Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Submitted: April 4th, 2013
The overall goal of this experiment is to understand and be familiar of SN1 reactivity. We also learned how to prepare 2-Bromobutane by learning how to distill and extract this product from its organic layer. Finally, another goal was to specifically understand the relative reactivity of alkyl halides under SN1 conditions by reacting the alkyl halide and silver nitrate in ethanol.
Results and Discussion
The Overall Reaction
The Proposed Mechanism
To prepare the 2-Bromobutane you must fill a 100 mL round bottom flask with 20 mL of 12M sulfuric acid and 7.4 mL of 2-butanol. Then add 8.0 g of ammonium bromide along with a magnetic stir bar. Then attach the flask to the apparatus, which is mounted on a Thermowell over a stirrer and a condenser attached to it, along with the thermometer in the flask. Then the mixture was heated at 90oC then kept at the range of 90oC-100oC for 30 minutes. When that is completed add 20 mL of water into the flask to perform a simple distillation to collect the distillate in a graduated cylinder, keep doing this until there is no more 2-Bromobutane collected. Use a Pasteur pipette to draw off the organic layer to another container. Add the potassium carbonate to allow the liquid to dry by swirling it.
Once this is completed the reactivity of alkyl halides under SN1 conditions was tested. Adding two drops of our product and the other different compounds into different test tubes along with 1mL of ethanolic silver nitrate reagent. We are comparing these by seeing how they react and if there is no reaction after 5 minutes we will place the test tubes in a beaker of water that is heated at a temperature of 70oC-80oC and observe what happens.
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