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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Joannes on May 04, 2022, 05:05:53 PM

Title: Hybridization of N in CH3NO2? ?
Post by: Joannes on May 04, 2022, 05:05:53 PM
I had to write the Lewis structure for CH3NO2 and had little to no problems (only insecurity wa about the other structure with no formal charges with one oxygen bonded to the carbon), but I still don't understand what is the hybridization of N in that structure. I think it's sp2 since there's a double bond but I don't know where the lone pair is "stationed" if that's the case.
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Babcock_Hall on May 04, 2022, 05:44:09 PM
Can you show us what you drew?
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Joannes on May 04, 2022, 06:04:42 PM
Quote from: Babcock_Hall on May 04, 2022, 05:44:09 PM
Can you show us what you drew?

This are the two structures I drew
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Babcock_Hall on May 04, 2022, 08:42:21 PM
The two structures you labeled "major" both look fine to me.  I am not sure what you mean regarding the lone pair being stationed.  Is there some reason that nitrogen would not follow the normal rules regarding hybridization?
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Joannes on May 06, 2022, 11:50:48 AM
Quote from: Babcock_Hall on May 04, 2022, 08:42:21 PM
The two structures you labeled "major" both look fine to me.  I am not sure what you mean regarding the lone pair being stationed.  Is there some reason that nitrogen would not follow the normal rules regarding hybridization?
Sorry for the late reply. My doubt was about how it hybridates. So what i figured out was that it forms 3 sp2 orbitals, two of them with one electron, and one with a pair of electrons. Then there's a p orbital with a single electron. So it uses the p and one of the two sp2 orbitals with a single electron to form the double bond with the oxygen, the other hybrid orbital with a single electron to form a bond with the carbon, and the last hybrid orbital with two electrons is used to form a coordinate bond with the oxygen which is connected to the nitrogen with only one bond. Is that right? And if so, does the nitrogen always form a coordinate bond when it has 4 bonds and no lone pair?
Title: Re: Hybridization of N in CH3NO2? ?
Post by: rolnor on May 08, 2022, 06:56:14 AM
The upper structure is a nitrite-ester.

I am not sure I understand, the electrons are not local?

https://www.google.com/search?rlz=1C9BKJA_enSE868SE868&source=univ&tbm=isch&q=nitro+compounds&hl=sv&fir=_eLntBK2PCY1xM%252C3Xc0u-QOEvYeNM%252C_%253BNO2beh9itLcFQM%252CRh_kbGA8CcHKjM%252C_%253BdBSJWxFQV6q6tM%252CWVFH4sK8M8vuxM%252C_%253BV-vGRqf3J18QBM%252CPOFq5FiiyzjEnM%252C_%253B4cExwTx2IAPNdM%252CxHC2dDBAGSFaZM%252C_%253B7Z5tfbDhdxRGFM%252CuXVzasmCYTNjrM%252C_%253BUSavZBXHP9XVUM%252CkiVgEjdzhv5CuM%252C_%253BLrS5DeYeEeVhQM%252CmHgOsE0tMKbqQM%252C_%253B4EizlcTc7vp4-M%252C0JMQJXfX48NVoM%252C_%253BpegFG6aASDxPTM%252CvCnZ8d9ZzP93fM%252C_%253BMN_PPz597SYtuM%252CuXVzasmCYTNjrM%252C_&usg=AI4_-kTne-cFYMUVyUcO0Vb7cieicW3llQ&sa=X&ved=2ahUKEwjq18eu38_3AhWMuosKHQvuCt8Q420oAHoECB0QBA&biw=1366&bih=915&dpr=2#imgrc=sYzCvC3EBNRbIM&imgdii=2auxZT6jaEw_IM
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Joannes on May 08, 2022, 09:22:42 AM
The problem I have is that I'm not sure what hybridization does the nitrogen have and how are the electrons placed in its orbitals once it's hybridized basically. Is it sp2? If yes does the nitrogen form a coordinate bond whenever it has 4 bonds and a + charge?
Title: Re: Hybridization of N in CH3NO2? ?
Post by: rolnor on May 08, 2022, 10:16:40 AM
Its SP2

https://simple.wikipedia.org/wiki/Nitro_compound
Title: Re: Hybridization of N in CH3NO2? ?
Post by: Babcock_Hall on May 10, 2022, 10:10:38 AM
Johannes, Just a general comment.  I usually look at the molecule as a whole to think about its hybridization, as opposed to imagining the atom hybridizing and then becoming a molecule.
Title: Re: Hybridization of N in CH3NO2? ?
Post by: rolnor on May 12, 2022, 06:10:05 AM
I think MO-theory is complicated, I wish I could say I am an expert, I am not.
Title: Re: Hybridization of N in CH3NO2? ?
Post by: hollytara on May 15, 2022, 08:25:53 PM
If you believe in hybridization, the N is sp2

Hybridization is a useful fiction to help us visualize the bonding.
Title: Re: Hybridization of N in CH3NO2? ?
Post by: rolnor on May 16, 2022, 04:36:12 AM
"Believe"? Its not religion, its a model?