I performed an aminolyzation of an acid halide a few days ago in lab, and I have a few questions about the process.
Now, as I understand it, you need two equivalents of ammonia: one to form the amide, and one to neutralize the hydrogen halide.
We used a solution of aqueous ammonia: NH3/H2O, so what would happen if I added this aqueous ammonia dropwise into my solution of acid halide, instead of adding the acid halide to the ammonia?
This is my prediction:
There would be an excess of acid halide, all of which would react with all of the ammonia. Effectively, there is only 1 equivalent of ammonia in this reaction.
So, formation of the amide would occur, but there would also be HX in the solution, along with the H2O. Normally, the second equivalent would neutralize the HX, producing a rather exothermic reaction and eliminating the NH4+X-
It seems the final result of using just one equivalent of ammonia will be the amide and hydrogen halide.
Will any subsequent reactions occur? I wonder if an acid-catalyzed hydrolysis of the amide might follow, reforming the carboxylic acid and producing an ammonium ion?
Basically, what's the difference between adding the acid halide to the aqueous ammonia versus adding the aqueous ammonia to the acid halide?