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- Finkelstein_reaction abstract "The Finkelstein reaction, named for the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one halogen atom for another. Halide exchange is an equilibrium reaction, but the reaction can be driven to completion by exploiting of differential solubility of halide salts, or by using a large excess of the halide salt.R-X + X′− 15px R-X′ + X−The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. Sodium iodide is soluble in acetone and sodium chloride and sodium bromide are not. The reaction is driven toward products by mass action due to the precipitation of the insoluble salt. For example, bromoethane can be converted to iodoethane:CH3CH2Br (acetone) + NaI (acetone) → CH3CH2I (acetone) + NaBr (s)Alkyl halides differ greatly in the ease with which they undergo the Finkelstein reaction. The reaction works well for primary (except for neopentyl) halides, and exceptionally well for allyl, benzyl, and α-carbonyl halides. Secondary halides are far less reactive. Vinyl, aryl and tertiary alkyl halides are unreactive. Below some relative rates of reaction (NaI in acetone at 60°):In modern usage the definition of the reaction has been expanded to include the conversion of alcohols to alkyl halides by first converting the alcohol to a sulfonate ester (tosylates or mesylates are usually used), and then performing the substitution. The example below is from a synthesis of chrysochlamic acid.550px↑ ↑ ↑ ↑ ↑ ↑".
- Finkelstein_reaction thumbnail Chrysochlamic-Acid-Finkelstein.png?width=300.
- Finkelstein_reaction wikiPageID "4705983".
- Finkelstein_reaction wikiPageLength "5258".
- Finkelstein_reaction wikiPageOutDegree "33".
- Finkelstein_reaction wikiPageRevisionID "678386468".
- Finkelstein_reaction wikiPageWikiLink Acetone.
- Finkelstein_reaction wikiPageWikiLink Alcohol.
- Finkelstein_reaction wikiPageWikiLink Alkyl_bromide.
- Finkelstein_reaction wikiPageWikiLink Alkyl_chloride.
- Finkelstein_reaction wikiPageWikiLink Alkyl_iodide.
- Finkelstein_reaction wikiPageWikiLink Allyl.
- Finkelstein_reaction wikiPageWikiLink Aryl.
- Finkelstein_reaction wikiPageWikiLink Benzyl.
- Finkelstein_reaction wikiPageWikiLink Bromoethane.
- Finkelstein_reaction wikiPageWikiLink Category:Name_reactions.
- Finkelstein_reaction wikiPageWikiLink Category:Substitution_reactions.
- Finkelstein_reaction wikiPageWikiLink Chemical_equilibrium.
- Finkelstein_reaction wikiPageWikiLink Copper(I)_iodide.
- Finkelstein_reaction wikiPageWikiLink Dimethyl_sulfoxide.
- Finkelstein_reaction wikiPageWikiLink Dimethylformamide.
- Finkelstein_reaction wikiPageWikiLink Electron-withdrawing_substituent.
- Finkelstein_reaction wikiPageWikiLink Ethyl_iodide.
- Finkelstein_reaction wikiPageWikiLink Fluorine.
- Finkelstein_reaction wikiPageWikiLink Halogen.
- Finkelstein_reaction wikiPageWikiLink Hans_Finkelstein.
- Finkelstein_reaction wikiPageWikiLink Iodoethane.
- Finkelstein_reaction wikiPageWikiLink Mesylate.
- Finkelstein_reaction wikiPageWikiLink Neopentane.
- Finkelstein_reaction wikiPageWikiLink Neopentyl.
- Finkelstein_reaction wikiPageWikiLink Nickel(II)_bromide.
- Finkelstein_reaction wikiPageWikiLink Nickel_bromide.
- Finkelstein_reaction wikiPageWikiLink Organobromine_compound.
- Finkelstein_reaction wikiPageWikiLink Organochloride.
- Finkelstein_reaction wikiPageWikiLink Organoiodine_compound.
- Finkelstein_reaction wikiPageWikiLink Polar_effect.
- Finkelstein_reaction wikiPageWikiLink Potassium_fluoride.
- Finkelstein_reaction wikiPageWikiLink SN2_reaction.
- Finkelstein_reaction wikiPageWikiLink Sodium_bromide.
- Finkelstein_reaction wikiPageWikiLink Sodium_chloride.
- Finkelstein_reaction wikiPageWikiLink Sodium_iodide.
- Finkelstein_reaction wikiPageWikiLink Sulfonate.
- Finkelstein_reaction wikiPageWikiLink Tosyl.
- Finkelstein_reaction wikiPageWikiLink Tosylate.
- Finkelstein_reaction wikiPageWikiLink Tri-n-butylphosphine.
- Finkelstein_reaction wikiPageWikiLink Tributylphosphine.
- Finkelstein_reaction wikiPageWikiLink Vinyl.
- Finkelstein_reaction wikiPageWikiLink File:Chrysochlamic-Acid-Finkelstein.png.
- Finkelstein_reaction wikiPageWikiLinkText "Finkelstein reaction".
- Finkelstein_reaction wikiPageWikiLinkText "Finkelstein reaction#Halex reaction".
- Finkelstein_reaction hasPhotoCollection Finkelstein_reaction.
- Finkelstein_reaction wikiPageUsesTemplate Template:Eqm.
- Finkelstein_reaction wikiPageUsesTemplate Template:Reflist.
- Finkelstein_reaction subject Category:Name_reactions.
- Finkelstein_reaction subject Category:Substitution_reactions.
- Finkelstein_reaction hypernym Reaction.
- Finkelstein_reaction type Disease.
- Finkelstein_reaction type Eponym.
- Finkelstein_reaction type Reaction.
- Finkelstein_reaction comment "The Finkelstein reaction, named for the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one halogen atom for another.".
- Finkelstein_reaction label "Finkelstein reaction".
- Finkelstein_reaction sameAs Finkelstein-Reaktion.
- Finkelstein_reaction sameAs Reacción_de_Finkelstein.
- Finkelstein_reaction sameAs Réaction_de_Finkelstein.
- Finkelstein_reaction sameAs Finkelstein-reakció.
- Finkelstein_reaction sameAs Reazione_di_Finkelstein.
- Finkelstein_reaction sameAs フィンケルシュタイン反応.
- Finkelstein_reaction sameAs Finkelstein-reactie.
- Finkelstein_reaction sameAs Reação_de_Finkelstein.
- Finkelstein_reaction sameAs m.0cj9pf.
- Finkelstein_reaction sameAs Реакция_Финкельштейна.
- Finkelstein_reaction sameAs Finkelsteinova_reakcia.
- Finkelstein_reaction sameAs Q899304.
- Finkelstein_reaction sameAs Q899304.
- Finkelstein_reaction sameAs 芬克尔斯坦反应.
- Finkelstein_reaction wasDerivedFrom Finkelstein_reaction?oldid=678386468.
- Finkelstein_reaction depiction Chrysochlamic-Acid-Finkelstein.png.
- Finkelstein_reaction isPrimaryTopicOf Finkelstein_reaction.