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AvBaeyer
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Loptr and JJay:
Good job! you figured it out. It's all about the electronics. The primary isolatable product from lactic acid in the Lucas reaction will be
3-chloropropionic acid as mentioned by Loptr above.
What may seem counter-intuitive in all this is the ready nucleophilic displacement of halide from alpha-haloacids and alpha-haloketones such as
phenacyl halides. Again, it's all about the electronics and effects on reaction mechanisms. It pays to become familiar with these mechanisms.
AvB
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Loptr
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Quote: Originally posted by AvBaeyer  | Loptr and JJay:
Good job! you figured it out. It's all about the electronics. The primary isolatable product from lactic acid in the Lucas reaction will be
3-chloropropionic acid as mentioned by Loptr above.
What may seem counter-intuitive in all this is the ready nucleophilic displacement of halide from alpha-haloacids and alpha-haloketones such as
phenacyl halides. Again, it's all about the electronics and effects on reaction mechanisms. It pays to become familiar with these mechanisms.
AvB |
I really appreciate what you did to help get us on the right track, AvB.
"Question everything generally thought to be obvious." - Dieter Rams
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solo
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.....with my recent bout with acid chlorides it seems to me if you made your acid chloride with your propionic acid in cyanuric chloride, then do
the Finkeltein reaction in acetone with bromine to acquire the desired product .....at least that's how i see it....solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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Texium
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| Quote: Originally posted by solo | | .....with my recent bout with acid chlorides it seems to me if you made your acid chloride with your propionic acid in cyanuric chloride, then do
the Finkeltein reaction in acetone with bromine to acquire the desired product .....at least that's how i see it....solo |
I don't understand what you're talking about. The thread is about brominating the alkyl chain of propionic acid, not making
propionyl bromide. Also the Finkelstein reaction only works for making iodides from chlorides or bromides by exploiting the relative solubility of NaI
in acetone. Converting a chloride to a bromide doesn't work since NaBr is insoluble in acetone. But it doesn't matter anyway. It's not like you can
use the Finkelstein reaction on acyl halides since you can't do an SN2 on a carbonyl carbon...
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solo
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.....i misunderstood the topic , still on the acid chloride mind,..solo
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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