Carboxylic acids with amines???

[CSU Undergrad]

Achiever has two questions, in the ochem portion of part two, it says that when you mix a carboxylic acid with an amine you get and amide??? my ochem book says that it wont work because an amine is basic and a carboxylic acid is acidic so when mixed the carboxylic acid would be deprotanated resulting in an ammonium carboxylate salt.

I was wondering what you guys know about this from your ochem knowledge?

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[rose786]

I've read the same thing in 2 different books, so I think destroyer is right.

 

[jntruong2003]

yup, i agree with rose. carboxylic acids and amines DO react to form amides as a result of condensation (loss of a water molecule).

 

[raiden117]

Your ochem book is correct. Acid/Base reactions occur much more rapidly than addition/substitution reactions involving carbonyls, so the amine would react with the acidic hydrogen of the -OH group in the carboxylic acid. However, with aldehydes/ketones this does not hold true and imines/enamines can be formed through amine reaction. Hope this helped.