So as the final lab of the year, we are supposed to identify an unknown based on various tests as well as IR, MS, and NMR. Now usually the unknowns come out to be three or four people for unknown so they are able to compare their test and see if they messed up anywhere. Unfortunately I had the amazing luck of being the only person with my unknown so right off the bat I'm not 100% sure if some of the tests I conducted were accurate although I am fairly sure.
Here is a breakdown of the tests and the results:
Observational Tests- Clear Liquid
- Smells like Wood Varnish (A lab mate said it smelled just like Menards and Home Depot)
Halogen Tests:- Beilstein Test: Negative
- Silver Nitrate Test: Negative
- NaI/Acetone Test: Negative
Unsaturation Tests- Bromine Test: Negative
- Baeyer Test: Negative
- Ignition Test: Positive
Aldehyde and Ketone Tests:- DNP test: Negative
- Chromic Acid Test: Negative
- Iodoform Test: Negative
Alcohol Tests:- Lucas Test: Positive
- Chromic Acid Test: Negative
- Iodoform Test: Negative
As you can see only the Lucas Test and the Ignition tests were positive which means there is an aromatic ring present(Ignition) and there is an alcohol present(Lucas). The lucas test is positive for Benzylic alcohols which furthers my idea that it contains a benzene ring. Now the thing is that I can't find a way to make this fit the data that I get from the IR, NMR, and MS.
Here are the spectras:
Mass SpecIRNMRI'm honestly at my wit's end here. I have no idea how to correlate my test results with the spectras. At first I thought it'd be a benzene ring with an alcohol group on one side, and then a ethyl group on the other, but that doesn't get me close to the mass that the MS says.
I don't expect to get a direct answer of what it is, although I wouldn't be opposed, but at this point I just need a new perspective on how to think this problem through as nothing I've tried seems to work.