The chemistry of the isomeric dichlorodiphenylacetaldehydes related to DDT was investigated to aid in delineating their possible role in the metabolism of this pesticide. In the case of the p,p'-isomer, the most important system under consideration, several literature syntheses were shown to be incorrect. The failure of at least one of these methods was attributed to the preferred oxidative involvement of the benzhydryl carbon via rearrangement of a beta-hydroxy enol ether which normally led to the isolation of the p,p'-dichlorobenzophenone instead of the desired aldehyde. The o,p'-isomer exhibited chemistry similar to that of the p,p'-isomer although the steric effect of the ortho-substituted chlorine on the benzhydryl proton was notable. The o,o'-isomer was normal in that it did not undergo reactions involving the benzhydryl carbon. Some possible mechanistic and biological implications of the work are discussed.