• C 3 H 4 O Practice Problem 1

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

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

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

• 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 5

You are complete?

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

Propose a structure consistent with the following IR spectrum and molecular formula 7 C 7 H 6 O

• 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

Propose a structure that is consistent with the following data: Mass spec shows a molecular ion at m/z = 69 9

Propose a structure that is consistent with the following data: Mass spec shows a molecular ion at m/z = 98 10