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Help using NMR/IR to identify an unknown?

Im at my wits end here... i've been using an NMR simulator (http://www.nmrdb.org/predictor) to try and find the identity of my unknown, but to no avail. What's perplexing all the more is somehow the IR produced peaks, around the mid 2300s, which, according to my text book and the internet so far, doesnt match ANYTHING.

the compound supposedly is made up of only Hydrogen, Oxygen, and Carbon, but if you can figure out something that works with another element, i'd be more than happy to hear it.

here are the data sheets:

IR spectrum: http://www.flickr.com/photos/49092395@N05/45002790...

13C-NMR: http://www.flickr.com/photos/49092395@N05/45009139...

and 1H-NMR: http://www.flickr.com/photos/49092395@N05/45009140...

on the 1H-NMR you will see many failed proposed structures, but maybe you can work from them. I swear, if I could give you 100 points for finding this compound, i would.

Update:

if you look at the top of the picture it'll say "all sizes" click on that to get a good view

Update 2:

also no... no mass spec. because apparently that would make it FAR too easy.

5 Answers

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  • 1 decade ago
    Favorite Answer

    You are right with what you had written on the 1H spectrum - it's propyl acetate (CH3COOCH2CH2CH3). The shifts for this compound from SDBS are:

    1H: 4.023 (t), 2.050 (s), 1.65 (m), 0.95 (t) ppm (it doesn't matter that these are out by ~0.05 ppm)

    13C: 171.09, 66.10, 22.14, 20.91, 10.41 ppm

    and the IR spectrum matches. The funny peak in the IR that you couldn't identify IS CO2 btw.

  • 1 decade ago

    Do you have the mass spec for the compound?

    Also, the images are a bit unclear so its hard to see the integrals/shifts/splitting for the 1D NMR.

    Edit: It doesn't appear to be methyl butyrate as the 13C NMR spectra doesn't match methyl butyrate's. The peaks at 77ppm should be lower at 50ppm. Also did you degas the system because the 2300 wavenumber peak on the IR spectra looks an awful lot like a CO2 peak. The intensity doesn't match but it at a spot where CO2 should appear.

    Edit2: I am pretty sure that the 2300 peak in the IR spectra is just CO2. If you look at the transmittance, it is really low. You must have had a VERY dilute sample.

  • 1 decade ago

    Ooh, I feel for you. We had the same problem when we were trying to defend our products in organic synthesis, but at least we knew what we were looking for. I think you should find a more detailed correlation table. The organic synthesis book that I have here at home only has a simplified one, and summer break has started so I can't check the library. Have you considered a nitrile group? Ideally, it's only around 100cm-1 from the IR absorbance of your weird peak.

  • ?
    Lv 4
    5 years ago

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  • 5 years ago

    Nmrdb.org

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