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A new chemist moved into an industrial lab where work was being done on oxygenated gasoline additives. Among the additives that had been tested, she found an old bottle containg a clear, pleasant-smelling liquid that was missing its label. She took a quick 1h nmr spectrum (shown below) and was able to determine the identity of the compound without any additional information. Propose a structure for this compound. (hint: this is a very pure sample.)

User Eladio
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solution:

The given specta of the unknow compound of the additive gasoline in the pure state are determined from the given spectral data is


\delta 0.9 triplet Area=3H\\</p><p>\delta 1.5 sextet area=2H\\</p><p>\delta 3.2 triplet,area =1H\\</p><p>\delta 3.5 quartert,area=2H\\</p><p>form the above spectral data the structure of the compound is\\</p><p>(3.5,q)(3.2,t)\\
</p><p>CH_(3)---CH_(2)---CH_(2)---OH\\</p><p>As the compound is very sample so there is interaction between the alcoholic proton and methylene proton.

User Alexander Lucas
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