9.11: Radical Additions to Alkenes - Chain-Growth Polymers
  134. 9.12: Biological Additions of Radicals to Alkenes
  135. 9.13: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene
  136. 9.14: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene
  137. 9.15: Chemistry Matters—Terpenes- Naturally Occurring Alkenes
  138. 9.16: Key Terms
  139. 9.17: Summary
  140. 9.18: Summary of Reactions
  141. 9.19: Additional Problems
  142. 10: Alkynes - An Introduction to Organic Synthesis
  143. 10.1: Why This Chapter?
  144. 10.2: Naming Alkynes
  145. 10.3: Preparation of Alkynes - Elimination Reactions of Dihalides
  146. 10.4: Reactions of Alkynes - Addition of HX and X₂
  147. 10.5: Hydration of Alkynes
  148. 10.6: Reduction of Alkynes
  149. 10.7: Oxidative Cleavage of Alkynes
  150. 10.8: Alkyne Acidity - Formation of Acetylide Anions
  151. 10.9: Alkylation of Acetylide Anions
  152. 10.10: An Introduction to Organic Synthesis
  153. 10.11: Chemistry Matters - The Art of Organic Synthesis
  154. 10.12: Key Terms
  155. 10.13: Summary
  156. 10.14: Summary of Reactions
  157. 10.15: Additional Problems
  158. 11: Organohalides
  159. 11.1: Why This Chapter?
  160. 11.2: Names and Properties of Alkyl Halides
  161. 11.3: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  162. 11.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  163. 11.5: Stability of the Allyl Radical - Resonance Revisited
  164. 11.6: Preparing Alkyl Halides from Alcohols
  165. 11.7: Reactions of Alkyl Halides - Grignard Reagents
  166. 11.8: Organometallic Coupling Reactions
  167. 11.9: Oxidation and Reduction in Organic Chemistry
  168. 11.10: Chemistry Matters - Naturally Occurring Organohalides
  169. 11.11: Key Terms
  170. 11.12: Summary
  171. 11.13: Summary of Reactions
  172. 11.14: Additional Problems
  173. 12: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  174. 12.1: Why This Chapter?
  175. 12.2: The Discovery of Nucleophilic Substitution Reactions
  176. 12.3: The Sₙ2 Reaction
  177. 12.4: Characteristics of the SN2 Reaction
  178. 12.5: Characteristics of the SN1 Reaction
  179. 12.6: Biological Substitution Reactions
  180. 12.7: Elimination Reactions- Zaitsev's Rule
  181. 12.8: The E2 Reaction and the Deuterium Isotope Effect
  182. 12.9: The E2 Reaction and Cyclohexane Conformation
  183. 12.10: The E1 and E1cB Reactions
  184. 12.11: Biological Elimination Reactions
  185. 12.12: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
  186. 12.13: Chemistry Matters—Green Chemistry
  187. 12.14: Key Terms
  188. 12.15: Summary
  189. 12.16: Summary of Reactions
  190. 12.17: Additional Problems
  191. 12.18: The SN1 Reaction
  192. Back Matter
  193. Index
  194. Glossary
  195. Detailed Licensing
  196. Detailed Licensing