SAINT MARY’S UNIVERSITY

3700 Bayombong, Nueva Vizcaya, Philippines

School of Health and Natural Sciences

CENTER FOR NATURAL SCIENCES
Course Descriptive Title: Chemistry for Engineers

CHEMICAL BONDING AND GEOMETRY OF MOLECULES

Introduction

A chemical bond is the attractive force that builds atoms together in a compound.
Chemical bonding is one of the most basic fundamentals of chemistry that explains other
concepts such as molecules and reactions. Without it, scientists wouldn't be able to explain why
atoms are attracted to each other or how products are formed after a chemical reaction has
taken place. To understand the concept of bonding, one must first know the basics behind
atomic structure.

A common atom contains a nucleus composed of protons and neutrons, with electrons
in certain energy levels revolving around the nucleus. In this section, the main focus will be on
these electrons. Elements are distinguishable from each other due to their "electron cloud," or the
area where electrons move around the nucleus of an atom. Because each element has a distinct
electron cloud, this determines their chemical properties as well as the extent of their reactivity
(i.e. noble gases are inert/not reactive while alkaline metals are highly reactive). In chemical
bonding, only valence electrons, electrons located in the orbitals of the outermost energy
level (valence shell) of an element, are involved.

The following are the important terms to remember:

 Metal – Electron donor to attain stability.
 Nonmetal – Electron acceptor to complete the atom’s outermost shell.
 Noble Gas – Neither an electron donor nor an electron acceptor.
 Valence electron – Electron in the outer energy level of an atom.
 Octet Rule – An atom tends to form bonds until it is surrounded by eight valence
electrons.
 Lewis Dot Symbol – Consists of the symbol of an element and one dot for
each valence in an atom.
Example: C6 = 1s22s22p2 → : C :
 Lewis Structure – A representation of covalent bonding using Lewis dot symbols in
which shared electron pairs are shown as either as lines or as pairs of dots between
two atoms, and lone pairs of dots on individual atoms.

I.Types of Chemical Bond

Chemical bonding, any of the interactions that account for the association of atoms into
molecules, ions, crystals, and other stable species that make up the familiar substances of the
everyday world. When atoms approach one another, their nuclei and electrons interact and
tend to distribute themselves in space in such a way that the total energy is lower than it would
be in any alternative arrangement. If the total energy of a group of atoms is lower than the sum
of the energies of the component atoms, they then bond together and the energy lowering is
the bonding energy.
 The ideas that helped to establish the nature of chemical bonding came to fruition
during the early 20th century, after the electron had been discovered and quantum
mechanics had provided a language for the description of the behavior of electrons in atoms.
However, even though chemists need quantum mechanics to attain a detailed quantitative
understanding of bond formation, much of their pragmatic understanding of bonds is expressed
in simple intuitive models. These models treat bonds as primarily of two kinds—namely, ionic and
covalent. The type of bond that is most likely to occur between two atoms can be predicted on
the basis of the location of the elements in the periodic table, and to some extent the
properties of the substances so formed can be related to the type of bonding.

A. Ionic Bond or Electrovalent

Ionic bond, also called
electrovalent bond, is a type of
linkage formed from the
electrostatic attraction between
oppositely charged ions in a
chemical compound. Such a
bond forms when the valence
(outermost) electrons of one atom
are transferred permanently to
another atom. The atom that loses
the electrons becomes a positively
charged ion (cation), while the
one that gains them becomes a
negatively charged ion (anion). The ions result from the transfer of electrons from one
atom
to the other. It forms when the electronegativity difference between the two bonding
atoms is 2.0 or more (100% Ionic character).

Ionic bonding results in compounds known as ionic, or electrovalent, compounds,

which are best exemplified by the compounds formed between nonmetals and the alkali
and alkaline-earth metals. In ionic crystalline solids of this kind, the electrostatic forces
of attraction between opposite charges and repulsion between similar charges orient the
ions in such a manner that every positive ion becomes surrounded by negative ions and
vice versa. In short, the ions are so arranged that the positive and negative charges
alternate and balance one another, the overall charge of the entire substance being
zero.
The magnitude of the electrostatic forces
in ionic crystals is considerable.
Accordingly, these substances tend to be
hard and nonvolatile.

At the macroscopic scale, ionic

compounds form lattices, are crystalline
solids under normal conditions, and have
high melting points. Most of these solids are
soluble in H2O and conduct electricity
when dissolved. The ability to conduct
electricity in solution is why these
substances are called electrolytes. Table
salt, NaCl, is a good example of this type of
compound.
B. Covalent Bond
Covalent bond, in chemistry, the interatomic linkage that results from the
sharing of an electron pair between two atoms. The binding arises from the electrostatic
attraction of their nuclei for the same electrons. A covalent bond forms when the
bonded atoms have a lower total energy than that of widely separated atoms.

Covalent bonding occurs when pairs of electrons are shared by atoms. Atoms will
covalently bond with other atoms in order to gain more stability, which is gained by
forming a full electron shell. By sharing their outer most (valence) electrons, atoms can
fill up their outer electron shell and gain stability. Nonmetals will readily form covalent
bonds with other nonmetals in order to obtain stability, and can form anywhere between
one to three covalent bonds with other nonmetals depending on how many valence
electrons they possess. Although it is said that atoms share electrons when they form
covalent bonds, they do not usually share the electrons equally.

Only when two atoms of the same element form a covalent bond are the shared
electrons actually shared equally between the atoms. When atoms of different elements
share electrons through covalent bonding, the electron will be drawn more toward the
atom with the higher electronegativity resulting in a polar covalent bond. When
compared to ionic compounds, covalent compounds usually have a lower melting and
boiling point, and have less of a tendency to dissolve in water. Covalent compounds
can be in a gas, liquid, or solid state and do not conduct electricity or heat well. The
types of covalent bonds can be distinguished by looking at the Lewis dot structure of the
molecule. For each molecule, there are different names for pairs of electrons, depending
if it is shared or not. A pair of electrons that is shared between two atoms is called a
bond pair. A pair of electrons that is not shared between two atoms is called a lone
pair.

Two important types of covalent bonds are nonpolar or pure covalent bonds and
polar covalent bonds. Nonpolar bonds occur when atoms equally share electron pairs.
Since only identical atoms (having the same electronegativity) truly engage in equal
sharing, the definition is expanded to include covalent bonding between any atoms with
an electronegativity difference less than 0.4. Examples of molecules with nonpolar bonds
are H2, N2, and CH4.

As the electronegativity difference increases, the electron pair in a bond is more

closely associated with one nucleus than the other. If the electronegativity difference is
between 0.4 and 1.7, the bond is polar. If the electronegativity difference is greater than
1.7, the bond is ionic.

1. Nonpolar Covalent Bond or Nonpolar Bond

It is a covalent bond between two atoms with the same electronegativity
value. The electrons are shared equally between the two atoms.

Examples: Diatomic Molecules

a. H2 [Single Bond]
 b. Br2 [Single Bond]

c. O2 [Double Bond]

2. Polar Covalent Bond or Polar Bond

Polar Covalent Bond is created when the shared electrons between atoms
are not equally shared. This occurs when one atom has a higher electronegativity
than the atom it is sharing with. The atom with the higher electronegativity will
have a stronger pull for electrons (Similiar to a Tug-O-War game, whoever is
stronger usually wins). As a result, the shared electrons will be closer to the
atom with the higher electronegativity, making it unequally shared. A polar
covalent bond will result in the molecule having a slightly positive side (the side
containing the atom with a lower electronegativity) and a slightly negative side
(containing the atom with the higher electronegativity) because the shared
electrons will be displaced toward the atom with the higher electronegativity.

As a result of polar covalent bonds, the covalent compound that forms

will have an electrostatic potential. This potential will make the resulting
molecule
slightly polar, allowing it to
form weak bonds with
other polar molecules. One
example of molecules
forming weak bonds with
each other as a result of an
unbalanced electrostatic
potential is hydrogen
bonding, where a hydrogen
atom will interact with an
electronegative hydrogen,
fluorine, or oxygen atom
from another molecule or
chemical group.

3. Types of Covalent Bonds

a. Single Bond
A single bond is when two electrons--one pair of electrons--are
shared between two atoms. It is depicted by a single line between the
two atoms. Although this form of bond is weaker and has a smaller
density than a double bond and a triple bond, it is the most stable
because it has a lower
 level of reactivity meaning less vulnerability in losing electrons to atoms that
want to steal electrons.

b. Double Bond
A Double bond is when two atoms share two pairs of electrons
with each other. It is depicted by two horizontal lines between two atoms
in a molecule. This type of bond is much stronger than a single bond, but
less stable; this is due to its greater amount of reactivity compared to a
single bond.

c. Triple Bond
A Triple bond is when three pairs of electrons are shared between
two atoms in a molecule. It is the least stable out of the three general types
of covalent bonds. It is very vulnerable to electron thieves!

C. Properties of Ionic and Covalent Compounds

IONIC COMPOUND VS COVALENT COMPOUND

Basis Ionic Compound Covalent Compound
1. Force of Attraction Electrostatic force Intermolecular force
2. Boiling Point High Low
3. Melting Point High Low
4. Physical state at 25 °C Solid Liquid/Gas
5. Electric Conductivity in water High No
6. Electronegativity Difference High Low

II. The Lewis Electron Dot Structure of Bond Formation

Lewis structures, also known as electron dot structures, are named after Gilbert N. Lewis,
who described them in a 1916 article titled, "The Atom and the Molecule." Lewis structures
depict the bonds between atoms of a molecule, as well as any unbonded electron pairs. You
can draw a Lewis dot structure for any covalent molecule or coordination compound.

A Lewis structure is a type of shorthand notation. Atoms are written using their element
symbols. Lines are drawn between atoms to indicate chemical bonds. Single lines are single
bonds, double lines are double bonds, and triple lines are triple bonds. (Sometimes pairs of dots
are used instead of lines, but this is uncommon.) Dots are drawn next to atoms to show
unbonded electrons. A pair of dots is a pair of excess electrons.

A Lewis electron dot diagram (or electron dot diagram or a Lewis diagram or a Lewis
structure) is a representation of the valence electrons of an atom that uses dots around the
symbol of the element. The number of dots equals the number of valence electrons in the
atom. These dots are arranged to the right and left and above and below the symbol, with no
more than two dots on a side. (It does not matter what order the positions are used.)

Nonbonding Electrons/Lone Pairs

- Valence electrons, which are not involved in covalent, bond formation.
Multiple Bonds
- Two atoms share two or more pairs of electrons.

For example, the Lewis electron dot diagram for calcium is simply:
A. The Octet Rule
The Octet Rule requires all atoms in a molecule to have 8 valence electrons--
either by sharing, losing or gaining electrons--to become stable. For Covalent bonds,
atoms tend to share their electrons with each other to satisfy the Octet Rule. It requires 8
electrons because that is the amount of electrons needed to fill a s- and p- orbital (electron
configuration); also known as a noble gas configuration. Each atom wants to become as
stable as the noble gases that have their outer valence shell filled because noble gases
have a charge of 0. Although it is important to remember the "magic number", 8, note
that there are many Octet rule exceptions.

When ions form, they conform to the octet rule by either losing or gaining
electrons in order to achieve the electron configuration of the nearest noble gas. In a
similar way, nonmetal atoms share electrons in the formation of a covalent in bond such
a way that each of the atoms involved in the bond can attain a noble-gas electron
configuration. The shared electrons are “counted” for each of the atoms involved in the
sharing. For hydrogen (H2), the shared pair of electrons means that each of the atoms is
able to attain the electron configuration of helium, the noble gas with two electrons. For
atoms other than hydrogen, the sharing of electrons will usually provide each of the
atoms with eight valence electrons.

1. Exceptions to the Octet Rule

a. Incomplete Octet
In some compounds, the number of electrons surrounding the
central atom in a stable molecule is fewer than eight.

Examples:
(1) Beryllium Hydride (BeH2)

(2) Boron Trifluoride (BF3)

 b. Odd – Electron Molecules
Some molecules contain an odd number of electrons

Examples:
(1) Nitric Oxide (NO)

(2) Nitrogen Dioxide (NO2)

c. Expanded Octet
In a number of compounds, there are more than eight valence
electrons around an atom. These are needed only for atoms of elements
in and beyond the third period.

Examples:
(1) Sulfur Hexafluoride (SF6)

(2) Phosphorus Pentafluoride (PF5)

B. Writing Lewis Structure Steps

1. Pick a central atom.
Start your structure by picking a central atom and writing its element
symbol. This will be the atom with the lowest electronegativity. Sometimes it's
difficult to know which atom is the least electronegative, but you can use the
periodic table trends to help you out. Electronegativity typically increases as you
move from left to right across the periodic table and decreases as you move
down the table from top to bottom. You can consult a table of
electronegativities, but be aware different tables may give you slightly different
values, since electronegativity is calculated. Once you've selected the central
atom, write it down and connect the other atoms to it with a single bond. (You
may change these bonds to double or triple bonds as you progress.)

2. Count electrons.
Lewis electron dot structures show the valence electrons for each atom.
You don't need to worry about the total number of electrons, only those in the
outer shells. The octet rule states that atoms with eight electrons in their outer
shells are
stable. This rule applies well up to period 4, when it takes 18 electrons to fill the
outer orbitals. Filling the outer orbitals of electrons from period 6 requires 32
electrons. However, most of the time when you're asked to draw a Lewis
structure, you can stick with the octet rule.

a. For polyatomic anions,

Add the number of negative charges to that total.
b. For polyatomic cations
Subtract the number of positive charges to that total.

3. Place electrons around atoms.

Once you have determined how many electrons to draw around each
atom, you can begin placing them on the structure. Start by placing one pair of
dots for each pair of valence electrons. Once the lone pairs are placed, you may
find that some atoms, particularly the central atom, don't have a complete octet
of electrons. This indicates there are double or possibly triple bonds. Remember,
it takes a pair of electrons to form a bond. Once the electrons have been placed,
put brackets around the entire structure. If there's a charge on the molecule,
write it as a superscript on the upper right, outside of the bracket.

4. Check for OCTET!

Complete the octets of the atoms bonded to the central atom. Electrons
belonging to the central or surrounding atoms must be shown as lone pairs if they
are not involved in bonding. If the octet rule is not met, try double or triple bonds
between the surrounding atoms and the central atom, using the lone pairs.

Example: Nitrogen Trifluoride (NF3)

a. Skeletal structure:

b. Outer shell configuration:

N7 = 1s22s22p3 → 5 valence electrons x 1 = 5 electrons

F9 = 1s22s22p5 → 7 valence electrons x 3 = 21 electrons
26 electrons

c. Draw a single covalent bond between N and F.

C. Formal Charge and Lewis Structure
The formal charge of an atom in a molecule is the hypothetical charge the atom
would have if we could redistribute the electrons in the bonds evenly between the atoms.
Another way of saying this is that formal charge results when we take the number of
valence electrons of a neutral atom, subtract the nonbonding electrons, and then
subtract the number of bonds connected to that atom in the Lewis structure.

A formal charge compares the number of electrons around a "neutral atom" (an
atom not in a molecule) versus the number of electrons around an atom in a molecule.
Formal charge is assigned to an atom in a molecule by assuming that electrons in all
chemical bonds are shared equally between atoms, regardless of relative
electronegativity. To calculate formal charges, we assign electrons in the molecule to
individual atoms according to these rules:
1. Non-bonding electrons are assigned to the atom on which they are located.
2. Bonding electrons are divided equally between the two bonded atoms, so
one electron from each bond goes to each atom. Two bonding electrons make
up a bonding pair

Formal Charge = Valence electrons – Bonding pairs – NonBonding electrons

FC = ve – bp – nbe
Example:
(1) Ozone (O3)

a. Formal charge (Central O atom) = +1

FC O1= 6 – 3 – 2 = +1
b. Formal charge (Terminal O atom in O=O) = 0
FC O2 = 6 – 2 – 4 = 0
c. Formal charge (Terminal O atom in O-O) = -1
FC O3 = 6 – 1 – 6 = -1

Formal Charge of O3 = Sum of the individual FC

FC of Ozone = (+1) + (0) + (-1) = 0

D. Resonance Structures (↔)

It is one of two or more Lewis structures for a single molecule that can be describe
fully one Lewis structure.

Example: (Resonance structure with formal charges)

(1) Carbonate ion (CO32-)
 (2) Nitrite ion (NO2-)

E. Coordinate Covalent Bond or Dative Bond

It is a covalent bond in which the shared pair of electrons is furnished by only
one of the bonded atoms. It is usually found in radicals.

Radical is a group of atoms acting as a single ion.

Example: Ammonium Ion (NH4+)

III. Molecular Geometry

The theory of molecular shape known as valence-shell electron-pair repulsion
(VSEPR) theory grew out of Lewis’s theory, and, like that approach to bonding, VSEPR focuses on
the role of electron pairs. It stems from the work of the British chemists H.M. Powell and Nevil V.
Sidgwick in the 1940s and was extensively developed by R.J. Gillespie in Canada and Ronald S.
Nyholm in London during the 1960s. As such, it postdates quantum mechanical theories of
bonding and shape but should be seen (as is so common a motivation in chemistry) as an
attempt to identify the essential features of a problem and to formulate them into a simple
qualitative procedure for rationalization and prediction.

The valence shell electron pair repulsion (VSEPR) model focuses on the bonding and
nonbonding electron pairs present in the outermost (valence) shell of an atom that connects
with two or more other atoms. Fundamentally, the VSEPR model theorizes that these regions of
negative electric charge will repel each other, causing them (and the chemical bonds that they
form) to stay as far apart as possible.

Molecular geometries (linear, trigonal, tetrahedral, trigonal bipyramidal, and octahedral)

are determined by the VSEPR theory. A table of geometries using the VSEPR theory can
facilitate drawing and understanding molecules. This is the three-dimensional (3-D)
arrangement of atoms in a molecule.
 Valence Shell
It is the outermost electron-occupied shell of an atom; it holds the electrons that are
usually involved in bonding.
 Valence Shell-Electron Pair Repulsion (VSEPR) Model
It accounts for the geometric arrangements of electron pairs around a central atom
in terms of repulsion between electronic pairs.

A. Guidelines for applying the VSEPR Model

1. Write the Lewis structure of the molecule, considering only the electron pairs
around the central atom (i.e. the atom that is bonded to more than one other
atom).
2. Count the number of electron pairs around the central atom (bonding pairs
and lone pairs). Treat double and triple bonds as though they were single
bonds.
3. Use table below to predict the geometry of the molecules.
 In predicting bond angles, note that a lone pair repels another bonding pair. Remember
that there is no easy way to predict the bond angles accurately when the central atom poses
one or more lone pairs. VSEPR table of molecular geometries: The bonded angles in the table
are ideal angles from the simple VSEPR theory; the actual angle for the example given is in the
following table.

IV.Hybridization
Hybridization was introduced
to explain molecular structure when
the valence bond theory failed to
correctly predict them. It is
experimentally observed that bond
angles in organic compounds are
close to 109°, 120°, or 180°.
According to Valence Shell Electron
Pair
Repulsion (VSEPR) theory, electron pairs repel each other and the bonds and lone pairs around
a central atom are generally separated by the largest possible angles. In this model, bonds are
considered to form from the overlapping of two atomic orbitals on different atoms, each orbital
containing a single electron. In looking at simple inorganic molecules such as H2 or HF, our
present understanding of s and p atomic orbitals will suffice. In order to explain the bonding in
organic molecules, however, we will need to introduce the concept of hybrid orbitals.

Hybridization happens when atomic orbitals mix to form a new atomic orbital. The new
orbital can hold the same total number of electrons as the old ones. The properties and energy of
the new, hybridized orbital are an 'average' of the original unhybridized orbitals.
A. Atomic Orbital
An atomic orbital is defined as the probability of finding an electron in an area
around an atom’s nucleus. Generally, orbital shapes are drawn to describe the region in
space in which electrons are likely to be found. This is referred to as “electron density.”
1. Sigma(σ)
Covalent bonding occurs when two atomic orbitals come together in close
proximity and their electron densities overlap. The strongest type of covalent
bonds are sigma bonds, which are formed by the direct overlap of orbitals from
each of the two bonded atoms. Regardless of the atomic orbital type, sigma
bonds can occur as long as the orbitals directly overlap between the nuclei of the

atoms.

Single covalent bonds occur when one pair of electrons is shared

between atoms as part of a molecule or compound. A single covalent bond can
be represented by a single line between the two atoms. For instance, the
diatomic hydrogen molecule, H2, can be written as H—H to indicate the single
covalent bond between the two hydrogen atoms.

2. Pi(π)
Pi bonds occur when there is overlap between unhybridized p orbitals of
two adjacent atoms. The overlap does not occur between the nuclei of the
atoms, and this is the key difference between sigma and pi bonds. For the bond
to form efficiently, there has to be a proper geometrical relationship between the
unhybridized p orbitals: they must be on the same plane.
 Overlap between adjacent unhybridized p orbitals produces a pi bond.
The electron density corresponding to the shared electrons is not concentrated
along the internuclear axis (i.e., between the two atoms), unlike in sigma bonds.

B. Hybrid Orbitals
Thinking in terms of overlapping atomic
orbitals is one way for us to explain how
chemical bonds form in diatomic molecules.
However, to understand how molecules with
more than two atoms form stable bonds, we
require a more detailed model. As an example,
let us consider the water molecule, in which we
have one oxygen atom bonding to two
hydrogen atoms. Oxygen has the electron
configuration 1s22s22p4, with two unpaired
electrons (one in each of the two 2p orbitals).
Valence bond theory would predict that the two
O–H bonds form from the overlap of these two
2p orbitals with the 1s orbitals of the hydrogen
atoms. If this were the case, the bond angle would be 90°, as shown in the figure,
because
p orbitals are perpendicular to each other.

Experimental evidence shows that the bond angle is 104.5°, not 90°. The prediction
of the valence bond theory model does not match the real-world observations of a water
molecule; a different model is needed. Quantum-mechanical calculations suggest why
the observed bond angles in H 2O differ from those predicted by the overlap of the 1s
orbital of the hydrogen atoms with the 2p orbitals of the oxygen atom. The
mathematical expression known as the wave function, ψ, contains information about
each orbital and the wavelike properties of electrons in an isolated atom. When atoms
are bound together in a molecule, the wave functions combine to produce new
mathematical descriptions that have different shapes. This process of combining the
wave functions for atomic orbitals is called hybridization and is mathematically
accomplished by the linear combination of atomic orbitals, LCAO, (a technique that
we will encounter again later). The new orbitals that result are called hybrid orbitals. The
valence orbitals in an isolated oxygen atom are a 2s orbital and three 2p orbitals. The
valence orbitals in an oxygen atom in a water molecule differ; they consist of four
equivalent hybrid orbitals that point approximately toward the corners of a tetrahedron
(Figure 2). Consequently, the overlap of the O and H orbitals should result in a
tetrahedral bond angle (109.5°). The observed angle of 104.5° is experimental evidence
for which quantum-mechanical calculations give a useful explanation: Valence bond
theory must include a hybridization component to give accurate predictions.

1. sp Hybridization
The beryllium atom in a gaseous BeCl 2 molecule is an example of a central
atom with no lone pairs of electrons in a linear arrangement of three atoms. There
are two regions of valence electron density in the BeCl2 molecule that correspond
to the two covalent Be–Cl bonds. To accommodate these two electron domains,
two of the Be atom’s four valence orbitals will mix to yield two hybrid orbitals. This
hybridization process involves mixing of the valence s orbital with one of the
valence p orbitals to yield two equivalent sp hybrid orbitals that are oriented in a
linear geometry.
 In this figure, the set of sp orbitals appears similar in shape to the
original p orbital, but there is an important difference. The number of atomic
orbitals combined always equals the number of hybrid orbitals formed. The p
orbital is one orbital that can hold up to two electrons. The sp set is two
equivalent orbitals that point 180° from each other. The two electrons that were
originally in the s orbital are now distributed to the two sp orbitals, which are
half filled. In gaseous BeCl2, these half-filled hybrid orbitals will overlap with
orbitals from the chlorine atoms to form two identical σ bonds.

2. sp2 Hybridization
The valence orbitals of a central atom surrounded by three regions of
electron density consist of a set of three sp 2 hybrid orbitals and one unhybridized p
orbital. This arrangement results from sp2 hybridization, the mixing of one s orbital
and two p orbitals to produce three identical hybrid orbitals oriented in a trigonal
planar geometry.
3. sp3 Hybridization
The valence orbitals of an atom surrounded by a tetrahedral arrangement
of bonding pairs and lone pairs consist of a set of four sp3 hybrid orbitals. The
hybrids result from the mixing of one s orbital and all three p orbitals that
produces four identical sp3 hybrid orbitals. Each of these hybrid orbitals points
toward a different corner of a tetrahedron.
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