[kirushanth]

In the Kolbe nitrile synthesis, why is that when we use AgCN in diethyl ether solvent for reacting with RX, the process involves a SN1 mechanism instead of SN2?

[kirushanth]

I dont think the reason behind these kind of questions is complicated. Anyone?

[discodermolide]

In the Kolbe nitrile synthesis, why is that when we use AgCN in diethyl ether solvent for reacting with RX, the process involves a SN1 mechanism instead of SN2?

Here is a quote from the Wiki page:
"When silver cyanide is reacted with diethyl ether as a solvent the reaction runs according to an SN1 reaction mechanism: the product is mainly isonitrile due to the attack of the more nucleophilic nitrogen atom."

[kirushanth]

Here is a quote from the Wiki page:
"When silver cyanide is reacted with diethyl ether as a solvent the reaction runs according to an SN1 reaction mechanism: the product is mainly isonitrile due to the attack of the more nucleophilic nitrogen atom."

The product is isonitrile because it is an SN1 reaction. But why is it SN1 is my question? I tried wiki already, but due to the incompleteness of the page, I posted here.

Anyway, thanks for the reply.

[camptzak]

the R must be a tertiary alkyl halide..