Diels-Adler Reaction Essay

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Abstract Otto Diels, Professor of Chemistry at the University of Kiel, Germany, and his student Kurt Alder published a paper in 1928 on additions of electron-poor alkenes and alkynes to electron-rich dienes to form cyclohexenes and cyclohexadienes. These [4+2] cycloadditions came to be known as Diels-Alder reactions. The Diels-Alder reaction is one of the most useful synthetic reactions in organic chemistry. In one step the reaction forms a six-membered ring with one or two double bonds forming an open-chain compound. A diene is the 4-pi-electron component. It is electron-rich. The 2-pi-electron component is called a dienophile. Dienophile contain relatively electron-poor double bonds. Because the reaction is concerted, bond breaking and bond forming take place in the same step- the stereochemistry of the reactants and the symmetry of their molecular orbitals control the stereochemistry of the products. Using well-chosen reactants a chemist can control the stereochemistry of a Diels-Alder product at up to four carbon atoms. (L.G. Wade Jr., Whitman College). The technique used for the Diels-Alder synthesis of cis-5-norbornene-2,3-endo-dicarboxylic anhydride is done by putting 5.00 grams of maleic anhydride (CAUTION Corrosive, toxic) in a 125 mL Erlenmeyer flask and adding 20 mL of ethyl acetate (CAUTION flammable) and heating it up on a hot plate until the maleic anhydride is dissolved. Allow the maleic anhydride to cool to room temperature, after cooling add 5 mL of fresh distilled anhydrous cyclopentadiene.( CAUTION flammable) The cyclopentadiene must be freshly distilled (cracked) from dicyclopentadiene and dried over CaCl2. Swirl the solution until the exothermic reaction subsides and the product precipitates as a color-less solid. Recrystallize the product by heating it on the hot plate until all the solid has dissolved remove
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