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Can hydrogen be abstracted from urea?

  • #1

Homework Statement


Urea is known to react with an acid to form salt. The carbonyl oxygen of urea is protonated in the process to form uronium ion. But, I have not seen conclusive reaction of urea with an alkali. So, if urea is dissolved in NaOH, what are the possible reactions? Can hydrogen be abstracted from one or both NH2 group? What reagent can afford this abstraction if any.

Homework Equations


(NH2)2CO + HCl --> (NH2)2COH+ Cl-
(NH2)2CO + NaOH --> ?
(NH2)2CO + ? --> HNCONH2 ]-
(NH2)2CO + ? --> HNCONH ]2-


The Attempt at a Solution

 

Answers and Replies

  • #2
DrDu
Science Advisor
6,023
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The reverse reaction, namely the hydrolysis of cyanamide is used in the preparation of urea. To reverse it, you will need a rather strong base. E.g. heating urea with metallic sodium.
 
  • #3
Borek
Mentor
28,327
2,714
You need to find pKa for these protons and then find a base strong enough. Definitely won't happen in water, and I doubt it will be possible to isolate such cations as salts, but organic chemists routinely use bases that should do the trick.

Edit: DrDu beat me.
 
  • #4
TeethWhitener
Science Advisor
Gold Member
1,602
911

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