Introduction
In 1950 the Nobel Prize for Chemistry was awarded to Otto Diels and Kurt Alder for their description of an invaluable chemical reaction (The Nobel Prize in Chemistry 1950). The reaction they described was for the formation of carbon-carbon bonds in a six membered ring with exceptional control of its stereochemistry in one step (Diels-Alder Reaction Gains Nobel Prize). This was an important discovery due to the fact that six membered rings are abundant natural products and man-made products. Several new compounds were synthesized as a result of the Diels-Alder reaction including: Reserpine, Cholesterol, Gibberellic acid, and various other organic compounds. Diels-Alder is an important reaction due to the fact that it is the easiest …show more content…
It is also important to note that the rate of the reaction is determined by the conformational exchange that takes place with the diene. This means that s-trans confirmation of a diene will never undergo a Diels-Alder reaction because the two terminal carbon atoms are far apart making any overlap between the diene and dienophile pointless. However, with the diene in s-cis conformation it is possible for the reaction to take place. Due to this when given a diene that is in s-trans conformation it is necessary that rotation occurs, and it is more favorable for the overall reaction is fixated in the s-cis conformation takes place (Clevenger, …show more content…
Anthracene (0.420 g, 2.36 mmol) was dissolved in a soln of isoamyl nitrite (0.4 mL, 0.5 g, 4 mmol) and glyme (4 mL) then placed into a large reaction tube with a boiling chip and heated to reflux in a sand bath. In another reaction tube anthranilic acid (0.540 g, 3.94 mmol) was dissolved in glyme (2 mL) then added dropwise into the refluxing soln over a 20 min period via a septum. Isoamyl nitrite (0.4 mL, 0.5 g, 4 mmol) was added, after which the soln was allowed to reflux for an additional 10 min. The soln was cooled and then ethanol (5 mL) and sodium hydroxide (10 mL) were added. The mixture was filtered and rinsed with cold ethanol and cold water to remove its brown color and a crude weight was taken (0.238 g, 0.936 mmol) The resulting solid was placed into a 25-mL round bottomed flask along with maleic anhydride (0.245 g, 2.50 mmol) and triglyme (4 mL). Then, the flask was fitted with a reflux condenser and refluxed in a sand bath for 5 min. The soln was cooled and had ethanol (2mL) and sodium hydroxide (6 mL) added. The resulting mixture was filtered and the solid was rinsed with cold ethanol and cold water to once again remove the brown color. Methanol was then used to recrystallize the resulting white solid (0.065 g, 0.256 mmol,
In 1950 the Nobel Prize for Chemistry was awarded to Otto Diels and Kurt Alder for their description of an invaluable chemical reaction (The Nobel Prize in Chemistry 1950). The reaction they described was for the formation of carbon-carbon bonds in a six membered ring with exceptional control of its stereochemistry in one step (Diels-Alder Reaction Gains Nobel Prize). This was an important discovery due to the fact that six membered rings are abundant natural products and man-made products. Several new compounds were synthesized as a result of the Diels-Alder reaction including: Reserpine, Cholesterol, Gibberellic acid, and various other organic compounds. Diels-Alder is an important reaction due to the fact that it is the easiest …show more content…
It is also important to note that the rate of the reaction is determined by the conformational exchange that takes place with the diene. This means that s-trans confirmation of a diene will never undergo a Diels-Alder reaction because the two terminal carbon atoms are far apart making any overlap between the diene and dienophile pointless. However, with the diene in s-cis conformation it is possible for the reaction to take place. Due to this when given a diene that is in s-trans conformation it is necessary that rotation occurs, and it is more favorable for the overall reaction is fixated in the s-cis conformation takes place (Clevenger, …show more content…
Anthracene (0.420 g, 2.36 mmol) was dissolved in a soln of isoamyl nitrite (0.4 mL, 0.5 g, 4 mmol) and glyme (4 mL) then placed into a large reaction tube with a boiling chip and heated to reflux in a sand bath. In another reaction tube anthranilic acid (0.540 g, 3.94 mmol) was dissolved in glyme (2 mL) then added dropwise into the refluxing soln over a 20 min period via a septum. Isoamyl nitrite (0.4 mL, 0.5 g, 4 mmol) was added, after which the soln was allowed to reflux for an additional 10 min. The soln was cooled and then ethanol (5 mL) and sodium hydroxide (10 mL) were added. The mixture was filtered and rinsed with cold ethanol and cold water to remove its brown color and a crude weight was taken (0.238 g, 0.936 mmol) The resulting solid was placed into a 25-mL round bottomed flask along with maleic anhydride (0.245 g, 2.50 mmol) and triglyme (4 mL). Then, the flask was fitted with a reflux condenser and refluxed in a sand bath for 5 min. The soln was cooled and had ethanol (2mL) and sodium hydroxide (6 mL) added. The resulting mixture was filtered and the solid was rinsed with cold ethanol and cold water to once again remove the brown color. Methanol was then used to recrystallize the resulting white solid (0.065 g, 0.256 mmol,