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Topic: Diazomethane  (Read 5956 times)

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Offline AdiDex

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Diazomethane
« on: July 24, 2014, 01:49:39 AM »

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..?

Offline Dan

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Re: Diazomethane
« Reply #1 on: July 24, 2014, 03:07:25 AM »

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?
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Offline AdiDex

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Re: Diazomethane
« Reply #2 on: August 04, 2014, 01:45:30 PM »
The structure having sp3 hyvridisation will contribute because it is more stable.. :)
Am i right....???

Offline PhDoc

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Re: Diazomethane
« Reply #3 on: August 07, 2014, 11:58:46 AM »
You're missing one resonance structure for diazomethane, i.e. the most important one.
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Offline AdiDex

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Re: Diazomethane
« Reply #4 on: August 12, 2014, 02:39:08 PM »


 Yep you were right..

Offline orgopete

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Re: Diazomethane
« Reply #5 on: August 12, 2014, 11:25:55 PM »
You're missing one resonance structure for diazomethane, i.e. the most important one.

Huh?
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Offline AdiDex

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Re: Diazomethane
« Reply #6 on: May 09, 2017, 02:14:03 AM »

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.

Offline clarkstill

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Re: Diazomethane
« Reply #7 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?

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