Organic Chemistry I

by Xin Liu

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An open textbook that is suitable for the first semester of Organic Chemistry. Basic concepts of the structures and reactivities of organic molecules are covered in this open textbook. Besides the fundamental discussions of organic acids-bases, stereochemistry, IR and NMR, this book also includes the topics of substitution and elimination reactions, radical substitution of alkanes, preparation and reactions of alkenes and alkynes.

Description from LibreTexts.

Publisher
Kwantlen Polytechnic University
Subjects
Chemistry, Organic Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
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. Front Matter
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. Licensing
  6. About the Author
  7. Acknowledgements
  8. Introduction
  9. 1: Basic Concepts in Chemical Bonding and Organic Molecules
  10. 1.1: Chemical Bonding
  11. 1.2: Lewis Structure
  12. 1.3: Resonance Structures
  13. 1.4: Resonance structures in Organic Chemistry
  14. 1.5: Valence-Shell Electron-Pair Repulsion Theory (VSEPR)
  15. 1.6: Valence Bond Theory and Hybridization
  16. 1.7: Answers to Practice Questions Chapter 1
  17. 2: Fundamental of Organic Structures
  18. 2.1: Structures of Alkanes
  19. 2.2: Nomenclature of Alkanes
  20. 2.3: Functional Groups
  21. 2.4: IUPAC Naming of Organic Compounds with Functional Groups
  22. 2.5: Degree of Unsaturation/Index of Hydrogen Deficiency
  23. 2.6: Intermolecular Force and Physical Properties of Organic Compounds
  24. 2.7: Answers to Practice Questions Chapter 2
  25. 3: Acids and Bases- Organic Reaction Mechanism Introduction
  26. 3.1: Review of Acids and Bases and Ka
  27. 3.2: Organic Acids and Bases and Organic Reaction Mechanism
  28. 3.3: pKa of Organic Acids and Application of pKa to Predict Acid-Base Reaction Outcome
  29. 3.4: Structural Effects on Acidity and Basicity
  30. 3.5: Lewis Acids and Lewis Bases
  31. 3.6: Answers to Practice Questions Chapter 3
  32. 4: Conformations of Alkanes and Cycloalkanes
  33. 4.1: Conformation Analysis of Alkanes
  34. 4.2: Cycloalkanes and Their Relative Stabilities
  35. 4.3: Conformation Analysis of Cyclohexane
  36. 4.4: Substituted Cyclohexanes
  37. 4.5: Answers to Practice Questions Chapter 4
  38. 5: Stereochemistry
  39. 5.1: Summary of Isomers
  40. 5.2: Geometric Isomers and E/Z Naming System
  41. 5.3: Chirality and R/S Naming System
  42. 5.4: Optical Activity
  43. 5.5: Fisher Projection
  44. 5.6: Compounds with More Than One Chirality Centers
  45. 5.7: Answers to Practice Questions Chapter 5
  46. 6: Structural Identification of Organic Compounds- IR and NMR Spectroscopy
  47. 6.1: Electromagnetic Radiation and Molecular Spectroscopy
  48. 6.2: Infrared (IR) Spectroscopy Theory
  49. 6.3: IR Spectrum and Characteristic Absorption Bands
  50. 6.4: IR Spectrum Interpretation Practice
  51. 6.5: NMR Theory and Experiment
  52. 6.6: ¹H NMR Spectra and Interpretation (Part I)
  53. 6.7: ¹H NMR Spectra and Interpretation (Part II)
  54. 6.8: ¹³C NMR Spectroscopy
  55. 6.9: Structure Determination Practice
  56. 6.10: Answers to Practice Questions Chapter 6
  57. 7: Nucleophilic Substitution Reactions
  58. 7.1: Nucleophilic Substitution Reaction Overview
  59. 7.2: SN2 Reaction Mechanism, Energy Diagram and Stereochemistry
  60. 7.3: Other Factors that Affect SN2 Reactions
  61. 7.4: SN1 Reaction Mechanism, Energy Diagram and Stereochemistry
  62. 7.5: SN1 vs SN2
  63. 7.6: Extra Topics on Nucleophilic Substitution Reaction
  64. 7.7: Answers to Practice Questions Chapter 7
  65. 8: Elimination Reactions
  66. 8.1: E2 Reaction
  67. 8.2: E1 Reaction
  68. 8.3: E1/E2 Summary
  69. 8.4: Comparison and Competition Between SN1, SN2, E1 and E2
  70. 8.5: Answers to Practice Questions Chapter 8
  71. 9: Free Radical Substitution Reaction of Alkanes
  72. 9.1: Homolytic and Heterolytic Cleavage
  73. 9.2: Halogenation Reaction of Alkanes
  74. 9.3: Stability of Alkyl Radicals
  75. 9.4: Chlorination vs Bromination
  76. 9.5: Stereochemistry for Halogenation of Alkanes
  77. 9.6: Synthesis of Target Molecules- Introduction of Retrosynthetic Analysis
  78. 9.7: Answers to Practice Questions Chapter 9
  79. 10: Alkenes and Alkynes
  80. 10.1: Synthesis of Alkenes
  81. 10.2: Reactions of Alkenes- Addition of Hydrogen Halide to Alkenes
  82. 10.3: Reactions of Alkenes- Addition of Water (or Alcohol) to Alkenes
  83. 10.4: Reactions of Alkenes- Addition of Bromine and Chlorine to Alkenes
  84. 10.5: Reaction of Alkenes- Hydrogenation
  85. 10.6: Two Other Hydration Reactions of Alkenes
  86. 10.7: Oxidation Reactions of Alkenes
  87. 10.8: Alkynes
  88. 10.9: Answers to Practice Questions Chapter 10
  89. Back Matter
  90. Index
  91. Glossary
  92. Detailed Licensing