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Organic : Unknown NMR help
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 Message 1 of 2 in Discussion 
From: MSN Nicknamewhat464  (Original Message)Sent: 3/22/2008 11:32 PM
We were doing an experiment to find the composition of an unknown compound. This compound has 71.9% C, 12.1 % H, and 16% O. So after doing an IR and some other tests I determined that the unknown compound had and aldehyde functional group, and with the % composition that was given to me, I determined that the compound was hexanal. So how do I prove that this h1 NMR spectrum that was given to me is one of hexanal. If you can, can you tell me which peak corresponds with which hydrogens. Thanks!
 Lab5 Uknwn 37 NMR.bmp  


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 Message 2 of 2 in Discussion 
From: MSN Nickname·Steve·Sent: 3/23/2008 3:29 AM
Comparing the spectrum to those of pentanal and heptanal at the Spectral Database for Organic Compounds, the spectrum of your compound looks similar in many respects.
 
The apparent triplet at 0.8 δ would be the CH3 hydrogens at the end of the chain.  This signal would integrate for 3H.
 
Going down the chain toward the carbonyl group, the large signal at 1.3 δ would be the overlapping signals of the next two CH2 hydrogens in the chain.  The integration signal looks like it could be for 4H.
 
The next signal at 1.6 δ would be the next CH2 hydrogens, integrating for 2H.
 
The signal at 2.4 δ would be the CH2 hydrogens next to the carbonyl group.  Spin-spin splitting by the neighboring two CH2 hydrogens would result in a triplet, which would further be doubled by the neighboring aldehyde H.  The signal looks more like a triplet, so the coupling constant to the aldehyde H must be small.
 
Finally, the aldehyde signal at 9.7 δ integrating for 1H should be split by the neighboring CH2 hydrogens into a triplet signal.  The signal looks like it might be a narrow triplet, but it's hard to tell with the integration line going right through the peak.

Any branching of the hexanal carbon chain would likely give some clearer signals, such as a clear doublet for a CH3 group in, for example, 3-methylpentanal, but your spectrum has no obvious doublet signals.
 
So, hexanal seems to me to be a reasonable identification. 

Steve