III.

Discussion & Conclusion In this lab, Dicyclopentadiene was used as the diene source to react with maleic anhydride (our dienophile) to give the Diels-Alder product, endo-s-norborneneendo-2,3-dicarboxylic anhydride (the reaction and structure are given in the attached data sheet). First of all we had to run a fractional distillation on the dicyclopentadiene dimmers to make monomers of cyclopentadienes to be able to perform the reaction. The distillate containing cyclopentadienes were collected in an ice/water bath in order to avoid any dimerizations at the higher temperatures. Then the monomer was reacted with maleic acid & ethyl acetate solution in the presence of petroleum ether. The precipitated crystals were separated from the solution using a vacuum filter and the % yield of the reaction was calculated after measuring the weight of the obtained crystals. The purity of the product and the success of the reaction were obtained through measuring the melting point and performing a KMnO4 reaction test respectively. After addition of the distillate (our monomer) to maleic acid, a white precipitate started to form. The formation of the crystals was continued for a couple of minutes by swirling the flask in the ice/water bath. The percent yield was calculated as 57.44% as it is shown in the attached data sheet. The melting point range of the obtained crystals was calculated as 157-158C. And the crystals turned the color of the magnesium permanganate from purple to dark brown. The reason we couldnt reach 100% yield in this experiment could be due to several errors. One could be loosing of the crystals while transferring from solution to the vacuum filter since we could not transfer all the crystals successfully. The other reason is that the reaction was not proceeded completely to the right (product side) because of dimerization of cylopentadienes, which prevents these monomers to react with maleic acid. However, maleic acid would readily react with the monomers and win the competition if it was present in the proper amount in the reaction. So low quantity of maleic acid would be the other reason for not reaching the 100% yield. The measured melting point of 157-158C, which is very close to the theoretical MP of this product (156C) indicates that the product is almost pure. The color change of KMnO4 from purple to brown shows the presence of double bonds, which could be due to cyclopentadiene or the product.

IV. Questions 1. Give an explanation for the following statements; a. Cyclopentadiene dimerizes more readily than acyclic dienes This is because the two double bonds in the cyclopentadiene are held in the s-cis configuration and this configuration makes it so reactive that it goes through a Diels-Alder reaction with the double bond of another cyclopentadiene in room temperature and creates a dimmer. On the other hand, the acyclic dienes are not usually in the s-cis form and should be forced to configure in s-cis form; therefore, they wont dimerize readily.

b. Cyclopentadiene reactions more readily with maleic anhydride than with another molecule of cyclopentadiene. The presence of two very electronegative oxygens on the maleic anhydride structure makes the double bond more reactive than the double bond in the cyclopentadiene. Therefore, the double bond in maleic anhydride reacts more readily than the double bond of the cyclopentadiene. 2. Predict the major Diels-Alder product of the following reaction, make sure to indicate stereochemistry.
H

3. Identify the diene and dienophile that would yield the following Diels-Alder adduct.
O