If you have an amino acid with both an amine and carboxylic acid, how can you know which one of them will react with the reagents? For example, if you have an acyl halide, does the reaction depend on whether it’s acid catalyzed (carboxylic acid + acyl halide -> anhydride) or base catalyzed (amine + acyl halide -> amide)? Or does it form whatever is more stable (amide = more stable = more favorable)?
