Chiral surfaces, capable of existing in two distinguishable mirror forms that cannot be superimposed, are attracting worldwide attention. The adsorption of complex organic molecules provides a means of introducing the ultimate discrimination function of chirality to a metal surface. Here, a comparison of the chiral tartaric acid (HOOC-CHOH-CHOH-COOH) molecule and the achiral succinic acid (HOOC-CH2-CH2-COOH) molecule on a Cu(1 10) surface is presented. For both molecules, two dimensional assembly is found to depend strongly on molecule-metal bonding interactions, whereas the presence/absence of the OH groups causes subtler, second-order effects on the-self-assembled structure. The driving force for creating chiral organisations is shown to arise from adsorption-induced asymmetrisation, via molecular distortion and/or metal reconstruction of the local adsorption unit. The macroscopic chirality of the surface is then determined by whether nucleation points of both chirality can be equally created, or whether non-degeneracy can be introduced to favour one chirality. (C) 2004 Elsevier B.V. All rights reserved.