Three series of zeroth to second generation chiral dendrimers, 7-9, 10-12, and 13-15, were prepared by convergent methods using chiral, nonracemic AB(2) monomers 1, 2, and 3, respectively. Chiroptical data revealed a significant change in molar rotation per subunit ([Phi](D)/n) as dendrimer generation increased for dendrimers 7-9 and 10-12, but not for dendrimers 13-15, a possible indication of chiral conformational order in the former two series of dendrimers, but not in the last. However, the optical activities ([Phi](D)) of low-molecular-weight model compounds 16 (+262) and 17 (+122), prepared to simulate different regions of the dendrimer structure, suggest that as generation size increases slight constitutional changes have a strong effect on the chiroptical properties of the dendrimer subunits. Using the [Phi](D) values of these and other (18-23) low-molecular-weight model compounds, we calculated [Phi](D) values for dendrimers 7-15 that agree within 14% of the observed values. Agreement between the optical activity of the model compounds and the dendrimers leads to the conclusion that the conformational equilibria of the dendrimer subunits are not perturbed relative to those of the model compounds. Therefore, we interpreted the change in [Phi](D)/n as dendrimer generation increased for dendrimers 7-12 to be based solely on constitutional changes in the dendritic structure and not chiral conformational order.