Help with unknown spectroscopy?

[Jayelle]

Hi all, I'd greatly appreciate some assistance with my unknown identification. I've attached my spectra to this post.

So far, I know that the molecular weight is 151 and that there is a benzene ring (indicated by peak in mass spectra at 77). I also think that there is a carboxylic acid present since there were peaks at 1698 and 3147 cm^-1 in the IR. I've also made some other notes on the spectra, but I'm not entirely certain if they are accurate or not. I believe the formula should be C₈H₉NO₂, but I'm having trouble fitting the pieces together and drawing the actual structure.

Any help you could offer would be amazing!

Thanks in advance!

Scanned_20141126-0011.pdf

Scanned_20141126-0013.pdf

Scanned_20141126-0014 (1).pdf

Scanned_20141126-0014.pdf

[Sensei]

Do you need to use spectroscopy to figure out substance?

Or do you just need to figure it out any way possible?

 

Looking at

http://en.wikipedia.org/wiki/C8H9NO2

They seem to have significant difference in properties, like melting/boiling points..

 

Another way that came to my mind is to do spectroscopy of all these known substances from list of possibilities, and compare with what you have unknown.

 

Edited November 26, 2014 by Sensei

[hypervalent_iodine]

Do you need to use spectroscopy to figure out substance?

Or do you just need to figure it out any way possible?

 

Looking at

http://en.wikipedia.org/wiki/C8H9NO2

They seem to have significant difference in properties, like melting/boiling points..

 

Another way that came to my mind is to do spectroscopy of all these known substances from list of possibilities, and compare with what you have unknown.

 

This looks like a homework question, so spectroscopy is probably all that's on offer (and would be preferable to just doing mp/bp regardless). Performing spectroscopic analysis on ever compound with that formula would be a waste of time. If the compounds are simple enough, there will already be data on them. Anyway, the spectra the OP has is more than sufficient to work it out.

 

OP: I will look at this later and come back with notes. You should work out the DBE in the meantime.