SEd Sci 221- ORGANIC CHEMISTRY

Chapter 2- Hybridization

Introduction
This chapter is focused on hybridization. It discusses the meaning of
hybridization and its types such as 1.) sp hybridization; 2.) sp 2 hybridization; 3.) sp3
hybridization; 4.) sp3d hybridization; and sp3d2 hybridization.

Learning Outcomes:
In this chapter, you are expected to:
1. Define hybridization; and
2. Explain and illustrate the types of hybridization.

Learning Contents:
This chapter contains the following lessons for you to be able to meet the
expected learning outcomes:
1. Meaning of hybridization
2. Types of hybridization such as
1.) sp hybridization;
2.) sp2 hybridization;
3.) sp3 hybridization;
4.) sp3d hybridization; and
5.) sp3d2 hybridization.
What is Hybridization?
Hybridization is defined as the concept of mixing two atomic orbitals with the
same energy levels to give a degenerated new type of orbitals. This intermixing is
based on quantum mechanics. The atomic orbitals of the same energy level can only
take part in hybridization and both full filled and half-filled orbitals can also take part
in this process, provided they have equal energy.
Hybridization is the idea that atomic orbitals fuse to form newly
hybridized orbitals, which in turn, influences molecular geometry and bonding
properties. Hybridization is also an expansion of the valence bond theory. In
order to explore this idea further, we will utilize three types of hydrocarbon
compounds to illustrate sp3, sp2, and sp hybridization.

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 Redistribution of the energy of orbitals of individual atoms to give orbitals of
equivalent energy happens when two atomic orbitals combine to form hybrid orbital
in a molecule. This process is called hybridization. The new orbitals thus formed
are known as hybrid orbitals.

During the process of hybridization, the atomic orbitals of similar energy are
mixed together such as the mixing of two ‘s’ orbitals or two ‘p’ orbital’s or mixing of
an ‘s’ orbital with a ‘p’ orbital or ‘s’ orbital with a ‘d’ orbital.
We all know from general chemistry that the s-orbital is spherical, and p-
orbitals are dumbbell-looking orbitals oriented along the x, y, and z axes of the
Cartesian system. We also know that VSEPR describes the 3D shape of the second
period elements reasonably well.

And here we have a problem: the atomic orbitals are at 90° to each
other, while the VSEPR theory predicts the 3D structure of, say, methane
(CH4) to be tetrahedral with bond angles around 109.5°. So, how can we
have 109.5° bond angles made by the orbitals which are at 90° to each

other? 

In 1931 the twice Nobel Laureate Linus Pauling proposed the model

of “mixing” the orbitals or “hybridizing” them to account for the observed
bonding pattern. Pauling proposed sort of a combination of the orbitals

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giving you an orbital that has partial characters. Not a complete s- or a p-
orbital, but rather something with a partial s- and partial p-character.

Let me emphasize one more time that hybridization is

a mathematical model. There’s no actual “process” that happens to
orbitals that causes the hybridization. The atomic orbitals don’t actually
change before going into the bonding with other atoms. Hybridization is a
mathematical model that describes how the atomic orbitals would’ve
looked like based on the observable molecular orbitals.

Types of Hybridization
Based on the types of orbitals involved in mixing, the hybridization can be
classified as sp3, sp2, sp, sp3d, sp3d2, sp3d3. Let us now discuss the various types
of hybridization, along with their examples.

Formation of the Hybridized Orbitals

Ok, now when we know that hybridization is a model and not an actual

process, let’s look at how this “process” happens.   Each bond takes 2 electrons to
complete. If we look at the carbon atom atomic orbitals, we’ll see the 2 electrons on
the 2s and 2 electrons on the 2p shells. This would only allow carbon to make 2
bonds since it only has 2 unpaired electrons. To make four bonds, carbon would have
to “decouple” its s-electrons onto the p shell.

Rearranging the electrons in an atom in this way also makes the orbitals closer
in energy making them virtually degenerate. This allows for easier “mixing” or
hybridization as we know it. Thus, when we mix those orbitals together, we end up
with a set of “hybrids” and any leftovers that were not hybridized.

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 An important thing to remember: # of AO’s = # of MO. So, when we mix the
atomic orbitals to make the hybrids, we will end up with the exactly the same
number of the the orbitals when we’re done. Thus, by mixing 4 orbitals (one s and
three p), we’ll always get 4 molecular orbitals (hybrids or not).

sp3 Hybridization

When one ‘s’ orbital and 3 ‘p’ orbitals belonging to the same shell of an atom mix
together to form four new equivalent orbital, the type of hybridization is called
a tetrahedral hybridization or sp3. The new orbitals formed are called sp3 hybrid
orbitals.

 These are directed towards the four corners of a regular tetrahedron and

make an angle of 109°28’ with one another.
  The angle between the sp3 hybrid orbitals is 109.28 0
 Each sp3 hybrid orbital has 25% s character and 75% p character.
 Example of sp3 hybridization: ethane (C2H6), methane.

Mixing an s-orbital and three p-orbitals gives four sp 3 orbitals.

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 The resulting four hybrid sp 3 orbitals are all degenerate in energy,
meaning they are all the same. Also, according to VSEPR theory, those
orbitals need to be as symmetric around each other as possible. This gives a
tetrahedral structure with bond angles around 109.5°.

When those hybrid orbitals make bonds, we get molecular orbitals

oriented in the same direction. So, as I’ve mentioned earlier, while the
hybridization and the hybrid orbitals might be the mathematical model, it
does help us predict and illustrate the actual molecular orbitals in the
molecule. BTW, the molecular orbital theory (MOT) is a mathematical model

as well. 

 However, we can perform calculations using the MOT to predict the

electron densities around the molecule congruent with the real physical
observations.

sp2 Hybridization

sp2 hybridization is observed when one s and two p orbitals of the same shell of
an atom mix to form 3 equivalent orbitals. The new orbitals formed are
called sp2 hybrid orbitals. 

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  hy2 bridization is also called trigonal hybridization.
 It involves mixing of one ‘s’ orbital and two ‘p’ orbital’s of equal energy to give
a new hybrid orbital known as sp2.
 A mixture of s and p orbital formed in trigonal symmetry and is maintained at
1200.
 All the three hybrid orbitals remain in one plane and make an angle of 120°
with one another. Each of the hybrid orbitals formed has 33.33% s character
and 66.66% ‘p’ character.
 The molecules in which the central atom is linked to 3 atoms and is sp2
hybridized have a triangular planar shape.

Examples of sp2 Hybridization

 All the compounds of Boron i.e. BF3, BH3

 All the compounds of carbon containing a carbon-carbon double bond,
Ethylene (C2H4)

When we mix one s-orbital and two p-orbitals, we get three

sp  hybridized orbitals. You’ll also have one leftover p-orbital that didn’t
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participate in the hybridization.

This hybridization gives you the trigonal planar geometry around the central
atom with the p-orbital sticking in the up and down vertical direction.

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 The “unused” p-orbital can make a π-bond or to participate in a complex
resonance conjugation.

sp Hybridization

sp hybridization is observed when one s and one p orbital in the same main shell
of an atom mix to form two new equivalent orbitals. The new orbitals formed are
called sp hybridized orbitals. It forms linear molecules with an angle of 180°

 This type of hybridization involves the mixing of one ‘s’ orbital and one ‘p’
orbital of equal energy to give a new hybrid orbital known as a sp hybridized
orbital.
 sp hybridization is also called diagonal hybridization.
 Each sp hybridized orbital has an equal amount of s and p character, i.e.,
50% s and p character.

Examples of sp Hybridization:

 All compounds of beryllium like BeF2, BeH2, BeCl2

 All compounds of carbon-containing triple Bond like C2H2.

In the case of the sp hybridization, only one s- and one p-orbital are mixed
together to make hybrids. This leaves two unused p-orbitals.

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 The unused sp orbitals force the structure to have a linear 3D geometry.

The unused p-orbitals can make two double bonds, a triple bond, or
potentially participate in resonance with other orbitals.

sp3d Hybridization
sp3d hybridization involves the mixing of 3p orbitals and 1d orbital to form 5
sp3d hybridized orbitals of equal energy. They have trigonal bipyramidal geometry.

 The mixture of s, p and d orbital forms trigonal bipyramidal symmetry.

 Three hybrid orbitals lie in the horizontal plane inclined at an angle of 120° to
each other known as the equatorial orbitals.
 The remaining two orbitals lie in the vertical plane at 90 degrees plane of the
equatorial orbitals known as axial orbitals.
 Example: Hybridization in Phosphorus pentachloride (PCl5)

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sp3d2 Hybridization
 Sp3d2 hybridization has 1s, 3p and 2d orbitals, that undergo intermixing to
form 6 identical sp3d2 hybrid orbitals.
 These 6 orbitals are directed towards the corners of an octahedron.
 They are inclined at an angle of 90 degrees to one another.

Key Features of Hybridization

 Atomic orbitals with equal energies undergo hybridization.
 The number of hybrid orbitals formed is equal to the number of atomic orbitals
mixing.
 It is not necessary that all the half-filled orbitals must participate in
hybridization. Even completely filled orbitals with slightly different energies
can also participate.
 Hybridization happens only during the bond formation and not in an isolated
gaseous atom.
 The shape of the molecule can be predicted if hybridization of the molecule is
known.
 The bigger lobe of the hybrid orbital always has a positive sign, while the
smaller lobe on the opposite side has a negative sign.

How Do We Determine Hybridization?

The easiest way to determine hybridization is to with the VSEPR theory and
determine the number of electron groups around your central atom. To put it plain, I
can summarize the hybridizations in the following picture:

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 So, the 3 groups around the central atom gives you the sp 3 hybridization, the
three groups give you sp2 hybridization, and the two groups yield the sp-hybridized
species. Also remember, we do count the spare electron pairs as the electron groups
too!

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 Unless the electron pair is next to a double or a triple bond (or an empty p-
orbital), the electron pair will be on the hybrid orbital and not the p-orbital. While
that is not 100% true in reality, that’s the way we treat it within the scope of a typical
organic chemistry class, so we’ll stick with it too.

Hybridization of Atoms with Electron Pairs next to Double or Triple Bonds

I’ve mentioned above, that a double or a triple bond next to an electron pair matters.
When you have an electron pair next to a p-orbital or a π-bond, there’s a resonance
between those.

This is a very typical “trick question” on the exam, so you want keep this in
mind. It’s also important to remember that the electron pair has to be physically able
to align with the p-orbital or a π-bond for this to happen. So, the isolated electron
pairs will still be sitting on the hybrid orbitals even when they are next to double
bonds.

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 Spotting the isolated electron pairs can be a little tricky, so you may want do
some practice to master this skill. There is a quick rule of thumb you can use. If you
have an electron pair on the atom that already has a double bond, chances are, it’s
going to be isolated. It’s not a 100% foolproof trick, but it works for cyclic structures

Teaching and Learning Activities:

Activity 1:

1. What are the different types of hybridization?

2. What are hybrid orbitals?

Activity 2:
Give the hybridization states of each of the carbon atoms in the given molecule.

1. H2C = CH – CN
2. HC ≡ C − C ≡ CH
3. H2C = C = C = CH2

Recommended learning materials and resources for supplementary reading:

The recommended learning materials and resources in this chapter include the URL
of the resources from the Internet (PDF, youtube, slideshare, etc.)

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Flexible Teaching Learning Modality (FTLM):

This chapter adopts the synchronous and asynchronous learning modalities for you
to have better access and learning of the lessons. This may include google classroom,
moodle, schoology, edmodo, Podcast, printed materials and other resources depending on
your needs and capacity to use the material.

Assessment Task

1. What is the difference among sp, sp2 and sp3 hybridization?

2. Explain the five basic shapes of Hybridization?

Answer Key:
Activity 1
1. The five basic shapes of hybridization are linear, trigonal planar, tetrahedral, trigonal
bipyramidal, and octahedral. b b
The geometry of the orbital arrangement:

 Linear: Two electron groups involved resulting in sp hybridization, the angle between the
orbitals is 180°.
 Trigonal planar: Three electron groups involved resulting in sp2 hybridization, the angle
between the orbitals is 120°.
 Tetrahedral: Four electron groups involved resulting in sp3 hybridization, the angle
between the orbitals is 109.5°.
 Trigonal bipyramidal: Five electron groups involved resulting in sp3d hybridization, the
angle between the orbitals is 90°, 120°.
 Octahedral: Six electron groups involved resulting in sp3d2 hybridization, the angle
between the orbitals is 90°.

2. Based on the nature of the mixing orbitals, the hybridization can be classified as,

 sp hybridization (beryllium chloride, acetylene)

 sp2 hybridization (boron trichloride, ethylene)
 sp3 hybridization (methane, ethane)
 sp3d hybridization (phosphorus pentachloride)
 sp3d2 hybridization (sulphur hexafluoride)
 sp3d3 hybridization (iodine heptafluoride)

References:
Carey, Francis A. Organic Chemistry. 3rd edition. © 1996. The Mc Graw-Hill Companies, Inc.

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Internet

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