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Economine Synthesis Lab Report

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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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The relative reactivity was found by setting the reactivity per hydrogen of 1,4-dichlorobutane to 1.0. As shown in Figure 4, 1,3 dichlorobutane had the highest yield of 48% and the highest relative reactivity of 3. This is because it replaced the C-H bond that was furthest from the chloro substituent and formed a stable secondary intermediate. Next, 1,4-dichlorobutane had the second highest yield of 24%, but the third lowest reactivity of 1.0. Even though it was the furthest C-H bond from the chloro substituent, it formed a less stable primary radical intermediate.

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Experiment 12: Dehydrobromination Discussion In this experiment, a double elimination reaction was performed on meso-stilbene dibromide, to form diphenylacetylene by eliminating two hydrogen and two bromine atoms in he presence of potassium hydroxide. The product was filtered and identified by comparing melting point data, and percent yield was calculated. Since an E2 reaction was performed in this experiment, the ideal conformation for the hydrogen and bromine would have been anticoplanar. However, since the phenyl groups were bulky and the atom was not symmetric, the hydrogen and bromine could at best be antiperiplanar.

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These tests were the silver nitrate test and the sodium iodide test. The goal of these tests was to verify that 1-bromobutane, a primary alkyl halide, had in fact been formed. Data and Results 0.844 grams of product were collected. As 1-bromobutane has a molecular weight of 137.02 grams/mole, this gives 0.00616 moles of 1-bromobutane. The limiting reagent in this reaction

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Camphor is produced by oxidizing a secondary alcohol, isoborneol, into a ketone. The melting point of the product was experimentally determined to be 169°C. Comparing 169°C litature value of 174-179°C, it can be assumed that the product was not completely purely.1 To improve purity, procdure could be examined. Allowing the reaction more time to occur, along with more through filtering may increasing purity. Additionally, the heating during sublimation could be done slowly inorder not to burn the product.

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Test such as Bromination, IR spectroscopy, refractive index, and measures physical properties confirmed that the product collected was the desired product, cyclohexene. A bromination

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By looking at our results, even though my partner and I didn’t obtain a high percent recovery for the unknown, we were still able to identified our unknown to be Acenapthene. We know that our unknown B8 is Acenapthene because of its melting range and its color. The unknown B8 was similar to the color of Acenapthene, and the mixed compound (Acenapthene and the recrystallized compound)’s melting range was close to Acenapthene’s literature melting range. With these two points, my partner and I believed our unknown B8 to be Acenapthene. According to our recrystallized vanillin, we know that our vanillin was pure because of its melting range.

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The goal of the experiment is to synthesize a bromohexane compound from 1-hexene and HBr(aq) under reflux conditions and use the silver nitrate and sodium iodide tests to determine if the product is a primary or secondary hydrocarbon. The heterogeneous reaction mixture contains 1-hexene, 48% HBr(aq), and tetrabutylammonium bromide and was heated to under reflux conditions. Heating under reflux means that the reaction mixture is heated at its boiling point so that the reaction can proceed at a faster rate. The attached reflux condenser allows volatile substances to return to the reaction flask so that no material is lost. Since alkenes are immiscible with concentrated HBr, tetrabutylammonium bromide is used as a phase-transfer catalyst.

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554 Words | 3 Pages

According to the results, the isoborneol was able to oxidized to the ketone, camphor. The melting point of the product from the sublimation can be determined to be purified camphor. One can potentially be concluded that the camphor was synthesized but since isoborneol can also be sublimes in elevated temperatures, the camphor product may contain some residual isoborneol affecting the final melting point to be higher than expected. Conclusion

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1125 Words | 5 Pages

This was proved by utilizing the IR spectrum to verify the C =O was not in the final product as it lacked the 1640 cm-1 peak. The melting point of 113-115 degrees C proved that the final product obtained was the E-Stilbene. The TLC plate proved that the E and the Z product was produced, show cased by the double intensity of the DCM spot to the final product’s spot, both which had an Rf of 0.92. The double intensity proved that both products were produced, but through heating and filtering, the Z-Stilbene was

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