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Addition, Elimination and Substitution: Markovnikov, Hofmann, Zaitsev and Walden
Discovery and Development
- 1st Edition - July 1, 2022
- Author: David E. Lewis
- Language: English
- Paperback ISBN:9 7 8 - 0 - 1 2 - 8 2 1 0 2 7 - 7
- eBook ISBN:9 7 8 - 0 - 1 2 - 8 2 1 0 2 6 - 0
Addition, Elimination and Substitution: Markovnikov, Hofmann, Zaitsev and Walden: Discovery and Development discusses foundational reactions in organic chemistry and their major… Read more
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Request a sales quoteAddition, Elimination and Substitution: Markovnikov, Hofmann, Zaitsev and Walden: Discovery and Development discusses foundational reactions in organic chemistry and their major protagonists, contributions to synthesis, and history. Hofmann, Zaitsev, and Markovnikov are introduced, along with their major discoveries and contributions to organic chemistry. The history of controversies around Markovnikov’s Rule are addressed. The book introduces Walden’s original demonstration of configuration inversion, then discusses bimolecular elimination reactions, regioselective addition reactions, regiospecific alkene synthesis, and the development of modern reactions with configuration inversion. With its unique perspective, focus, and comprehensive coverage, this book belongs on the shelf of every organic chemist.
- Introduces Markovnikov, Zaitsev, Hofmann, and Walden as actual persons, rather than just an abstract term used as a form of short-hand to describe the rules
- Discusses, in depth, the discovery and usage of these reactions and rules, from their discovery to their most recent applications
- Includes biographical materials about chemists responsible for major changes in application of the rules
- Traces the history of the applications of these reactions, e.g., anti-Markovnikov additions in catalytic organic synthesis, and reactions such as the Mitsunobu reaction improving the original SN2 displacement
Researchers and advanced chemistry students in academia and in chemical, pharmaceutical and biotechnology industries
- Cover image
- Title page
- Table of Contents
- Copyright
- Chapter one. Introduction: Organic Chemistry in the Nineteenth Century
- A 19th-century chronology of organic chemistry
- Theories of organic chemistry
- Chapter TWO. Vladimir Vasil'evich Markovnikov and his rule for addition
- Vladimir Vasil'evich Markovnikov (1837–1904)
- Markovnikov's resignation from Kazan
- Markovnikov's move to Moscow
- Chapter Three. Markovnikov's rule: history and development
- The first decades: early challenges to the validity of the rule
- What is in a name? Markovnikov and anti-Markovnikov
- Chapter Four. Aleksandr Mikhailovich Zaitsev and his empirical rule for elimination
- Aleksandr Mikhailovich Zaitsev (1841–1910)
- In Western Europe
- Theoretician no more: the synthetic organic chemist emerges
- Sulfur compounds in Marburg
- The return to Kazan
- Moving into leadership of the Kazan Chemical School
- Scientific work as professor at Kazan
- Zaitsev's later career and legacy
- Chapter Five. August Wilhelm von Hofmann and Hofmann's rule for elimination
- August Wilhelm von Hofmann (1818–92)4,5
- Hofmann's career
- Hofmann's chemistry
- Chapter Six. Paul Walden and the Walden inversion
- Introduction
- Paul Walden (Pauls Valdens, Pavel Ivanovich Val'den)
- Education
- Leader at the Riga Polytechnic Institute
- World War I: evacuation of Riga
- Walden's scientific career as an independent researcher
- Research in organic chemistry
- Walden in the Third Reich
- Walden in retirement
- Walden, the historian of chemistry
- Afterword
- Chapter Seven. Mechanistic studies
- Early mechanistic and stereochemical investigations
- The beginnings of modern mechanistic studies
- Isotope effect evidence for the mechanisms of elimination
- Chapter Eight. Development of highly regioselective addition reactions of alkenes and alkynes
- Factors affecting reaction regiochemistry: the alkene
- Heteroatom-stabilized electrophilic carbocations: The Prins, Mannich, and Mukaiyama reactions
- Carbocation rearrangements in synthesis
- Anti-Markovnikov additions to alkenes
- Chapter Nine. Development of highly regiospecific alkene syntheses: elimination and its substitutes
- Introduction
- β-Eliminations not involving deprotonation: reductive elimination
- Elimination during Wolff–Kishner and related reactions4
- The Bamford–Stevens and Shapiro reactions
- Alkenes by 1,3-elimination and extrusion
- Chapter Ten. Inversion of configuration in modern synthesis
- Introduction
- Effects of solvent on the mechanism and rates of nucleophilic substitutions
- Phase transfer catalysis
- SN2 displacement driven by the formation of a phosphoryl group
- The Mitsunobu reaction
- The substoichiometric Mitsunobu reaction
- Changing the paradigm: the Denton variant
- Index
- No. of pages: 280
- Language: English
- Edition: 1
- Published: July 1, 2022
- Imprint: Elsevier
- Paperback ISBN: 9780128210277
- eBook ISBN: 9780128210260
DL
David E. Lewis
David Lewis is Professor of Chemistry at the University of Wisconsin-Eau Claire, and holds B.Sc., Ph.D., and D.Sc. degrees from the University of Adelaide, in South Australia. His research over the last decade has been divided between synthetic organic chemistry and the history of chemistry (specifically, the history of organic chemistry in Russia). He is the author of over 100 refereed publications, of Advanced Organic Chemistry (Oxford: New York, 2016) and of The Wolff-Kishner Reduction and Related Reactions. Discovery and Development (Elsevier: Amsterdam, 2019). He is the recipient of the 2018 HIST Award for Outstanding Achievement in the History of Chemistry, and a 2019 Laureate of the V. V. Markovnikov Medal. He is a member of the Editorial Advisory Board of Minireviews in Organic Chemistry, and of the ad hoc Editorial Advisory Board of The Bulletin for the History of Chemistry, and a Fellow of the Royal Society of Chemistry and the Royal Australian Chemical Institute.
Affiliations and expertise
Professor of Chemistry, Department of Chemistry, University of Wisconsin-Eau Claire, Eau Claire, WI, USA