Understanding the Hybridization and Formation of Pi Bonds in Ammonia and Ethyne

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Discussion Overview

The discussion centers on the hybridization of nitrogen in ammonia and the formation of pi bonds in ethyne. Participants explore the reasoning behind the sp3 hybridization of nitrogen despite having three bonding pairs and the role of unhybridized orbitals in the formation of pi bonds in ethyne.

Discussion Character

  • Technical explanation
  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • One participant questions why nitrogen in ammonia is sp3 hybridized given that there are only three bonding pairs, suggesting a need for clarification on the role of the lone pair.
  • Another participant explains that in ethyne, the triple bond consists of a sigma bond formed from one of the 2s electrons and two pi bonds formed from the 2p electrons, arguing that the pi bonds involve the lower energy 2px and 2py orbitals.
  • A participant expresses confusion regarding the energy levels of orbitals in the same subshell, referencing textbook information that states they are at the same energy level.
  • Another participant clarifies that while isolated carbon atoms have degenerate 2p orbitals, the presence of other atoms during bonding alters their energy levels and hybridization behavior.
  • It is noted that a pz pi molecular orbital would align with the sigma bond axis, which may help clarify the orbital interactions involved.

Areas of Agreement / Disagreement

Participants express differing views on the hybridization and energy levels of orbitals during bonding, indicating that multiple competing perspectives remain without a clear consensus.

Contextual Notes

There are limitations regarding the assumptions made about orbital energy levels in different contexts, particularly between isolated atoms and bonded states, which remain unresolved in the discussion.

Clari
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In ammonia, why the N atom is sp3 hybridized and not sp2 hybridized...since there are only 3 bondings...

Also, in ethyne, that is H-C(triple bond)C-H...for the formation of 2 pi bonds, why it is the unhybridized 2px orbital and 2py orbital of each C atom overlap with each other? How about the 2pz orbital?


any help would be appreciated
 
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In NH3, there are 4 electron pairs about the N atom - you're omitting the lone pair.

The triple bond in [itex]H-C \equiv C-H[/itex] is basically a sigma bond using one of the two 2s electrons (the other 2s electron is used for the sigma bond with H), and a pair of pi bonds using both of the 2p electrons. Since C has only 2 electrons in the 2p subshell, and since px and py are lower energy orbitals than pz, the pi bonds must involve an overlap of only these orbitals.
 
Gokul43201:

but in my textbook, it is said that orbitals in the same subshell is at the same energy level...I am confused now...
 
Clari said:
Gokul43201:

but in my textbook, it is said that orbitals in the same subshell is at the same energy level...I am confused now...

For isolated Carbon atoms they do:[itex]2p_{x},2p_{y} & 2p_{z}[/itex] have all the same energy.But when the Carbon atom reacts with nonmetalic elements,like Hydrogen,those orbitals do not behave in the same manner.That's because 2 of them have one electron and the remaining one ([itex]2p_{z}[/itex]) has none.The 2 orbitals with one electron they "hybridize" with the [itex]2s[/itex] orbital which has 2 electrons,resulting in 4 hybridized orbitals of smaller energy than the unhybridized [itex]2p_{z}[/itex].Since it overlaps 3 hybrid orbitals (one [itex]\sigma[/itex] and 2 [itex]\pi[/itex]) with another C atom,it has a triple bond.Since 2 of the bonds are [itex]\pi[/itex],and another 2 are [itex]\sigma[/itex],it id hybridized [itex]sp[/itex].


Daniel.

PS.Maybe Gokul can put it in a more coherent way... :wink:
 
As Dexter mentioned, your textbook is right only when it talks about isolated atoms.

However, when a molecule is being formed, the direction along the line joining the atoms breaks the degeneracy (x, y and z are not symmetric anymore; the z direction is the internuclear direction and so, is different from x and y) between px, py and pz.
 
A "pz" pi molecular orbital would be along the same axis as the sigma, perhaps this clarifies things a bit more.
 

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