Find the molecules by interpreting the H NMR spectroscopy

[STLCards002]

Homework Statement

I have a 3 compounds with the same formula: C6H12O2
I need to find the molecules by interpreting the H NMR spectroscopy

http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1867_430.jpg
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1869_524.jpg
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1871_526.jpg

The Attempt at a Solution

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I've tried so many structures that it would be pointless to name them off.

 

[Borek]

Don't start with structures - start with the spectrum. What does integration tell you about number of hydrogens? What does formula tell about saturation?

 

[STLCards002]

Well I know (atleast I think) the integrations;
1st graph: 2:3:2:2:3; One degree of unsaturation
2nd graph: 1:3:2:3:3; One degree of unsaturation
3rd graph: 1:3; One degree of unsaturation

But then I can't put everything together. I spend atleast an hour one each of these but can't figure out there connectivity.

 

[Borek]

3rd seems to be the simplest. 1:3 - you have two types of protons. How many of each type?

 

[STLCards002]

Each spike counts as 3 Hydrogens...so a CH3 and then 4 CH3?

 

[STLCards002]

I figured them out. Thanks for the help.