Unknown Compound HNMR, IR, CNMR and Mass spec HELP??

[steelhead]

I have worked on these last two Unknown compounds for a total of 6 hours now and cannot seem to come up with an expanded structure. Can anyone help me it is really crucial I figure this out I have spent 6 hours trying to figure this out today instead of studying for my Organic 2 exam I have at 7:30 tomorrow morning please help. This problem set is also due after my 7:30 am exam ugh.

 

[BabcockHall]

We don't dump answers at this site. Please show your work before we attempt to help you.

[hypervalent_iodine]

Those problem sheets bring back memories. Pretty sure we used the same ones at the uni I went to.

 

Start with your mass spec and work out the molecular formula. They give you a molecular ion m/z with an isotopic ratio for one of them. This is a big hint. Once you have that, calculate your DBE and go from there. If you can show your working and where you are struggling, we'll be happy to give further direction.