Dissociation of individual cyclopentene molecules on the Si(100) surface is induced and investigated using cryogenic ultrahigh vacuum scanning tunneling microscopy (STM). Using a secondary feedback loop during elevated tunneling current and sample biasing conditions, the cyclopentene dissociation products are isolated and then characterized with atomic-scale spatial resolution. Using multibias STM and density functional theory, the cyclopentene dissociation products are shown to consist of a C(5)H(7) fragment and an individual H atom. The C(5)H(7) fragment contains a C=C double bond and is bound to the Si(100) surface via a single Si-C covalent bond, while the individual H atom can be induced to hop between two sites on a single silicon dimer with the STM tip. This study shows that the use of feedback control during STM-induced single molecule reactions allows transient reaction products to be captured and thus more thoroughly studied. While demonstrated here for cyclopentene on Si(100), this feedback-controlled approach can likely be applied to a wide array of chemical reactions on semiconductor surfaces.