The Vespiary

The Hive => Newbee Forum => Topic started by: ning on August 27, 2003, 10:07:00 AM

Title: toluene + ethyl acetate -> P2P : would it work?
Post by: ning on August 27, 2003, 10:07:00 AM

I saw a nice, interesting article on organic syntheses web page, and it got me thinking.

alpha-PHENYLACETOACETONITRILE (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0487)

(http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0487)

They are using Sodium ethoxide to condense ethyl acetate with benzyl cyanide. But I got to wondering--
the cyanide part is not affected at all by this synthesis.
What if it wasn't there?

By performing the same procedure with toluene instead, could we have completely OTC p2p?

I don't know how much effect my suggested change would have on the attack on the toluene, but I can hope...

Any beez out there feel like commenting?

Title: no go
Post by: hypo on August 27, 2003, 10:38:00 AM

> the cyanide part is not affected at all by this synthesis.
> What if it wasn't there?

then the Hs on the adjacent C wouldn't be acidic enough.
see any organic chemistry book for details.

Title: But...But....
Post by: ning on August 27, 2003, 04:41:00 PM

But...benzyl chloride et al can be made by attaching to toluene, right? I don't know much about how different functional groups affect reactivity. Is there a digest or good post on this at the hive? If not, I see a job for Aurelius... :)
Couldn't just a stronger base be used?

Title: Do not forget
Post by: moo on August 27, 2003, 06:05:00 PM

There are a lot of good sites with information on reaction mechanisms, the subject you are asking about. There are a lot of good links here too. Then there are libraries full of books full of information. Why don't you start reading and digging up information instead of asking questions? The answers are all there and I promise that in the end you won't regret it. If you wan't to understand things it's the only way to go.

Title: no buts.
Post by: hypo on August 28, 2003, 12:26:00 AM

> But...benzyl chloride et al can be made by attaching to toluene, right?

so what? entirely different reaction mechanism.

>  don't know much about how different functional groups affect reactivity.

try to get a cheap, used version of this book:

http://www.amazon.com/exec/obidos/tg/detail/-/0716734605/ (http://www.amazon.com/exec/obidos/tg/detail/-/0716734605/)

Title: well, thanks...
Post by: ning on August 28, 2003, 07:59:00 AM

I'll look into that book. But I have to say, sometimes it is much more efficient to ask a question and get to the heart of the matter than to drill away randomly till I hit the target myself. Please be aware, I am reading also. I still don't know exactly how different groups guide reactions to different places on a molecule, and that seems to be something that is not covered *concisely* in any of my textbooks. I would love to see some wonderful, wise bee produce a little, distilled tutorial on that. I'm sure I'm not the only one...
Sure, it would be easier in many ways to answer most questions with "go read some more, and you will understand". And I know, perhaps some questions deserve that answer. But ultimately, this site exists for people to question and answer, and I am glad some bees decide it's worth their time to answer my questions. I am certain someday I will have enough experience to reciprocate. We were all newbees once...

Title: Claisen Condensation
Post by: Aurelius on August 28, 2003, 07:34:00 PM

Is a good place to start.

Title: A thread!
Post by: ning on August 30, 2003, 09:32:00 PM

To unknown territory! Thanks, Aurelias! :)