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9. Propose a structure for a molecule that has the following H NMR spectrum and a molecular formula of C3H30. The peak at 2.

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Answer #1

The compound is saturated and can be an alcohol(-OH) , as the -OH proton is labile with D2O and gets exchanged . The resonance of -OH proton also occurs in the region 2- 5 ppm.

Thus we can say the compound is isopropanol CH3-CH(OH) -CH3

From the 1HNMR

we see both the -CH3 as doublet at 1.1 ppm,

the middle CH , is seen as a heptet at 4.0 ppm(deshielded due to the attached -OH)

and the oH proton at 2.2ppm that disappears on addition of D2O.

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