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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 while sodium chloride and sodium bromide are not; [ 3 ] therefore, the reaction is driven toward products by mass action due to the ...
This reaction does not depend much on the strength of the nucleophile, unlike the S N 2 mechanism. This type of mechanism involves two steps. The first step is the ionization of alkyl halide in the presence of aqueous acetone or ethyl alcohol. This step provides a carbocation as an intermediate.
A common method is halide metathesis. An example is the conversion of alkyl chloride into alkyl fluoride: . C 3 H 5-Cl + NaF → R-F + NaCl. This kind of reaction is called Finkelstein reaction. [2]
Another proposed mechanism involves single electron transfer with the generation of radicals. In reactions of secondary and tertiary alkyllithium and alkyl halides, radical species were detected by EPR spectroscopy. [9] [6] The mechanistic studies of lithium–halogen exchange are complicated by the formation of aggregates of organolithium species.
In chemistry, the haloform reaction (also referred to as the Lieben haloform reaction) is a chemical reaction in which a haloform (CHX 3, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (R−C(=O)CH 3, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base.
The scope of the Corey-House synthesis is exceptionally broad, and a range of lithium diorganylcuprates (R 2 CuLi, R = 1°, 2°, or 3° alkyl, aryl, or alkenyl) and organyl (pseudo)halides (RX, R = methyl, benzylic, allylic, 1°, or cyclic 2° alkyl, aryl, or alkenyl and X = Br, I, OTs, or OTf; X = Cl is marginal) will undergo coupling as the nucleophilic and electrophilic coupling partners ...
The coupling of an acetylide and tertiary alkyl halide is an example of a reaction that cannot be accomplished with alkali metal acetylides, which displace halides in an S N 2 fashion. The corresponding alkynylalanes are able to couple to tertiary halides via an S N 1-like mechanism. [4] (11)
Traditionally, the alkylating agents are alkyl halides. Many alkylating agents can be used instead of alkyl halides. For example, enones and epoxides can be used in presence of protons. The reaction typically employs a strong Lewis acid, such as aluminium chloride as catalyst, to increase the electrophilicity of the alkylating agent. [6]