SN2 of Cyanide with Alkyl Halides to give Nitriles
Description: Alkyl halides (or tosylates) will react with cyanide ion to give alkyl cyanides (nitriles) in an SN2 reaction.
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Real-Life Examples:
Org. Synth. 1922, 2, 9
DOI link: 10.15227/orgsyn.002.0009
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/1872-Front-OS-I-pg-107-rxng-166.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/1872-Reverse-OS-I-pg-107-rxng-166.gif)
Org. Synth. 1928, 8, 52
DOI link: 10.15227/orgsyn.008.0052
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/1887-Front-OS-I-pg-156-rxng-166.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/1887-Reverse-OS-I-pg-156-rxng-166.gif)
Org. Synth. 1925, 5, 103
DOI link: 10.15227/orgsyn.005.0103
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1924-Front-OS-I-pg-536-rxng-166.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1924-Reverse-OS-I-pg-536-rxng-166.gif)
Org. Synth. 1936, 16, 35
DOI link: 10.15227/orgsyn.016.0035
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1952-Front-OS-II-pg-292.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1952-Reverse-OS-II-pg-292.gif)
Org. Synth. 1938, 18, 50
DOI link: 10.15227/orgsyn.018.0050
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1965-Front-OS-II-pg-376-2.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2021/08/1965-Reverse-OS-II-pg-376-2.gif)
Org. Synth. 1943, 23, 33
DOI link: 10.15227/orgsyn.023.0033
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/2026-Front-OS-III-pg-372.gif)
![](https://cdn.masterorganicchemistry.com/wp-content/uploads/2022/10/2026-Reverse-OS-III-pg-372.gif)
What if you add CH2CN to the reaction as well? Instead of just CN?
Do you mean CH3CN ? Acetonitrile? That’s a polar aprotic solvent, should be a great solvent for a reaction like this.
Hi,
The first example reaction is for acetal formation…not alkyl halides for nitriles. Other than that, this is fantastic! Finally understand reactions properly! :)
the work is good, i real like it.