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Phthalates are the most prevalent plasticizers in poly(vinyl chloride) (PVC), the most commonly used polymer for drinking water distribution pipes. Though typically considered inert to the free chlorine necessary for drinking water disinfection, we found that certain commercially relevant phthalates leach from PVC and transform in the presence of free chlorine. The extent of aqueous phthalate leaching was alkyl chain length-dependent; the greatest leaching was observed for the most soluble 1-carbon chain phthalate, which was unaffected by free chlorine. In contrast, 2- and 4-carbon chain phthalates leached significantly less, and their concentrations decreased further in the presence of free chlorine. These observations were rationalized by experiments showing increased chlorine consumption with increasing phthalate alkyl chain length, indicative of structure-dependent chemical transformations of the parent phthalate with free chlorine. Using gas and liquid chromatography, high-resolution mass spectrometry, and nuclear magnetic resonance spectroscopy, we identified 13 disinfection byproducts of diisobutyl phthalate, 2 of which were confirmed using reference materials. The presence of both chlorinated and hydroxylated transformation products suggests reactions with both free chlorine and chlorine-derived reactive intermediates. This study underscores the need for consideration of chemical structure in predicting phthalate reactivity and highlights potential exposure risks in drinking water infrastructure.