November 21, 2024, 10:27:15 PM
Forum Rules: Read This Before Posting


Topic: Acid - Base reactions  (Read 3841 times)

0 Members and 1 Guest are viewing this topic.

Offline gsel

  • Regular Member
  • ***
  • Posts: 19
  • Mole Snacks: +0/-0
Acid - Base reactions
« on: January 09, 2014, 06:24:56 AM »
How come these two reactions* are not likely to occur according to their pKa values?
* HCN + CH3CO2-NA+  --> NA+-CN + CH3CO2H
* CH3CH2OH +NA+-CN  --> CH3CH2O-NA+ + HCN

Thanks!

Offline TheUnassuming

  • Chemist
  • Full Member
  • *
  • Posts: 461
  • Mole Snacks: +48/-1
Re: Acid - Base reactions
« Reply #1 on: January 09, 2014, 01:00:43 PM »
Correct me if I'm wrong, but it looks like you have two equations showing the equilibrium between HCN and sodium acetate or acetic acid and sodium cyanide:

HCN + CH3CO2Na <-> NaCN + CH3CO2H

So given the pKa of the two protonated forms (HCN and CH3CO2H), only one of the reactions shown is most likely to occur.  That said its an acid/base equilibrium so technically the other does happen just very slowly and is almost immediately reversed by the other.
When in doubt, avoid the Stille coupling.

Sponsored Links