Qualitative Organic

[Soulwraith56]

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!

[Greippi]

What sort of NMR was it? 1H?

[Fuzzwood]

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

[Greippi]

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