DIals Alder
Abstract: The objective of this experiment was to successfully prepare an endo,cis-diacid from the synthesis of the bicyclic anhydride (cis-Norbonene-5,6-endo-dicarboxylic anhydride). The percent yield of the product was calculated and found to be 39.01%. The infrared spectroscopy confirmed the presence of a O-H group with a stretch at 2948.03 1/cm and the presence of C=O with a stretch at 1698.93 1/cm. Melting point determination found the melting point range of the products to be 149.2-164.1 for the bicyclic anhydride and 169.4-179.5 for the endo-cis,diacid.
Introduction:
The Diels-Alder reaction is one of the most powerful tools used in the preparation of important organic molecules. When two carbon-carbon double bonds are positioned next to one another, a conjugated diene is formed. Conjugated dienes undergo a cycloaddition reaction (also called pericyclic addition) with certain double bonds to afford cyclohexenes and related compounds. The reaction of Cyclopentadiene with Maleic anhydride is an example of a Diels-Alder reaction. This reaction forms a six-membered ring from two reagents: a conjugated "diene" (which provides four of the ring atoms) and a "dienophile" (which provides two of the ring atoms). In this case, the dienophile is Maleic anhydride and the diene is cyclopentadiene. The Diels-Alder reaction is facilitated by the presence of electron donating groups (EDG) on the diene and by the presence of electron withdrawing groups (EWG) on the dienophile. For instance, maleic anhydride is a very good dienophile because it contains two highly electron withdrawing carbonyl groups.
Experimental:
To a 100 mL flask, 22 mL of Diclopentadiene was added and arranged for fractional distillation into an ice-cooled receiver. In order for the diene to distill, heat was applied to the dimer with a microburner. Into a 50 ml round bottom flask boiling chips were added before starting the distillation . Within about 5 mins while reaching a steady boiling point
Introduction:
The Diels-Alder reaction is one of the most powerful tools used in the preparation of important organic molecules. When two carbon-carbon double bonds are positioned next to one another, a conjugated diene is formed. Conjugated dienes undergo a cycloaddition reaction (also called pericyclic addition) with certain double bonds to afford cyclohexenes and related compounds. The reaction of Cyclopentadiene with Maleic anhydride is an example of a Diels-Alder reaction. This reaction forms a six-membered ring from two reagents: a conjugated "diene" (which provides four of the ring atoms) and a "dienophile" (which provides two of the ring atoms). In this case, the dienophile is Maleic anhydride and the diene is cyclopentadiene. The Diels-Alder reaction is facilitated by the presence of electron donating groups (EDG) on the diene and by the presence of electron withdrawing groups (EWG) on the dienophile. For instance, maleic anhydride is a very good dienophile because it contains two highly electron withdrawing carbonyl groups.
Experimental:
To a 100 mL flask, 22 mL of Diclopentadiene was added and arranged for fractional distillation into an ice-cooled receiver. In order for the diene to distill, heat was applied to the dimer with a microburner. Into a 50 ml round bottom flask boiling chips were added before starting the distillation . Within about 5 mins while reaching a steady boiling point