An ambident nucleophile is one that can attack from two or more places, resulting in two or more products. For example, the thiocyanate ion (SCN) may attack from either the S or the N. For this reason, the S2 reaction of an alkyl halide with SCN often leads to a mixture of RSCN (an alkyl thiocyanate) and RNCS (an alkyl isothiocyanate). Similar mixtures will happen in the Kolbe nitrile synthesis.