I was handed a paper today and told to try the reaction and see if it works.
I placed my aldehyde (benzaldehyde, 5 mmol) into a soluton of Iodine (5.5 mmol), 28% ammonium hydroxide ( 30 mL) and THF 5 mL. This all stirred together for one hour. The solution should go colorless after 1 hour. It did NOT after 1 hour or 2 hours. So I continued with the solution being a slight peach color, adding 3 mL of 35% hydrogen peroxide. This should "trap" the formed nitrile and produce the amide.
Upon extracting with DCM, washing with brine, drying over sodium sulfate and removing solvent i.v., there was no amide. The GC shows product and no starting material. I am convinced that it is the nitrile, not benzamide. The product at rt is a viscous liquid, not a solid as benzamide should be.
What do you all think is the next move?
I am doing the reaction again and just going to wait until the solution goes colorless. If that means letting it stir overnight, so be it.
I will also try and add excess hydrogen peroxide. 6 mL and then 9 mL on the next trial.
After all a nice chemist once said to me, "Chemistry is an experimental science"
Cheers,
thanks in advance