[m3lm4k]

Hello!

I wonder what would happen if we add thionyl chloride to such alcohol ( image below ). I know that this reagent can give us alkyl chloride in the case of primary and secondary alcohols. There isn't a lot of data concerning this topic on the internet unfortunately. However I found that it can cause dehydratation, which doesn't seem nice for me because next step of sequence of reaction is addition of KCN in DMF solution. All in all I hope that somebody is able to help me

[Yarr]

Is your purpose to convert the hydroxyl group into a cyanide group? Then your method doesn't seem reasonable, because even if you are able to make the conversion -OH --> -Cl, then adding KCN will probably induce elimination instead of substitution. A much better method would be to treat your alcohol with NaCN and TMSCl (with a catalytic amount of NaI) in DMF.

[m3lm4k]

To be honest my purpose is to pass the test and by the way learn how it works. I see that your method seem more reasonable. The thing is whether thionyl chloride chlorinate tertiary alcohols. I've read that CN- may induce elimination, however it was one remark too. If I perform introduction of KCN within DMF solution its high dielectric polarizability may give desired nitrile.

Thanks!