[SemonSays]

I can't figure out why urea is basic and not acidic. I can't find any information on the internet and i have to use the molecular structure or Lewis structure of urea to prove it. I also need to find out how urea is chemically changed to nitrate ions.

Can anyone help me out?

[Sam (NG)]

Please read the Forum Rules, specifically:

4.) Please show that you've at least attempted the problem.  We don't mind helping you solve problems but we are ethically opposed to doing homework for you. Violators will have their topic deleted or locked.

If you draw resonance structures for urea, that would be a good start.
Think about conjugate acids and bases.

[SemonSays]

there are 4 i think.                                                                             http://academic.evergreen.edu/curricular/MANDM2000/Spring/homework/hw6/Image950.gif

That is the Lewis structure of urea (hope the link works). But how does that help? Im so confused.

[SemonSays]

I thought it had something to do with the amino groups or amidogens (NH2), but im not so sure.

[Sam (NG)]

The lone pairs of electrons in the molecule are available despite resonance because in all of the resonance structures, at least one of the nitrogen atoms has a lone pair on it.

[constant thinker]

Don't forget what Brønsted-Lowry said about a base, the whole part about a base being simply a proton acceptor.

The nitrogen has that nice lone pair. Looks like a good place to accept a proton to me.

[P]

Hi guys - sorry for being dumb, but, why is it then that urea dissolved in water is quite acidic - pH being about 1 when I put it in water at about 20%.

[Sam (NG)]

Hi guys - sorry for being dumb, but, why is it then that urea dissolved in water is quite acidic - pH being about 1 when I put it in water at about 20%.

This is a good point, the pKa for urea is low, why have you assumed that it is basic Semonsays?

[P]

Yea  -  my first assumption (which was wrong) was that the solution would be basic   - I guess it was the 2 NH2's that threw me  -  it just 'looks' as though it should be basic to me.  It is, however, quite acidic in solution   -  I might be missing something simple here, but, at the moment I'm not sure why it is acidic.

[Sam (NG)]

Yea  -  my first assumption (which was wrong) was that the solution would be basic   - I guess it was the 2 NH2's that threw me  -  it just 'looks' as though it should be basic to me.  It is, however, quite acidic in solution   -  I might be missing something simple here, but, at the moment I'm not sure why it is acidic.

If you push the electrons from the nitrogen into the C-N bond and make it C=N, then you have a positive charge on the NH2 group, loss of hydrogen would fix this?

[constant thinker]

Hmmm, so it is acidic. The NH₂'s also threw me.

[UnintentionalChaos]

Google Search: *urea basic*...second result: http://answers.yahoo.com/question/index?qid=20070508144240AAqawz0

[Sam (NG)]

Google Search: *urea basic*...second result: http://answers.yahoo.com/question/index?qid=20070508144240AAqawz0

Strange, because the pKa of urea is ~0.2.

[P]

I'm really sorry gents - feel free to eat my snacks   

It was the urea phosphate I was using that gave the very low pH's (0.2 in water).  The urea in water was around 7.5.  Apologies.

[Sam (NG)]

I'm really sorry gents - feel free to eat my snacks   

It was the urea phosphate I was using that gave the very low pH's (0.2 in water).  The urea in water was around 7.5.  Apologies.

That clears up some confusion i guess.