What Isomer of C6H12O2 Matches This NMR Spectrum?

Click For Summary

Discussion Overview

The discussion revolves around identifying the isomer of C6H12O2 that corresponds to a provided NMR spectrum. Participants explore various aspects of the spectrum, including functional groups, splitting patterns, and the implications of unsaturation.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant notes the difficulty in listing all attempts to identify the isomer based on the NMR spectrum.
  • Another participant suggests considering whether the compound is likely an alcohol and prompts a discussion on the number of methyl groups and their splitting patterns.
  • A different participant identifies an unsaturation number of 1 and hypothesizes the presence of a C=C bond, questioning the complexity of the multiplet observed in the spectrum.
  • One participant challenges the calculation of the unsaturation number, asking how the presence of oxygens affects this assessment.
  • Another participant recommends counting the methyl groups and analyzing their splitting and chemical shifts to piece together the overall structure that fits the spectrum.

Areas of Agreement / Disagreement

Participants express differing views on the interpretation of the NMR spectrum, particularly regarding the unsaturation number and the implications of the observed splitting patterns. No consensus is reached on the identification of the isomer.

Contextual Notes

Participants do not fully agree on the role of oxygen in determining the unsaturation number, and there are unresolved questions about the complexity of the multiplet in the spectrum.

mychelle0430
Messages
2
Reaction score
0

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.
 
Physics news on Phys.org
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.
 

Similar threads

  • · Replies 5 ·
Replies
5
Views
6K
  • · Replies 2 ·
Replies
2
Views
4K
  • · Replies 2 ·
Replies
2
Views
4K
Replies
2
Views
6K
  • · Replies 1 ·
Replies
1
Views
4K
  • · Replies 3 ·
Replies
3
Views
5K
  • · Replies 3 ·
Replies
3
Views
3K
  • · Replies 1 ·
Replies
1
Views
3K
  • · Replies 6 ·
Replies
6
Views
6K
  • · Replies 4 ·
Replies
4
Views
3K