This thesis is outlined as five different projects, each of which relates to the topic of cleavage of silicone bonds in various chemical environments. Preparative chemistry was important, and multiple methods of introducing reactive silicon-based groups into silicone elastomers were developed, including syntheses of reactive group - containing crosslinkers which can function as a "Part C" in standard two-part hydrosilylation-cured silicone formulations. Studies of the degradation kinetics of these materials in different hydrolytic environments were also a significant component of the research. In addition to silicone elastomer studies, the hydrolytic stability and performance of a superspreading trisiloxane-polyethylene glycol surfactant was detailed and improved. The core message of the thesis can be summarized by the fact that there is an interplay between the local concentration of water around the reactive silicon-based group and the chemical reactivity of said groups, both of which are crucial for the cleavage of the group and degradation of the material. Local concentration of water is lowered by incorporating the reactive groups within a bulk silicone matrix or adding a small amount of an immiscible hydrophobic phase in the surfactant mixture. Reactivity can be augmented by changing the chemistry of the group to become more susceptible to hydrolysis or altering the environment to become more acidic or basic. Chapter 1, the introduction section, provides a brief overview of silicone chemistry and an in-depth review of silyl ethers and silyl esters. Chapter 2 demonstrates various methods for the synthesis of resins that contain vinyl groups bridged by silyl ethers. These resins are prepared by either modifying existing silicone resins with commercial silanes and then further reacting the silane groups with alkenols to create silyl ether-bridged vinyls, or functionalizing compounds with multiple hydroxyl groups, including natural carbohydrates, by vinyldimethylsilyl protection. These resins are capable of forming crosslinks with hydride-containing silicones by hydrosilylation between Si-H and alkenes. Their hydrolytic susceptibility under exposure to hydrogen chloride-water solution vapor is compared in terms of the degree of mechanical property change based on the crosslinker structure. Chapter 3 discusses the incorporation of silyl ester bonds into silicone matrices, which result in solids with much higher degradability than those with silyl ethers. This was achieved by two methods: 1) the vinyldimethylsilyl protection of 10-undecenoic acid followed by crosslinking with poly(dimethylsiloxane-hydromethylsiloxane) copolymer, and 2) the hydrosilylation of 10-undecenoic acid with hydride-terminated linear polydimethylsiloxane using excess polymer, which can then be oxidatively crosslinked under air exposure. Exposure of the crosslinked solids to water vapor without added acidic catalyst is able to cause mechanical property changes by cleavage of the silyl ester bonds. Chapter 4 describes studies of the hydrosilylation of alkenols by two different types of platinum catalysts, Lamoreaux and Karstedt. Although the Karstedt catalyst is widely used in silicone chemistry, the Lamoreaux catalyst, a mixture of Pt(II) and Pt(IV) in 1-octanol and 1-octanal, has been neglected in comparison. We show the results of hydrosilylation of various alkenols with hydrosilane-terminated poly(dimethylsiloxane) catalyzed by the Lamoreaux and Karstedt catalysts. The Karstedt catalyst always results in alkene silylation to form Si-C bonds as the major product, the Lamoreaux catalyst may selectively promote either the alkene silylation (Si-C bonds) or the dehydrogenative hydroxyl silylation (Si-O-C bonds) depending on the alkenol. We also establish the utility of the Lamoreaux catalyst in silyl ether materials chemistry as a catalyst with which vinyl-terminated silyl ether-containing crosslinkers can be synthesized. In Chapter 5, the hydrolytic properties of trisiloxane surfactants in aqueous solutions have been studied. Trisiloxane surfactants increase surface spreading areas compared to most other amphiphiles. However, due to the water-cleavable nature of the Si-O-Si bond, their structures are degraded over time in water, which causes the solutions to lose their spreading capabilities. Chemical evidence of trisiloxane surfactant hydrolysis when dissolved in water and exposed to high temperature and lower pH is presented. Additionally, it was found that the addition of a small amount of heptane as an immiscible second phase was able to dramatically protect the siloxane bonds from cleavage and allow the mixtures to retain their superspreading properties. In Chapter 6, cleavage of the siloxane bond between two hydromethylsiloxane groups, catalyzed by guanidine or amine in very low concentrations, is explored. With silanol-terminated PDMS as the initiator, polyhydromethylsiloxane was formed from the cyclic precursor 1,3,5,7-tetramethylcyclotetrasiloxane with only ~1% of hydrosilane groups being oxidized. This reaction was further used to synthesize crosslinked silicone solids by mixing silanol-terminated PDMS, 1,3,5,7-tetramethylcyclotetrasiloxane, methyltriacetoxysilane, and ppm levels of the guanidine catalyst, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). The solid contained unreacted polyhydromethylsiloxane chains, whose presence imparted degradability to the solid under exposure to diethylamine while being stable under normal conditions.