Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cathi_ on October 25, 2020, 05:33:50 AM
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Hey there,
I cant figure out the mechanism of a reaction I need to explain in a homework for uni as nothing seems to make sense.
The reaction is an acid-katalysed reaction from a Fluor-substituted pyridine to a pyridone. The reaction is carried out at 100°C with 100%acetic acid as the acid component.
How is this reaction able to work with Flour being such a bad leaving group an acetic acid as a weak nucleophile? Is this even a nucleophilic substitution or something else (cant think of anything else actually)?
Help would be so appreciated!
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This is the reaction:
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What is Ka of HF? At what pH does the reaction take place?
(I am not saying it explains anything, but it is an obvious thing to consider)
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The reaction takes place at pH 2,5 as 100% acetic acid is used an other solvents were removed before hand. the Ka oh HF is 3.15
Im not really sure what to do about this information ???
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If it is in pure acetic acid speaking of pH doesn't make much sense, as pH is a property of a water solution.
Still, do you think you have F- in the liquid phase, or is it mostly protonated?
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The reaction takes place at pH 2,5 as 100% acetic acid is used an other solvents were removed before hand. the Ka oh HF is 3.15
Im not really sure what to do about this information ???
pH 2.5 shows ~4% or ~0.6 M acetic acid.