Keto-enol content

Main Question or Discussion Point

hi
i'm trying to figure out the percent enol content of 2-acetylcyclohexanone but with little success. i have been given an H-nmr of 2-acetylcyclohexanone and one of the deuterated derivative.
i know that the proton from the -OH group of the enol form shows up at around 16ppm but the other peaks are a little more confusing.
i need a little help in assigning the peaks and finding the percent enol content.
thanks in advance
 

Answers and Replies

chemisttree
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The deuterated version won't have the beta hydrogen or the hydroxyl hydrogen. That will help you identify those peaks since those are present in one spectrum and not the other. They should both be singlets with the hydroxyl one being somewhat broad... you might not even see it. 16 ppm doesn't sound like a hydroxyl proton, though.

Were you given the integrated intensities for the spectra?
 

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