1. C 3 H 4 O Practice Problem 1

2. 2 m/z = 128 (M) m/z = 113 m/z = 58 m/z = 43

3. 3 m/z = 73 (M) m/z = 58

4. 4 m/z = 150 (M) m/z = 107 m/z = 43

5. 5 Propose structures for compounds that meet the following descriptions: – An optically active compound C 5 H 10 O with an IR absorption at 1730 cm -1 – A non-optically active compound C 5 H 9 N with an IR absorption at 2215 cm -1

6. You are carrying out the dehydration of 1- methylcyclohexanol to yield 1-methylcyclohexene. How could you use IR to determine when the reaction is complete? 6

7. Propose a structure consistent with the following IR spectrum and molecular formula 7 C7H6OC7H6O

8. Nitriles undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the product of hydrolysis of propanenitrile (CH 3 CH 2 CN) if it has IR absorptions at 2500 to 3100 cm -1 (br) and 1710 cm -1 (s) and has a parent peak in MS at 74? 8

9. 9

10. 10