The four-stereospecific Diels-Alder transition structures for the cyclopentadiene and methyl acrylate cycloaddition have been computed using the Becke three-parameter density functional tiieory widi the 6-31G(d) basis set within basic and acidic ionic melt approximations. The computational model includes 1-ethyl-3-memylimidazolium cation (EMI+) and chloroaluminates (AlCl4- and Al2Cl 7-) in a stacked configuration which exploits lessons learned from other Lewis acid catalyzed Diels-Alder reactions. Several orientations and possible interactions have been attempted in stationary point determinations. The computed activation energies, structures and vibrations indicate that stacked models may explain experimental data. Large scale density functional computations are necessary to probe larger models including several anion and cation layers, and the inclusion of bulk phase effects.