Can Two Halides on a Phenyl Ring Be Replaced with Just One KCN Molecule?

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SUMMARY

The discussion centers on the reactivity of a phenyl ring with two halides, specifically bromine (Br) and iodine (I), when treated with potassium cyanide (KCN). It is established that a single KCN molecule cannot replace both halides on the phenyl ring; stoichiometry dictates that two moles of KCN are required for complete substitution. The consensus is that the phenyl ring's structure significantly influences the reaction, as it does not behave like a typical alkyl halide.

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Huej
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So if an alkyl halide reacts with KCN, the halide gets replaced with CN. But what if I was using a phenyl ring with two halides, Br and I attached, let's say, para to each other. If I react with KCN, do both halides get replaced, or would I need double moles of KCN to do that?
 
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Regardless of everything else stoichiometry tells you you can't replace quantitatively TWO halides with ONE -CN.

Phenyl hardly counts as an alkyl.
 

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