Chapter 19, Problem 19.53SP

A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. The barrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample, which she takes to her laboratory for analysis.

The mass spectrum shows a molecular ion at m/z 101, and the most abundant fragment is at m/z 86. The IR spectrum shows no absorptions above 3000cm−1, many absorptions between 2800 and 3000cm−1, no absorptions between 1500 and 2800cm−1, and a strong absorption at 1200cm−1. The proton NMR spectrum shows a triplet (J=7Hz) at δ1.0 and a quartet (J=7Hz) at δ2.4, with integrals of 17 spaces and 11 spaces, respectively.

1. a. Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.
2. b. Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers. Propose an inexpensive method for converting this waste to a solid, relatively odorless form for reburial.
3. c. Suggest how the chemist can remove the fishy smell from her clothing.