[DM7000]

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 Spec
IR
NMR

I'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.

[kryptoniitti]

Boiling point and refractive index should also be measured. Often they give away the answer right there if it isn't a mixture.
However, you can solve the problem here without them.

Check the mass spectra 128 / 126 peaks' proportions to each other. This should give you a hint that one of your functional group tests have failed.

Use webdatabase like
http://www.colby.edu/chemistry/cmp/cmp.html
to narrow down the possible matches.

Study the NMR spectra to for the fine structure to get the right isomer.

[Honclbrif]

Something weird is going on. Your chemical tests are not matching your IR data. Since these are really the best ways of determining functionality, they really should agree.

[DM7000]

I was afraid that my tests were wrong. Unfortunately we only got one day to perform the tests. At this point i'm really down to just using the Spectras to figure it out. I had performed a boiling point test, although I didn't trust it very much as we later found out the equipment set up was messed up but it recorded about ~140 degrees. From what I could gather from the link kryptoniitii posted (thank you so much), the test for a halogen failed, especifically the test for chlorine as all the possible results for my data seem to point to cholorotoluene.