text: Epoxides react with a broad range of nucleophiles, for example, alcohols, water, amines, thiols, and even halides. With two often nearly equivalent sites of attack, epoxides are examples "ambident substrates."  The regioselectivity of ring-opening in asymmetric epoxides generally follows the S2 pattern of attack at the least-substituted carbon, but can be affected by carbocation stability under acidic conditions.  This class of reactions is the basis of epoxy glues and the production of glycols.