Question

During the past two semesters, we have talked about infrared spectros-

copy (IR), 1H-NMR spectroscopy, 13C-NMR spectroscopy, and Mass spec-

trometry (MS). We've also talked about using information gathered from

the mass spectrum to generate a molecular formula and the index of hydro-

gen deficiency which helps us determine information about our compound

when there isn't any available.

The moment has come in which we piece all of these together. There are

8 problems in this chapter; each problem comes with an IR, both H- and

C-NMR spectra, and a mass spectrum. With this information, you need to do

the following for each problem:

• Identify all major functional groups in the IR spectra

• Identify all peaks in 1H'- and 13C-NMR spectra

• Identify the molecular mass of the unknown from the mass spectrum

• Determine the pattern of fragmentation from the mass spectrum

• Generate a molecular formula

• Determine the Index of Hydrogen Deficiency

° Determine the structure of the unknown compound

Spectroscopic Analysis 200 180 160 10 120 00 0 4020 11 0 ppmm L00 1000 100 80 60 40 20 10 15 20 25 30 35 40 45 50 5S 60 65 70 75 m/z