Finkelstein reaction

Finkelstein Reaction

Finkelstein reaction

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The Finkelstein reaction, named for the German chemist Hans Finkelstein , is an S<sub>N</sub>2 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 taking advantage of differential solubility of halide salts, or by using a large excess of the halide salt.

For conversion of Chlorides to Fluorides,it is done in the presence of 18-Crown-6 (ether).

R-X + X′<sup>−</sup> R-X′ + X<sup>−</sup>

The classic Finkelstein reaction involves the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by the addition of sodium iodide in acetone. Because sodium iodide is soluble in acetone and sodium chloride and sodium bromide are not, the equilibrium is shifted by the precipitation of the insoluble salt. For example, bromoethane can be converted to iodoethane:

CH<sub>3</sub>CH<sub>2</sub>Br <sub>(acetone)</sub> + NaI <sub>(acetone)</sub> → CH<sub>3</sub>CH<sub>2</sub>I <sub>(acetone)</sub> + NaBr <sub>(s)</sub>

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 substrates are...
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