I\'m doing an organic chemistry \"unknowns\" lab and I\'m in need of some help.

Question

I'm doing an organic chemistry "unknowns" lab and I'm in need of some help. I already figured out one of my unknowns, but the other is still unknown to me! This is what I know about the compound, and has been confirmed by my professor. I just need the name and the structure, but I'm having the hardest time piecing it together!

Refractive index is roughly ~1.46...

What I know: 2° Alcohol Neutral Reactive C-C bonds High degree of unsaturation Non-aromatic NO halides NO nitro groups IR Spectra: Unk A 110 100 80 70 60 50 40 3500 3000 2500 2000 Wavenumbers (cm-1) 1500 1000 FriApr 10 11:38.08 2015 (GMT07:00) FIND PEAKS Spectrum: Absolute threshold: 90.413 Peak list Bender UnkA 4000.00 400.00 Position: 611.44 Intensity: 87.212 Position: 889.48 Intensity: 83,490 Position: 968.40 Intensity: 60.509 Position: 1025.00 Intensity: 73.353 Position 1085.71 Intensity 42.300 Position: 1362.80 Intensity 80.445 Position 450.82 Intensity: 66.615 Position: 2854.17 Intensity: 61.861

Explanation / Answer

From the spectroscopic data there is no double bond because double bonds appear in C RMN at 110-125 ppm.

IR indicates that there is an alcohol aliphatic

C RMN indicates that it is an alcohol, from the peak height you can see that there are 6 carbons, two of them are equivalent and one different what could suggest there is simmetry in the molecule.

proton RMN confirms there is no aromaticity and the non resolved peaks suggest there is complexes couplings, so there is no much electronegativity difference between C atoms.

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