Organic chemistry emergency?

Question

An unknown compound with molecular formula C9H18O3 shows only one signal in its proton nmr spectrum.In the IR spectrum a strong band is seen near 1300cm^-1. propose a structure for this compound.. what do i do and where do i start from........ ???????????????

Answer 1

Hmmm, well, according to my CRC Handbook, there are three compounds that will fit the molecular formula, and all three are carbonic acids:

Di n-butyl carbonate, Di-isobutyl carbonate, and Di-tert-butyl carbonate.

Based on the fact that you have a single proton NMR peak, it is most likely the di-tert-butyl carbonate, since all the protons are in methyl groups.

Answer 2

The formula indicates that there is only one unsaturation in the molecule, either a double bond or a ring. The strong band at 1300 is usually typical of an ester, which would take up your unsaturation.

The one signal in the proton NMR means all 18 of the hydrogens are equivalent, so you need some sort of symmetric molecule. The only real conceivable way to do that would be to have 2 t-butyl groups, meaning that your 3 oxygens are all bonded to the same carbon in such a way to make the molecule symmetric.

My guess would be di-t-butylcarbonate, which would be (CH3)3C-O-C(=O)-O-C(CH3)3.

Answer 3

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