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Bromination Of Alkene Lab Report

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For this experiment, an addition mechanism for the bromination of an alkene was observed along with studying chirality. The bromination of the substituted alkenes was known as an oxidation reaction and it produced different stereoisomers based on the alkene’s geometry. The E-stilbene when exposed to bromine produced dibromostilbene. Three products can potentially form from this reaction which are meso, D, and L stilbene bromide. The goal of this experiment was to identify which stereoisomer predominated in the reaction and determine the most favored cation intermediate. The first step of the mechanism was to break the alkene pi bond and form a new C-Br bond. When the alkene broke, a secondary carbocation formed. The bromide anion attached to …show more content…

In a round bottom flask, both the E-stilbene and the DCM were added along with a rice stir bar. When stirring the solution containing the bromine, it is safer to place a keck clamp on the top of the round bottom flask and rest the stopper on top, so no solution flies out of the round bottom flask. This prevents sealing to occur and protects against bromine exposure. Sealing is dangerous because DCM is a high vapor pressure and if the system is sealed then this can lead to a pressurized system which is not safe. The stir bar was used to dissolve the solid. Then bromine was also added to the solution. Then the solution was stirred once more for ten to fifteen minutes or until the orange color had mostly disappeared and a white solid had formed in a colorless solution. After this, the precipitate product was isolated and filtered by using a Buchner funnel and was washed with cold DCM to ensure the removal of most of the bromine and any unreacted starting material as well as most of the D/L isomer. Once the product has dried, the weight of the product was recorded and the percent yield. The melting point was also taken to ensure that all of the unreacted starting material along with the D/L isomers had been removed from the

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