Dtsch. This is an equilibrium process and it is driven forward by taking advantage of the poor solubility in acetone of the newly formed metal halide salt (Le Chatelier's principle). The reaction works well for primary (except for neopentyl) halides, and exceptionally well for allyl, benzyl, and α-carbonyl halides. Hans Finkelstein came from a liberal Jewish family and joined the Protestant Church when he was 10 years old. For instance: The bromoethane can be converted to iodoethane: $$CH_{3} CH_{2}Br \ _{(acetone)} + Nal \ _{(acetone)} \rightarrow CH_{3} CH_{2} I \ _{(acetone)} + NaBr \ \ _{(s)}$$. cleanly to fluoroalkanes, because fluoride is such a poor leaving group due to For example, reactions with KF will thus lead of metal salts that have a high lattice energy require the addition of a crown It is used to synthesize one alkyl halide from another. better stabilized than the other in a given solvent (see Nucleophilic Substitution). Finkelstein Reaction Treatment of a primary alkyl halide or pseudohalide with an alkali metal halide (e.g. [8], The halex reaction describes any aryl HALogen EXchange. In the modern usage of Finkelstein reaction, it has expanded including in the process of changing alcohols to alkyl halides by converting the alcohol to a sulfonate ester in the first stage, and then the substitution changes. [7] Nickel bromide and tri-n-butylphosphine have been found to be suitable catalysts as well. [3] The reaction is driven toward products by mass action due to the precipitation of the insoluble salt. A. Taher, K. C. Lee, H. J. Han, D. W. Kim, Org. Below some relative rates of reaction (NaI in acetone at 60 °C):[7][8], 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. Nucleophilic Substitution. Sulfonate Esters by Recyclable Ionic Liquids [bmim][X] The flask was then equipped with a reflux condenser and, after placing the reaction under a nitrogen atmosphere, was heated to reflux. For Example: Synthesis of chrysochlamic acid. For Example: Synthesis of chrysochlamic acid. (e.g. The mechanism of the Finkelstein reaction is single-step $$S_{N}2$$ reaction with stereochemistry inversion. The success of this reaction depends on the below conditions. The reaction works good with the primary halides but better with Î±-carbonyl halides and allyl benzyl. This solid was triturated with a 1:1 v./v. For instance: The bromoethane can be converted to iodoethane: $$CH_{3} CH_{2}Br \ _{(acetone)} + Nal \ _{(acetone)} \rightarrow CH_{3} CH_{2} I \ _{(acetone)} + NaBr \ \ _{(s)}$$. An example involves the conversion of the ethyl ester of 5-bromovaleric acid to the iodide:[4], Potassium fluoride is used for the conversion of chlorocarbons into fluorocarbons. The use The mixture was allowed to react for 24 hours. The Finkelstein reaction is an organic reaction where an alkyl halide is converted into another alkyl halide by reacting with a metal halide salt. [10] Nickel bromide and tri-n-butylphosphine have been found to be suitable catalysts as well.[11]. [2], 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. This reaction is important because there are many ways to make $\ce{RCH2Cl}$, but making $\ce{R-CH2-I}$ is difficult. In the classical version of Finkelstein reaction, a primary alkyl halide, RX is treated with an alkali metal halide, like NaX' or KX', in excess in acetone. Vinyl, aryl and tertiary alkyl halides are unreactive; as a result, the reaction of NaI in acetone can be used as a qualitative test to determine which of the aforementioned classes an unknown alkyl halide belongs to, with the exception of alkyl iodides, as they yield the same product upon substitution. It is named after the Hans Finkelstein, a German chemist. The flask was then equipped with a reflux condenser and, after placing the reaction under a nitrogen atmosphere, was heated to reflux. The Finkelstein reaction is a Substitution Nucleophilic Bimolecular reaction ($$S_{N}2$$ Reaction) involves the exchange of halogen atom. Darwish, T. A.; James, M.; Triani, G.; Hanley, T.L. chloroalkanes with KI in acetone leads cleanly to the desired iodoalkane Lett., It is named after German Chemist Hans Finkelstein. SN2 Reaction. The solvent was removed by rotary evaporation to afford pure 3-iodo-1-propanol as a pale yellow oil (7.78 g, 84%). the anion, whether a good leaving group is present, and whether one anion is Thus, the substitution of bromo- and This page was last modified on 13 December 2015, at 22:12. 3-Chloro-1-Propanol (98% Purity, Sigma Aldrich)Acetone (CHROMASOLV®, for HPLC, ≥99.9%, Sigma Aldrich)Sodium Iodide (ACS reagent, ≥99.5%, Sigma Aldrich)Diethyl Ether (anhydrous, ≥99.7%, 1 ppm BHT, Sigma Aldrich)Hexanes (mixture of isomers, anhydrous, ≥99%, Purchased from Sigma Aldrich)Sodium thiosulfate (ReagentPlus®, 99%)Sodium Sulfate (ACS reagent, ≥99.0%, anhydrous, granular). [9], From Infogalactic: the planetary knowledge core. The so-called "aromatic Finkelstein reaction" is catalyzed by copper(I) iodide in combination with diamine ligands. It is named after the Hans Finkelstein, a German chemist. 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