What Isomer of C6H12O2 Matches This NMR Spectrum?

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SUMMARY

The discussion focuses on identifying the isomer of C6H12O2 that corresponds to a specific NMR spectrum. Participants analyze the spectrum, noting an unsaturation number of 1, indicating the presence of a C=C bond. They discuss the splitting patterns of methyl and methylene groups, emphasizing the importance of determining the adjacency of protons to accurately deduce the structure. The conversation highlights the complexity of interpreting NMR data and the necessity of systematic analysis to arrive at the correct isomer.

PREREQUISITES
  • Understanding of NMR spectroscopy principles
  • Knowledge of organic chemistry isomerism
  • Familiarity with interpreting splitting patterns in NMR
  • Experience with molecular formula analysis
NEXT STEPS
  • Study NMR spectroscopy interpretation techniques
  • Learn about isomer classification in organic compounds
  • Research the significance of unsaturation numbers in molecular structures
  • Explore software tools for NMR spectrum analysis
USEFUL FOR

Chemistry students, organic chemists, and researchers involved in structural analysis of organic compounds will benefit from this discussion.

mychelle0430
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Homework Statement



Which isomer with formula C6H12O2 has the following NMR spectrum?
http://aceorganic.pearsoncmg.com/epoch-plugin/tempfiles/1869_4119.jpg




3. The Attempt at a Solution
It's hard (and probably unhelpful) to list all the tries I've had at this.
 
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OK then, talk us through your logic. Is it likely to be an alcohol, for example? How many methyl groups do you see? From its (their) splitting patterns, is it (are they) adjacent to methylene? Methine? Something else?
 
Well to start it has an unsaturation number of 1, I was figuring it has a C=C, since the vinyl hydrogens would have the downfield resonance near 5. It looks like a multiplet? So I'm confused how you could have that many adjacent protons on the double bond?
 
How did you figure that it had an unsaturation number of 1? What about the oxygens?
 
As a start, count the number of methyl groups. From their splitting and chemical shift, determine what they are next to. Then assemble the pieces so it fits the overall spectrum.
 

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