Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Carbene mechanism with malononitrile
JAVA
Hazard to Self
**




Posts: 71
Registered: 9-1-2014
Member Is Offline

Mood: No Mood

[*] posted on 9-1-2014 at 09:00
Carbene mechanism with malononitrile


Hello guys,

I just get a practical problem: what happens if malononitrile is reacted with sodium in EtOH, is it right that a carbanion intermediate exists?

If this is true, what reaction mechanism takes place with this pyranone?

Since I suffering for a while about insertion mechanisms and carbene chemistry it seems impossible for me to explain what the product is?

Reaction scheme is given below

Additional background is very welcome!

ScreenHunter_101 Jan. 09 17.40.jpg - 12kB
View user's profile View All Posts By User
UnintentionalChaos
International Hazard
*****




Posts: 1454
Registered: 9-12-2006
Location: Mars
Member Is Offline

Mood: Nucleophilic

[*] posted on 9-1-2014 at 09:50


There is no carbene there. That is a carbanion. A carbene is a charge-neutral carbon species with two substituents and a pair of electrons (whose configuration can be singlet or triplet). You have a carbanion (a relatively weak one) and an activated alkene.

http://www.organic-chemistry.org/namedreactions/michael-addi...




Department of Redundancy Department - Now with paperwork!

'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
View user's profile View All Posts By User
solo
International Hazard
*****




Posts: 3967
Registered: 9-12-2002
Location: Estados Unidos de La Republica Mexicana
Member Is Offline

Mood: ....getting old and drowning in a sea of knowledge

[*] posted on 9-1-2014 at 15:32


.....just to clarify, this JAVA is not the java of the hive or any other forum.......java is solo here ....i just thought i clarify that since many know me as java .....solo/java




It's better to die on your feet, than live on your knees....Emiliano Zapata.
View user's profile View All Posts By User
JAVA
Hazard to Self
**




Posts: 71
Registered: 9-1-2014
Member Is Offline

Mood: No Mood

[*] posted on 28-2-2014 at 08:53


Thank you UnintentionalChaos. It wasn't explained on the university. Then I suppose that this is the mechanism for the 1,4-Michael Addition:

ScreenHunter_147 Feb. 28 17.38.jpg - 9kB

solo: don't mix subjects in scientific discussions, JAVA - solo:P




www.versuchschemie.de

"Keep sportive it's like Soccer: play on the ball, not on the players"
View user's profile View All Posts By User

  Go To Top