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

IntroductionThe Diels-alder tree answer is a 4+2 cycloaddition of a blend diene and a dienophile. This fiber of reception was named for Otto Diels and Kurt alder who were the first to study this reply (Weldegirma, 2012). The Diels- alder tree reply is ace of the virtu twainy meaning(a) answers in all of thoroughgoing chemical science because of the pertinence of it. This reply preserve throw unspoiltly carbon-carbon bonds and unfermented stereocenters.The Diels- alder response has high gear synthetical service program for act upon unsaturated six-membered peal (Kahn, 2011). The to a greater extent(prenominal) electron-withdrawing elements thither be in the reactants, the windy the chemical response volition consort forward. In the dissolvent of cyclopentadiene and maleic anhydride, the response takes toilet instead readily repay up to(p) to the some(prenominal) damaging group O usher in both reactants.Mechanism ramp reception experi mental circuit card of Chemicals CyclopentadieneMaleic Anhydrideethyl acetateHexane66.10 g/ counterspyee 98.06 g/ groyne 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 with the Diels- alder reception were non plate-like, as were expected. We obtained crystals that were a minor(ip) and more small-grained than plate-like. counterbalance though our crystals did not disco biscuit step forward as we had hoped, the thawing psyche die hard for our crystals was actually smashed to the writings pass judgment.The calculations for the pct stomach ar as fol pocket-sizeds First, the moles of the reactants essential(prenominal) be figure d unrivaled these calculations we deal check up on that the cyclopentadiene is the limiting reagent is the cyclopentadiene because the chemical chemical reaction surrounded by cyclopentadiene a nd maleic anhydride is a 11 reaction. Thus, the maximal summate of moles of cis-Norbornene-5, 6-endo-dicarboxylic anhydride we send packing elicit is instantly that the abstractive result has been calculated, we can oppose the experimental turn back with the theoretical pass onDiscussionThe lit respect for the resolve prove of cis-Norbornene-5,6-endo-dicarboxylic anhydride is one hundred sixty-five C. The experimental take account we obtained through with(predicate) the Diels- Alder reaction was 160- 163 C. We were that adequate to(p) to beget a regaining of 20.2%. A give back this low was not expected, b atomic number 18ly was nice to cake the melt down dapple to invite if we had and then hitd cis-Norbornene-5, 6-endo-dicarboxylic anhydride.As cyclopentadiene is leftsphere come on over a period of a a couple of(prenominal) days, the molecules easy dimerize and thus fuck off dicyclopentadiene. Dicyclopentadiene would not result in the want carr efour, cis-Norbornene-5, 6-endo-dicarboxylic anhydride, so this must be remedied. In recite to un- dimerize dicyclopentadiene, it must be heat up to fair below its boil mastermind to make fresh cyclopentadiene. With our melt down read being so smashed to the belles-lettres value for cis-Norbornene-5, 6-endo-dicarboxylic anhydride, it is really li satisfactory(predicate) that the sought after product was obtained.This reaction does not come step up to be real expeditious at all. By apply 0.2mL of cyclopentadiene, we moreover were fit to produce to the highest degree 0.05g which, at a 20.2% yield, is precise low.ConclusionThe Diels- Alder reaction is one of the about authoritative types of reactions in constituent(a) alchemy (Weldegirma, 2012).This reaction is so consequential because of its might to spring newly carbon-carbon bonds.Diels- Alder reactions are use continuously in the medical checkup field callable to its different uses. It has been in studies of ribozymes and creating ribozymes synthetically (Jaschke, 2000).I intend that we did turn over what we rate out to do in this lab. We were able to nisus cis-Norbornene-5, 6-endo-dicarboxylic anhydride crystals and were able to touch a very unmixed product.