Synthesis of Cis-Norbornene-5, 6-Endo-Dicarboxylic Anhydride

IntroductionThe Diels-Alder reply is a 4+2 cycloaddition of a conjugated diene and a dienophile. This persona of answer was named for Otto Diels and Kurt Alder who were the first to check into this chemical reaction (Weldegirma, 2012). The Diels- Alder reaction is sensation of the most important reactions in either of organic chemistry because of the applicability of it. This reaction bath form innovative carbon-carbon bonds and modern stereocenters.The Diels-Alder reaction has high synthetic service for making unsaturated 6-membered go (Kahn, 2011). The more electron-withdrawing elements there are in the reactants, the faster the reaction will hightail it forward. In the case of cyclopentadiene and maleic anhydride, the reaction takes get into quite quickly collect to the numerous electronegative oxygen present in both reactants.MechanismSide Reaction data-basedT able-bodied of Chemicals CyclopentadieneMaleic AnhydrideEthyl ethanoateHexane66.10 g/mol 98.06 g/mol 88.11 g/mol 86.18 g/mol MP -90 C BP 39-43 C MP 52.8 C BP 202 C MP -83.6 C BP 77.1 C MP -9694 C BP 68-69 C Cyclopenta-1,3-diene Furan-2,5-diene Ethyl Acetate HexaneResultsThe crystals obtained through the Diels-Alder reaction were not plate-like, as were expected. We obtained crystals that were a small and more powdery than plate-like. Even though our crystals did not develop out as we had hoped, the resolve straits range for our crystals was very nasty to the literary productions repute.The calculations for the percent outturn are as follows First, the moles of the reactants must be calculatedthrough and through these calculations we can see that the cyclopentadiene is the limiting reagent is the cyclopentadiene because the reaction between cyclopentadiene and maleic anhydride is a 11 reaction. Thus, the maximum amount of moles of cis-Norbornene-5, 6-endo-dicarboxylic anhydride we can put out isNow that the speculative yield has been calculated, we can compare the experimental y ield with the theoretical yieldDiscussionThe literature value for the thawing point of cis-Norbornene-5,6-endo-dicarboxylic anhydride is 165 C. The experimental value we obtained through the Diels- Alder reaction was 160- 163 C. We were totally able to produce a yield of 20.2%. A yield this low was not expected, but was enough to measure the thaw point to see if we had indeed produced cis-Norbornene-5, 6-endo-dicarboxylic anhydride.As cyclopentadiene is odd out over a distributor point of a few days, the molecules slowly dimerize and thusly become dicyclopentadiene. Dicyclopentadiene would not result in the desired product, cis-Norbornene-5, 6-endo-dicarboxylic anhydride, so this must be remedied. In order to un- dimerize dicyclopentadiene, it must be heated to just under its simmering point to make fresh cyclopentadiene. With our melting point being so close to the literature value for cis-Norbornene-5, 6-endo-dicarboxylic anhydride, it is very in all likelihood that the desi red product was obtained.This reaction does not seem to be very cost-efficient at all. By using 0.2mL of cyclopentadiene, we only were able to produce about 0.05g which, at a 20.2% yield, is very low.ConclusionThe Diels- Alder reaction is one of the most important types of reactions in organic chemistry (Weldegirma, 2012).This reaction is so important because of its ability to form new carbon-carbon bonds.Diels- Alder reactions are used eer in the medical field due to its diverse uses. It has been in studies of ribozymes and creating ribozymes synthetically (Jaschke, 2000).I call up that we did accomplish what we set out to do in this lab. We were able to form cis-Norbornene-5, 6-endo-dicarboxylic anhydride crystals and were able to achieve a very sensitive product.