Jump to content
Main menu
Main menu
move to sidebar
hide
Navigation
Main page
Recent changes
Random page
Help about MediaWiki
Special pages
Niidae Wiki
Search
Search
Appearance
Create account
Log in
Personal tools
Create account
Log in
Pages for logged out editors
learn more
Contributions
Talk
Editing
Vladimir Markovnikov
(section)
Page
Discussion
English
Read
Edit
View history
Tools
Tools
move to sidebar
hide
Actions
Read
Edit
View history
General
What links here
Related changes
Page information
Appearance
move to sidebar
hide
Warning:
You are not logged in. Your IP address will be publicly visible if you make any edits. If you
log in
or
create an account
, your edits will be attributed to your username, along with other benefits.
Anti-spam check. Do
not
fill this in!
===Work=== Markovnikov is best known for [[Markovnikov's rule]], elucidated in 1869 to describe addition reactions of H-X (where 'X' represents a [[halogen]]) to [[alkene]]s. According to this rule, the nucleophilic X- binds to the carbon (C) atom with fewer hydrogen atoms, while the proton binds to the carbon atom with more hydrogen atoms bonded to it. Thus, hydrogen chloride (HCl) reacts with propene, CH<sub>3</sub>-CH=CH<sub>2</sub> to produce 2-chloropropane CH<sub>3</sub>CHClCH<sub>3</sub> rather than the isomeric 1-chloropropane CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cl.<ref>{{cite journal | title=Ueber die Abhängigkeit der verschiedenen Vertretbarkeit des Radicalwasserstoffs in den isomeren Buttersäuren | author=Markownikoff, W. | journal=Annalen der Pharmacie | year=1870 | volume=153 | issue=1 | pages=228–259 | doi=10.1002/jlac.18701530204 | language=de| url=https://zenodo.org/record/1427295 }}</ref> 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.<ref>{{cite journal | doi = 10.1021/ed083p1152 | author = Hughes, Peter | title = Was Markovnikov's Rule an Inspired Guess? | journal = The Journal of Chemical Education | volume = 83 | issue = 8 | pages = 1152–1154 | year = 2006 |bibcode = 2006JChEd..83.1152H }}</ref> 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.<ref>{{cite journal | doi = 10.1002/anie.202008228 | author = Lewis, David E.| title = The Logic Behind Markovnikov's Rule: Was It an Inspired Guess? …No!| journal = Angewandte Chemie International Edition| volume = 60| issue = 9| pages = 4412–4421| year = 2021| s2cid = 230570680| language=en}}</ref> 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 (C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>) but different structures; i.e., they are isomers.
Summary:
Please note that all contributions to Niidae Wiki may be edited, altered, or removed by other contributors. If you do not want your writing to be edited mercilessly, then do not submit it here.
You are also promising us that you wrote this yourself, or copied it from a public domain or similar free resource (see
Encyclopedia:Copyrights
for details).
Do not submit copyrighted work without permission!
Cancel
Editing help
(opens in new window)
Search
Search
Editing
Vladimir Markovnikov
(section)
Add topic