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Swarts reaction

  1. Nov 19, 2015 #1
    CH3Cl +AgF :CH3F +AgCl
    Guys if I'm correct this is a nucleophilic substitution reaction and here I'm not getting the reaction because from my view chlorine atom is more nucleophilic than fluorine atom and carbon atom is more electronegative than silver atom so how the reaction is taking place?
     
  2. jcsd
  3. Nov 19, 2015 #2

    Borek

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    What do you know about the stability of AgCl?
     
  4. Nov 19, 2015 #3
    I think thaf AgF is more stable than AgCl and I'm studying in FYJC science. So please can you provide answers according to my level of education
     
  5. Nov 19, 2015 #4

    Borek

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    Which is more soluble?
     
  6. Nov 19, 2015 #5
    If in water i think so AgF
     
  7. Nov 19, 2015 #6
    But from this how i will understand the reaction?
     
  8. Nov 19, 2015 #7

    Borek

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    AgCl is much more stable than AgF - this is reflected by their solubilities in water. Thus conversion of AgF to AgCl is a driving force for many reactions.
     
  9. Nov 19, 2015 #8
    Can you explain it a little better....I'm not getting that. If swarts reaction is happening than the electronegativity and nucleophilicness of atoms in this reaction are not working.
     
  10. Nov 19, 2015 #9

    Borek

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    They do, but the fact that AgCl is much stable counteracts it. AgCl stability means you are effectively removing chlorine from the reaction mixture.
     
  11. Nov 19, 2015 #10
    Ok i understood, then there would be many reactions like this case. Correct? Can you also tell me on what basis is the AgCl more stable than AgF
     
  12. Nov 20, 2015 #11

    DrDu

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    As Borek said, AgCl has a very low solubility in water in contrast to AgF which is completely soluble (under the conditions of the reaction).
    Solubility is not mainly a question of stability of the salt, but also of the energetic stabilization of the ions in the solution. Fluorine anions are much smaller than Cl- anions and can also form hydrogen bonds, which increases solution enthalpy of AgF. Hence AgF is very soluble in contrast to AgCl.
    The nucleophilic substitution is an equilibrium reaction. With comparable amounts of Cl- and F- present, it may well be that the equilibrium is on the side of CH3Cl. But the formation of AgCl removes almost all Cl- anions from the solution as soon as they are formed whence the reaction will be pulled on the side of CH3F.
     
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