BG Orgo Chem

[Cream Soda]

Looking over the notes, we didn't haven't covered the mechanism for this and its needed for the lab report.

Anyone able to assist?

http://a3.sphotos.ak.fbcdn.net/hphot..._1940901_n.jpg

[Yabby]

chicken

[Heavencloud]

NH3 maybe? lol what section are you doing? I can pull out my ochem book and check

[Cream Soda]

Well, we have to actually do the mechanism, to the mystery product will become apparent. I'm just not sure which mechanism to follow, since the only nitrile we've messed with was reacted w/ H2O OH-, H+ instead of NaOH, H+

But its definitely a nitrile (orgo II by the way). We use his power point notes, so I wouldn't be able to tell you the exact section in any book.

[plue]

I took this class.
I passed this class.
I cheated...

Wish I could help.

[Heavencloud]

It's gotta be something to do with resonance, where you make the N negative and the ring have a +charged carbon. I'm in orgo chem II but it's been a few months since we looked at nitriles :C

[Cream Soda]

lol I'm stumped. Wish I could find a nitrile NaOH mechanism, then I'd just follow that, haha.

[Eliseos]

If your lab TAs are anything like mine, you could just ask him/her and they'll do it for you.

[Gwathuial]

H2O OH-, H+ instead of NaOH, H+

I... really? Have you not learnt anything on this course?

(Where do you think the OH- in the first case came from?)

[Heavencloud]

Maybe it's just Phenol and NaCN? SN2 reaction with CN as leaving group? lol

Also NaOH is the same as OH- D:

[Cream Soda]

I... really? Have you not learnt anything on this course?

(Where do you think the OH- in the first case came from?)

Well, I was running through the H2O oh-, h+ mechanism the the thing is the OH- part matches up, but then the h20 comes in, which there is none of in the NaOH problem, so it's not the same after that point.

[Gwathuial]

Anyway, my first guess at a mechanism would just be attack OH- at the C and gradually remove the N bonds, in equilibria all the way.

[Daemien]

I'm assuming this is in water. Nucleophilic addition of OH to form amide intermediate, then that reacts with H20 and H+ to form NH3 and benzoic acid

[Gwathuial]

Well, I was running through the H2O oh-, h+ mechanism the the thing is the OH- part matches up, but then the h20 comes in, which there is none of in the NaOH problem, so it's not the same after that point.

Uh... isn't the H2O the solvent? Or at least any polar proton donating solvent

[Cream Soda]

Uh... isn't the H2O the solvent? Or at least any polar proton donating solvent

Doesn't seem to be the case in the said mechanism. Looking at it in my handout right now, and it's part of the mechanism. Let me see if I can pull it up and post it.

[Cream Soda]

http://a3.sphotos.ak.fbcdn.net/hphot...5_427439_n.jpg

[Gwathuial]

The water in that mechanism is solvent.

[synistar]

Neucleophilic addition sounds about right. Should all be aqueous. Hydroxide attacks -C(triple bond)N. Mechanism gets fuzzy around that point because it has been 8 years since my last brush in with O-Chem.

[Heavencloud]

It shows... NH3 on your paper. NaOH is only found in h2o btw, you can't just have pure NaOH as an organic reactant because that's a solid.

[Cream Soda]

Yea, lol my teacher has this Australian accent and I just went to his office and he was like "We didn't use solid NaOH, did weeee?!?!" lol was funny as fuck. I can take it from here. Thanks guys.