what happens when you add sodium hydroxide to urea?

[the guy]

what do you get when you add sodium hydroxide to urea?

what is the equation?

[UC]

http://www.chemguide.co.uk/organicprops/amides/hydrolysis.html

Urea is just carbonic acid diamide.

Edited June 16, 2009 by UC

[bob000555]

I am fairly sure urea is actually a special case. So the reaction of urea with sodium hydroxide is a bit more complex then is described in the article. Urea can be produced produced by the reaction of sodium cyanate (NaOCN) with ammonium chloride.

NaOCN + NH4Cl -> NH2CONH2 + NaCl

by adding NaOH to urea you are essentially reversing the process and will get sodium cyanate, ammonia and water.

NaOH + (NH2)2CO -> NaOCN + NH3 + H2O

[UC]

I am fairly sure urea is actually a special case. So the reaction of urea with sodium hydroxide is a bit more complex then is described in the article. Urea can be produced produced by the reaction of sodium cyanate (NaOCN) with ammonium chloride.

NaOCN + NH4Cl -> NH2CONH2 + NaCl

by adding NaOH to urea you are essentially reversing the process and will get sodium cyanate, ammonia and water.

NaOH + (NH2)2CO -> NaOCN + NH3 + H2O

 

References, if you please.

 

Cyanic acid undergoes nucleophilic attack at the carbon by ammonia, followed by tautomerization, yielding urea. Simply adding something like NaOH will not reverse the reaction mechanism.

 

The hydrolysis of urea proceeds like normal base-catalyzed amide hydrolysis, giving first sodium carbamate and ammonia. The carbamate readily undergoes a second hydrolysis reaction to give sodium carbonate and another equivalent of ammonia.