Explanation

If there was an unhybridized 2p orbital, then the central atom would be either sp2^22 or sp
hybridized. This would produce a trigonal planar species or linear species, respectively.

Q1.23 - Level 2
Review
What is the hybridization of the nitrogen atom in ammonia?
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answer.
a
sp
b

sp
c

sp

Explanation

A tetrahedral shape is the result of sp3^33 hybridization. Here, one 2s orbital and three 2p
orbitals hybridize to produce four sp3^33 orbitals.

This is your recorded answer from classroom or homework

Explanation

Explanation

A tetrahedral shape is the result of sp3^33 hybridization. Here, one 2s orbital and three 2p
orbitals hybridize to produce four sp3^33 orbitals.

The hybridization of nitrogen involves the combination of one atomic 2s orbital with three
atomic 2p orbitals to produce four sp3 hybridized molecular orbitals oriented ~107° from each
other. The reason the bond angle is less than the ideal 109.5° is because lone pairs of electrons
occupy more space than bond pairs and thus cause greater electron-electron repulsion. The sp 3
energy diagram is the same as carbons. The only difference is the number of electrons as
indicated by the dotted circle.

In Figure 1.37 is a summary of the hybridization of nitrogen and the relative energies of the
hybridized orbitals with respect to the ground state s and p orbitals.
Figure 1.37. Electron configuration diagram and hybridization states of nitrogen.

3D Molecule*: ammonia

3D Molecule*: methanimine

3D Molecule*: formonitrile

As seen above, in order to determine the hybridization of an atom in a molecule, you must
realize that each lone pair and σ bond localized on an atom requires one hybrid orbital. For
example, consider the molecule acetaldehyde (Figure 1.38).
Figure 1.38. Hybridization of atoms in acetaldehyde.

3D Molecule*: acetaldehyde

The carbon on the left has four σ bonds, so it requires four hybrid orbitals. In order to construct
four hybrid orbitals, its 2s, 2px, 2py, and 2pz orbitals mix to form four sp3 hybrid orbitals.
Therefore, we say that the carbon on the left is sp3 hybridized. The carbonyl (C=O) carbon has
three σ bonds, so it requires only three hybrid orbitals. In order to construct the three required
hybrid orbitals, the 2s orbital is mixed with two 2p orbitals to form three sp 2 hybrid orbitals. The
coordinate axes are arbitrary. The oxygen atom is also sp2 hybridized. In the case of oxygen,
however, two of the three sp2 hybrid orbitals are used to house lone pairs. Note that hydrogen
atoms are incapable of hybridization since they only have one valence orbital (1s).

Q1.24 - Level 3
Review
Which of the following diagrams correctly represents the hybridization of the oxygen atom in
methoxymethane?
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answer.
a
Energy Diagram 1
b
Energy Diagram 2
c
Energy Diagram 3

Explanation

Since there are 4 electron dense regions (2 bonds and 2 electron pairs), this is sp3^33 hybridized.

This is your recorded answer from classroom or homework

Explanation

Explanation

Since there are 4 electron dense regions (2 bonds and 2 electron pairs), this is sp3^33 hybridized.

In addition to allowing us to reconcile quantum mechanics with observed molecular geometries,

Figure 1.39. Effect of hybridization on bond length and hence strength.

Note that in ethane the C-H bond is formed via C(sp 3)/H(1s). In ethene, the C bond is due to
C(sp2)/H(1s) overlap. In ethyne, the C-H bond comes from C(sp)/H(1s) overlap. As the “p-
character” increases, the bond length increases, since the orbital extends further into space. Being
able to predict and explain bond lengths is important since bond length and bond strength are
inversely related and weak bonds are often reactive sites in organic molecules.

As you can see from the above, it is important to keep track of the lone pairs of electrons because
the electrons occupy space and dictate the shape of the molecule. A very common term used to
signify both atoms and lone pairs around a central atom is steric number and electron group
geometry. The steric number is the total number of lone pairs and atoms around a central atom.
For example, the steric number of C in methane, N in ammonia, and O in water is 4. Since they
all have a steric number of 4, they will all have the same electron group geometry, based on
VSEPR: approximately tetrahedral. However, their molecular shapes will be tetrahedral, trigonal
pyramidal, and bent, respectively.
Figure 1.40. Summary of electron domain geometries.

Q1.26 - Level 1
Review
What is the hybridization about the central carbon atom in the drawing below?

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answer.
a
sp
b

sp
c

sp

Explanation

The central carbon has 3 different ligands. Therefore, it is sp2^22 hybridized.

This is your recorded answer from classroom or homework

Explanation
Explanation

The central carbon has 3 different ligands. Therefore, it is sp2^22 hybridized.

Q1.27 - Level 1
Review
What is the hybridization about the nitrogen atom in the drawing below?

Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a
sp
b

sp
c

sp

Explanation

Since there are 4 ligands, the nitrogen is sp3^33 hybridized.

This is your recorded answer from classroom or homework

Explanation

Explanation

Since there are 4 ligands, the nitrogen is sp3^33 hybridized.

Q1.29 - Level 2
Review
What type of orbital overlap is responsible for the sigma bond between the carbon atoms in the
molecule below?
Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a

sp/sp
b

sp/sp
c

sp /sp
d

sp /sp
e

sp /sp

Explanation

One of the carbons is sp3^33 hybridized, while the second carbon is sp hybridized. The end-to-
end overlap of these two hybridized orbitals causes the sigma bond.

This is your recorded answer from classroom or homework

Explanation

Explanation

One of the carbons is sp3^33 hybridized, while the second carbon is sp hybridized. The end-to-
end overlap of these two hybridized orbitals causes the sigma bond.

1.2.2F Molecular Orbital Theory

Lewis theory, VSEPR theory, and hybrid orbital theory are sometimes collectively called valence
bond theory. In valence bond theory, bonding electrons are treated as being localized between
two atoms participating in a covalent bond. We have seen that this treatment of bonding
electrons does not always lead to a satisfactory description of bonding, especially in cases when
we must arbitrarily choose where to place non-bonding and π bonding electrons (e.g. NO 3-;
Figure 1.53). A more realistic, albeit more complicated, description of electron density in
molecules is offered by Molecular Orbital (MO) theory.

In MO theory, the valence atomic orbitals of each atom in the molecule are combined according
to a series of rules in order to generate new, molecular orbitals where bonding, non-bonding, and
antibonding electrons reside. One of the simplest methods for combining atomic orbitals to form
molecular orbitals is called the Linear Combination of Atomic Orbitals (LCAO) method. In this
method, the wave functions for each atomic orbital are added together via a linear, weighted
superpositioning. For example, if you were to create a molecular orbital for the hypothetical
molecule AB, you would use the equation in Figure 1.41.

Figure 1.41. Mathematical basis for linear combination

The rules for combining atomic orbitals to generate molecular orbitals are as follows:

Rule 1: For each atomic orbital in the basis set, comprising all valence orbitals for all atoms in
the molecule, one molecular orbital will be generated. Each molecular orbital results from a
unique linear combination of atomic orbitals (Figure 1.42).
Figure
1.42. Atomic orbitals combine constructively and destructively to form bonding and antibonding
molecular orbitals. A node is a region in which the probability density is zero.

Rule 2: When n atomic orbitals are combined to make n molecular orbitals, n/2 of the molecular
orbitals are lower in energy than the parent atomic orbitals; the bonding molecular orbitals.
Moreover, n/2 of the molecular orbitals are higher in energy than the parent atomic orbitals, the
antibonding molecular orbitals (Figure 1.43).

Figure 1.43. Molecular orbital energy level diagram for

Bonding molecular orbitals result from constructive interference between atomic orbitals (i.e.
overlap of orbital lobes with same sign), and antibonding molecular orbitals result from
destructive interference between atomic orbitals (i.e. overlap of orbital lobes of opposite sign).
Note that when we draw a bonding molecular orbital, the constructive interference is depicted by