3-Hydroxy-5,5-dimethylcyclohex-2-en-1-one
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C8H12O2
Molecular Weight: 140.180
InChI= 1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3,9H,4-5H2,1-2H3
IUPAC Name:  3-Hydroxy-5,5-dimethylcyclohex-2-en-1-one
CAS Number: 3471-13-4
PubChem: 137957
NMRShiftDB: 10016776
Spectrometer: 500 MHz
Solvent: CDCl3
Provided by:  E. Pretsch et al., Computer-Aided Structure Elucidation, WILEY-VCH 2002.


 

1D Proton Resonances From Book:


$> cat proton.ll
7.47    1.08
5.49    1.00
2.26    4.14
1.09    6.12
			
 

1D Carbon Resonances From Book:


$> cat carbon.ll
191.05
103.14
46.25
32.71
28.29
			
 

Automated VerifyIt Proton Assignments:

Proton Assignments
 

Automated VerifyIt Carbon Assignments:

Carbon Assignments

Top 10 FindIt Molecular Structures Consistent With Molecular Formula and Proton Resonances:

The correct structure is at position 2.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.988389 (  220834)    2: 0.982597 (  137957)    3: 0.977365 ( 9903087)
    4: 0.972260 ( 5071309)    5: 0.970741 (  565424)    6: 0.969081 (  558500)
    7: 0.968231 (  587702)    8: 0.965263 (  574370)    9: 0.965188 ( 3271948)
   10: 0.963141 (  528706)
			

Top 10 FindIt Molecular Structures Consistent With Proton and Carbon Resonances:

The correct structure is at position 5.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.848558 (  558012)    2: 0.830848 ( 3374825)    3: 0.825304 (  138318)
    4: 0.824368 ( 1523228)    5: 0.816880 (  137957)    6: 0.807871 (  258158)
    7: 0.805222 ( 4131611)    8: 0.800149 ( 5082151)    9: 0.799342 ( 5256901)
   10: 0.798053 (  566977)
			

Comments:

The first two structures for the molecular formula and proton results are keto/enol tautomers of the same compound. The shift of the corresponding carbon clearly identifies which of these tautomers is predominent.


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