Orbital hybridization and lone electrons

In summary, in a free radical such as the methyl radical, the lone electron will typically occupy a p orbital rather than an sp3 orbital due to the p orbital being higher in energy. This is energetically advantageous as it allows for the maximum occupancy of the low lying s orbital. Alternatively, using sp2 hybridization for the bonds can also maximize the occupancy of the s orbital. The concept of a "hole" is used to explain the lack of energy in the electron occupying the p orbital. However, this explanation may not be intuitive for some.
  • #1
CrimpJiggler
149
1
Do single non bonding electrons (i.e. on a free radical) always occupy non hybrid orbitals? For example the methyl radical has trigonal planar molecular geometry so the lone electron must occupy a p orbital. Why doesn't it occupy an sp3 orbital instead?
 
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  • #2
Think of it as a hole occupying a p orbital. A p orbital is higher in energy than an s orbital or a sp hybrid. So it is energetically advantageous for the hole being in a pure p orbital than in an sp hybrid.
Alternatively you can say that using sp2 for the bonds you maximize the occupancy of the low lying s orbital.
 
  • #3
A hole? I don't understand your explanation at all. By hole, do you mean a lack of energy? In other words, the electron has less energy than an electron pair and therefore occupies the p orbital to account for this lack of energy?

As for your 2nd explanation, wouldn't using sp3 maximize the occupancy for the s orbital regardless of whether one of the sp3 orbitals is only occupied by a lone electron? Inversely, you could say that sp2 hybridizing minimizes the occupancy of the p orbitals but it doesn't really because either way there are just as many electrons occupying the orbitals, regardless of how many of them are hybridized.

EDIT: Ah wait, I see what you mean now. By only putting pairs into hybrid orbitals then there are no vacant spaces left in the s orbital.
 
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1. How does orbital hybridization affect the shape of a molecule?

Orbital hybridization is the process of mixing atomic orbitals to form new hybrid orbitals that have different shapes and energies than the original orbitals. This affects the shape of a molecule because the hybrid orbitals will determine the arrangement of atoms and bonding angles, ultimately determining the overall shape of the molecule.

2. What is the difference between sp, sp2, and sp3 hybridization?

Sp, sp2, and sp3 are different types of hybridization that occur when atomic orbitals mix. In sp hybridization, one s orbital and one p orbital combine to form two sp hybrid orbitals. In sp2 hybridization, one s orbital and two p orbitals combine to form three sp2 hybrid orbitals. In sp3 hybridization, one s orbital and three p orbitals combine to form four sp3 hybrid orbitals. The number of hybrid orbitals formed depends on the number of atomic orbitals that are mixed.

3. How do lone electrons affect the hybridization of a molecule?

Lone electrons refer to the unpaired electrons in an atom that are not involved in bonding. These electrons can affect the hybridization of a molecule by influencing the shape and orientation of the hybrid orbitals. For example, lone pairs of electrons can cause a deviation from the ideal bond angle in a molecule, leading to a distorted shape.

4. Can lone electrons participate in bonding?

Yes, lone electrons can participate in bonding. For example, in molecules with double or triple bonds, one of the bonded atoms may have a lone pair of electrons that is involved in bonding with another atom. This is known as a coordinate covalent bond, where the shared pair of electrons comes from only one atom.

5. How does orbital hybridization explain the bonding in molecules with multiple bonds?

Orbital hybridization explains the bonding in molecules with multiple bonds by showing how the atomic orbitals of different atoms mix to form hybrid orbitals that allow for the formation of double or triple bonds. For example, in molecules with a double bond, one sp2 hybrid orbital from each atom overlaps to form a sigma bond, while the remaining p orbitals overlap to form a pi bond. In molecules with a triple bond, one sp hybrid orbital and two p orbitals from each atom overlap to form a sigma bond, while the remaining p orbitals overlap to form two pi bonds.

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