Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ace on October 21, 2007, 05:26:19 PM

Title: Reacting chloroacetic acid with an amine
Post by: ace 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?

Title: Re: Reacting chloroacetic acid with an amine
Post by: Fry 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?

Title: Re: Reacting chloroacetic acid with an amine
Post by: ace on October 21, 2007, 08:11:56 PM

Thanks Fry for your response.   I do meant chloroacetic acid.  thanks

Title: Re: Reacting chloroacetic acid with an amine
Post by: gaurang 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.