[walt1120]

Hi everyone this is my first post here.

Ive been trying to identify this compound and the NMR is stumping me because im having trouble matching it to a known compound.

Based on my in lab work and the IR i already know a few things
-its aromatic
-has a halide (i think Br)
-melting point of it is 63 degrees C (white solid with hints of yellow before i crushed it to powder)
-has an OH group

im going to post two pictures of the compounds H-NMR with integration lines and numbers. the second photo is a blown up version of the first one.

Any help with possibly piecing together a structure would be appreciated!

The NMR was taken with CDCl3 and i circled the peak from that, also ignore the peak right around 0

[salteen]

Hi,

Your aromatic peaks indicate a para-disubstituted compound.  You've indicated the compound has an OH and Br group.  There are no other peaks present.... this really only leaves one possibility.

[walt1120]

I wasn't 100% sure about Br but it sure looks like Br based on the IR. so do you think it's BROMOPHENOL? It's really the only conclusion I can make

[Altered State]

You've got 4 aromatic protons that are equal 2/2, that is an obvious sign of an aromatic ring disustituted in para orientation.
The only other proton is a width singlet about ~4.7ppm, that must be OH (that agrees with the 63ºC melting point, you definetly need hydrogen bonds, stronger than NH ones).

You absolutely need to have para-X-phenol
where X can't be easily identified.

Don't you have mass spectra??

It must be totally clarifier, you will get something like this:



(Molecular ion +2 with aprox. the same abundance than molecular ion, since we know bromine 79 and 81 isotopes are both about 50% abundance).


I vote for this:



But I'm afraid you won't be able to tell exactly which must be the other substitutent just with 1H NMR shifts.

[Altered State]

I've just tried it out on ChemNMR, and this is what I got:



Hope it helps.

I would say Chlorine, but I'm still not sure.

[Babcock_Hall]

I would look up the melting points of the most likely candidates.

[Altered State]

I would look up the melting points of the most likely candidates.

Nice point!
I've just definetly solved it out with that tip.
Hope OP did aswell.

[walt1120]

Yeah thats what helped me eliminate the other halides. the only halide close to my melting point is Br. im going with para-Bromophenol

Thanks everyone, you guys have been a big help.

[orgopete]

Since this is a known compound, the IR spectra can be matched with literature spectra. They should match peak for peak, especially the fingerprint region.