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

IntroductionThe Diels-alder tree reply is a 4+2 cycloaddition of a conjugated diene and a dienophile. This type of reaction was named for Otto Diels and Kurt Alder who were the first to investigate this reaction (Weldegirma, 2012). The Diels- Alder reaction is atomic number 53 of the most important reactions in all of radical chemistry because of the applicability of it. This reaction can form unsanded carbon-carbon bonds and new stereocenters.The Diels-Alder reaction has high synthetic utility for making unsaturated six-membered rings (Kahn, 2011). The more(prenominal) electron-withdrawing elements there are in the reactants, the faster the reaction will move forward. In the case of cyclopentadiene and maleic anhydride, the reaction takes place instead quickly due to the many electronegative oxygen present in both reactants.MechanismSide Reaction ExperimentalTable of Chemicals CyclopentadieneMaleic AnhydrideEthyl acetateHexane66.10 g/ seawall 98.06 g/mol 88.11 g/mol 86.18 g/m ol 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 turn taboo as we had hoped, the melting elevation range for our crystals was very close to the literature esteem.The calculations for the percent acquit are as follows First, the moles of the reactants essential be calculated by dint of 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 introduce isNow that the conjectural yield has been calculated, we can compare the experimental yield with the theoretical yi eldDiscussionThe literature value for the melting 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 only able to produce a yield of 20.2%. A yield this low was not expected, but was tolerable to measure the melting point to see if we had indeed produced cis-Norbornene-5, 6-endo-dicarboxylic anhydride.As cyclopentadiene is left out over a period 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 bonny under its boiling 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 liable(predicate) that the desired product was obtained.This reaction does not seem to be very 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 apply constantly in the medical field due to its diverse uses. It has been in studies of ribozymes and creating ribozymes synthetically (Jaschke, 2000).I believe 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 splendid product.