Organic Chemistry IR and NMR problem solving

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Discussion Overview

The discussion revolves around determining the structure of a carbon compound with seven carbons, 14 hydrogens, and one oxygen, specifically focusing on its interpretation through NMR spectroscopy and the implications of the carbonyl group. The scope includes homework-related problem solving in organic chemistry.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant suggests that the compound has 4 hydrogens with 3 neighboring hydrogens, 2 hydrogens with 4 neighboring hydrogens, 2 hydrogens with 5 neighboring hydrogens, and 3 hydrogens with 2 neighboring hydrogens.
  • Another participant questions what the NMR shifts indicate about the relative distances from the carbonyl functional group.
  • There is a proposal that the four most shifted hydrogens may represent a superposition of triplets.
  • A later reply speculates that the "quartet" might actually be a pair of triplets overlapping, which could simplify the interpretation.
  • One participant expresses frustration with the asymmetry in the data.
  • It is noted that the data may be flawed, leading to a revised interpretation of the structure as a linear arrangement of carbon atoms with a double bond to oxygen.

Areas of Agreement / Disagreement

Participants express varying interpretations of the NMR data and its implications for the compound's structure. There is no consensus on the correct interpretation, and some participants acknowledge potential errors in the data.

Contextual Notes

Participants mention the possibility of misinterpretation due to bad data and the complexity of the NMR shifts, indicating that assumptions about the hydrogen environments may need to be revisited.

montoyas7940
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NMR.png

Homework Statement


I am trying to help my daughter determine the structure of this carbon compound. It has seven carbons, 14 hydrogens and one oxygen. The oxygen must be in a ketone group. Also each carbon is different (as indicated by the carbon 13 NMR).

Homework Equations




The Attempt at a Solution


We think that the correct interpertation of the NMR shown is that there are 4 hydrogens with 3 neighboring hydrogens, 2 hydrogens with 4 nieghboring hydrogens, 2 hydrogens with 5 neighboring hydrogens, 3 hydrogens with 2 neighboring hydrogens and 3 hydrogens with 2 neighboring hydrogens. [/B]

Are we correct so far? Any suggestions?
 

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Looks reasonable. What do the NMR shifts tell you about relative distances from the carbonyl functional group?
 
Bystander said:
Looks reasonable. What do the NMR shifts tell you about relative distances from the carbonyl functional group?
The 4 hydrogens will be closest to the carbonyl and the 3 hydrogens will be farthest from the carbonyl. And one of the groups of 3 hydrogens will be closer than the other group of three hydrogens.
 
montoyas7940 said:
group of three hydrogens.
Might as well call these two methyl groups.
Next, the four most shifted hydrogens: possibility of superposition of triplets?
 
By triplets do you mean the four most shifted hydrogens having three (hydrogen) neighbors? That is the premise we have been working with but we must be missing something obvious.
 
I was wondering if the "quartet" might actually be a pair of triplets sitting almost on top of each other. Haven't got Silverstein and Basler handy, and I'm winging it right now on that part. If it is, the whole thing becomes "trivial." Hah, hah --- sure.
 
Arrgh! Taking a break. Then we will play with it some more. Thanks for the suggestion.
 
Asymmetry baffles me.
 
As it turns out, the data is bad.

Scratch the 4 hydrogens with 3 neighbors. So it becomes 7 carbon atoms in a line with the third having a double bond with oxygen.

Thanks for looking at it!
 
  • #10
montoyas7940 said:
As it turns out, the data is bad.
And this was a teaching exercise for your daughter? I would demand my money back.
 
  • #11
Bystander said:
I would demand my money back.

Full scholarship...

I guess you really do get what you pay for.
 

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