achiever orgo question 100

[jlee1986]

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hey guys,

when i looked at the solution for this question (achiever test #2), i got a little confused because i thought carboxylic acids didn't make amides when reacted with amines (the amine will just deprotonate the carboxylic acid). i understand that imines are formed when they hydrazines with aldehydes or ketones only, but i also thought that carboxylic acids and amines didn't produce amides. please help me out! thanks

 

[jlee1986]

anyone? pleeeeeeease 😀

 

[smec]

hey guys,

when i looked at the solution for this question (achiever test #2), i got a little confused because i thought carboxylic acids didn't make amides when reacted with amines (the amine will just deprotonate the carboxylic acid). i understand that imines are formed when they hydrazines with aldehydes or ketones only, but i also thought that carboxylic acids and amines didn't produce amides. please help me out! thanks

It'll be a two-step process outlined below:

Carboxylic acid + Amine ----> Ammonium carboxylate salt --(heat)--> Amide + Water

or, if you prefer, both steps may be combined in a single operation by simply heating a carboxylic acid with an amine together, eg.:

Benzoic acid + Aniline --(225 degree celcius)--> N-Phenylbenzamide + Water