Sunday 10 May 2015

organic chemistry - Does the reaction of 1-bromobutane with cyanide ion follow an SN1 or SN2 mechanism?


Reaction of 1-bromobutane with cyanide in ethanol/water to form pentanenitrile


In my textbook it's mentioned that the reaction undergoes $\mathrm{S_N2}$ mechanism. I understand that the carbon attached to the bromine is primary, but both solvents here are polar protic solvents, which favour the $\mathrm{S_N1}$ mechanism. Can anybody explain how to reconcile these?




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