ChemActivity

25
Electron Orbitals

Model 1: Orbital Representation of n=2 Shell

Electrons are small and move very fast, so it is useful to think about them as a mist of negative
charge concentrated in a region of space (e.g. a bond). This is sometimes referred to as an
electron cloud.
An orbital is a three-dimensional region of space where this electron cloud is likely to be found.
In our previous Shell Model of the atom, electrons were shown as an orbit, circling the nucleus a
fixed distance away. The n=1 shell could hold up to two electrons and the n=2 shell could hold up
to eight. In this model, the n=2 shell is shown as four orbitals: 2s, 2px, 2py, and 2pz. Each orbital
can be empty (zero e), half-filled (one e), or full (two e).

Figure 1. Shell (orbit) and Orbital Representations of the n=2 Shell

Critical Thinking Questions

1. What is the maximum number of electrons that can fit in a single orbital (2s, 2px, 2py, or
2pz)?

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

Model 2: Electron Configuration

Previously we assigned electrons to orbital
on an electron configuration diagram or an
energy level diagram. Recall that within the
n=2 shell an electron in the 2s orbital has
lower potential energy than an electron in the
2p orbital because the area of an s orbital is
closer (on average) to the nucleus than that of
a p orbital.

Critical Thinking Questions

2. What neutral atom is represented by the electron configuration in Model 2?

Model 3: Sigma () Bonds and Pi () Bonds

We have represented bonds as electron domains between two atoms and say that the atoms
share the electrons. A bond is actually formed by an overlap of orbitals. We will mostly
encounter two types of bonds: head-to-head overlaps called () sigma bonds and side-to-side
overlaps called () pi bonds. Most often a bond is an overlap of two half-filled orbitals. This
results in two electrons per bond.
head-to head overlap of p orbitals

Single bond = one bond

Double bond = one bond plus one bond

Triple bond = one bond plus two bonds

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

Critical Thinking Questions

3. A student says the picture at the right must represent a triple
bond formed by the overlap of three 2p orbitals surrounding
each of the two nuclei represented by the symbol .
a) Agree or disagree with this statement and explain your
reasoning.

b) How many electrons are there in a triple bond and how many electrons are there in the
bond represented at the right?
c) What misconception may have caused this student to think this was a representation of
a triple bond?

d) You are supposed to imagine that an orbital is a 3D object like a balloon. In the picture
of a double bond in Model 3, all the balloons are centered in the plane of the paper.
Where is their space to add a second bond linking these same two nuclei so they
generate a triple bond?

e) Recall that the major experimentally determined bond angles around a central atom are
109.5, 120 and 180. What angle do the p orbitals form (hint: see Model 1)?

f) Which of the 2p orbitals, 2px, 2py, or 2pz, can form one of the three major bond angles?

Information
None of the p orbitals point in the right direction to make 109.5, 120 or even 180 bond angles.
To solve this problem Nobel Prize winner Linus Pauling described orbitals he called hybrid
orbitals which pointed in the right directions. For s and p orbitals there are three hybrid orbital
sets, one to explain each family of experimentally observed bond angles.
A hybrid orbital is a mixture of multiple orbitals. The number of hybrid orbitals that results
from mixing orbitals is the same as the number of orbitals used. For example, a hybrid of the 2s
and all three 2p orbitals results in four identical hybrid orbitals. A hybrid of the 2s and only two
2p orbitals results in three identical hybrid orbitals.

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

Critical Thinking Questions

4. How many electron domains are there around an atom in the 109.5 angle set?
5. How many hybrid orbitals are needed to arrive at that many electron domains?
6. Which orbitals would be used to form these hybrid domains?
7. Explain the name s(1/4)-p(3/4) hybrid orbital for each of the four orbitals.

8. In fact, each of the four hybrid orbitals in the 109.5 set is called an sp3-hybrid orbital.
Explain that name.

Model 4: Hybrid Orbital Picture of Bonding in Ammonia

Any central atom with bond angles close to 109.5 is sp3-hybridized.

Critical Thinking Questions

9. Circle each central atom that you expect to be sp3-hybridized.

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

Model 5: The 120-Hybrid Orbital Set

A 109.5 hybrid orbital set was needed to explain the
bond angles of NH3, H2O, etc. Similarly, a 120 hybrid
ortbital set is needed to explain 120 bond angles.

Critical Thinking Questions

10. Construct an explanation for why each hybrid
orbital in the 120-hybrid orbital set is called an
sp2-hybrid orbital.

11. Circle each central atom you expect to be sp2-hybridized.

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

Model 6: Orbital Description of a Double Bond

Recall that side-on overlap

of two half-filled p-orbitals
results in a bond.

Orbital overlap between two sp2-hybridized atoms can result in a bond and a bond.

Critical Thinking Questions

12. On the left side of the figure above, label the areas shown with a dotted line where
a) One bond can form.
b) One bond can form.
13. Draw a Lewis structure of the molecule represented
with the orbitals on the right side of the figure.

14. Label the and bond on both the Lewis structure you just drew and the orbital
representation on the right side of the figure.

Information
Single bonds can freely rotate, but double bonds cannot because the portion of a double bond
prevents the bond axis from rotating.

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009

15. Construct an explanation for why structure K and L are different molecules while M and N are
two representations of the same molecule.

Model 7: Orbitals Descriptions of a Triple Bond

Critical Thinking Questions

16. On the left side of the figure, dotted lines are used to show the bond that can form between
the two black p orbitals.
a) Add dotted lines showing where the bond can form between the two white p orbitals.
b) Add dotted lines showing where the bond can form.
17. Now consider the fully formed molecule to the right side of the figure.
a) Draw a Lewis structure of this molecule.

b) Identify orbital representations of the two bonds and three bonds in the figure and
match these with the representation of the bonds on the Lewis structure you just drew.
c) Construct a name for the hybrid orbital set that gives rise to 180 bond angles.

Adapted from Straumanis, Organic Chemistry: a Guided Inquiry 2nd Edition, Houghlin Mifflin Publishing Company 2009