[morlord]

Hey,

I'm new here, but I'm in undergrad Ochem, and we're doing some qual analysis. I've run into some problems with one of my unknowns, and I'm guessing that I'm just lacking experience. Any assistance with pointing me in the right direction would be appreciated.

Here's what I've got (assuming I've done my tests correctly):
SOLUBILITY:
H20: Very poor
NaOH (aq) 5%: poor
HCl (aq) 5%: poor
H2SO4 (aq): dissolves readily
Ether: dissolves readily

PHYSICAL PROPERTIES:
Compound is an off-white solid, with the very thin flaky kind of crystals (I've seen them before with aromatics).
m.p. is around 131-133C

SODIUM FUSION:
There are no halogens, nitrogen or sulfur groups present.

FUNCTIONAL GROUPS (where I'm confused):
2,4 DNP (aldehyde ketone): Dissolving compound in 95% EtOH and adding to a 2,4DNP solution did not give any immediate results. However, almost 30 minutes later, I hate a discrete red ppt "floating" at the top of the test tube. It's not like the results I've seen for most carbonyls.

Lucas Test: Zinc Chloride solution stayed clear (no 2nd or 3rd degree ROH).

Chromic Acid Test: Dissolved in Acetone and added Chromic Acid; no ppt was generated (no 1st or 2nd degree ROH)

AlCl3 test for Aromaticity: Dropped compound down the side of a test tube with AlCl3 on the side. Gave a faint orange color.

Bromine in CCl4 for Unsaturation: Compound doesn't show any signs of sp2, sp or activated aromatic rings.

Ferric Hydroximate: It's not an ether.

Here is an IR for the compound. No NMR available.
http://www.flickr.com/photos/55619050@N06/5707706763/in/photostream


MY CONCLUSIONS:
The IR seems to show an alcohol peak (I'm really not sure, it's not very rounded). Also, I'm thinking that I have a C=O bond due to the peak around 1600. Also, it seems that I have some unsaturated bonds due to subtle peaking just above 3000. Other than that, I'm not sure what to conclude; could it be a Benzoic acid? It's not soluble in water, but maybe that's because it's high m.w.?


Any help is appreciated.

[Sepelio]

Definately looks like something aromatic to me, lots of noise low down and a few peaks around 3000. An ester or an amide maybe? An aromatic amide looks quite likely I think.