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Organic Chemistry: 100 Must-know Mechanisms in pdf


Download this PDF book: Organic Chemistry: 100 Must-know Mechanisms: In Organic Chemistry by Roman Valiulin

This book summarizes 100 essential mechanisms in organic chemistry ranging from classical such as the Reformatsky Reaction from 1887 to recently elucidated mechanism such as the copper(I)-catalyzed alkyne-azide cycloaddition. 

The reactions are easy to grasp, well-illustrated and underpinned with explanations and additional information.

Pedagogical Principles. At first, every body of knowledge that is new to us seems to have boundless complexity and creates the initial impression of incomprehensibility and even fear. 

Organic chemistry provides an excellent example of this phenomenon. The discipline is replete with complex and initially abstract concepts, as a result the information may seem overwhelming, particularly for the young chemist. 

But as with most new subjects, consistent study and practice reveals patterns, commonalities, rules, and an apparent logic. Eventually, an “architecture” becomes more appar- ent as we grow to become more experienced chemists. To develop this intuition, it requires close study, repetition, and breadth of exposure. 

A significant element of that learning is intrinsic and simply requires time and immersion. However, to help with the development of this intuition, an organic chemist would also be wise to focus on mechanisms for organic reactions as a foundation or anchoring point. This, in combination with deep study, can help organize knowledge into skill and expertise. 

An understanding of reaction mechanisms provides a solid foundation for the field and a scaffold for further study and life-long learning. Mechanisms are highly useful because they can logically explain how a chemical bond in a molecule was formed or broken and help to rationalize the formation of the final synthetic target or an unde- sired side-product. 

Moreover, as we parse an increasing number of mechanisms, we begin to see the similarities and an invisible conceptual “thread” then forms in our mind’s eye that was not previously apparent. 

It helps to organize thinking and brings sense to the otherwise foreign concepts such as reactive intermediates, transition states, charges, radicals, and mechanistic arrows.


1 Electrophilic Addition Mechanism 

2 Nucleophilic Substitution Mechanism 

3 Aromatic Electrophilic Substitution Mechanism 

4 Aromatic Nucleophilic Substitution Mechanism 

5 Aromatic Radical Nucleophilic Substitution Mechanism 

6 Elimination Mechanism 

7 Acyloin Condensation 

8 Alkyne Zipper Reaction 

9 Arbuzov Reaction 

10 Arndt‒Eistert Synthesis 

11 Baeyer‒Villiger Oxidation 

12 Barton Decarboxylation 

13 Baylis‒Hillman Reaction 

14 Beckmann Rearrangement 

15 Benzoin Condensation 

16 Benzyne Mechanism 

17 Bergman Cyclization 

18 Birch Reduction 

19 Bischler‒Napieralski Cyclization 

20 Brown Hydroboration 

21 Buchwald‒Hartwig Cross Coupling 

22 Cannizzaro Reaction 

23 Chan‒Evans‒Lam Cross Coupling 

24 Chichibabin Amination 

25 Claisen Condensation 

26 Claisen Rearrangement 

27 Cope Elimination 

28 Cope Rearrangement 

29 Criegee & Malaprade Oxidation 

30 CuAAC 

31 Curtius Rearrangement 

32 Darzens Condensation 

33 Dess‒Martin Oxidation 

34 Diazotization (Diazonium Salt) 

35 Diels‒Alder Cycloaddition 

36 Di‒π‒Methane Rearrangement 

37 Favorskii Rearrangement 

38 Fischer Indole Synthesis 

39 Friedel‒Crafts Acylation & Alkylation 

40 Gabriel Synthesis 

41 Gewald Reaction 

42 Glaser–Eglinton–Hay Coupling 

43 Grignard Reaction 

44 Grob Fragmentation 

45 Haloform Reaction 

46 Heck Cross Coupling 

47 Hell–Volhard–Zelinsky Reaction 

48 Hiyama Cross Coupling 

49 Hofmann Elimination 

50 Horner–Wadsworth–Emmons Olefination 

51 Jones Oxidation 

52 Kucherov Reaction 

53 Kumada Cross Coupling 

54 Ley–Griffith Oxidation 

55 Liebeskind–Srogl Cross Coupling 

56 Mannich Reaction 

57 McMurry Coupling 

58 Meerwein–Ponndorf–Verley Reduction 

59 Michael Addition 

60 Minisci Reaction 

61 Mitsunobu Reaction 

62 Miyaura Borylation 

63 Mukaiyama RedOx Hydration 

64 Nazarov Cyclization 

65 Nef Reaction 

66 Negishi Cross Coupling 

67 Norrish Type I & II Reaction 

68 Olefin (Alkene) Metathesis 

69 Oppenauer Oxidation 

70 Ozonolysis 

71 Paal–Knorr Syntheses 

72 Paternò–Büchi Reaction 

73 Pauson–Khand Reaction 

74 Peptide (Amide) Coupling 

75 Pictet–Spengler Reaction 

76 Pinacol–Pinacolone Rearrangement 

77 Polonovski Reaction 

78 Prilezhaev Epoxidation 

79 Prins Reaction 

80 Pummerer Rearrangement 

81 Ramberg–Bäcklund Rearrangement 

82 Reformatsky Reaction 

83 Robinson Annulation 

84 Shapiro Reaction 

85 Sonogashira Cross Coupling 

86 Staudinger Reaction 

87 Steglich Esterification 

88 Stille Cross Coupling 

89 Suzuki Cross Coupling 

90 Swern Oxidation 

91 Ugi Reaction 

92 Ullmann Aryl–Aryl Coupling 

93 Upjohn Dihydroxylation 

94 Vilsmeier–Haack Reaction 

95 Wacker Oxidation 

96 Wagner–Meerwein Rearrangement 

97 Weinreb Ketone Synthesis 

98 Wittig Reaction 

99 Wohl–Ziegler Reaction 

100 Wolff–Kishner Reduction

About the book: 

Publisher ‏ : ‎ De Gruyter (April 20, 2020)

Language ‏ : ‎ English

Pages ‏ : ‎ 251

File : PDF, 15MB


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