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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: AdiDex on July 24, 2014, 01:49:39 AM

Title: Diazomethane
Post by: AdiDex on July 24, 2014, 01:49:39 AM
(http://upload.wikimedia.org/wikipedia/commons/thumb/3/38/Diazomethane-resonance-structures-2D.png/320px-Diazomethane-resonance-structures-2D.png)
According to first structure carbon is in sp3 hybridizations nd N is in sp  hybridization where as in second structure Both C nd N in Sp2..
So what can we comment on the hybridization of C nd N in its hybrid structure..?
Title: Re: Diazomethane
Post by: Dan on July 24, 2014, 03:07:25 AM
(http://upload.wikimedia.org/wikipedia/commons/thumb/3/38/Diazomethane-resonance-structures-2D.png/320px-Diazomethane-resonance-structures-2D.png)
According to first structure carbon is in sp3 hybridizations

It's not that simple, that drawing does not tell you the hybridisation - will the lone pair be more stable in an sp3 orbital or a p orbital?
Title: Re: Diazomethane
Post by: AdiDex on August 04, 2014, 01:45:30 PM
The structure having sp3 hyvridisation will contribute because it is more stable.. :)
Am i right....???
Title: Re: Diazomethane
Post by: PhDoc on August 07, 2014, 11:58:46 AM
You're missing one resonance structure for diazomethane, i.e. the most important one.
Title: Re: Diazomethane
Post by: AdiDex on August 12, 2014, 02:39:08 PM
(http://www.chemaxon.com/marvin-archive/4.0.3/marvin/chemaxon/marvin/help/calculator-plugins_files/diazomethane.png)

 Yep you were right..
Title: Re: Diazomethane
Post by: orgopete on August 12, 2014, 11:25:55 PM
You're missing one resonance structure for diazomethane, i.e. the most important one.

Huh?
Title: Re: Diazomethane
Post by: AdiDex on May 09, 2017, 02:14:03 AM
(http://upload.wikimedia.org/wikipedia/commons/thumb/3/38/Diazomethane-resonance-structures-2D.png/320px-Diazomethane-resonance-structures-2D.png)
According to first structure carbon is in sp3 hybridizations

It's not that simple, that drawing does not tell you the hybridisation - will the lone pair be more stable in an sp3 orbital or a p orbital?

I think , Lone pair will be stable in sp3 hybrid orbital . Because it has more s character. Hence more electronegative.
Title: Re: Diazomethane
Post by: clarkstill on May 09, 2017, 10:44:52 AM
The structure on the right is likely to be lower in energy, since the negative charge is held on an electronegative nitrogen atom, and since a C=N bond replaces a weaker N≡N pi bond, so any interactions that allow this mesomer to form will lower the molecule's energy.

It will help if you can think, in orbital terms, about what you mean when you draw this resonance. What is the pair of electrons on the carbon atom interacting with to lead to the structure on the right? And what hybridization on carbon allows this interaction to be maximized?