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Economine Synthesis Lab Report

579 Words3 Pages

In this experiment, 1,2-diphenylacetylene was synthesized from trans-stilbene via bromination reaction using the "greener" reaction of HBr and hydrogen peroxide followed by elimination reaction involving potassium hydroxide. The theoretical yield of stilbene-dibromide due to the bromination of trans-stilbene was calculated to be 2.0519 grams, with 1.4797 grams recovered experimentally, for a 72.1% yield. The theoretical yield of 1,2-diphenylacetylene due to an elimination reaction involving KOH was found to be 1.07547 grams using 1.4598 grams of recrystallized stilbene dibromide. The percent yield based on the recovered 0.9221 grams was calculated at 85.7%. Bromination is the process by which two bromines are added across an alkene anti …show more content…

The bromination preformed had a theoretical yield of 2.0519 grams, 1.4797 grams of crude stilbene dibromide were recovered for a 72.1% yield. The product was then recrystallized from the ethyl acetate for a final weight of 1.4598 grams. The calculated Rf values were 0.6363 for stilbene dibromide and 0.5454 for the more polar trans-stilbene. TLC analysis showed a small amount trans-stilbene was still present, however, purity was sufficient enough to proceed with synthesis. Melting point analysis was preformed and showed impurities were present as the mixed melting point was broadened and decreased from its 236.3°C in the pure sample to 228°C in the recovered. IR confirmed some impurities were present as peaks were still present in the C=C double bond area around 1600 cm-1 to 1680 cm-1. Peak at 625.81 cm-1 is indicative of a C-Br bond showing the bromination was successful. Based on 1.4598 grams of recrystallized stilbene dibromide the theoretical yield of the target 1,2-diphenylacetylene was found to be 1.0754 grams. With 0.9221 grams recovered the % yield was an acceptable 85.7%. Impurities after bromination may have been due to some HBr not forming into Br2 or due to the presence of remaining water. Some product may have been lost due during vacuum filtration. Based on

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