Surface anchoring of the nematic liquid crystal 5CB (4'-n-pentyl-4-cyanobiphenyl) responds to chemical and mechanical surface modification. If an octadecyltriethoxysilane (OTES) self-assembled monolayer (SAM) is partially degraded with UV irradiation, a hydrophobicity gradient forms that corresponds with a transition from homeotropic to planar alignment. We propose this hydrophobicity gradient is caused by sequential shortening of the alkyl chain length of the SAM. This explanation is corroborated by studying un-degraded SAM/5CB systems with varying alkyl chain lengths between 1 and 18. In agreement with hydrophobicity data from irradiated SAMs, the contact angle (Θ) decreases with decreasing alkyl chain length. Also, there is a transition from homeotropic to various pretilt angles at a contact angle of Θ~ 70o in both irradiated OTES SAMs and the SAMs of chain length of 5. We will also discuss the relationship of contact angle and birefringence. Mechanical rubbing also induced azimuthal alignment of the nematic phase in specific conditions.