Question

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.)

Answer 1

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