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Question 8.4.1: Use the formal charge for each atom in the cyanide ion, CN^−......

Use the formal charge for each atom in the cyanide ion, CN^{−}, to predict whether H^{+} is more likely to attach to carbon or nitrogen when forming hydrocyanic acid.

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You are asked to identify the formal charge for every atom in a polyatomic ion and to use formal charge to predict the attachment site of H^{+}.
You are given the chemical formula for the polyatomic ion.
First draw the Lewis structure of CN^{-}.

\left[\begin{matrix}:C\equiv N: \end{matrix} \right]^{-}

Use Equation 8.3 to calculate the formal charge for carbon and nitrogen.

\text{formal charge}=\left(\text{number of } \text{valence electrons}\right)-\left[\left(\text{number of } \text{nonbonding electrons}\right) + \frac{1}{2}\left(\text{number of } \text{bonding electrons}\right) \right]      (8.3)

C formal charge = (4) − [2 + ½(6)] = −1
N formal charge = (5) − [2 + ½(6)] = 0

When the positively charged H^{+} ion attaches to CN^{-}, it is more likely to attach to the atom with the negative formal charge, forming H-C≡N.

Is your answer reasonable? Notice that the sum of the formal charges is equal to the overall charge on the ion (−1).

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