Proton NMR spectral analysis

[mychelle0430]

1. The problem statement, all variables and given/known data

Which isomer with formula C6H12O2 has the following NMR spectrum?
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1869_4119.jpg




[b]3. The attempt at a solution
It's hard (and probably unhelpful) to list all the tries I've had at this.

[chemisttree]

OK then, talk us through your logic. Is it likely to be an alcohol, for example? How many methyl groups do you see? From its (their) splitting patterns, is it (are they) adjacent to methylene? Methine? Something else?

[mychelle0430]

Well to start it has an unsaturation number of 1, I was figuring it has a C=C, since the vinyl hydrogens would have the downfield resonance near 5. It looks like a multiplet? So I'm confused how you could have that many adjacent protons on the double bond?

[chemisttree]

How did you figure that it had an unsaturation number of 1? What about the oxygens?

[chemisttree]

As a start, count the number of methyl groups. From their splitting and chemical shift, determine what they are next to. Then assemble the pieces so it fits the overall spectrum.