[kevin_lofgren]

I'm trying to get some help with this unknown compound. The C-13 NMR has two peaks.  One of the peaks is for aromatic carbons. I know this because aromaticity is evident in the IR NMR and is the only stretch on my H NMR chart (singlet).  The other C-13 stretch is at around 95. I don't know what that peak is from!!!  The compound is soluble in 5% sodium hydroxide and ether. It's not soluble in 5% hydrochloric acid, water and 30% sulfuric acid. It appeared to be slightly soluble in 5% sodium bicarbonate.  Since it dissolves in two bases I would assume that there is something like an oxygen or nitrogen with a hydrogen that could be removed. Also, sodium fusion showed the compound contains no nitrogen, sulfur or halogens. What should my next step be???  Thanks! 

[kevin_lofgren]

I feel like there must be more than one aromatic ring. 

[MOTOBALL]

1. Elemental analysis; this will let you calculate molecular formula

2. Molecular formula will enable you to determine the number of rings & double bonds (i.e. degrees of unsaturation)

3. Mass spectrum will (a) confirm Mol. Wt. (b) detect characteristic structural features

4. Proton NMR for determination of different H environments

Combine ALL information to obtain a structure that is consistent with ALL data.

Good Luck.

[kevin_lofgren]

Thanks for the reply. I also found out why I was having so much trouble trying to determine the structure...he gave me the wrong C-13 and H NMR for my compound!!  Glad that is resolved.