H NMR of unknown sample (organic chem)

AI Thread Summary
The discussion revolves around analyzing an H NMR spectrum of an unknown compound, C7H5NO3, suspected to be 4-nitrobenzaldehyde. A puzzling signal at 7.2 ppm, not integrated for any hydrogens, raises questions about its origin, with possible interpretations including aromatic, conjugated vinylic, or phenolic protons. Participants suggest that this signal is likely due to contamination from the solvent, specifically chloroform, which also produces a signal in that region. The consensus indicates that the signal does not correlate with the compound's structure. Overall, it emphasizes the importance of considering solvent effects in NMR analysis.
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Homework Statement


Last week in organic chem lab, we were provided with an H NMR spectrum of an unknown compound with the formula C7H5NO3. I'm not terribly good at analyzing these spectra, but I've managed to figure out that I'm looking at 4-nitrobenzaldehyde. The only thing that's bothering me is this tiny signal, which shows up at about 7.2 ppm and is not integrated for any hydrogens. Known chemical shift data gives three possibilities: (1) aromatic proton, (2) conjugated vinylic proton, and (3) phenolic proton. I don't really see how this signal could represent any of those. Would it be possible that the signal is representative of the tiny amount of the enol form of the aldehyde? If not, what do you think it might be?

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Chloroform gives an H-NMR signal around 7.2 ppm. Was your sample dissolved in CDCl3?
 
Ygggdrasil said:
Chloroform gives an H-NMR signal around 7.2 ppm. Was your sample dissolved in CDCl3?
Yes it was. I would assume that means the signal really has nothing to do with the structure of the sample?
 
Yes, it's likely contamination from the solvent. A very common occurrence in NMR.
 
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