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Chapter 22: Summary of Major Reaction Mechanisms

Recommended Article: 【Organic Chemistry】 Organic Chemistry Table of Contents



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Difficulty Level ★: Sophomore college level → Able to solve problems by rote memorization

Difficulty Level ★★: Senior college level → Capable of making deductions after some trials and errors

Difficulty Level ★★★: Exam candidate level for professional exams → Frequently tested complex reactions

Difficulty Level ★★★★: Highly difficult exam questions → Rarely tested complex reactions


1. Acetoacetic ester synthesis (Difficulty Level: ★)

2. Acyloin condensation (Difficulty Level: ★★)

3. Aldol addition (Difficulty Level: ★★)

4. Aldol condensation (Difficulty Level: ★★)

5. Arbuzov reaction (Difficulty Level: ★)

6. Arndt-Eistert synthesis (Difficulty Level: ★★)

7. Aza-Cope rearrangement (Difficulty Level: ★)

8. azo coupling (Difficulty Level: ★)

9. Baeyer-Villiger oxidation (Difficulty Level: ★★★)

10. Baylis-Hillman reaction (Difficulty Level: ★★★★)

11. Beckmann rearrangement (Difficulty Level: ★★★)

12. benzilic acid rearrangement (Difficulty Level: ★★★★)

13. benzoin condensation (Difficulty Level: ★★★★)

14. Birch reduction (Difficulty Level: ★)

15. Bischler-Napieralski reaction (Difficulty Level: ★★★★)

16. boronic acid Mannich reaction (Difficulty Level: ★★★★)

17. brown hydroboration (Difficulty Level: ★★)

18. Cannizzaro reaction (Difficulty Level: ★★★)

19. Claisen condensation (Difficulty Level: ★★)

20. Claisen rearrangement (Difficulty Level: ★)

21. Claisen-Schmidt reaction (Difficulty Level: ★★)

22. Clemmensen reduction (Difficulty Level: ★)

23. Cope elimination (Difficulty Level: ★★★)

24. Cope rearrangement (Difficulty Level: ★)

25. Corey-Posner-Whitesides-House Reaction (Difficulty Level: ★)

26. Corey-Seebach reaction (Difficulty Level: ★)

27. Cumene process (Difficulty Level: ★★★)

28. Curtius rearrangement (Difficulty Level: ★★★)

29. Darzens condensation (Difficulty Level: ★★)

30. Dess-Martin oxidation (Difficulty Level: ★)

31. Diazotisation (Difficulty Level: ★)

32. Dieckmann condensation (Difficulty Level: ★★)

33. Diels-Alder reaction (Difficulty Level: ★)

34. 1,3-dipolar cycloaddition (Difficulty Level: ★)

35. Eschweiler-Clarke reaction (Difficulty Level: ★★★★)

36. Ester pyrolysis (Difficulty Level: ★)

37. Favorskii rearrangement (Difficulty Level: ★★★)

38. Fischer esterification (Difficulty Level: ★)

39. Friedel-Crafts acylation (Difficulty Level: ★)

40. Friedel-Crafts alkylation (Difficulty Level: ★)

41. Fries rearrangement (Difficulty Level: ★★★)

42. Gabriel synthesis (Difficulty Level: ★★)

43. Gattermann-Koch reaction (Difficulty Level: ★)

44. Grob fragmentation (Difficulty Level: ★★)

45. Grubbs reaction (Olefin metathesis) (Difficulty Level: ★★)

46. Haloform reaction (Difficulty Level: ★★)

47. Heck reaction (Difficulty Level: ★)

48. Hell-Volhard-Zelinsky(HVZ) reaction (Difficulty Level: ★★★★)

49. Hofmann elimination (Difficulty Level: ★★★)

50. Horner-Wadsworth-Emmons reaction (Difficulty Level: ★★★★)

51. Hundsdiecker reaction (Difficulty Level: ★★★★)

52. Ireland-Claisen rearrangement (Difficulty Level: ★★★★)

53. Johnson-Claisen rearrangement (Difficulty Level: ★★★★)

54. Johnson-Corey-Chaykovsky reaction (Difficulty Level: ★★★)

55. Jones oxidation (Difficulty Level: ★)

56. Knoevenagel condensation (Difficulty Level: ★★)

57. Kochi reaction (Difficulty Level: ★★★★)

58. Kolbe nitrile synthesis (Difficulty Level: ★)

59. Kolbe-Schmitt reaction (Difficulty Level: ★)

60. Malonic ester synthesis (Difficulty Level: ★★)

61. Mannich reaction (Difficulty Level: ★★)

62. McMurry reaction (Difficulty Level: ★★★★)

63. Meerwein-Ponndorf-Verley reduction (Difficulty Level: ★★★★)

64. Michael addition (Difficulty Level: ★★)

65. Mukaiyama aldol reaction (Difficulty Level: ★★)

66. Negishi coupling (Difficulty Level: ★)

67. oxy-Cope rearrangement (Difficulty Level: ★)

68. oxymercuration-demercuration reaction (Difficulty Level: ★)

69. ozonolysis (Difficulty Level: ★)

70. para-Claisen rearrangement (Difficulty Level: ★★)

71. Payne epoxidation (Difficulty Level: ★★)

72. Perkin’s condensation (Difficulty Level: ★★★★)

73. Pictet-Spengler reaction (Difficulty Level: ★★★)

74. Pinacol coupling reaction (Difficulty Level: ★★)

75. Pinacol rearrangement (Difficulty Level: ★★)

76.Pomeranz-Fritsch reaction (Difficulty Level: ★★★)

77. Reductive amination reaction (Difficulty Level: ★★)

78. Reimer-Tiemann reaction (Difficulty Level: ★★)

79. Reformatsky reaction (Difficulty Level: ★★★)

80. Ring expansion reaction (Difficulty Level: ★)

81. Ring contraction reaction (Difficulty Level: ★)

82. Ring formation reaction (Difficulty Level: ★)

83. Ring opening reaction (Difficulty Level: ★)

84. Ritter reaction (Difficulty Level: ★★)

85. Robinson annulation (Difficulty Level: ★★)

86. Rosenmund reduction (Difficulty Level: ★)

87. Sandmeyer reaction (Difficulty Level: ★)

88. Schmidt reaction (Difficulty Level: ★★★★)

89. semi-pinacol rearrangement (Difficulty Level: ★★)

90. Shapiro reaction (Difficulty Level: ★★★★)

91. Simmons-Smith reaction (Difficulty Level: ★)

92. Stetter reaction (Difficulty Level: ★★)

93. Strecker synthesis (Difficulty Level: ★)

94. Stork-Enamine reaction (Difficulty Level: ★★★)

95. Suzuki coupling (Difficulty Level: ★)

96. Swern oxidation (Difficulty Level: ★)

97. Tiffeneau-Demjanov rearrangement (Difficulty Level: ★★★)

98. tautomerization (Difficulty Level: ★)

99. Wilsmeier reaction (Difficulty Level: ★★)

100. Williamson ether synthesis (Difficulty Level: ★)

101. Wittig reaction (Difficulty Level: ★)

102. Wolff-Kishner reduction (Difficulty Level: ★★★)

103. Wolff rearrangement (Difficulty Level: ★★★)

104. Wurtz reaction (Difficulty Level: ★★)

105. Wurtz-Fittig reaction (Difficulty Level: ★★)



Input: 2022.02.02 17:55

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