What is the hybridization of the nitrogen atom in this molecule?

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

Kobebucsfan

Full Member
10+ Year Member
Joined
Apr 20, 2010
Messages
736
Reaction score
16
plz see attachment,
so is it sp3 or sp2 ??


i heard that when there are lone pairs on an atom and it is next to a double bond, it is sp2





Second question) - when a question asks which of the following is NOT aromatic, are they looking for answers that are both non-aromatic and anti-aromatic ?

Members don't see this ad.
 

Attachments

  • sp3.docx
    220.6 KB · Views: 129
I think you don't count the lone pair of nitrogen in this molecule because it is under the aromaticity and so the hybridization will be sp2? (in my opinion..)

And I believe not aromatic = non-aromatic
 
it's sp3......nitrogen bonded to one hydrogen and two carbons so the lone pair must be in the p orbital making a total of 4 domains..one S and three Ps....this kind of the question you can get in DAT to find which one of the given compounds is/are aromatic..although aromatics do not have any sp3 atoms in ring ...this one is exception because the lone pair is contributing to pi bond system of aromatic ring....remember odd numbers of pi bonds ( or pi electrons in ring)....aromatic.
 
Last edited:
It's sp2, Nitrogen lone pair can donate towards resonance and counts towards pi electrons.

"i heard that when there are lone pairs on an atom and it is next to a double bond, it is sp2"
Partially right but if Nitrogen was bound to two hydrogen, then there would have been no lone pairs on nitrogen(sp3) and this will be Non-Aromatic

Hey if you have Chad's subscription,he clears out all doubts.
 
Members don't see this ad :)
I confirmed from chad's video and the answer is although it looks like its sp3 it's not ..so the correct answer is it's sp2 hybridize

chad explained it this way
"It looks like it should be sp3 hybridized but it's not. Taking into account the delocalization of the lone pair (note that the lone pair is involved in resonance) it must be sp2 hybridized. To be part of the deloclized pi system, the lone pair must be in an unhybridized 'p' orbital. This only leaves the other 2 'p' orbitals left to be used to make the hybrid orbitals which is why the nitrogen is actually sp2 hybridized. If an atom in a ring has a lone pair and if including a single lone pair from that atom will result in the compound being aromatic, then the atom will be sp2 hybridized rather than sp3 hybridized."
 
Top