ANSWER:
There is only one unsaturation in the compound. It could be a C=C, C=O or a ring.
13C-NMR Data:
Chemical Shift | Assigment | Chemical Shift | Assigment |
176 ppm | C=O | 22 ppm | CH3, CH2 or CH |
68 ppm | C-O | 17 ppm | -CH3 |
40 ppm | C-C=O | 10 ppm | -CH3 |
28 ppm | CH3, CH2 or CH |
IR Data:
Signal | Assigment |
3000-2900 cm-1 | C-H stretch (sp3 carbons) |
1720 cm-1 | C=O stretch |
1200 cm-1 | C-O stretch |
1H-NMR Data:
Chemical Shift | Integration | Multiplicity | Assigment |
5.00 ppm | 1H | m | >CH-OR |
2.30 ppm | 1H | m | >CH-C=O |
1.70 ppm | 1H | m | -CH2-CH3 |
1.40 ppm | 1H | m | -CH2-CH3 |
1.25 ppm | 6H | d | CH3-CH |
1.10 ppm | 3H | d | CH3-CH |
0.80 ppm | 3H | t | CH3-CH2 |
Using all data, we get the structure of compound C8H16O2 as
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