Numford
Name reaction

Swarts reaction

Alkyl fluorides are made by heating an alkyl chloride or bromide with a metallic fluoride such as AgF, Hg2F2, CoF2 or SbF3.

Class 12, Chapter 6 Haloalkanes and Haloarenes

  1. Br
    BromoethaneCH₃CH₂BrHaloalkane
  2. Step 1

    AgF (or Hg₂F₂, CoF₂, SbF₃)

    Swarts reaction
    i

    Swarts reaction: the way to make an alkyl fluoride from a bromide or chloride.

    F
    FluoroethaneCH₃CH₂FHaloalkane

Reagents: AgF, Hg₂F₂, CoF₂ or SbF₃

Mechanism

How it works

  1. The metallic fluoride supplies fluoride ions.
  2. Fluoride replaces the halogen by nucleophilic substitution.
  3. The insoluble silver or mercury halide is left behind.
Used to prepare

What it makes

Alkyl fluorides.

Limitations

Where it fails

Direct fluorination or HF addition is not used because fluorine is too reactive.

Which chapter

Class 12, Chapter 6 Haloalkanes and Haloarenes

Questions

Swarts reaction: quick answers

Which reagent is used in the Swarts reaction?

AgF, Hg2F2, CoF2 or SbF3.

Why is direct fluorination not used?

Fluorine is too reactive to control, so a metallic fluoride supplies the fluoride ion instead.

Is the Swarts reaction the same as Finkelstein?

No. Finkelstein gives iodides with NaI; Swarts gives fluorides with metallic fluorides.

Plan an organic conversion