Organic Chemistry I

by Jeffrey Turk

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Organic chemistry studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and theoretically.

Description from LibreTexts.

Publisher
Alma College
Subjects
Chemistry
Licence
CC BY-SA 4.0, as LibreTexts states it
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: Structure and Bonding
  7. 1.1: Describing Chemical Bonds - Valence Bond Theory
  8. 1.2: Describing Chemical Bonds- Molecular Orbital Theory
  9. 1.3: Polar Covalent Bonds - Electronegativity
  10. 1.4: Development of Chemical Bonding Theory
  11. 1.5: Formal Charges
  12. 1.6: Drawing Chemical Structures
  13. 1.7: sp³ Hybrid Orbitals and the Structure of Methane
  14. 1.8: sp³ Hybrid Orbitals and the Structure of Ethane
  15. 1.9: sp² Hybrid Orbitals and the Structure of Ethylene
  16. 1.10: sp Hybrid Orbitals and the Structure of Acetylene
  17. 1.11: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  18. 1.12: Polar Covalent Bonds - Dipole Moments
  19. 2: Conjugation, Resonance, and Aromaticity
  20. 2.1: Conjugation, Color, and the Chemistry of Vision
  21. 2.2: Stability of Conjugated Dienes- Molecular Orbital Theory
  22. 2.3: Resonance
  23. 2.4: Rules for Resonance Forms
  24. 2.5: Drawing Resonance Forms
  25. 2.5.1: Orbital Picture of Delocalization
  26. 2.6: Structure and Stability of Benzene
  27. 2.7: Aromaticity and the Hückel 4n + 2 Rule
  28. 2.8: Aromatic Ions
  29. 2.9: Aromatic Heterocycles - Pyridine and Pyrrole
  30. 2.10: Polycyclic Aromatic Compounds
  31. 3: Organic Compounds- Alkanes and Their Stereochemistry
  32. 3.1: Gasoline - A Deeper Look
  33. 3.2: Properties of Alkanes
  34. 3.3: Alkanes and Alkane Isomers
  35. 3.4: Alkyl Groups
  36. 3.5: Naming Alkanes
  37. 3.6: Conformations of Ethane
  38. 3.7: Conformations of Other Alkanes
  39. 4: Organic Compounds - Cycloalkanes and their Stereochemistry
  40. 4.1: Naming Cycloalkanes
  41. 4.2: Cis-Trans Isomerism in Cycloalkanes
  42. 4.3: Stability of Cycloalkanes - Ring Strain
  43. 4.4: Conformations of Cycloalkanes
  44. 4.5: Conformations of Cyclohexane
  45. 4.6: Axial and Equatorial Bonds in Cyclohexane
  46. 4.7: Conformations of Monosubstituted Cyclohexanes
  47. 4.8: Conformations of Disubstituted Cyclohexanes
  48. 4.9: Conformations of Polycyclic Molecules
  49. 5: Stereochemistry at Tetrahedral Centers
  50. 5.1: Chapter Objectives and Introduction
  51. 5.2: Optical Activity
  52. 5.3: Chirality in Nature and Chiral Environments
  53. 5.4: Enantiomers and the Tetrahedral Carbon
  54. 5.5: The Reason for Handedness in Molecules - Chirality
  55. 5.6: Sequence Rules for Specifying Configuration
  56. 5.7: Diastereomers
  57. 5.8: Meso Compounds
  58. 5.9: Racemic Mixtures and the Resolution of Enantiomers
  59. 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
  60. 5.11: Prochirality
  61. 6: An Overview of Organic Reactions
  62. 6.1: Kinds of Organic Reactions
  63. 6.2: How Organic Reactions Occur - Mechanisms
  64. 6.3: Radical Reactions
  65. 6.4: Polar Reactions
  66. 6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene
  67. 6.6: Using Curved Arrows in Polar Reaction Mechanisms
  68. 6.7: Describing a Reaction - Equilibria, Rates, and Energy Changes
  69. 6.8: Describing a Reaction - Bond Dissociation Energies
  70. 6.9: Describing a Reaction - Energy Diagrams and Transition States
  71. 6.10: Describing a Reaction- Intermediates
  72. 6.11: A Comparison between Biological Reactions and Laboratory Reactions
  73. 6.12: Oxidation and Reduction in Organic Chemistry
  74. 7: Acids and Bases
  75. 7.1: Acids and Bases - The Brønsted-Lowry Definition
  76. 7.2: Acid and Base Strength
  77. 7.3: Predicting Acid-Base Reactions from pKa Values
  78. 7.4: Organic Acids and Organic Bases
  79. 7.5: Acids and Bases - The Lewis Definition
  80. 8: Organohalides- Radical Halogenation of Alkanes and Alkenes
  81. 8.1: Introduction to Organohalides
  82. 8.2: Names and Properties of Alkyl Halides
  83. 8.3: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  84. 8.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  85. 8.5: Stability of the Allyl Radical - Resonance Revisited
  86. 9: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  87. 9.1: Introduction
  88. 9.2: The Discovery of Nucleophilic Substitution Reactions
  89. 9.3: The SN2 Reaction
  90. 9.4: Characteristics of the SN2 Reaction
  91. 9.5: The SN1 Reaction
  92. 9.6: Characteristics of the SN1 Reaction
  93. 9.7: Biological Substitution Reactions
  94. 9.8: Elimination Reactions- Zaitsev's Rule
  95. 9.9: The E2 Reaction and the Deuterium Isotope Effect
  96. 9.10: The E2 Reaction and Cyclohexane Conformation
  97. 9.11: The E1 and E1cB Reactions
  98. 9.12: Biological Elimination Reactions
  99. 9.13: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
  100. 10: Alkenes- Structure and Reactivity
  101. 10.1: Introduction to Alkenes
  102. 10.2: Industrial Preparation and Use of Alkenes
  103. 10.3: Naming Alkenes
  104. 10.4: Cis-Trans Isomerism in Alkenes
  105. 10.5: Sequence Rules - The E,Z Designation
  106. 10.6: Stability of Alkenes
  107. 10.7: Electrophilic Addition Reactions of Alkenes
  108. 10.8: Orientation of Electrophilic Additions - Markovnikov's Rule
  109. 10.9: Carbocation Structure and Stability
  110. 10.10: The Hammond Postulate
  111. 10.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
  112. 11: Alkenes- Reactions and Synthesis
  113. 11.1: Chapter Objectives
  114. 11.2: Preparation of Alkenes - A Preview of Elimination Reactions
  115. 11.3: Halogenation of Alkenes - Addition of X₂
  116. 11.4: Halohydrins from Alkenes - Addition of HOX
  117. 11.5: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  118. 11.6: Hydration of Alkenes - Addition of H₂O by Hydroboration
  119. 11.7: Reduction of Alkenes - Hydrogenation
  120. 11.8: Oxidation of Alkenes to Vicinal Diols
  121. 11.9: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  122. 12: Alkynes - An Introduction to Organic Synthesis
  123. 12.1: Naming Alkynes
  124. 12.2: Preparation of Alkynes - Elimination Reactions of Dihalides
  125. 12.3: Alkylation of Acetylide Anions
  126. 12.4: Alkyne Acidity - Formation of Acetylide Anions
  127. 12.5: Reactions of Alkynes - Addition of HX and X₂
  128. 12.6: Hydration of Alkynes
  129. 12.7: Reduction of Alkynes
  130. 12.8: Oxidative Cleavage of Alkynes
  131. 12.9: An Introduction to Organic Synthesis
  132. Back Matter
  133. Index
  134. Glossary
  135. Detailed Licensing
  136. Detailed Licensing