[radlations]

I've spent 2 hours straight looking at this thing and no luck.


Here are pics I've scanned of my IR and NMR.

Overall IR



Overall NMR




Zoomed In NMR



I dont want to make it seem like I haven't tried.

I've narrowed down the IR to be either a saturated Alcohol, an alkyne, or an Amine.

I'm really thinking its an Alcohol though. Now to look at my NMR. Someone please help me figure out the integrals And we can work from there.

[radlations]

I don't mean to *Ignore me, I am impatient* my own thread but I have to add this information.


My AIM screenname is "RADLATIONS" if you want to talk about this more quickly.

Here are the direct links. I noticed you couldnt ZOOM IN on the pictures here, but on direct link you can zoom in.

http://img.photobucket.com/albums/v259/liVilike/IR_0003.jpg
http://img.photobucket.com/albums/v259/liVilike/IMG.jpg
http://img.photobucket.com/albums/v259/liVilike/IMG2_0002.jpg

[Squirmy]

I agree with your alcohol assignment of an alcohol.

Have you made any progress on the NMR? What information do you get from the chemical shifts, integration, and splitting (or lack of splitting, in your case)?

[radlations]

Well I assumed the peak on the far right is the CH3 peak.

But It doesnt look like a multiplet. Looks like a singlet to me, suggesting no neighbors. I've measured it multiple ways and I end up with a measurement of either 60millimeters or 75 millimeters.

I can't work with 75, so I use 60 or 6 hydrogens. Leading to 2 Methyl groups.

The other peaks look like they have an integral of 1. Which really confuses me because the molecular weight won't add up to my assigned MW. HERES the thing that determines whether im right or wrong.

The assigned molecular weight is 84g/mol.

If OH= 17g/mol
2 CH3= 30g/mol

I'm still missing 37g/mol and I dont know how to make this work.

The unassigned peak also has a integral of 1 suggesting its a hydrogen bonding to a carbon that is bonded to 3 other things. This would lead to a MW of 13(12+1).

ARGH This isnt working 

[Squirmy]

I agree this is a bit of an evil one    I've seen it before and it still threw me off.

I don't see anything wrong with your work so far.  The pieces you have so far are:

OH = 17
2 CH3 = 30
CH = 13

For a total of 60 g/mol. You're missing 24 g/mol. The question is how are these pieces attached and how can you get another 24 without adding hydrogens?

Earlier you mentioned other functional group possibilities from your IR analysis. Keep in mind it doesn't have to be either/or. The shoulder off of the OH peak is significant.

[radlations]

An ALKYNE would do it!

I could either have 3-Methyl-1-butyn-1-ol

or I could have 2-methyl-3-butyn-2-ol

I think I might have 2-methyl-3-butyn-2-ol. The nmr/IR database on the website SDBS is similar to my IR, but my NMR has weaker peaks. The peaks found on the NMR in the SDBS website has weaker peaks. Does this matter?


Could it also be 3-Methyl-1-butyn-1-ol? I can't find this molecule. I'm guessing its unstable or somthing.

NO it can't be 3-methyl-1-butyn-1-ol, because there would be no SP3 CH stretch which would lead to a normal broad OH stretch.