The chemistry department custodian was cleaning the organic lab when an unmarked bottle fell off a shelf and smashed on the floor, leaving a puddle of volatile liquid. The custodian began to wipe up the puddle, but he was overcome with burning in his eyes and a feeling of having an electric drill thrust up his nose. He left the room and called the fire department, who used breathing equipment to go in and clean up the chemical. Three students were asked to identify the chemical quickly so the custodian could be treated and the chemical could be handled properly. The students took IR and NMR spectra, which follow. The UV spectrum showed λmax at 220 nm (ε = 16,000). The mass spectrometer was down, so no molecular weight was available. Determine the structure of this nasty compound, and show how your structure fits the spectra.

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wavelength (m) 5 5.5 6 2.5 100 3.5 4 4.5 7 8 9 10 11 12 13 14 15 16 Problem 18-70 3000 2000 1800 1600 1400 1200 1000 800 wavenumher (cm 500 400 200 100 60 MHz NMR spectrum 18-70 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 L.O (ppm)