Questions tagged [nitriles]

For questions about nitriles and isonitriles and their organic derivatives such as organic cyanates. Not to be used for inorganic cyanides or related structures; for those, one of the tags ionic-compounds or coordination-compounds will be appropriate.

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Why do SN2 reactions of alkyl halides proceed differently with KCN and AgCN?

Alkyl halides react with $\ce{KCN}$ to form alkyl cyanides as the main product, whereas the use of $\ce{AgCN}$ leads to isocyanides as the chief product. Why does this happen?
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What is a reasonable mechanism for the following reaction?

Hello all! I'm stuck on this one question and am not sure how to finish the mechanism. What I did was attack the alkyne first with the N farthest to the left. I'm not sure what do to after that though....