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Organic Chemistry - Textbook for Chem 2443

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Organic Chemistry - Textbook for Chem 2443

This online textbook will serve as a resource for organic chemistry students taking Chem 2443. All materials are in conjunction with the course schedule. This material was compiled by Dr. Kiet Tran.

Chemistry
Author
Kiet Tran
Publisher
University of Connecticut
Source
LibreTexts
Language
EN
Category
Basic Sciences
Read online Download PDF (open licence)
Contents· 128 sections
  1. 01: General Chemistry Topics Review
  2. 1.01: Ionic and Covalent Bonds - The Octet Rule
  3. 1.02: Electron-Dot Model of Bonding - Lewis Structures
  4. 1.03: Resonance Forms
  5. 1.04: Hybrid Orbitals- Bonding in Complex Molecules and Practice Problems
  6. 1.05: Structures and Formulas of Organic Molecules
  7. 1.06: Polar Covalent Bonds - Electronegativity
  8. 1.07: Polar Covalent Bonds - Dipole Moments
  9. 02: Alkanes
  10. 2.01: Alkanes and Alkane Isomers
  11. 2.02: Alkyl Groups
  12. 2.03: Naming Alkanes
  13. 2.04: Properties of Alkanes
  14. 2.05: Conformations of Ethane
  15. 2.06: Conformations of Other Alkanes
  16. 2.07: Videos
  17. 03: Acids and Bases
  18. 3.01: Acids and Bases - The Brnsted-Lowry Definition
  19. 3.02: Acid and Base Strength
  20. 3.03: Organic Acids and Organic Bases
  21. 3.04: Acids and Bases - The Lewis Definition
  22. 3.05: Videos
  23. 3.S: Polar Covalent Bonds Acids and Bases (Summary)
  24. 04: Alkenes and Alkynes
  25. 4.01: Introduction to Alkenes
  26. 4.02: Calculating Degree of Unsaturation
  27. 4.03: Naming Alkenes
  28. 4.04: Cis-Trans Isomerism in Alkenes
  29. 4.05: Sequence Rules - The EZ Designation
  30. 4.06: Sequence Rules - The EZ Designation
  31. 4.07: Electrophilic Addition Reactions of Alkenes
  32. 4.08: Naming the Alkynes
  33. 4.09: Properties and Bonding in the Alkynes
  34. 4.10: Reduction of Alkynes- The Relative Reactivity of the Two (pi) Bonds
  35. 4.11: Electrophilic Addition Reactions of Alkynes
  36. 4.12: Videos
  37. 05: Electrophilic Addition Reactions
  38. 5.01: Why Addition Reactions Proceed- Thermodynamic Feasibility
  39. 5.02: Catalytic Hydrogenation
  40. 5.03: Nucleophilic Character of the Pi Bond- Electrophilic Addition of Hydrogen Halides
  41. 5.04: The Generality of Electrophilic Addition
  42. 5.05: Electrophilic Addition of Halogens to Alkenes
  43. 5.06: Alcohol Synthesis by Electrophilic Hydration- Thermodynamic Control
  44. 5.07: Oxymncuration-Demercuration- A Special Elcctrophilic Addition
  45. 5.08: Hydroboration-Oxidation- A Stereospecific Anti-Markovnikov Hydration
  46. 5.09: Vicinal SYn Dihydroxylation with Osmium Tetroxide
  47. 5.10: Oxidative Cleavage- Ozonolysis
  48. 5.11: Anti-Markovnikov Additions to Triple Bonds
  49. 5.12: Video (all videos on this website are recommended)
  50. 06: Stereochemistry
  51. 6.01: All Stereochemistry Topics
  52. 6.1.01: Chiral Molecules
  53. 6.1.02: Optical Activity
  54. 6.1.03: Absolute Configuration- R-S Sequence Rules
  55. 6.1.04: Fischer Projections
  56. 6.1.05: Molecules Incorporating Several Stereocenters- Diastereomers
  57. 6.1.06: Meso Compounds
  58. 6.1.07: Stereochemistry in Chemical Reactions
  59. 6.1.08: Resolution- Separation of Enantiomers
  60. 6.1.E: Stereoisomers (Exercises)
  61. 6.02: Videos
  62. 07: Cycloalkanes
  63. 7.01: All Cycloalkane Topics
  64. 7.1.01: Names and Physical Properties of Cycloalkanes
  65. 7.1.02: Ring Strain and the Structure of Cycloalkanes
  66. 7.1.03: Cyclohexane- A Strain-Free Cycloalkane
  67. 7.1.04: Substituted Cyclohexanes
  68. 7.1.05: Larger Cycloalkanes
  69. 7.1.06: Polycyclic Alkanes
  70. 7.1.07: Carbocyclic Products in Nature
  71. 7.1.E: Cycloalkanes (Exercises)
  72. 7.02: Videos
  73. 08: Nomenclature of Functional Groups and Intermolecular Interactions
  74. 8.01: Naming Alcohols and Phenols
  75. 8.02: Properties of Alcohols and Phenols
  76. 8.03: Thiols and Sulfides
  77. 8.04: Names and Properties of Ethers
  78. 8.05: Physical Properties of Haloalkanes
  79. 8.06: Videos
  80. 09: Reactions of Alkyl Halides
  81. 9.01: Preparation of Alkynes by Double Elimination
  82. 9.02: Alkyl Halide Reactivity - Substitution Reactions
  83. 9.2.01: Physical Properties of Haloalkanes
  84. 9.2.02: Nucleophilic Substitution
  85. 9.2.03: Reaction Mechanisms Involving Polar Functional Groups- Using Electron-Pushing' Arrows
  86. 9.2.04: A Closer Look at the Nucleophilic Substitution Mechanism- Kinetics
  87. 9.2.05: Frontside or Backside Attack Stereochemistry of the SN2 Reaction
  88. 9.2.06: Consequences of Inversion in SN2 Reactions
  89. 9.2.07: Structure and (S N2) Reactivity- The Leaving Group
  90. 9.2.08: Structure and SN2 Reactivity- The Nucleophile
  91. 9.2.09: Keys to Success- Choosing Among Multiple Mechanistic Pathways
  92. 9.2.10: Reaction Mechanisms Involving Polar Functional Groups- Using Electron-Pushing' Arrows
  93. 9.2.11: Structure and SN2 Reactivity- The Substrate
  94. 9.2.12: The Sn2 Reaction at a Glance
  95. 9.2.13: Stereochemical Consequences of SN1 Reactions
  96. 9.2.14: Stereochemical Consequences of SN1 Reactions
  97. 9.2.15: Effect of the Alkyl Group on the SN 1 Reaction- Carbocation Stability
  98. 9.2.E: Properties and Reactions of Haloalkanes- Bimolecular Nucleophilic Substitution (Exercises)
  99. 9.03: Alkyl Halide Reactivity - Elimination Reactions
  100. 9.3.01: Unimolecular Elimination- E1
  101. 9.3.02: Bimolecular Elimination- E2
  102. 9.04: Keys to Success- Substitutin Versus Elimination-Structure Determines Function
  103. 9.05: Summary of Reactivity of Haloalkanes
  104. 9.06: Videos
  105. 9.E: Further Reactions of Haloalkanes- Unimolecular Substitution (Exercises)
  106. 10: Carbenes and Free-Radicals
  107. 10.01: Diazomethane Carbenes and Cyclopropane Synthesis
  108. 10.02: 12.13-Radical Additions- Anti-Markovnikov Product Formation
  109. 10.03: Dimerization Oligomerization. and Polymerization of Alkenes
  110. 10.04: Synthesis of Polymers
  111. 10.05: Videos - Intro to Free Radical Halogenation
  112. 10.06: Video - Polymerization of Alkenes
  113. 11: Reactions of Alcohols
  114. 11.01: Alcohols as Acids and Bases
  115. 11.02: Reactions of Alcohols with Base- Preparation of Alkoxides
  116. 11.03: Synthesis of Alcohols by Nucleophilic Substitution
  117. 11.04: Synthesis of Alcohols- Oxidation-Reduction Relation Between Alcohols and Carbonyl Compounds
  118. 11.05: Organometallic Reagents- Sources of Nucleophilic Carbon for Alcohol Synthesis
  119. 11.06: Organometallic Reagents in the Synthesis of Alcohols
  120. 11.07: Keys to Success- An Introduction to Synthetic Strategy
  121. 11.08: Williamson Ether Synthesis
  122. 11.09: Synthesis of Ethers- Alcohols and Mineral Acids
  123. 11.10: Videos
  124. 12: Ethers and Epoxides
  125. 12.01: Reactions of Ethers
  126. 12.02: Reactions of Oxacyclopropanes (Epoxides)
  127. 12.03: Videos - Preparation of epoxides
  128. 12.04: Video - Reactivity of epoxides