Dehydration of formic acid w/sulfuric acid

[BurningKrome]

Can anyone point me to, or diagram out, an electron pushing diag for the dehydration of formic acid by sulfuric acid to form carbon monoxide. I'm especially interested in how the the CO forms with a lone pair without picking up the free H+ to form either COH of formaldahyde (CH2O). I'm also curious abot how the dative bond forms, without picking up a free H+.

 

Thanks!

[Horza2002]

I've just had a very quick look at it and heres what I came up with.

 

Sulfuric acid pronates and then eliminates the water to leave you with prononated CO. This is simply deprotonated by the water you just eliminated to give you the CO

 

 

untitled.bmp

[BurningKrome]

So the impression I get is the H2SO4 does nothing but provide free H+ for the protonation of the OH group. Would the reaction work as well with any strong acid (HCl or whatever)? Would this be considered an E2 reaction?

 

Thanks!

Edited October 8, 2010 by BurningKrome

[Horza2002]

The sulphuric acid is there purely to provide a proton to catalyse the reaction. Any acid strong enough to protonate formic acid will work. HCl might not be strong enough but there are some others that would also do nicely.

 

It would mainly depend on what the rate determining step was. However I dont think it'l be an E2 reaction. The elimination of water is probally the rds in which case this would be an E1 reaction as there is only one molecule involved in the rds.