Table of Contents

I. 100 Must Know Mechanisms	4

1. Arbuzov Reaction (1898–1906)	4

2. Acyloin Condensation 1903	5

3. Alkyne (acetylene) Zipper 1975	5

4. Arndt-Eistert Synthesis 1935	6

5. Copper-Catalyzed Alkyne Azide Cycloaddition	7

6. Baeyer-Villiger Oxidation 1899	8

7. Bergman Cyclization 1972	8

8. Beckmann Rearrangement 1886	9

9. Baylis-Hillman Reaction 1972	10

10. Benzoin Condensation 1832	11

11. Buchwald-Hartwig Cross Coupling 1994	12

12. Claisen Condensation 1887	13

13. Cannizzaro Reaction 1853	13

14. Curtius Rearrangement 1890	14

15. Claisen Rearrangement 1912	16

16. Cope Rearrangement 1940	17

17. Chan-Evans-Lam Cross Coupling 1998	18

18. Darzens Condensation 1904	19

19. Dess-Martin Oxidation 1983	19

20. Diels-Alder Cycloaddition 1928	20

21. Favorskii Rearrangement 1894	21

22. Friedel-Crafts Acylation & Alkylation 1877	22

23. Fischer Indole Synthesis 1883	23

24. Grob Fragmentation 1955	24

25. Grignard Reaction 1900	24

26. Haloform Reaction 1822	25

27. Hofmann Elimination 1851	25

28. Heck Cross Coupling 1968	26

29. Hiyama Cross Coupling 1988	27

30. Kumada Cross Coupling 1972	27

31. Michael Addition 1887	28

32. Mannich Reaction 1912	29

33. McMurry Coupling 1974	30

34. Meerwein-Ponndorf-Verley Reduction 1924	30

35. Mitsunobu Reaction 1967	31

36. Negishi Cross Coupling 1977	32

37. Nef Reaction 1894	33

38. Nazarov Cyclization 1941	34

39. Oppenauer Oxidation 1937	35

40. Ozonolysis 1840	36

41. Pinacol Rearrangement 1860	36

42. Pummerer Rearrangement 1909	37

43. Polonovski Reaction 1927	37

44. Prins Reaction 1919	38

45. Paternò-Büchi Reaction (1909, 1954)	39

46. Ramberg-Bäcklund Rearrangement 1940	40

47. Robinson Annulation 1935	40

48. Reformatsky Reaction 1887	41

49. Suzuki Cross Coupling 1979	41

50. Stille Cross Coupling 1978	42

51. Shapiro Reaction 1975	42

52. Staudinger Ligation 1919	43

53. Swern Oxidation 1978	43

54. Sonogashira Cross Coupling 1975	44

55. Wacker Oxidation 1959	45

56. Birch Reduction 1944	46

57. Barton Decarboxylation 1983	46

58. Benzyne Mechanism 1953	47

59. Diazotisation 1900	48

60. Electrophilic Addition	49

61. Electrophilic Aromatic Substitution	50

62. Beta-Elimination	51

63. Cope Elimination 1949	52

64. Brown Hydroboration 1956	53

65. Bischer-Napieralski Reaction 1903	54

66. Chichibabin Amination 1914	55

67. Criegee Oxidation 1931 – Malaprade Oxidation 1934	56

68. Di-pi-Methane (DPM) Rearrangement (Zimmerman Reaction) 1967	57

69. Gewald Reaction 1966	58

70. Gabriel Synthesis 1887	59

71. Glaser-Hay Coupling 1869	60

72. Hell-Volhard-Zelinsky Reaction 1881-1887	61

73. Horner-Wadsworth-Emmons (HWE) Olefination 1958	62

74. Jones Oxidation 1946	63

75. Kucherov Reaction 1881	64

76. Ley-Griffith Oxidation 1987	65

77. Liebeskind-Srogl Coupling 2000	66

78. Mukaiyama Hydration 1989	67

79. Miyaura Borylation 1995	68

80. Olefin (Alkene) Metathesis 1955	69

81. Minisci Reaction 1968	69

82. Norrish Type I and II Fragmentation 1937	70

83. Prilezhaev Epoxidation 1909	71

84. Paal-Knorr Syntheses 1884	72

85. Pictet-Spengler Reaction 1911	73

86. Passerini Three-Component Reaction 1921	74

87. Pauson–Khand Reaction 1977	75

88. Nucleophilic Substitution	76

89. Nucleophilic Aromatic Substitution	77

90. Radical Nucleophilic Aromatic Substitution 1970	78

91. Steglich Esterification 1978	79

92. Upjohn Dihydroxylation 1976	80

93. Ugi Reaction 1959	81

94. Ullmann Aryl-Aryl Coupling 1901	82

95. Vilsmeier-Haak Formylation 1927	83

96. Wagner-Meerwein Rearrangement (1899–1914)	84

97. Weinreb Ketone Synthesis 1981	84

98. Wittig Reaction 1954	85

99. Wolff-Kishner Reduction 1911	85

100. Wohl-Ziegler Reaction (1919–1942)	86

II. 100 Must Know Reagents	87

1. Lawesson’s Reagent 1956	87

2. Grubbs’ Catalyst First Generation 1995	88

3. Grignard Reagent 1900	89

4. Weinreb Amide 1981	92

5. 3-Chloroperoxybenzoic Acid – mCPBA 1970	93

III. Misc	94

1. Fundamental Organic Mechanisms	94

2. Isomerism	95

3. Constitutional Isomerism	95

4. Stereoisomerism	96

5. Alkenes	97

6. Terminal Alkynes	98

7. Internal Alkynes	99

8. Nucleophylic Substitution	100

9. Diazonium Chemistry	101

10. Condensation	102

11. Aryl-Aryl Coupling	103

12. Thiophene Synthesis A	104

13. Thiophene Synthesis B	105

100 Must Know Mechanisms

Arbuzov Reaction (1898–1906)

Acyloin Condensation 1903

Alkyne (acetylene) Zipper 1975

Arndt-Eistert Synthesis 1935

Copper-Catalyzed Alkyne Azide Cycloaddition

Baeyer-Villiger Oxidation 1899

Bergman Cyclization 1972

Beckmann Rearrangement 1886

Baylis-Hillman Reaction 1972

Benzoin Condensation 1832

Buchwald-Hartwig Cross Coupling 1994

Claisen Condensation 1887

Cannizzaro Reaction 1853

Curtius Rearrangement 1890

Claisen Rearrangement 1912

Cope Rearrangement 1940

Chan-Evans-Lam Cross Coupling 1998

Darzens Condensation 1904

Dess-Martin Oxidation 1983

Diels-Alder Cycloaddition 1928

Favorskii Rearrangement 1894

Friedel-Crafts Acylation & Alkylation 1877

Fischer Indole Synthesis 1883

Grob Fragmentation 1955

Grignard Reaction 1900

Haloform Reaction 1822

Hofmann Elimination 1851

Heck Cross Coupling 1968

Hiyama Cross Coupling 1988

Kumada Cross Coupling 1972

Michael Addition 1887

Mannich Reaction 1912

McMurry Coupling 1974

Meerwein-Ponndorf-Verley Reduction 1924

Mitsunobu Reaction 1967

Negishi Cross Coupling 1977

Nef Reaction 1894

Nazarov Cyclization 1941

Oppenauer Oxidation 1937

Ozonolysis 1840

Pinacol Rearrangement 1860

Pummerer Rearrangement 1909

Polonovski Reaction 1927

Prins Reaction 1919

Paternò-Büchi Reaction (1909, 1954)

Ramberg-Bäcklund Rearrangement 1940

Robinson Annulation 1935

Reformatsky Reaction 1887

Suzuki Cross Coupling 1979

Stille Cross Coupling 1978

Shapiro Reaction 1975

Staudinger Ligation 1919

Swern Oxidation 1978

Sonogashira Cross Coupling 1975

Wacker Oxidation 1959

Birch Reduction 1944

Barton Decarboxylation 1983

Benzyne Mechanism 1953

Diazotisation 1900

Electrophilic Addition

Electrophilic Aromatic Substitution

Beta-Elimination

Cope Elimination 1949

Brown Hydroboration 1956

Bischer-Napieralski Reaction 1903

Chichibabin Amination 1914

Criegee Oxidation 1931 – Malaprade Oxidation 1934

Di-pi-Methane (DPM) Rearrangement (Zimmerman Reaction) 1967

Gewald Reaction 1966

Gabriel Synthesis 1887

Glaser-Hay Coupling 1869

Hell-Volhard-Zelinsky Reaction 1881-1887

Horner-Wadsworth-Emmons (HWE) Olefination 1958

Jones Oxidation 1946

Kucherov Reaction 1881

Ley-Griffith Oxidation 1987

Liebeskind-Srogl Coupling 2000

Mukaiyama Hydration 1989

Miyaura Borylation 1995

Olefin (Alkene) Metathesis 1955

Minisci Reaction 1968

Norrish Type I and II Fragmentation 1937

Prilezhaev Epoxidation 1909

Paal-Knorr Syntheses 1884

Pictet-Spengler Reaction 1911

Passerini Three-Component Reaction 1921

Pauson–Khand Reaction 1977

Nucleophilic Substitution

Nucleophilic Aromatic Substitution

Radical Nucleophilic Aromatic Substitution 1970

Steglich Esterification 1978

Upjohn Dihydroxylation 1976

Ugi Reaction 1959

Ullmann Aryl-Aryl Coupling 1901

Vilsmeier-Haak Formylation 1927

Wagner-Meerwein Rearrangement (1899–1914)

Weinreb Ketone Synthesis 1981

Wittig Reaction 1954

Wolff-Kishner Reduction 1911

Wohl-Ziegler Reaction (1919–1942)

100 Must Know Reagents

Lawesson’s Reagent 1956

Grubbs’ Catalyst First Generation 1995

Grignard Reagent 1900

Grignard Reagent C-C Bond

Grignard Reagent C-X Bond

Weinreb Amide 1981

3-Chloroperoxybenzoic Acid – mCPBA 1970

AIBN 1896

Misc

Fundamental Organic Mechanisms

Isomerism

Constitutional Isomerism

Stereoisomerism

Alkenes

Terminal Alkynes

Internal Alkynes

Nucleophylic Substitution

Diazonium Chemistry

Condensation

Aryl-Aryl Coupling

Thiophene Synthesis A

Thiophene Synthesis B