Republic of the Philippines

CEBU TECHNOLOGICAL UNIVERSITY

MAIN CAMPUS
M. J. Cuenco Avenue Cor. R. Palma Street, Cebu City,
Philippines
Website: http://www.ctu.edu.ph E-mail: casdean@ctu.edu.ph
Phone: +6332 402 4060 loc. 1109

ATOMIC AND MOLECULAR MODELS

Activity no. _______ Date: _____________

Introduction
Organic compounds occur throughout in our everyday lives and countless products – like jelly beans in a plastic container, Jelly beans are composed
of sugar, gelatin and starch which are all organic compounds. And the plastic container is a combination of polymeric organic compounds. In fact, for
some of the few salts and ever -present water, nearly everything you put into your body or on your body, everything is consisting of organic
compounds.

Purpose:
1. Create various kinds of atomic models of selected hydrocarbons
2. Recognize chemical bonds with the use of tetrahedral models

Discussion:
Hydrocarbons, the simplest type of organic compounds are large group of substances containing only Carbon and Hydrogen atoms. Most organic
molecules, including all hydrocarbons like alkanes, are not planar but instead characterized by three dimensional structures. Methane for example,
has the shape of a regular tetrahedron with carbon at the center and a hydrogen atom at each other. Higher alkanes such as butane have bonds that are
in tetrahedral disposed on each carbon except that the resulting C-C-C and H-C-H angles are slightly larger and smaller, respectively, than the ideal
value of 109.50 characteristic of a perfectly symmetrical tetrahedron. Carbon- Carbon bond distance in alkanes are normally close to 1.53 angstroms.

An important aspect of the three-dimensional shape of alkanes and other organic molecules is their conformations, the non identical
arrangements of atoms that are generated by rotation about single bonds. Of the infinite number of conformations possible for ethane
—which are related by tiny increments of rotation of one CH 3 group with respect to the other—the eclipsed conformation is the least
stable, and the staggered conformation is the most stable. The eclipsed conformation is said to suffer torsional strain because of
repulsive forces between electron pairs in the C―H bonds of adjacent carbons. These repulsive forces are minimized in the staggered
conformation since all C―H bonds are as far from one another as possible. Although rotation about the C―C bond of ethane is
exceedingly rapid (millions of times per second at room temperature), at any instant most of the molecules exist in the staggered
conformation.
 Republic of the Philippines
CEBU TECHNOLOGICAL UNIVERSITY
MAIN CAMPUS
M. J. Cuenco Avenue Cor. R. Palma Street, Cebu City,
Philippines
Website: http://www.ctu.edu.ph E-mail: casdean@ctu.edu.ph
Phone: +6332 402 4060 loc. 1109

Atomic orbitals can be combined and reshaped – much like a dough- to make other orbitals of different shapes and properties.
There are two basic types of orbitals that can result from such processes. They are:

1. Hybrid orbitals is an orbital formed by the combination of two or more atomic orbitals. The resulting orbital has a different shape and
energy than the component orbitals that form it. Hybridization is used to model molecular geometry and to explain atomic bonding.

2. Molecular orbital states that each atom tends to combine together and form molecular orbitals. As a result, they result from the
combination of orbitals between atoms as bonding takes place to form molecules.

Orbital Hybridization
Hybridization was introduced to explain molecular structure when the valence bond theory failed to predict them. It is experimentally observed that
bond angles in organic compounds are close to 109 0, 1200, or 1800. . According to Valence Shell Electron Pair Repulsion (VSEPR) theory, electrons
pairs repel each other and the bonds and lone pairs around a central atom are generally separated by the largest possible angles.

Let’s take a look at Carbon the perfect example showing the value of hybrid orbitals.

A neutral carbon atom has atomic number is 6, with 6 protons and 6 electrons. The ground state electron configuration for carbon is 1s 2 2s2 2p2 .

If we look at the valence shell configuration of carbon, we find two paired electrons in the 2s orbital, and two unpaired electrons in the 2p x and py
orbitals, one in each:

In order to fulfill the octet rule, carbon must use its 4 valence electrons when bonding to other atoms. However, only unpaired electrons can bond.
That means that the two paired electrons occupying the 2s orbital must become unpaired before they can bond. Since the energy gap between the 2s
and 2 p orbital is very small, one of the 2s electrons can be promoted to the 2p orbital, leading to the following situation:

Now the four electrons appear to be ready for bonding, but there is a problem. The 2p orbitals are known to be right angles to each other. The
simplest hydrocarbon – methane- CH4 – is known to have tetrahedral geometry, where the four C-H bonds are all equivalent and positioned at 109.5 0
angles to each other. In addition, there are some carbon compounds where the bond angles are 120 0 or even 1800 .
 Republic of the Philippines
CEBU TECHNOLOGICAL UNIVERSITY
MAIN CAMPUS
M. J. Cuenco Avenue Cor. R. Palma Street, Cebu City,
Philippines
Website: http://www.ctu.edu.ph E-mail: casdean@ctu.edu.ph
Phone: +6332 402 4060 loc. 1109

All four sp3 orbitals that result from this process are equivalent. That means that they have the same shape, size, and energy. According to VSEPR
(valence shell electron repulsion) theory, such orbitals will orient themselves in 3-D space to be as far apart from each other as possible. The
resulting shape is then a tetrahedron, where the carbon nucleus is at the center and the orbitals point to the corners of the tetrahedron.

LET’S A LOOK AT THE HYDROCARBON METHANE

Methane (CH4 ) , the three 2p orbitals of the carbon atom are combined with its 2s orbital to form four new orbitals called “sp 3” hybrid orbitals. The
name is simply a tally of all the orbitals that were blended together to form these new hybrid orbitals. Four hybrid orbitals were required since there
are four atoms attached to the central atom. These orbitals will have energy slightly above the 2s orbital and below the 2p orbitals as show in the
following illustration. There will be no change for 1s. (not shown)

These hybrid orbitals have 75% p- character and 25% s-character which gives them a shape that is shorter and fatter than a p-orbital. A stick and
wedge drawing of methane shows the tetrahedral angles… (The wedge is coming out of the paper and the dashed line is going behind the paper. The
solid lines are in the plane of the paper.
 Republic of the Philippines
CEBU TECHNOLOGICAL UNIVERSITY
MAIN CAMPUS
M. J. Cuenco Avenue Cor. R. Palma Street, Cebu City,
Philippines
Website: http://www.ctu.edu.ph E-mail: casdean@ctu.edu.ph
Phone: +6332 402 4060 loc. 1109

LET’S TAKE A LOOK AT THE HYDROCARBON MOLECULE ETHENE, C 2 H4 both carbon atoms will be sp2 hybridized and have one unpaired
electron in a non-hybridized p orbital.

These p- orbitals will undergo parallel overlap and form one pi bond with bean-shaped probability areas above and below the plane of the six atoms.
This pair of bean-shaped probability areas constitutes one- pi-bond and the pair of electrons in this bond can be found in either bean-shaped area.

Now let’s take at a look at H2 C2 (acetylene). Both carbon atoms will be sp hybridized and have one electron in each of two unhybridized p orbitals.

These p orbitals will undergo parallel overlap to form two pi-bonds at right angles to each other.
 Republic of the Philippines
CEBU TECHNOLOGICAL UNIVERSITY
MAIN CAMPUS
M. J. Cuenco Avenue Cor. R. Palma Street, Cebu City,
Philippines
Website: http://www.ctu.edu.ph E-mail: casdean@ctu.edu.ph
Phone: +6332 402 4060 loc. 1109

Questions to be answered: Free response (always include and write the references of your answer)

1.What is the purpose of orbital diagrams?

2. Explain the following explicitly
a. Aufbau principle
b. The Pauli-Exclusion principle
c. Hund’s rule
3. Show / illustrate (need to be handwritten, no copy paste)
Sigma bond combinations
a. s-s overlapping b. s-p overlapping c. p-p overlapping
4. Pi bonding molecular orbital
5. What are the differences between a sigma and pi bonds?

References:

1.USC Chemistry 25NL Laboratory manual

2.Cebu Doctors’ University, Chemistry 112 L Inorganic and Organic Chemistry
3. Petrucci et. al. General Chemistry Principles and Modern Applications. Pearson. Canada
4. https://www.thoughtco.com/definition-of-hybrid-orbital-605218
5. https://nigerianscholars.com/tutorials/covalent-bonding-continued/sp3-hybridization/

Prepared by: Lucia T. Ballesta, LPT