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Grignard reaction
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==History and definitions== Grignard reactions and reagents were discovered by and are named after the French chemist [[François Auguste Victor Grignard]] ([[University of Nancy]], France), who described them in 1900.<ref name=":0">{{Cite web |last=texte |first=Académie des sciences (France) Auteur du |date=1900-01-01 |title=Comptes rendus hebdomadaires des séances de l'Académie des sciences / publiés... par MM. les secrétaires perpétuels |url=https://gallica.bnf.fr/ark:/12148/bpt6k3086n |access-date=2023-04-23 |website=Gallica |language=EN}}</ref> He was awarded the 1912 [[Nobel Prize in Chemistry]] for this work.<ref>{{cite journal |author=Grignard, V. |author-link=Victor Grignard |year=1900 |title=Sur quelques nouvelles combinaisons organométaliques du magnésium et leur application à des synthèses d'alcools et d'hydrocabures |url=http://gallica.bnf.fr/ark:/12148/bpt6k3086n/f1322.table |journal=Compt. Rend. |volume=130 |pages=1322–25}}</ref> The reaction of an organic halide with magnesium is ''not'' a Grignard reaction, but provides a Grignard reagent.<ref name=":2">IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). {{ISBN|0-9678550-9-8}}. {{doi|10.1351/goldbook}}.</ref> [[Image:Grignard with carbonyl.png|thumb|560x560px|Although [[Grignard reagent#Reactions of Grignard reagents|Grignard reagents]] undergo many reactions, the classical ''Grignard reaction'' refers only to the reaction of RMgX with ketones and aldehydes, shown in red. X = Cl, Br, I.|center]] Classically, the Grignard reaction refers to the reaction between a ketone or aldehyde group with a Grignard reagent to form a primary or tertiary alcohol.<ref name=":1" /> However, some chemists understand the definition to mean all reactions of any electrophiles with Grignard reagents.<ref name=":3" /> Therefore, there is some dispute about the modern definition of the Grignard reaction. In the ''Merck Index'', published online by the [[Royal Society of Chemistry]], the classical definition is acknowledged, followed by "A more modern interpretation extends the scope of the reaction to include the addition of Grignard reagents to a wide variety of electrophilic substrates."<ref name=":3">{{Cite web |title=Grignard Reaction {{!}} The Merck Index Online |url=https://www.rsc.org/Merck-Index/reaction/r177/ |access-date=2023-04-23 |website=www.rsc.org}}</ref> This variety of definitions illustrates that there is some dispute within the chemistry community about the definition of a Grignard reaction. Shown below are some reactions involving [[Grignard reagent]]s, but they themselves are not classically understood as Grignard reactions. [[File:Grignard_with_others.png|alt=Reactions of Grignard reagents with various electrophiles|center|494x494px|Additional reactions which involve Grignard reagents, but are not considered to be Grignard reactions by the classical definition. X = Cl, Br, I.]]
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