Vladimir Markovnikov
Vladimir Markovnikov | |
---|---|
Born | Knyaginino, Nizhny Novgorod Governorate, Russian Empire | December 25, 1837
Died | February 11, 1904 Saint Petersburg, Russian Empire | (aged 65)
Alma mater | University of Kazan |
Scientific career | |
Institutions | University of Kazan University of Saint Petersburg University of Odessa |
Doctoral advisor | Alexander Butlerov |
Vladimir Vasilyevich Markovnikov (Russian: Влади́мир Васи́льевич Марко́вников), also spelled as Markownikoff,[1] (December 22, 1838 – February 11, 1904), was a Russian chemist.
Early life and education[]
Markovnikov studied economics at the University of Kazan; during his studies, under the Russian cameral system, he also studied chemistry.
Career[]
After a conflict with that university, Markovnikov was appointed professor at the University of Odessa in 1871 and, two years later, at the University of Moscow, where he stayed the rest of his career. He was elected as a member to the American Philosophical Society in 1901.[2]
Work[]
Markovnikov is best known for Markovnikov's rule, elucidated in 1869 to describe addition reactions of H-X ('X' represents a halogen) to alkenes. According to this rule, the nucleophilic X- adds to the carbon atom with fewer hydrogen atoms, while the proton adds to the carbon atom with more hydrogen atoms bonded to it. Thus, hydrogen chloride (HCl) adds to propene, CH3-CH=CH2 to produce 2-chloropropane CH3CHClCH3 rather than the isomeric 1-chloropropane CH3CH2CH2Cl.[3] The rule is useful in predicting the molecular structures of products of addition reactions. Why hydrogen bromide exhibited both Markovnikov as well as reversed-order, or anti-Markovnikov, addition, however, was not understood until Morris S. Kharasch offered an explanation in 1933. It is also called The Peroxide effect sometimes.
Hughes has discussed the reasons for Markovnikov's lack of recognition during his lifetime.[4] Although he published mostly in Russian which was not understood by most Western European chemists, the 1870 article in which he first stated his rule was written in German. However the rule was included in a 4-page addendum to a 26-page article on isomeric butyric acids, and based on very slight experimental evidence even by the standards of the time. Hughes concludes that the rule was an inspired guess, unjustified by the evidence of the time, but which turned out later to be correct (in most cases). A more recent assessment, based on a reading of Markovnikov's Magistr Khimii and Doktor Khimii dissertations, contradicts this view, and points out that Markovnikov's Rule arises logically from his dissertations.[5]
Markovnikov also contributed to organic chemistry by finding carbon rings with more than six carbon atoms, a ring with four carbon atoms in 1879, and a ring with seven in 1889.
Markovnikov also showed that butyric and isobutyric acids have the same chemical formula (C4H8O2) but different structures; i.e., they are isomers.
References[]
- ^ Zerong, Wang (2010). "Markovnikov Rule and Anti-Markovnikov Rule". Comprehensive Organic Name Reactions and Reagents. 411: 1833–1837. doi:10.1002/9780470638859.conrr411. ISBN 9780470638859.
- ^ "APS Member History". search.amphilsoc.org. Retrieved 2021-05-19.
- ^ Markownikoff, W. (1870). "Ueber die Abhängigkeit der verschiedenen Vertretbarkeit des Radicalwasserstoffs in den isomeren Buttersäuren". Annalen der Pharmacie (in German). 153 (1): 228–259. doi:10.1002/jlac.18701530204.
- ^ Hughes, Peter (2006). "Was Markovnikov's Rule an Inspired Guess?". The Journal of Chemical Education. 83 (8): 1152–1154. Bibcode:2006JChEd..83.1152H. doi:10.1021/ed083p1152.
- ^ Lewis, David E. (2021). "The Logic Behind Markovnikov's Rule: Was It an Inspired Guess? …No!". Angewandte Chemie International Edition. 60 (9): 4412–4421. doi:10.1002/anie.202008228.
External links[]
Wikiquote has quotations related to: Vladimir Markovnikov |
- 1838 births
- 1904 deaths
- Chemists of the Russian Empire
- Organic chemists
- Russian inventors