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Victor Grignard

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Françoisthe Auguste Victor Grignard
Born(1871-05-06)6 May 1871
Cherbourg, France
Died(1935-12-13)13 December 1935
Lyon, France
Resting placeGuillotière Cemetery, Lyon
NationalityFrance
Alma materUniversity of Lyon
Known forGrignard reaction
SpouseAugustine Marie Boulant
ChildrenRoger Grignard
AwardsNobel Prize for Chemistry (1912)
Scientific career
FieldsOrganic chemistry
InstitutionsUniversity of Nancy
Doctoral advisorPhilippe Barbier[1]

François Auguste Victor Grignard (6 May 1871 in Cherbourg – 13 December 1935 in Lyon) was a Nobel Prize-winning French chemist.

Biography

Victor Grignard in 1912. Taken for Nobel Prize publication.

Grignard was the son of a sail maker. His character was described as having humble and friendly attitude.[2] After attempting to major in mathematics, Grignard failed his entrance exams before being enlisted into the army in 1892. [3]After one year of service, he went back to pursue mathematics at the University of Lyon and finally obtained his degree Licencié ès Sciences Mathématiques in 1894.[4] In December of the same year, he transferred to chemistry and began working with Professors Philippe Barbier (1848–1922) and Louis Bouveault (1864–1909). After working with stereochemistry and enines, Grignard was not impressed with the subject matter and asked Barbier about a new direction for his doctoral research.[5] Barbier advised that Grignard research how a failed Saytzeff reaction, using zinc, was successful, in low yields, after using magnesium.[6][5] They sought to synthesize alcohols from alkyl halides, aldehydes, ketones, and alkenes.[5] Grignard hypothesized that the aldehyde/ketone prevented the magnesium from reacting with the alkyl halide which resulted in the low yields. He tested his hypothesis by first adding the alkyl halide and magnesium filings to a solution of anhydrous ether and then adding the aldehyde/ketone. This resulted in a drastic increase in the yield of the reaction.[5]

A couple of years later, Grignard was able to isolate the intermediate.[6] He had heated a mixture of magnesium turnings, isobutyl iodide, and added dry ethyl ether to the mixture and a reaction was observed.[2] The product is known as a Grignard Reagent. Named after him, this organo-magnesium compound (R-MgX) (R = alkyl ; X = Halogen) readily reacts with ketones, aldehydes, and alkenes to produce their respective alcohols in impressive yields. Grignard had discovered the synthetic reaction which now bears his name (the Grignard reaction) in 1900. In 1901, Grignard published his doctoral thesis titled "Thèses sur les combinaisons organomagnesiennes mixtes et leur application à des synthèses d‘acides, d‘alcools et d‘hydrocarbures".[7] He became a professor at the University of Nancy in 1910. That same year, he and Paul Sabatier (1854-1941) were awarded the Nobel Prize in Chemistry in 1912.[8] During World War I he studied chemical warfare agents with Georges Urbain at Sorbonne University, particularly the manufacture of phosgene and the detection of mustard gas.[6]In 1918, Grignard discovered that sodium iodide could be used as a battlefield test for mustard gas. Sodium iodide converts mustard gas to diiododiethyl sulfide, which crystallizes more easily than mustard gas. This test could detect as little as 0.01 gram of mustard gas in one cubic meter of air and was successfully used on the battlefield.[9] His counterpart on the German side was another Nobel Prize–winning chemist, Fritz Haber.

Grignard reaction

Grignard is most noted for devising a new method for generating carbon-carbon bonds using magnesium to couple ketones and alkyl halides.[10] This reaction is valuable in organic synthesis. It occurs in two steps:

  1. Formation of the "Grignard reagent", which is an organomagnesium compound made by the reaction an organohalide, R-X (R = alkyl or aryl; and X is a halide, usually bromide or iodide) with magnesium metal. The Grignard reagent is usually described with the general chemical formula R-Mg-X, although its structure is more complex.
  2. Addition of the carbonyl, in which a ketone or an aldehyde is added to the solution containing the Grignard reagent. The carbon atom that is bonded to Mg transfers to the carbonyl carbon atom, and the oxygen of the carbonyl carbon becomes attached to the magnesium to give an alkoxide. The process is an example of a nucleophilic addition to a carbonyl. After the addition, the reaction mixture is treated with aqueous acid to give an alcohol, and the magnesium salts are subsequently discarded.

Military service

Grignard was drafted into the French military as part of obligatory military service in 1892. Within the two years of his first session of service he rose to the rank of corporal.[11] He was demobilized in 1894 and returned to Lyon to pursue his education.[11] He was awarded a medal of the Legion of Honour and made a Chevalier in 1912 after winning the Nobel Prize.[11] When World War I broke out, Grignard was drafted back into the military, keeping his rank of corporal.[11] He was placed on sentry duty, and served there for several months until he was brought to the attention of the General Staff.[11] Grignard had been wearing his Medal of the Legion of Honour, despite being ordered to take it off by a superior.[11] After looking more into Grignard, the General Staff decided that he would be better suited for research than sentry duty, so they assigned him to the explosives division.[11] Grignard's research shifted to antidotes to chemical weapons when production of TNT was no longer sustainable, and eventually Grignard was assigned to research new chemical weapons for the French army.[11]

Honors

Notes

  1. ^ Newbold, Brian T. "Victor Grignard Ancestor of Organic Synthesis: Victor Grignard was a brilliant French chemist who became famous at age 29 for the discovery of the organomagnesium halides and their versatility in chemical synthesis. (Feature/Chronique)." Canadian Chemical News Oct. 2001: 25+. Business Insights: Global. Web. 16 Nov. 2018
  2. ^ a b Newbold, Brian (Fall 2001). "Victor Grignard Ancestor of Organic Synthesis: Victor Grignard was a brilliant French chemist who became famous at age 29 for the discovery of the organomagnesium halides and their versatility in chemical synthesis. (Feature/Chronique)". Business Insights: Global.
  3. ^ Wisniak, Jaime. “François Auguste Victor Grignard.” Educación Química, vol. 15, no. 4, 2018, p. 425., doi:10.22201/fq.18708404e.2004.4.66168.
  4. ^ “The Nobel Prize in Chemistry 1912.” Nobelprize.org, www.nobelprize.org/prizes/chemistry/1912/grignard/biographical/. Accessed 18 Nov. 2018.
  5. ^ a b c d Nye, Mary Jo. (1986). Science in the provinces : scientific communities and provincial leadership in France, 1860-1930. Berkeley: University of California Press. ISBN 0-520-05561-6. OCLC 12081738.
  6. ^ a b c Hodson, Derek (February 1987). "Victor Grignard (1871-1935)". Chemistry in Britain. 23: 141–142.
  7. ^ "Philippe Barbier (1848–1922) and Victor Grignard (1871–1935): Pioneers of Organomagnesium Chemistry" (PDF). Synfacts. 14 (10): A155–A159. 2018. doi:10.1055/s-0037-1609791.
  8. ^ "The Nobel Prize in Chemistry 1912". NobelPrize.org. Retrieved 2018-11-18.
  9. ^ Nye, Mary Jo (1986). Science in the Provinces. Berkeley: University of California. p. 189. ISBN 9780520055612.
  10. ^ V. Grignard (1900). "Sur quelques nouvelles combinaisons organométalliques du magnèsium et leur application à des synthèses d'alcools et d'hydrocarbures (On some new organometallic compounds of magnesium and their application to syntheses of alcohols and hydrocarbons)". Compt. Rend. 130: 1322.
  11. ^ a b c d e f g h Dieringer, Rachael; North, Hunter; Lewis, David (September 17, 2018). "Philippe Barbier (1848–1922) and Victor Grignard (1871–1935): Pioneers of Organomagnesium Chemistry" (PDF). Synform. 50: 156–158.
  12. ^ Nobel Prize in Chemistry, 1912, Victor Grignard bio notes
  13. ^ Newbold, Brian T. "Victor Grignard Ancestor of Organic Synthesis," Canadian Chemical News. October 1, 2001.

References

  • G. Bram; E. Peralez; J.-C. Negrel; M. Chanon (1997). "Victor Grignard et la naissance de son réactif". Comptes Rendus de l'Académie des Sciences, Série IIB. 325 (4): 235–240. Bibcode:1997CRASB.325..235B. doi:10.1016/S1251-8069(97)88283-8.
  • Blondel-Megrelis M (2004). "Victor Grignard Conference and Traité de Chimie organique". Actualité Chimique. 275: 35–45.
  • Hodson, D. (1987). "Victor Grignard (1871-1935)". Chemistry in Britain. 23: 141–2.
  • Philippe Jaussaud (2002). "Grignard et les terpènes". Actualité Chimique. 258: 30.
  • Victor Grignard on Nobelprize.org Edit this at Wikidata including the Nobel Lecture, December 11, 1912 The Use of Organomagnesium Compunds in Preparative Organic Chemistry
  • Comptes Rendus
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