The 2-phenylethyl halides were prepared from the treatment of 2-phenylethanol-1-C14with thionyl chloride alone, thionyl chloride in pyridine, 48% hydrobromic acid, 55% hydroiodic acid, or phosphorus and iodine. Except for the reaction with thionyl chloride in pyridine, these reactions gave rise to some rearrangement of the C14activity from the C-1 to the C-2 position. It appears probable that these rearrangements resulted from reactions having the SN1 type of mechanism with the phenylethyl cation as reaction intermediate. The fact that the thionyl chloride in pyridine treatment leads to a product without rearrangement is of interest in that this method may have further applications in synthetic tracer chemistry.