The purpose of this lab is to form 4-cyclohexene-cis-1,2-dicarboxylic anhydride using 3sulfolene and maleic anhyride using microscale reflux.

The product was then characterized by using the melting point set up and IR. The Diers-Alder Reaction is a thermal reaction that forms six-membered rings from a diene and a dienophile. The dienophile (almost any non-conjugated alkene) reacts with the cisdiene (alkene that contains two conjugated pi bonds) through a [4+2] pi cycloaddition. In this addition, the 3 pi bonds of the diene and dienophile are broken, and the six- membered ring is then created when 2 sigma and 1 pi bond is formed from the 6 electrons of the 3 pi bonds broken. The Diers-Alder Reaction occurs as a single step mechanism, occurs only if the diene is in the cis conformation, and proceeds the quickest when the dienophile has more electron- withdrawing substituents. The mass of the 3-sulfolene reactant was that of 0.408g, and the mass of the maleic anhydride reactant was 0.181g. Based of the mass on the reactants, it was determined that the maleic anhydride was the limiting reactant, and since it was the limiting reactant, the theoretical mass of the product was calculated to be 0.281g. The experimental mass of the product, 4- cyclohexane-cis-1,2-dicarboxylic anhydride, was 0.183g. The percent yield was calculated using the equation: [experimental mass/ theoretical mass] * 100%. From the equation, it was determined that the percent yield of the product was 64.9%. The melting point of the product was between 92.0 to 96.0 degrees Celsius. However, the theoretical melting point of 4-cyclohexane- cis- 1,2- dicarboxylic anhydride was 103 degrees Celsius. This lowered melting point indicates impurites in the compound, either from unreacted reactants or from contamination. The IR obtained for the product showed two peaks, a large one at 1760cm-1, and a smaller one at 1830cm-1. These peaks corresponded to the theoretical IR bands, which called for 2 carbonyl peaks between 1880cm-1 and 1780cm-1 to be observed, and indicated the purity of the product obtained. Several sources of error occurred throughout the experiment. Firstly, the transfer of product from the conical vial to the Hirsch funnel resulted in some products left behind in the vial as the spatula could not fully transfer some of the products left in the bottom of the vial. This loss of product would account for the decreased percent yield. Secondly, despite the vacuum filtration, there might have been some water left in the product to contribute to its mass and therefore resulting in a falsely inflated theoretical yield. Lastly, there was contamination from the spin vane used, resulting in the product obtained being slightly brown rather than clear as it was supposed to be. This contamination from the spin vane might have resulted in the lower and broader melting point of 92.0 - 96.0 degrees Celsuis observed, rather than that of the theoretical 103 degrees Celsius.