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SN2 Reaction. Ges., 1910, 43, 1528. [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. $$^9$$Persuasive arguments have been made that many $$\text{E}2$$ reactions proceed by the sequence The reaction works good with the primary halides but better with Î±-carbonyl halides and allyl benzyl. After this time, the now yellow solution was filtered through a medium porosity fritted funnel, eluting with ≈200 mL of acetone into a 500 mL round-bottom flask.1 The solvent was removed by rotary evaporation to afford a dry orange solid. Since $\ce{KCl}$ keeps precipitating the reaction will be driven to the desired product. It is used in the preparation of haloalkanes or alkyl halides. Chem. For instance: The bromoethane can be converted to iodoethane: $$CH_{3} CH_{2}Br \ _{(acetone)} + Nal \ _{(acetone)} \rightarrow CH_{3} CH_{2} I \ _{(acetone)} + NaBr \ \ _{(s)}$$. Sodium iodide (37.47 g, 0.250 mol) was then added all at once to the flask . ether (compare the reaction times for KF and CsF in the example above). Darwish, T. A.; James, M.; Triani, G.; Hanley, T.L. It is an organic reaction that uses an alkyl halide exchange into another alkyl halide through a reaction wherein the metal halide salt is used. [7] Nickel bromide and tri-n-butylphosphine have been found to be suitable catalysts as well. "Darstellung organischer Jodide aus den entsprechenden Bromiden und Chloriden", https://en.wikipedia.org/w/index.php?title=Finkelstein_reaction&oldid=987174453, Creative Commons Attribution-ShareAlike License, This page was last edited on 5 November 2020, at 11:11. Thus, the substitution of bromo- and KF, KI) leads to replacement of the halogen via an The reaction works good with the primary halides but better with α-carbonyl halides and allyl benzyl. The Finkelstein reaction is another one of the important name reactions of organic chemistry. Y. Liu, Y. Xu, S. H. Jung, J. Chae, Synlett, 2012, 23, Lett., Finkelstein reaction allows to convert available $\ce{R-CH2-Cl}$ to $\ce{R-CH2-I}$. This page was last modified on 13 December 2015, at 22:12. A spatula was used to break up any large orange aggregates 3. It is an organic reaction that uses an alkyl halide exchange into another alkyl halide through a reaction wherein the metal halide salt is used. 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). For example, bromoethane can be converted to iodoethane: Alkyl halides differ greatly in the ease with which they undergo the Finkelstein reaction. The so-called "aromatic Finkelstein reaction" is catalyzed by copper(I) iodide in combination with diamine ligands. 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