Nucleophilic Substitution Reaction: CH3Cl + AgF

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Discussion Overview

The discussion revolves around the nucleophilic substitution reaction between CH3Cl and AgF, exploring the stability and solubility of the resulting compounds, AgCl and AgF. Participants examine the implications of these properties on the reaction dynamics and the role of electronegativity and nucleophilicity in this context.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Mathematical reasoning

Main Points Raised

  • One participant suggests that CH3Cl reacts with AgF to produce CH3F and AgCl, questioning the reaction due to the perceived nucleophilicity of chlorine compared to fluorine.
  • Another participant raises a question about the stability of AgCl, indicating a need for clarity on this aspect.
  • A participant expresses a belief that AgF is more stable than AgCl and requests explanations suitable for their educational level.
  • Several participants inquire about the solubility of AgF and AgCl in water, with some asserting that AgF is more soluble.
  • One participant states that AgCl is much more stable than AgF, citing solubility differences as a driving force for reactions involving these compounds.
  • Another participant seeks clarification on the stability of AgCl compared to AgF, questioning how electronegativity and nucleophilicity influence the reaction.
  • A participant explains that AgCl's stability counteracts the nucleophilicity of the reactants, effectively removing Cl- from the reaction mixture.
  • One participant elaborates on the solubility differences, noting that the energetic stabilization of ions in solution plays a role, and discusses the equilibrium nature of the nucleophilic substitution reaction.

Areas of Agreement / Disagreement

Participants express differing views on the stability and solubility of AgCl and AgF, with no consensus reached on the implications of these properties for the nucleophilic substitution reaction. The discussion remains unresolved regarding the overall dynamics of the reaction.

Contextual Notes

Participants mention the solubility of AgCl and AgF in water, but do not resolve the underlying assumptions about the reaction conditions or the specific energetic factors influencing solubility and stability.

Karan Punjabi
Messages
127
Reaction score
3
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?
 
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What do you know about the stability of AgCl?
 
Borek said:
What do you know about the stability of AgCl?
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
 
Which is more soluble?
 
Borek said:
Which is more soluble?
If in water i think so AgF
 
Karan Punjabi said:
If in water i think so AgF
But from this how i will understand the reaction?
 
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.
 
Borek said:
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.
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.
 
They do, but the fact that AgCl is much stable counteracts it. AgCl stability means you are effectively removing chlorine from the reaction mixture.
 
  • #10
Borek said:
They do, but the fact that AgCl is much stable counteracts it. AgCl stability means you are effectively removing chlorine from the reaction mixture.
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
 
  • #11
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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