Use Halogen
Posted in Restaurant & Catering Equipment on 12/10/2007 07:34 am by adminUse Halogen
Devise a synthesis for propyl cyanide. How do you know which halogen to use(Cl,Br,I)?
In which a nucleophilic substitution reaction is used.
I can do this reaction using an Sn2 reaction, however the only halogen used would be in the sulfonate I would use to remove an OH (alcohol group).
Difficult to draw a mechanism here but if required I can scan and send.
Take propanol, and react with 4-toluenesulfonyl chloride. This attaches to the oxygen of OH group. Use base to remove the proton of OH group....don't forget the O is +ve charged at the moment. Suitable base would be NEt3. This would leave with the tosylate leaving group. Introduce your nucleophile....to add the cyanide, NaCN would be fine. This adds on to your C-O carbon, the tosylate leaves and you end up with this (stabilised by resonance), along with H-N+Et3 and NaCl....and of course propyl cyanide!
If you need the mechanism give me a shout.
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