有机化学课件the dielsalder reaction.ppt

10.12 The Diels-Alder Reaction;conjugated diene;transition state;concerted mechanism cycloaddition pericyclic reaction a concerted reaction that proceeds through a cyclic transition state;conjugated diene;What makes a reactive dienophile?;+;+;+;+;+;syn addition to alkene cis-trans relationship of substituents on alkene retained in cyclohexene product;only product;only product;Cyclic dienes yield bridged bicyclicDiels-Alder adducts.;+;is thesame as;10.13 The p Molecular OrbitalsofEthylene and 1,3-Butadiene;Orbitals and Chemical Reactions;We can illustrate HOMO-LUMO interactions by way of the Diels-Alder reaction between ethylene and 1,3-butadiene. We need only consider only the p electrons of ethylene and 1,3-butadiene. We can ignore the framework of s bonds in each molecule.;The p MOs of Ethylene;The p MOs of Ethylene;Four p orbitals contribute to the p system of 1,3-butadiene; therefore, there are four p molecular orbitals. Two of these orbitals are bonding; two are antibonding.;The Two Bonding p MOs of 1,3-Butadiene;The Two Antibonding p MOs of 1,3-Butadiene;10.14A p Molecular Orbital Analysisof theDiels-Alder Reaction;MO Analysis of Diels-Alder Reaction;LUMO of ethylene (dienophile);LUMO of ethylene (dienophile);A forbidden reaction;A forbidden reaction