Solved Problems Employing IR and NMR Spectra

Most structure determination problems that are encountered in real-life situations in the laboratory rely on a combination of these spectral methods for solution. A general strategy that is often successful is as follows  

Step 1. Calculate the degree of unsaturation if the formula is available. 

Step 2. Examine the IR spectrum to determine the functional group. Do not 

Although the H-NMR spectrum has not provided much helpful information in this case, the nC-NMR spectrum is quite useful. The spectrum has only four peaks, indicating that the compound has symmetry. There are probably two carbons of each type. 

There are three CH2 groups and one CH3 group. These fragments can be assembled only into a butyl group. This group is attached to a nitrogen. The carbons closer to the nitrogen are shifted farther downfield  

---