Polymers possess bulk elastic properties due to entanglement of the polymer chains, not due to an inherit elasticity found within the monomers. An appropriately disubstituted bicyclo[8.8.8]hexacosane monomer should impart inherit elasticity when utilized in a polymer. A stochastic search of disubstituted bicyclo[m.m.m]alkanes demonstrated that these systems will adopt an out,out configuration and bicycles with medium and large values of m possess variable bridgehead-bridgehead distances. A stochastic search of disubstituted bicyclo[8.8.n]alkanes demonstrated an even-odd effect within the bite-angle of the bicycle. Two model compounds with methyl and hydroxyl groups at the bridgehead carbons were synthesized that demonstrated solid-state structures that correlated extremely well with the computational search. The solid-state structures were observed with both an out,out configuration and variable bridgehead-bridgehead distances. To investigate this hypothesis, polyurethanes will be made from the following diol monomers: 1,10-decanediol, a monocyclic diol, and a bicyclo[8.8.8]hexacosane diol.