What is the Difference Between Finkelstein and Swarts Reaction?

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The Finkelstein and Swarts reactions are both halogen exchange reactions associated with the synthesis of alkyl halides, which are important in organic synthesis processes. The key difference between the two reactions lies in the end products:

  • Finkelstein Reaction: This process produces alkyl iodide as the end product. The reactant for the Finkelstein reaction can be primary halides, secondary halides, allyl halides, and benzyl halides, but it is not applicable for tertiary reactions, vinyl, and aryl halides.
  • Swarts Reaction: This reaction produces alkyl fluoride as the end product. It is generally used to obtain fluorides from alkyl chlorides or alkyl bromides by heating the alkyl chloride/bromide in the presence of the fluoride of some heavy metals.

Both reactions involve the exchange of halides according to their reactivity, with sodium iodide being the nucleophile in the Finkelstein reaction and metallic fluorides like AgF, Hg2F2, CoF2, or SbF3 being used in the Swarts reaction.

Comparative Table: Finkelstein vs Swarts Reaction

The Finkelstein and Swarts reactions are both halogen exchange reactions involving alkyl halides. Here is a table comparing the differences between the two reactions:

Finkelstein Reaction Swarts Reaction
End product is an alkyl iodide End product is an alkyl fluoride
Reactants can be primary halides, secondary halides, allyl halides, and benzyl halides. Does not occur for tertiary reactions, vinyl, and aryl halides Reactants are either alkyl chloride or alkyl bromide along with a fluorinating agent (Swarts Reagent)
Uses an excess amount of halide salt to drive the reaction towards completion Converts alkyl chlorides or alkyl bromides into alkyl fluorides by heating them with metallic fluorides
Reaction is an SN2 reaction or bimolecular reaction Follows an SN2 reaction mechanism

Both reactions involve the exchange of halides between organic compounds (or organic and inorganic compounds), but their products and specific conditions vary.