Spectroscopy Homework Student Name_________________________

The following homework packet contains 27 problems. Your assignment is to do 10 of these.

• Problems 1-6 (parts A, B, and C): Do either all of the A problems, or all of the B problems, or all of the C problems, as assigned by your TA.

• Problems 7-15: Do any four of these problems. Turn in only the pages for the problems you choose to do, but make sure your name is on the front of the pages you turn in! For each problem, you must: 1) Calculate the degree of unsaturation. 2) Assign the principal IR absorption bands above 1500 cm-1 3) Draw the structure of the compound 4) Label the protons on your structure with letters and assign them to peaks on the NMR spectrum

(see the example below).

Each problem contains the formula of the compound, the IR spectrum (with axes in cm-1 vs. % transmission), and the 1H NMR spectrum (with axis in PPM shift). Some NMR spectra show a peak hovering above the baseline. This is a magnified view of one of the actual peaks, to allow you to see splitting more clearly.

1A: C5H10O

1B: C7H14O

1C: C7H14O

2A: C5H12O

2B: C3H8O

2C: C5H12O

3A: C6H12O2

3B: C7H14O2

3C: C5H10O2

4A: C9H21N

4B: C6H15N

4C: C6H15N

5A: C7H6O2

5B: C8H8O2

5C: C8H8O

6A: C8H8O3

6B: C11H14O2

6C: C7H6O3

7: C5H8O4

8: C9H16O3

9: C11H14O2

10: C4H9NO

11: C6H10

12: C6H14O2

13: C9H11Cl

14: C4H6O2

15: C10H10O2