So, I synthesized 4-bromoacetanilide in the lab by brominating acetanilide. Acetic acid was used as a catalyst. Sodium bisulfide was used to neutralize the reaction product. Then it was washed with water and recrystallized in ethanol. After that I let it dry for a week. Then I added a little water by accident but decided to store it anyways, and a few weeks later I opened the stored product and I smelt almonds. It wasn't even a weak odour, it was much like benzaldehyde, but not that strong. How would this even be possible? I can't figure it out.
2-bromoacetanilide might have been formed. I did search a little bit, and found that the decomposition of 2-nitroacetanilide - a similar product - results in hydrogen cyanide (almonds smell; very toxic). But it cannot be that, can it? Wouldn't I be like dead by now? Sniffed it three times. Or is it not really toxic at very low concentrations, but smellable?
The smell was kindof pleasant, less aromatic-like than benzaldehyde. Not strong, but also not weak when I held it close. People say HCN smells like burned or roasted almonds, but it was more like a sweet but bitter maybe ester-like odour. Something probably most similar to marzipan.