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Photobromination of Toluene Procedure: 500 mL of toluene was added to a 2 liter beaker and equipped with a magnetic stir bar. The beaker was placed atop a stir plate and stirring commenced. . A high intensity UV light source was placed inside the beaker and secured to a ring stand using a clamp. The exterior of the UV light bulb was in direct contact with the toluene solution. • 50 mL of liquid bromine, Br₂, was added to the beaker causing the solution to change from colorless (before Br2 was added) to a dark orange color. With the entire assembly located inside a fume hood, the UV light source was turned on. Over the course of 10 minutes, the color of the solution changed from dark orange to light orange to colorless, after which time the UV light source was tuned off. During the reaction, gaseous fumes were observed to emanate from the beaker. These fumes turned wetted pH paper red. As the solution slowly turned colorless, the formation of these fumes slowed and then eventually stopped. . The reaction mixture was transferred to a 1 L round bottom flask and a simple distillation apparatus was assembled.
Photobromination of Toluene Procedure: 500 mL of toluene was added to a 2 liter beaker and equipped with a magnetic stir bar. The beaker was placed atop a stir plate and stirring commenced. . A high intensity UV light source was placed inside the beaker and secured to a ring stand using a clamp. The exterior of the UV light bulb was in direct contact with the toluene solution. • 50 mL of liquid bromine, Br₂, was added to the beaker causing the solution to change from colorless (before Br2 was added) to a dark orange color. With the entire assembly located inside a fume hood, the UV light source was turned on. Over the course of 10 minutes, the color of the solution changed from dark orange to light orange to colorless, after which time the UV light source was tuned off. During the reaction, gaseous fumes were observed to emanate from the beaker. These fumes turned wetted pH paper red. As the solution slowly turned colorless, the formation of these fumes slowed and then eventually stopped. . The reaction mixture was transferred to a 1 L round bottom flask and a simple distillation apparatus was assembled.
Look carefully at the 13C NMR spectra shown below. Which one photobromination product of this reaction? corresponds to the B U O 200 D B A 200 180 160 140 A 180 160 140 120 C 120 100 ppm 100 porn 6 signals total 80 60 80 5 signals total, including 3 at about 128 ppm 40 20 60 40 20 0 0 200 180 160 140 D 200 180 160 140 120 120 100 ppm 100 ppm 80 50 5 signals total, including 2 at about 130 ppm 60 40 60 6 signals total, including 2 at about 128 ppm 20 40 -8 0 0