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Organic Chemistry: 100 Must-Know Mechanisms
Language:
English
Published/Copyright:
2023
About this book
In chemistry, good problem-solving requires a balanced combination of scientific intuition and
methodical analysis. Additionally, thoughtfully presented diagrams and infographics can convey
a large amount of complex information in a more intuitive and accessible manner. 100 Must-Know
Mechanisms (Second Edition) strives to be at the intersection of these two key principles. Its
thorough visualizations enable experienced readers to use it as a quick reference for specific
mechanisms of interest. At the same time, the book’s breadth of covered reactions, from classic to
cutting-edge, make it a good study-aid for the developing chemist. A slow and consistent study of
the entire series of mechanisms can help set the foundation for good scientific intuition, while its
detailed infographics and careful navigation features encourage coming back to it frequently. This
edition includes over 40 new illustrations, numerous new mechanistic schemes, enhanced original
figures with a variety of real-case examples, and more
methodical analysis. Additionally, thoughtfully presented diagrams and infographics can convey
a large amount of complex information in a more intuitive and accessible manner. 100 Must-Know
Mechanisms (Second Edition) strives to be at the intersection of these two key principles. Its
thorough visualizations enable experienced readers to use it as a quick reference for specific
mechanisms of interest. At the same time, the book’s breadth of covered reactions, from classic to
cutting-edge, make it a good study-aid for the developing chemist. A slow and consistent study of
the entire series of mechanisms can help set the foundation for good scientific intuition, while its
detailed infographics and careful navigation features encourage coming back to it frequently. This
edition includes over 40 new illustrations, numerous new mechanistic schemes, enhanced original
figures with a variety of real-case examples, and more
New in this edition:
- Dot structure added for most mechanisms.
- Selected mechanisms accompanied by specific examples with step-by-step explanation using Lewis dot structures.
- Name reactions accompanied by additional detailed mechanisms.
Author / Editor information
Dr. Valiulin obtained his dual B.S. and M.S. in Organic Chemistry at Lomonosov Moscow State
University - MSU (Russia, Moscow). MSU is one of the oldest established and most competitive
universities in the country. He then moved across the ocean to the United States where he earned
a Ph.D. in Organic Chemistry at the University of Denver. Afterward, he completed two
postdoctoral fellowships, one with Professor K. C. Nicolaou at the Scripps Research Institute in
La Jolla, California, and another with Professor M. G. Finn at the Georgia Institute of Technology
in Atlanta, Georgia. His industrial career started in Boston, Massachusetts where he joined the
formulation development group in a medium-sized biopharmaceutical company. He gained
experience in drug development and early discovery with an emphasis on physical organic
chemistry, nuclear magnetic resonance (NMR), formulation development techniques, and
materials science before joining the medicinal chemistry group as a synthetic chemist. After six
years working in a biotech hub on the East Coast, he continues his career path as an organic chemist
in San Diego.
In the course of his career, he has published over twenty research and review articles and is a coinventor on numerous patents. As a Ph.D. scientist, he believes in staying engaged with the
learning community, and draws inspiration through teaching and by making visually-engaging and
educational chemistry infographics, which he shares on The ChemInfoGraphic Blog:
www.cheminfographic.com/
Dr. Valiulin’s scientific research focuses on chemical synthesis and includes collaboration with
researchers who are driven by a passion to deliver novel chemical compounds that may help save
lives
University - MSU (Russia, Moscow). MSU is one of the oldest established and most competitive
universities in the country. He then moved across the ocean to the United States where he earned
a Ph.D. in Organic Chemistry at the University of Denver. Afterward, he completed two
postdoctoral fellowships, one with Professor K. C. Nicolaou at the Scripps Research Institute in
La Jolla, California, and another with Professor M. G. Finn at the Georgia Institute of Technology
in Atlanta, Georgia. His industrial career started in Boston, Massachusetts where he joined the
formulation development group in a medium-sized biopharmaceutical company. He gained
experience in drug development and early discovery with an emphasis on physical organic
chemistry, nuclear magnetic resonance (NMR), formulation development techniques, and
materials science before joining the medicinal chemistry group as a synthetic chemist. After six
years working in a biotech hub on the East Coast, he continues his career path as an organic chemist
in San Diego.
In the course of his career, he has published over twenty research and review articles and is a coinventor on numerous patents. As a Ph.D. scientist, he believes in staying engaged with the
learning community, and draws inspiration through teaching and by making visually-engaging and
educational chemistry infographics, which he shares on The ChemInfoGraphic Blog:
www.cheminfographic.com/
Dr. Valiulin’s scientific research focuses on chemical synthesis and includes collaboration with
researchers who are driven by a passion to deliver novel chemical compounds that may help save
lives
Topics
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Frontmatter
I -
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Second Edition
VII -
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Preface and Overview
IX -
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Contents
XIII -
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List of Acronyms and Abbreviations
XIX -
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1 Electrophilic Addition Mechanism
1 -
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2 Nucleophilic Substitution Mechanism
4 -
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3 Aromatic Electrophilic Substitution Mechanism
6 -
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4 Aromatic Nucleophilic Substitution Mechanism
10 -
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5 Aromatic Radical Nucleophilic Substitution Mechanism
12 -
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6 Elimination Mechanism
16 -
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7 Acyloin Condensation
20 -
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8 Alkyne Zipper Reaction
24 -
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9 Arbuzov Reaction
26 -
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10 Arndt–Eistert Synthesis
28 -
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11 Baeyer–Villiger Oxidation
32 -
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12 Barton Decarboxylation
34 -
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13 Baylis–Hillman Reaction
36 -
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14 Beckmann Rearrangement
38 -
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15 Benzoin Condensation
40 -
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16 Benzyne Mechanism
42 -
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17 Bergman Cyclization
44 -
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18 Birch Reduction
46 -
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19 Bischler‒Napieralski Cyclization
48 -
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20 Brown Hydroboration
50 -
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21 Buchwald–Hartwig Cross-Coupling
52 -
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22 Cannizzaro Reaction
54 -
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23 Chan–Evans–Lam Cross-Coupling
56 -
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24 Chichibabin Amination
58 -
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25 Claisen Condensation
60 -
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26 Claisen Rearrangement
62 -
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27 Cope Elimination
64 -
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28 Cope Rearrangement
66 -
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29 Criegee and Malaprade Oxidation
70 -
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30 CuAAC
72 -
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31 Curtius Rearrangement
74 -
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32 Darzens Condensation
78 -
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33 Dess–Martin Oxidation
80 -
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34 Diazotization (Diazonium Salt)
82 -
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35 Diels–Alder Cycloaddition
84 -
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36 Di-π-Methane Rearrangement
90 -
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37 Favorskii Rearrangement
92 -
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38 Fischer Indole Synthesis
96 -
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39 Friedel–Crafts Acylation and Alkylation
98 -
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40 Gabriel Synthesis
102 -
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41 Gewald Reaction
104 -
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42 Glaser–Eglinton–Hay Coupling
106 -
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43 Grignard Reaction
108 -
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44 Grob Fragmentation
110 -
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45 Haloform Reaction
112 -
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46 Heck Cross-Coupling
114 -
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47 Hell–Volhard–Zelinsky Reaction
116 -
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48 Hiyama Cross-Coupling
118 -
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49 Hofmann Elimination
120 -
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50 Horner–Wadsworth–Emmons Olefination
122 -
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51 Jones Oxidation
126 -
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52 Kucherov Reaction
128 -
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53 Kumada Cross-Coupling
130 -
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54 Ley–Griffith Oxidation
132 -
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55 Liebeskind–Srogl Cross-Coupling
134 -
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56 Mannich Reaction
136 -
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57 McMurry Coupling Fig.
140 -
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58 Meerwein–Ponndorf–Verley Reduction
142 -
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59 Michael Addition
144 -
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60 Minisci Reaction
148 -
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61 Mitsunobu Reaction
150 -
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62 Miyaura Borylation
154 -
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63 Mukaiyama RedOx Hydration
156 -
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64 Nazarov Cyclization
158 -
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65 Nef Reaction
160 -
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66 Negishi Cross-Coupling
162 -
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67 Norrish Type I and II Reactions
164 -
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68 Olefin (Alkene) Metathesis
166 -
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69 Oppenauer Oxidation
170 -
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70 Ozonolysis
172 -
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71 Paal–Knorr Syntheses
176 -
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72 Paternò–Büchi Reaction
180 -
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73 Pauson–Khand Reaction
182 -
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74 Peptide (Amide) Coupling
184 -
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75 Pictet–Spengler Reaction
188 -
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76 Pinacol–Pinacolone Rearrangement
192 -
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77 Polonovski Reaction
194 -
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78 Prilezhaev Epoxidation
196 -
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79 Prins Reaction
198 -
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80 Pummerer Rearrangement
200 -
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81 Ramberg–Bäcklund Rearrangement
202 -
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82 Reformatsky Reaction
204 -
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83 Robinson Annulation
206 -
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84 Shapiro Reaction
208 -
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85 Sonogashira Cross-Coupling
210 -
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86 Staudinger Reaction
212 -
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87 Steglich Esterification
216 -
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88 Stille Cross-Coupling
218 -
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89 Suzuki Cross-Coupling
220 -
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90 Swern Oxidation
224 -
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91 Ugi Reaction
226 -
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92 Ullmann Aryl–Aryl Coupling
228 -
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93 Upjohn Dihydroxylation
232 -
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94 Vilsmeier–Haack Reaction
234 -
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95 Wacker Oxidation
236 -
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96 Wagner–Meerwein Rearrangement Fi
238 -
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97 Weinreb Ketone Synthesis
242 -
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98 Wittig Reaction
244 -
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99 Wohl–Ziegler Reaction
246 -
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100 Wolff–Kishner Reduction
248 -
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Acknowledgments
251 -
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Bibliography and References
253
Publishing information
Pages and Images/Illustrations in book
eBook published on:
July 4, 2023
eBook ISBN:
9783110786835
Paperback published on:
July 4, 2023
Paperback ISBN:
9783110786828
Edition:
2nd, Completely Revised Edition
Pages and Images/Illustrations in book
Front matter:
22
Main content:
267
Coloured Illustrations:
363
Tables:
10
Audience(s) for this book
Students, Organic Chemists
Safety & product resources
- Manufacturer information:
- Walter de Gruyter GmbH
Genthiner Straße 13
10785 Berlin - productsafety@degruyterbrill.com