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Topic: IR/NMR question!!! Please help, making me angryyyy.  (Read 11167 times)

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Offline arbz101

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IR/NMR question!!! Please help, making me angryyyy.
« on: August 03, 2012, 06:11:12 PM »
Provide a structure for the following compound: C6H13N; IR: 3280, 1653, 898 cm–1; 1H
NMR spectrum: 2H in a doublet, 2H in a singlet, 2H in a quartet, 3H in a singlet, 3H in a doublet, 1H in a singlet

I'm think the 2H in a quartet and the 3H in a doublet would have to be Ch2-Ch3 on a central carbon with no hydrogens attached to that central carbon; I am also thinking this is a primary amine with (R-NH2); what i'm stuck on is how you can have a split 2H doublet and no splitting on the 1H singlet?
Any help would be appreciated; this question is making me angry!


Offline discodermolide

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Re: IR/NMR question!!! Please help, making me angryyyy.
« Reply #1 on: August 03, 2012, 11:51:37 PM »
Provide a structure for the following compound: C6H13N; IR: 3280, 1653, 898 cm–1; 1H
NMR spectrum: 2H in a doublet, 2H in a singlet, 2H in a quartet, 3H in a singlet, 3H in a doublet, 1H in a singlet

I'm think the 2H in a quartet and the 3H in a doublet would have to be Ch2-Ch3 on a central carbon with no hydrogens attached to that central carbon; I am also thinking this is a primary amine with (R-NH2); what i'm stuck on is how you can have a split 2H doublet and no splitting on the 1H singlet?
Any help would be appreciated; this question is making me angry!



If it had CH2-CH3 then you would see a 2H quartet and a 3H triplet.
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Offline orgopete

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Re: IR/NMR question!!! Please help, making me angryyyy.
« Reply #2 on: August 04, 2012, 08:29:30 AM »
There isn't a lot to go on here, but with the MF, there is a ring or double bond. I'd suggest a ring. Just put the pieces together. If a 3H is a CH3 or NH3(+), the 2H are CH2's, etc, there cannot be that many possibilities. Suggest at least one of them. For example, start with N,2-dimethylpyrrolidine. Is there anything right or wrong with it? Can you use something from it to come up with another structure?
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