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NMR problem

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magnumbreaker

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Can someone help me with this? I already spent 2 hours on this.
1.4 ppm, multiplet, 1H
2.5 ppm, singlet, 1H
3.7 ppm, doublet, 4H
7.3 ppm, singlet, 10H
Formula C15 H16 O
My teacher doesn't want me to have more information than necessary, therefore NMR is all I am allowed to have
THANKS.
 

Me+PharmD

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Can someone help me with this? I already spent 2 hours on this.
1.4 ppm, multiplet, 1H
2.5 ppm, singlet, 1H
3.7 ppm, doublet, 4H
7.3 ppm, singlet, 10H
Formula C15 H16 O
My teacher doesn't want me to have more information than necessary, therefore NMR is all I am allowed to have
THANKS.

12,12-dimethyl-4,6,8,10-tetra-tridecyn-3-ol, something I through together that I'm still trying to check. The IUPAC may be a little off but your carbon count is friggin' high.
 

magnumbreaker

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From 10 H singlet in aromatic region, I think there are 2 benzene rings attached to a carbon.
 

Farmercyst

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From 10 H singlet in aromatic region, I think there are 2 benzene rings attached to a carbon.

That would explain the unsaturation and the H way the heck down field (probably an OH). Also gives symmetry again pointing to 10H singlet.
 

Me+PharmD

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That wasn't nice of your teacher to withhold IR, but I'm thinking your molecule might be 1,1-diphenyl-2-propen-1-ol. Let me know what you think.
 

magnumbreaker

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I think your hydrogen count is off, but thanks for the help. I think the formula should be 1,3-dimphenyl-2-propanol.
 

disboifan

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that site was my lifeline in orgo lab. hope we don't need nmr in rx school, cuz i don't remember anything.

from what i remember, my organic professor said nmr, mass spec, IR, etc. are used regularly by chemistry majors so they have to learn it really well.
 

Eleen

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hope we don't need nmr in rx school, cuz i don't remember anything.

Ditto, I haven't used any of that info since I graduated (Chem major), and I work in an analytical lab. Surely we would be able to pick it back up quickly if needed; hopefully, it's not.
 
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