The reaction of cyclopropylmethamine with sodium nitrite in dilute aqueous perchloric acid solution yielded a mixture of 48% cyclopropylmethyl alcohol, 47% cyclobutanol, and 5% homoallylic alcohol (but-3-en-1-ol). In the non-classical perspective, the positive charge is delocalized throughout the carbocation intermediate structure via resonance, resulting in partial (electron-deficient) bonds. Evidently, the relatively low yield of the homoallylic alcohol implies that the homoallylic structure is the weakest resonance contributor.