The objective of the experiment is to perform the Diels-Alder[4+2] cycloaddition of Furan and Maleic Anhydride and use NMRspectroscopy to determine the product formed. This type of reaction hasthe possibility of forming both endo or exo furan-maleic anhydrideadducts.
The Diels-alder reaction occurs when a conjugated diene and anisolated alkene are added together in one step. The bonding electronsredistribute forming two carbon-carbon bonds to create a cyclic product.With a cyclic diene and cyclic dienophile, two products form that havedifferent stereochemistries. They are the exo and endo-adducts. The endo-adduct is the kinetic product as it is faster and takes lessenergy to form. It is less stable than the exo-adduct, which is thethermodynamic product, so the endo is easily reversible in equilibriumconditions. When equilibration occurs, the fast reversal of the endoallows for gradual build up of the exo so that the exo will be the majorproduct.Furan (C
O), the diene of the reaction, is a five-memberedconjugated ring. It reacts with maleic anhydride (C
), the dienophileof the reaction, which has a five-membered ring with an isolated pibond. The possible products formed are the endo and exo furan-maleicanhydride adducts (C
). The experiment can be carried out under specific conditions inorder to contol what the major product will be. If the reaction is donequickly, isolating the endo, it will be the major product. If the reaction isdone over a longer period of time, exo will be the major product.