[discodermolide]

Where would i look to determine what the IR sample was recorded in?

As for the NMR, wouldn't all of the Hydrogen's in it not be equivalent?

What about axial and equatorial protons are they equivalent?

[Orgodude]

I wasn't aware that i should be looking at the hydrogen's in the context of whether or not they are in the axial or equatorial position. I'm not exactly sure how to approach that..

I would guess that they are not. 2 axial protons wouldn't be equivalent when an electronegative atom is effecting the symmetry of a compound. does my thinking make sense?

[discodermolide]

Well the axial and equatorial protons are not magnetically equivalent. When the spectrum is recorded at RT you see time averaged signals for both sets of protons, i.e. one big lump of protons. This is due to the ring flip mechanism. If you cool the sample down to say liquid nitrogen temperatures you see two distinct sets of signals, each of 6 protons each, one for the axial one for the equatorial protons. If you do this experiment properly you can actually measure the rate of the ring flipping process.
Your NMR does not look like the one shown on that web site provided by the other poster.

[jdpaul88]

It appears that you have two different compounds. The carbon NMR matches exactly the one you have listed

[Orgodude]

Ahh every time i feel like i'm beginning to grasp the material a new variable is introduced.

 Is it possible that the reason the NMR from the website doesn't resemble the NMR from my homework is due to such a scenario as you've described? The problem is entirely hypothetical, and the readings are not from any actual product that I have produced.

When I'm looking at a cyclohexanol drawing, to me it looks like the environment's of the hydrogens differ from carbon to carbon, but i'm not sure (certainty seems like a luxury in Organic.) I'm able to identify 7 distinct groups,a hypothesis which is supported by my NMR. This is partly why the data from the website is so confusing to me.

[jdpaul88]

Your NMR also accounts for 12 Hydrogens, right

[Orgodude]

It appears that you have two different compounds. The carbon NMR matches exactly the one you have listed

I was wondering if this was the case. We were only supposed to have one compound though, so maybe it was a mistake?

The range of peaks on my NMR (to the right of the OH peak) fall within the same range as those spikes in the NMR from the site. I dont know if that's significant.

Also, the IR from the website doesn't have the alcohol bend around the 3500-3200 range. I know disco mentioned the conditions of the sample can affect this, but i think it'd be strange that the site would would throw that kind of curve ball. Maybe there's a mistake on the sites part?

[jdpaul88]

The aromatic portion would show a higher proton shift than what it is - something such as 7.5 ppm...this makes me wonder if the carbon is referring to cyclohexanol and the h nmr is referring to something different

[Orgodude]

Your NMR also accounts for 12 Hydrogens, right

I'm not so good with the splitting and whatnot, so i'm not sure.

It does fit in when u consider the H on the OH, the one on the C-OH, and then each of the pairs on the remaining 5 carbons. That adds up to 7 environments, 12 H's total.

[discodermolide]

The OH is present in the IR. As I said the intensity is dependant upon concentration. You can used these dilution effects to establish H-bonding in a compound.
Maybe the ¹H-NMR was run at low temperature?

[Orgodude]

The aromatic portion would show a higher proton shift than what it is - something such as 7.5 ppm.

Is it aromatic though? I thought aromatic indicates double bonds.

[jdpaul88]

Nevermind that is the shift of a carboxylic acid

[jdpaul88]

The aromatic portion would show a higher proton shift than what it is - something such as 7.5 ppm.

Is it aromatic though? I thought aromatic indicates double bonds.

Oh yes, I was thinking of aromatic, sorry. You're right

[Orgodude]

The OH is present in the IR. As I said the intensity is dependant upon concentration. You can used these dilution effects to establish H-bonding in a compound.
Maybe the ¹H-NMR was run at low temperature?

Do you mean the IR from the website or the one i provided?
I'm only familiar with alcohols showing like this on IR spectra:
http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ch13/figures/iriproh.gif
Doesn't it seem strange that the site would have an IR for an alcohol, but under unique conditions in which the most recognizable signifiers are not there?

[Orgodude]

Ohhh i just saw, the IR from the site i posted was in CCl4 solution; the IR in "liquid film" matches the one from my example.

http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/IMG.cgi?imgdir=ir&fname=NIDA8688&sdbsno=581

vs

http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/IMG.cgi?imgdir=ir&fname=NIDA9018&sdbsno=581

HNMR
90 mhz
http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/IMG.cgi?fname=HSP00009&imgdir=hspW

vs

400 mhz
http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/IMG.cgi?fname=HSP40238&imgdir=hspW

So it is indeed cyclohexanol.