The classical molecular dynamics simulations presented here examine the compression and friction of monolayers composed of linear hydrocarbon chains with 8, 13, or 22 carbon atoms that are chemically bound (or anchored) to a diamond (111) substrate. The roles structural defects and their formation play in compression, friction, and energy dissipation processes are examined. The number of defects increases under increasing load, reaching a plateau at a specified Toad. Defects are also clearly implicated in the energy dissipation associated with sliding friction. The friction is found to be highest in shorter chains and disordered surfaces, in agreement with previous atomic force microscopy studies.