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Synthesis Of Stilbene Dibromide

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Synthesis of an Alkyne: Bromination of Stilbene and Dehydrohalogenation of Dibromide Maya Yagan Fall 2015 Lab Section 355-01 Lab Partner: Kristine Thao Abstract Trans-stilbene (1,2-diphenylethene) was synthesized in a two-step reaction. Trans-stilbene was brominated to give meso-stilbene dibromide in the first reaction. The stilbene dibromide was heated with base in order to induce dehydrobromination. One of the methods used throughout this experiment was vacuum filtration. An 81% yield was obtained due to a few minor errors. The compound seemed to be pure due to the relatively close melting point ranges. Introduction The experiment that was conducted in lab was synthesis of an alkyne. Now, what exactly is an alkyne? An …show more content…

In the first reaction, trans-stilbene was brominated to give meso-stilbene dibromide. In the second reaction, the stilbene dibromide was heated with base to induce dehydrobromination (net loss of HBr) and formation of diphenylacetylene. The purpose of this lab experiment is to carry out the bromination of E-stilbene and characterize the product, meso-stilbene dibromide, by its melting point. In the following experiment, the dibromide is converted into diphenylacetylene. Pyridinium hydrobromide perbromide (PHPB), a crystalline solid which is much less corrosive and easier to handle than liquid bromine was the brominating agent used in this …show more content…

The mixture was warmed in a hot water bath until the solid dissolved and then 1.0 g of pyridinium hydrobromide perbromide was added. With a little acetic acid, the crystals of reagent from the sides of the flask were rinsed and then heated for an additional 1-2 minutes. Immediately, stilbene dibromide precipitated as small plates. Once the mixture has been cooled under tap water, the product was collected by vacuum filtration. Ice cold methanol was used to wash and the isolated solid continued to dry for a few minutes. To achieve maximum drying, the crystals were pressed with a spatula. The yield, percent yield, and melting point of the product was recorded. About 0.8 g of stilbene bromide should’ve been obtained with an expected melting point range of 236℃-237℃. The IR spectrum was obtained and compared to that reported for the pure

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