Intramolecular Sn2

[Chemik]

Hello,

is the product of this reaction correct? I'm just not sure if the oxetane is stable enough to form. Are there other possible products? The instructions say it should be an Sn2 reaction but none of the other reactions in this exercise have been intramolecular so I would like to be sure.

[chenbeier]

The question is why cyanide is used and not only hydroxide. I guess chlorine is exchanged by cyanide and in a further reaction the nitrile will react with the alcohol group to form a ring. Look for Pinner reaction.

Edited January 12, 2023 by chenbeier

[Sensei]

4 hours ago, Chemik said:

is the product of this reaction correct?

Where on the right side do you have Chlorine and Nitrogen atoms?

 

[Chemik]

10 hours ago, chenbeier said:

The question is why cyanide is used and not only hydroxide. I guess chlorine is exchanged by cyanide and in a further reaction the nitrile will react with the alcohol group to form a ring. Look for Pinner reaction.

But I thought the acid-base reaction leading to deprotonation of –OH was preferred over the Sn2 reaction. Why does NaCN react differently from NaOH?

Edited January 12, 2023 by Chemik

[chenbeier]

CN is not OH. CN will react with Halogen by exchange. CN is also called Pseudohalogen.