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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.

acetanilide, 4-bromoacetanilide, 2-bromoacetanilide

SDS Source

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    $\begingroup$ Just because two compounds are different doesn't mean that they don't smell the same... $\endgroup$ – Zhe Jan 11 at 21:29
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    $\begingroup$ 4-bromoacetanilide isn't supposed to smell like almonds though. It's one step away from being paracetamol, and acetanilide itself doesn't smell either. $\endgroup$ – Eli Jan 11 at 21:33
  • $\begingroup$ I haven't heard anybody using the word 'bromizing' until I checked google. I use the word 'brominating'. $\endgroup$ – Nilay Ghosh Jan 12 at 16:56
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    $\begingroup$ That's because I'm Dutch, not sure how that got in my mind but I guess it's closest to the Dutch word: bromeren. $\endgroup$ – Eli Jan 12 at 17:42
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    $\begingroup$ It might be hydrolysis product of 4-bromoacetanilide, 4-bromoaniline, which is described to have “sweet odor”. $\endgroup$ – mykhal Jan 14 at 16:38

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