Procedure: Place 6.2 mL of 1-butanol into a 100 mL round bottom flask. Add 10 mL of 48 % hydrobromic acid (HBr) to the flask with swirling. Slowly, cautiously, and with swirling, add 4 mL of concentrated sulfuric acid (H₂SO4) to the flask. If the flask gets extremely hot, cool it in an ice bath. Add 1-2 boiling chips to the flask and connect a reflux condenser to the top of the round bottom flask. Connect the water hoses to the condenser (water goes in the bottom nozzle, out the top nozzle). Since some noxious fumes may be generated during the heating period, connect a vacuum connecting tube to the top of the condenser. Leave the ground glass joint open, and connect a vacuum hose to the gas outlet of the connecting tube. Be sure that the other end of the vacuum hose is connected to the SINK aspirator (via the trap) and turn the aspirator water on full blast. Feel for a slight suction when you place one of your fingers over the open joint of the vacuum connecting tube. Once the apparatus is connected and the sink aspirator is working correctly, heat the reaction mixture at reflux for 45 minutes. During the reflux period, perform EXPT. SB, Syl reaction rate studies. Allow the flask and its contents to cool to almost room temperature (cooling in an ice bath is acceptable). Slowly, carefully and with swirling, add 10 mL of de-ionized water to the mixture by pouring it through the condenser. Add a new boiling chip (or two) and convert the apparatus to a simple distillation apparatus (disconnect the vacuum). Distill the contents of the flask into a 25 mL round bottom flask which has been immersed in an ice bath. Stop distilling when the temperature of the distillate reaches 100°C. Remove the aqueous layer from the distillate using a transfer pipet. DO NOT THROW ANYTHING AWAY UNTIL YOU GET VERIFICATION OF PRODUCT BY IR SPECTROSCOPY!!! Add 5 mL of de-ionized water to the organic layer of the distillate, mixing well with the transfer pipet. Separate the aqueous layer from the organic layer. Combine the aqueous layer with the original aqueous layer. Wash the organic layer with 5 mL of 5% sodium bicarbonate solution, again separating the layers and combining the aqueous layers in a "waste flask". Wash the organic layer once more with 5 mL of de-ionized water, separating the layers and combining the aqueous layer with the other aqueous washes. Dry the organic layer over anhydrous sodium sulfate. Decant or pipet the dry organic layer into a clean, dry, pre- weighed sample bottle (with a cap). Weigh the product and run an IR spectrum on the product. Calculate the % yield of the reaction.