Nucleophiles bidentate, cyanide

Cyanide is a bidentate nucleophile. Draw the product that results from a reaction with 1-bromopentane where carbon is the nucleophile. Draw the product that results from the reaction where nitrogen is the nucleophile. Calculate the formal charge, if any, on both products. Assuming there is a mixture of these two products, suggest a simple way that you might separate them. 

Extensive studies on the molybednum complex XXXVI with various bidentate phosphorus and sulfur, ligands demonstrate that hydride, n-butyllithium and cyanide nucleophiles add to the arene to give XXXVII ... 

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