u/Judethenotdude

While in an unknowns lab I took a IR which I initially thought was an aromatic carboxylic acid of some sorts. But then after doing H-NMR I don’t have a carboxylic acid peak but I do have an aldehyde peak. After running some aldehyde tests and ester tests they’re all inconclusive, not a positive but also not an affirmed negative. When testing solubility in NaHCO3 it was soluble and I saw bubbles which pointed towards carboxylic acids again. I’m so lost on what is going on. I’m going to attempt to redo my H-NMR since the machine was acting up but I was curious to hear theories on what might be happening.