[pfnm]

This is a combined structure problem; using the spectral data provided we are to identify the compound. I've attached the image of the spectra here.



Uploaded with ImageShack.us

My thinking is:

The IR suggests an aromatic alcohol: the stretch at 1600cm-1 is too low to be attributed to a carbonyl. The sp2 and sp3 C-H stretches and the stretches in the 1450-1600cm-1 range suggest an aromatic ring.

From the mass spec and thep revous IR data, I think the formula is C12H14O.

From the proton NMR I get: the upfield triplet is from a CH3, the multiplet at 1.9ppm is from  the CH2 in a Ar-CH2-CH3 substituent.

The 3.4ppm quartet is from a Ar-CH(OH)-CH3.

The signals in the aromatic region are from the four aromatic hydrogens in an ortho-disubstituted arrangement (two doublets, two triplets).

The singlet at 5.9 ppm or so is from the O-H.

I believe the molecule to be:


Uploaded with ImageShack.us

http://imageshack.us/photo/my-images/845/aromaticalcohol.jpg/

I'm not sure what it's called.

Would this be correct:? Have I missed anything?

Thanks alot

[fledarmus]

I believe you meant C₁₀H₁₄O? That matches both your MS and your proposed structure. Other than that, it all looks right.

[pfnm]

Yep that's right, I meant C10H14O.

Thanks very much.

Do you know if this structure is called anything other than 1-(2-ethylphenyl)ethanol?

I would like to find it on SBDS, the spectral database, but I can't find it under that above name (which ChemDraw and ACD ChemSketch give as the name).

Thanks again

[fledarmus]

A Scifinder search gives three different CAS numbers (racemic and two enantiomers), but none of them are in the SDBS. I think you're out of luck there.