So, I was given an unknown chemical that I was to identify. Along with that chemical, I was given an NMR and a series of 7 tests to complete to identify this unknown chemical. I have all the results now, but I have been trying to figure out what this chemical is, but I can't. I know that it is either a ketone, aldehyde, alkene, or an alcohol due to a series of solubility tests.

 

1) My IR that I took showed a strong O-H and a strong C=O stretch.

2) The 2,4-DNP test produced a yellow precipitate (no conjugation

3) It reacted with CrO3 to produce a brown product (either a primary or secondary alcohol)

4) When mixed with Bromine, there was a color change to orange (double bonds present)

5) when burned on a copper wire, it produced a yellow flame (no halogens)

6) My NMR data showed 4 peaks:

a) singlet at about 2.0 with an integration of 1

b) doublet at about 4.2 with an integration of 2

c) triplet at about 5.2 with an integration of 2

d) multiplet at about 5.9 with an integration of 1

 

 

I have searched through everything... including going through my list of possible unknowns and could not find out what it was. Any help would be greatly appreciated!

 

Thank you!

What sort of NMR was it? 1H?

That is usually the case if people speak of things like doublets and multplets, no?

Oh okay fair enough maybe I am going mad, but I thought e.g. 13C could too.