Thispaper is dedicated to Professor Charles A. McDowell on the occasion of his seventieth birthdayRALPH M. PAROLI, NANCY T. KAWAI, IAN S. BUTLER, and DENIS F. R. GILSON. Can. J. Chem. 66, 1973 (1988. The phase transition behaviour of 2-chloroadamantane, 2-CloHlsC1, has been investigated by differential scanning calorimetry (DSC), and FT-IR and Raman spectroscopy. Two transitions were detected by both DSC and vibrational spectroscopy at 23 1 and 178 K, on cooling, and at 242 and 227 K, on heating. The measuredenthalpies were 8.3 kJ mol-' for the first transition (phase I + phase 11), and 0.47 kJ mol-' for the second (phase I1 + phase 111). The entropies were 35 and 2.3 J K-' mol-I, respectively. These are similar to those observed for other 2-substituted adamantanes, but significantly different from those for 1 -substituted derivatives. The large hystereses observed for the two transitions are independent of the DSC scanning rate and are characteristic of first-order phase transitions. The dramatic differences observed in the vibrational spectra of phases I and I1 provide clear evidence of an order-disorder transition at about 235 K.