Find the molecules by interpreting the H NMR spectroscopy

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Discussion Overview

The discussion revolves around interpreting H NMR spectroscopy data for three compounds with the same molecular formula, C6H12O2. Participants explore how to deduce the structures of these compounds based on the provided NMR spectra.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant suggests starting the analysis with the spectrum rather than proposing structures immediately, emphasizing the importance of integration and saturation.
  • Another participant provides integration values for the spectra: 1st graph (2:3:2:2:3), 2nd graph (1:3:2:3:3), and 3rd graph (1:3), all indicating one degree of unsaturation.
  • A participant expresses difficulty in determining connectivity despite having integration values, indicating a struggle with synthesizing the information from the spectra.
  • One participant notes that the third spectrum appears to be the simplest, prompting a question about the number of each type of proton present.
  • There is a claim that each spike in the spectrum corresponds to three hydrogens, suggesting a CH3 group and potentially multiple CH3 groups.
  • A later reply indicates that one participant has figured out the structures, thanking others for their help.

Areas of Agreement / Disagreement

The discussion shows a mix of agreement on the approach to interpreting the spectra, but there is uncertainty regarding the connectivity and specific structures until one participant claims to have resolved the issue.

Contextual Notes

Participants express limitations in their understanding of how to connect the integration values to the molecular structures, indicating unresolved aspects of the analysis.

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Homework Statement


I have a 3 compounds with the same formula: C6H12O2
I need to find the molecules by interpreting the H NMR spectroscopy

http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1867_430.jpg
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1869_524.jpg
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1871_526.jpg

The Attempt at a Solution

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I've tried so many structures that it would be pointless to name them off.
 
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Don't start with structures - start with the spectrum. What does integration tell you about number of hydrogens? What does formula tell about saturation?
 
Well I know (atleast I think) the integrations;
1st graph: 2:3:2:2:3; One degree of unsaturation
2nd graph: 1:3:2:3:3; One degree of unsaturation
3rd graph: 1:3; One degree of unsaturation

But then I can't put everything together. I spend atleast an hour one each of these but can't figure out there connectivity.
 
3rd seems to be the simplest. 1:3 - you have two types of protons. How many of each type?
 
Each spike counts as 3 Hydrogens...so a CH3 and then 4 CH3?
 
I figured them out. Thanks for the help.
 

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