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In page Nucleophile:
"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 sulfur or the nitrogen. For this reason, the SN2 reaction of an alkyl halide with SCN− often leads to a mixture of an alkyl thiocyanate (R-SCN) and an alkyl isothiocyanate (R-NCS). Similar considerations apply in the Kolbe nitrile synthesis.[citation needed]
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