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Topic: Reacting chloroacetic acid with an amine  (Read 6222 times)

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Offline ace

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Reacting chloroacetic acid with an amine
« on: October 21, 2007, 05:26:19 PM »
What is the mechanism tht is involved in adding chloroacetic acid to an amine?  Does this reaction require basic conditions or will it simply add at neutral pH?

Offline Fry

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Re: Reacting chloroacetic acid with an amine
« Reply #1 on: October 21, 2007, 07:47:57 PM »
Slightly basic conditions may be optimal. Otherwise the acidic proton may slow down the reaction rate by interferring with the nucleophilicity of the amine. It would be an a nucleophillic substitution reaction that avoids the need for a carbocation intermediate.

You didnt actually mean acid chloride, right?

Offline ace

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Re: Reacting chloroacetic acid with an amine
« Reply #2 on: October 21, 2007, 08:11:56 PM »
Thanks Fry for your response.   I do meant chloroacetic acid.  thanks

Offline gaurang

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Re: Reacting chloroacetic acid with an amine
« Reply #3 on: October 23, 2007, 02:32:10 AM »
Take a reaction in EDC add amines and KOH and heat to reflux now start addition of Chloro acetic acid in EDC .

You will find salt KCl which shows your reaction is going on.

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