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Hey /sci/ just looking for some help with a chemistry question, would it be possible to replace the Cl on an acyl chloride with a nitrile group while preserving the carbonyl bond? I'm having trouble finding any confirmation on the internet suggesting that it is or isn't possible
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Why cant you just add HCN
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>>8484103
or KCN
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>>8483769
look in your organic book i'm pretty sure you'll find the rxn scheme for acetyl chloride reactions.
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better to add hcn becouse u can not use water as a solvent. it would be the best to use an boiling ether
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HCN should protonate carbonyl O. Then the protonated acyl chloride should be in equilibrium with an chlorohydroxynitrile intermediate and the protonated acyl cyanide product, by nucleophilic substitution.
The equilibrium will favour acyl cyanide because Cl- (pKaH -7) is a better leaving group than CN- (pKaH ~9).
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>>8484167
i cant use acidic conditions because the next step of the synthesis is an aldol condensation
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