How to interpret this pair of IR and 1H NMR spectra?

Question

I need to figure out the structure of a $C_{8}H_{14}O_{2}$ molecule with this IR spectrum:

and these $^{1}$H NMR spectrum signals:

m means 4 or more spikes.

I worked out that the degree of unsaturation is 2 and I think the first IR trough is OH alcohol or C-H alkene, but the rest of the IR spectrum doesn't seem to correspond to anything. I can interpret some of the NMR signals, but it seems like there are a lot of possibilities that I don't know how to organize, especially when symmetry is involved.

Here are the IR and NMR reference tables I'm given:

Any help is much appreciated!

Answer 1

I was spoiled working with a FTIR with digital spectra and libraries. I no longer have access so I can give some bits and pieces. First there is no OH! the blip at 3400 and strong peak at 1730 indicate ketone or ester the peaks at 1180 and 950 suggest ester that takes care of the 2 Os and 1 unsaturation. The nmr shows a typical ethanol ethyl group so likely an ethyl ester. That leaves C5H9 one unsaturation and the bond to the carbonyl There is a singlet methyl group down field, 2 methylenes and 2 vinyl. That leaves a -CH2CH2- bound to a carbonyl and a C=C The ethylene has 2 H's and one methyl attached. The peak at 940 suggests a trans double bond [ I forget what the trans coupling constants are]. The sharp peak at 3100 for the vinyl is troublesome possibly the symmetrical stretch is inactive. Another possibility is a methyl ester and ethyl group on the double bond. The chemical shifts will tell.