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Help interpreting NMR and IR spectrum

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ASensation:
Hi, first time posting, I need some help trying to interpret and relate between these 2 spectra
1H NMR


IR

Borek:
Please read the forum rules. You have to show your attempts at answering the question/solving the problem to receive help, it is a forum policy.

mjc123:
The IR is massively saturated; is it possible you could run it again with less sample?

ASensation:

--- Quote from: Borek on April 24, 2022, 01:52:26 PM ---Please read the forum rules. You have to show your attempts at answering the question/solving the problem to receive help, it is a forum policy.

--- End quote ---
Ah my bad, I am very sorry. Mr. Admin.

My Attempts so far
This homework of mine in particular is to identify a given unknown compound supplied by my instructor and I would need to run multiple qualitative analysis before obtaining the IR and NMR spectrum to verify my qualitative analysis results as well as determining possible structures. The results for my qualitative analysis has been:

Alcohol (-OH) group: Present
Carboxylic acid group: Not present
Ester group: Not present
Any nitrogen group: Not present
Carboxyl group: Not present

NMR
My interpretations for the NMR spectra has been consistent with the results of qualitative analysis with the peaks appearing at chemical shift region of <2 ppm and a signal appearing >3 ppm for the presence of the -OH group. However the integration of the peaks seem to me to be quite odd to make out the structure of as it is shown to be 2 high signals of triplets and 1 medium sized triplet signal. What is more confusing is the lack of a quartet or maybe multiplet signal and the quartet shape for what I deemed to be the -OH group's signal, I have yet to find a possible structure that would explain such a signal shape while also falling in line with the rest of the spectra.

IR
For the IR Spectra, the shape of the spectrum itself is quite worrying to me. My interpretations so far has left me with:
Broad peak at 3368: -OH stretch
Peak at 2934: alkyl C-H stretch
sharp peak at 1651: possible Amide stretch or alkenyl C-C stretch

The rest of the spectrum seem quite hard to interpret as said here:

--- Quote from: mjc123 on April 24, 2022, 03:30:17 PM ---The IR is massively saturated; is it possible you could run it again with less sample?

--- End quote ---
However the IR was simply given to me by the instructor and was generated even before this assignment was given out.

I hope this satisfies the forum rules as well as some relevant information on my predicament.
Thank you.


Babcock_Hall:
The behavior of -OH groups in NMR is a complex subject.  Only sometimes do they show coupling to other hydrogen atoms.  I seem to recall that this is because of their ability to exchange with small and variable amounts of H2O that are almost always present (there is also exchange between one hydroxyl group and another to consider).
EDT
You should express your integrals as ratios; this might help in their quantitative interpretation.  I would also apply the n+1 rule to each NMR signal.

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