Question

An unknown compound (X) wiht a molecular formula C4H10O gives four C NMR signals: 10, 24, 33, and 10 ppm. Propose a structure for the unknown explain your anwser.

Answer 1

This compound is an alcohol, and the proposed structure is the following:

Now, this is the proposed structure basically because if you look at the signs, you have the same spectra in carbon 1 and 4 (10 ppm), which means that these two carbons needs to be the same kind (in these case a CH₃). The second carbon has a higher ppm range, and the third is higher than the second. However, this raising is because in one of those carbons you have the alcohol, it could be either 2nd or 3rd, but in this case it's does not matter because it would be the same compound.

I discart the possibility of an ether, because the carbon 2 and 3 would have to be in the same spectra, and they don't have the same spectra.

Hope this helps