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Two new methods for the formation of Si−C monolayers from reactions with Si(111)−H are reported. Besides the photochemical method previously reported by Chidsey, Lewis acid-catalyzed hydrosilylation of alkenes and direct reaction of alkylmagnesium bromide produce a surface with similar chemical composition. These processes are demonstrated and compared using reactions of a C₁₀ precursor. The surfaces are chemically stable and can be stored for several weeks without measurable deterioration. The availability of a variety of synthetic approaches leading to the same chemical product is key to the development of flexible surface synthetic strategies. It is expected that these approaches will underpin the development of stepwise solid-phase-like syntheses of more complex organic/bioorganic species on these surfaces.