UNIVERSITY OF CALOOCAN CITY

Biglang Awa St., Corner Catleya St., EDSA, Caloocan City

COLLEGE OF EDUCATION

SCIENCE TECHNOLOGY AND SOCIETY

SUBJECT CODE: MBS 322
TOPIC OR LESSON 1: Chapter 1: Structure and Bonding; Acids and Bases
WEEK: 1
SUBTOPIC/S: Lesson 1: Classification of Organic Compound
Lesson 2: Atomic Structure (Electron Configuration)
Lesson 3: Chemical Bonding (Development of Chemical
Bonding Theory, Nature of chemical bonds, Valence bond
theory)
Lesson 4: sp3 Hybrid Orbitals (Methane and Ethane Structure)
Lesson 5: Polar Covalent Bonds: Electronegativity
Lesson 6: Acids and Bases (Bronsted Lowry Definition and
Lewis Definition)

OVERVIEW OF THE TOPIC

Hello everyone! How are you today?

I hope you are feeling okay this another academic year of

new normal setup.

This week you are tasked to learn and accomplish several

activities about the classification of organic compound, atomic
structures, chemical bonding its development, nature as well as
valence bond theory. It also discusses the sp3 hybrid orbitals in methane and ethane
structure, likewise with the polar covalent bonds as well as acids and bases based on
Bronsted Lowry and Lewis definition.

Organic chemistry is all around us. The reactions and interactions of organic
molecules allows us to see, smell, fight, and fear. Organic chemistry provides the
molecules that feed us, treat our illnesses, protect our crops, and clean our clothes (Mc
Murry, 2011) All of these are because of the curiosity of the people studying organic
chemistry. Are you wondering how those things can be processed? Let us know more first
the classification of Organic compound.

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 LEARNING OUTCOMES

At the end of this module, learners are expected to develop an in-depth

understanding of the modern concepts of organic chemistry, and answer the activities
in relation to atomic structure, chemical bonding, and electronegativity.

LEARNING OBJECTIVES

Today you will be learning some ideas about Organic compound. But before you
proceed, here are the goals that you need to accomplish as you finished this module:

1. classify different kinds of organic compounds;

2. familiarize the rules in writing the electron configurations of the elements;
3. discuss the development, nature, and the valences of chemical bonding;
4. explain the concept of sp3 orbitals in methane and ethane structure;
5. explain the electronegativity of polar covalent bond; and
6. differentiate Bronsted-Lowry definition and Lewis’s definition.

ENGAGE

Can you give some idea/s that associated or relevant to the word located inside the box
then explain briefly why your answers are significant to the given word? (3-minute
activity)? You can write your answers in the separate sheet of paper.

Organic Chemistry

Source: https://www.template.net/business/word-templates/concept-map-template/

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 EXPLORE

Are the learning goals above clear to you? Remember that those are the things that
will keep you on the right track as you explore our topic. I know that you are already
excited with our lesson! At this point you are tasked to unscramble the jumbled letters to
reveal the word appropriate on the given description below.

1. GAORINC SPOUCOMND

➢ It can be defined as any type of chemical compounds in which atoms of

carbon, that could be one or more than one is covalently linked to the
other elements’ atoms.

2. AYCCICL MOCDNSPOU

➢ A classification of compound that is also called an open chain compound

because they have a linear structure

3. LYCCIC CPMNDSOO

➢ Commonly known as a ring compounds or closed chain compounds

4. CRMATIOA SPOUMNDCO

➢ Compounds that have a distinctive stability and usually referred to us

aromaticity or a major concerned with odor.

5. LANTIONCNUF POUGR

➢ It can be defined as a process in which a molecule receives its

characteristics chemical properties by one or group of atoms which exist in
the molecule.

When you’re done, the instructor will call the students randomly to answer the
above activity.

Let us now begin to discuss the world of CARBON COMPOUND

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 EXPLAIN

Lesson 1: Classification of Organic Compounds

What do you know about organic compounds? As far a chemistry is concerned

ORGANIC COMPOUNDS can be defined as any type of chemical compounds in which
atoms of carbon, that could be one or more than one, are covalently linked to other
elements’ atoms (vedantu.com). Organic compounds are simply any chemical
compounds that have carbon, but it doesn’t mean that every carbon containing
compound can be known as organic. Why do you think so? Because they contain
hydrocarbons or carbon bonded to hydrogen. Thus, when you are determining whether
a carbon compound is organic or not, look to see whether it contains hydrogen in
addition to carbon or the carbon is bonded to the hydrogen. The table below shows the
difference between organic and non-organic compounds.

Table 1: Difference from Organic and Non-organic Compounds

Organic Structure Non-organic Structure
Compounds compounds

Cyclohexane Cyanides

Carbonates
Ethyne
(Acetylene)

Carbides
Ethane

Note: Images of the structure are crafted to google images

Classification of Organic Compounds

Organic compounds can be classified on two bases. The first one is based on the
STRUCTURE and the second part is based on its FUNCTION.

A. Classification of Organic Compounds According to the STRUCTURE

➢ Acyclic or Open chain compounds
➢ Cyclic or Closed chain compounds

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 • Acyclic or Open chain compounds- These are just opposite to cyclic compounds
because their molecules don’t form any ring. It is called an open chain compound
because they have a linear structure
Examples: Aliphatic compounds and Alkanes

• Cyclic or Closed chain compounds- it is also known as “Ring Compounds”. Cyclic

compounds are those kinds of compounds where one or more than one number
of atoms get connected to forms a closed ring. It is not mandatory that everything
of these compounds is to be on the same size.
Examples: Cyclic hydrocarbons

Categories of Closed chain compounds:

a) Heterocyclic- this is a kind of cyclic compound in which the ring structure

exists. This is an organic compound in which two or more than two atoms
join in the ring shape in their molecules.
Examples: Synthetic dyes, nucleic acids,
and most of the drugs

Synthetic dyes
b) Homocyclic- a cyclic compound in which the ring structure is formed by
the atoms. This ring structure is made up of the same elements’ atoms and
this element is the carbon. This is called a carbocyclic compound. No
element other than carbon can exist in this compound.
Examples: naphthalene, tetracene, and
benzene

Benzene
Heterocyclic- compounds are divided into two broad categories which are named as
Alicyclic heterocyclic compounds and Aromatic heterocyclic compounds

➢ Alicyclic heterocyclic compounds- Ring structures of these compounds have one

or more one heteroatoms.
Examples: tetrahydrothiopene, tetrahydrofuran

➢ Aromatic heterocyclic compounds- molecules of these compounds

have one or more than one heteroatom.
Examples: Thiopene, furan

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 B. Classification of Organic Compounds based on functional group

A functional group can be defined as a process in which a molecule receives its

characteristics of a chemical properties by one or group of atoms which exist in the
molecule. Why do we need to classify organic compounds based on functional group?
It is simply because it classifies the chemical behavior of an organic compound. We need
to understand that the nature of functional groups draws impacts on the reactions of
compounds and at some level their physical properties. Below are some of the
compounds with their functional group.

Table2: Some of the Compounds with their functional group

Class Functional Group Class Functional Group
Amides (Alkanamides) Amid (-CONH2) Isocyanides – NC (Isocyano)
Alcohols (Alkanols) –OH (Hydroxy) Olefins/Alkenes (ene)
(Carbonyl)
Amines (Amino) NH2 Ketones (Alkanones) C=O
Nitro compounds
Acetylenes/Alkynes (yne) (Nitroalkanes) (Nitro) ¯NO2
(Anhydride)
−COOOC−

Acid anhydrides (Alkanoic (Ester)

anhydrides) Esters (Alkylalkanoates) R–COO–R′
(Aldehydic) -CHO

Aldehydes (Alkanals) Alkyl Halides

(Acylhalide) Cyanides/Nitriles (Cyano)
Acid halides (Alkanoyl halids)
R-CO-X (Alkanenitrile) –C=N
(Carboxyl)
Carboxylic acid (Alkanoic
Ethers (Alkoxyalkanes) R-O-R acid) R−COOH
https://www.vedantu.com/chemistry/classification-of-organic-compounds

Lesson 2: ATOMIC STRUCTURE: Electron Configuration

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An atom consists of a dense, positively
charged nucleus surrounded at a relatively
large distance by negatively charged
electrons (see figure 1 ). The nucleus consists
of subatomic particles called neutrons
which are electrically neutral, and protons,
which are positively charged. Because an
atom is neutral overall, the number of Figure 1: Schematic view of an atom
positive protons in the nucleus and
The number of negative electrons surrounding
The nucleus is the same. (Mc Murry, 2011)

Electrons move continuously. Like anything that moves, electrons have kinetic
energy, and this energy counteracts the attractive force of the positively charged
protons that pull the negatively charged electrons toward the nucleus.
Protons and neutrons have approximately the same mass and are about 1800 times more
massive than an electron. Most of the mass of an atom, therefore, is in its nucleus. Most
of the volume of an atom, however, is occupied by its electron cloud. This is where our
focus will be because it is the electrons that form chemical bonds.

• Atomic number vs. Mass number

Atomic number of an atom is the number of protons in its nucleus. The atomic
number is unique to a particular element. For example, the atomic number of carbons is
6, which means that all uncharged carbon atoms have six protons and six electrons.
Although atoms can gain electrons and become negatively charged or lose electrons
and become positively charged, the number of protons in an atom of a particular
element never changes.

The mass number of an atom is the sum of its protons and neutrons. Although all
carbon atoms have the same atomic number, they do not all have the same mass
number. Why? Because carbon atoms can have varying numbers of neutrons. For
example, 98.89% of all carbon atoms have six neutrons—giving them a mass number of
12—and 1.11% have seven neutrons—giving them a mass number of 13. These two
different kinds of carbon atoms (12C and 13C) are called isotopes. (See Illustration 2)

Figure 2: Isotopes of Carbon (Bruice, 2016)

• Atomic mass vs. Molecular mass

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 The atomic mass is the weighted average of the isotopes in the element. Because
an atomic mass unit (amu) is defined as exactly 1/12 of the mass of 12C, the mass of 12C
is 12.0000 amu; the mass of 13C is 13.0035 amu. Therefore, the atomic mass of carbon is
12.011 amu because (0.9889 * 12.0000) + (0.0111 * 13.0035) = 12.011. The molecular mass
is the sum of the atomic masses of all the atoms in the molecule. (Refer to the periodic
table at the last page of your module)

• How the Electrons in an atom are Distributed?

According to Quantum mechanical model (Quantum Mechanics) the behavior

of a specific electrons can be described by a mathematical expression called a wave
equation. The version of quantum mechanics was proposed by Erwin Schrödinger in 1926.

According to Schrödinger, the electrons in an atom can be thought of as

occupying a set of concentric shells that surround the nucleus (Table 3).
Table 3: Distribution of an electrons in the first four shells
First shell Second shell Third shell Fourth shell
Atomic orbitals s s, p s, p, d s, p, d, f
Number of 1 1, 3 1, 3, 5 1, 3, 5, 7
atomic orbitals
Maximum 2 8 18 32
numbers of
electrons

• The first shell is the one closest to the nucleus. The second shell lies farther from the
nucleus. The third and higher numbered shells lie even farther out.
• The shells contain subshells known as atomic orbitals. We will see that an atomic
orbital has a characteristic shape and energy and occupies a characteristic
volume of space
• Each shell contains one s atomic orbital. Each second and higher shell—in
addition to its s atomic orbital—contains three degenerate p atomic orbitals.
Degenerate orbitals are orbitals that have the same energy. The third and higher
shells—in addition to their s and p atomic orbitals—contain five degenerate d
atomic orbitals, and the fourth and higher shells also contain seven degenerate f
atomic orbitals.
• A maximum of two electrons can coexist in an atomic orbital. (Based on the idea
of Pauli exclusion principle) Therefore, the first four shells, with 1, 4, 9, and 16 atomic
orbitals, respectively, can contain a maximum of 2, 8, 18, and 32 electrons.

The first shell holds a maximum of 2

electrons in one 1s orbital; the
second shell holds a maximum of 8
electrons in one 2s and three 2p
orbitals; the third shell holds a
maximum of 18 electrons in one 3s,
three 3p, and five 3d orbitals; and so
on. The 2 electrons in each orbital
are represented by up and
down arrows, . Although not shown,
8 |the energy level of the 4s orbital falls
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between 3p and 3d.
 Figure 3: Energy levels of electrons in an atom (McMurry, 2011)

➢ Atomic Structure: Ground State Electron Configuration

The ground-state electronic configuration of an atom describes the atomic

orbitals occupied by the atom’s electrons when they are all in the available orbitals with
the lowest energy. If energy is applied to an atom in the ground state, one or more
electrons can jump into a higher-energy orbital. The ground state electronic
configuration of the smallest atoms is shown in the Table 4 (each arrow represents one
electron)

Table 4: The Electronic Configurations of the smallest atoms (Bruice, 2016)

Three Rules Predicting Arrangement of Electrons

1. The Aufbau Principle (German term meaning “building up”)

• It states that an electron always goes into the available orbital with the
lowest energy.

When using the aufbau principle rule, it is important to remember that the closer
the atomic orbital is to the nucleus, the lower is its energy. Because the 1s orbital is closer
to the nucleus, it is lower in energy than the 2s orbital, which is lower in energy—and closer
to the nucleus—than the 3s orbital. When comparing atomic orbitals in the same shell,
we see that an s orbital is lower in energy than a p orbital, and a p orbital is lower in
energy than a d orbital.

Illustration 1: Atomic Orbitals (Bruice, 2016)

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2. The Pauli exclusion principle
• States that no more than two electrons can occupy each atomic orbital,
and the two electrons must be of opposite spin.

This is called an exclusion principle because it limits the number of electrons that
can occupy an atomic orbital and, therefore, any shell. (Notice in Illustration 4 that
opposite spins are designated by ↑ and ↓.)
These first two rules allow us to assign electrons to atomic orbitals for atoms that
contain one, two, three, four, or five electrons.
■ The single electron of a hydrogen atom occupies a 1s orbital.
■ The second electron of a helium atom fills the 1s orbital.
■ The third electron of a lithium atom occupies a 2s orbital.
■ The fourth electron of a beryllium atom fills the 2s orbital.
■ The fifth electron of a boron atom occupies one of the 2p orbitals. (The subscripts
x, y, and z distinguish the three 2p orbitals.) Because the three p orbitals are degenerate,
the electron can be put into any one of them.

3. Hund’s Rule
• States that when two or more atomic orbitals with the same energy, an
electron will occupy an empty orbital before it pairs up with another
electron.

In this way, electron repulsion is minimized.

■ Therefore, the sixth electron of a carbon atom goes into an empty 2p orbital,
rather than pairing up with the electron already occupying a 2p orbital (see Illustration
4).
■ There is one more empty 2p orbital, so that is where nitrogen’s seventh electron
goes.
■ The eighth electron of an oxygen atom pairs up with an electron occupying a
2p orbital rather than going into the higher energy 3s orbital.

➢ Valence and Core electrons

The major factor that determines the chemical behavior of an element is the number
of valence electrons it has. Valence electrons are electrons in an atom’s outermost shell.
Electrons in inner shells (below the outermost shell) are called core electrons. For
example, carbon has four valence electrons and two core electrons (Illustration 4).
Valence electrons participate in chemical bonding; core electrons do not. Elements in
the same column of the periodic table have similar chemical properties because they
have the same number of valence electrons. If you examine the periodic table inside the
back cover of this book, you will see that lithium and sodium, which have similar chemical
properties, are in the same column because each has one valence electron.

Lesson 3: Chemical Bonding

➢ Development of Chemical Bonding Theory

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 ➢ In 1858, August Kekulé and Archibald Couper independently proposed that, in all
organic compounds, carbon is tetravalent; that is, it always forms four bonds when
it joins other elements to form chemical compounds. Furthermore, said Kekulé,
carbon atoms can bond to one another to form extended chains of linked atoms
and chains can double back on themselves to form rings.
➢ In 1874, Jacobus van’t Hoff and Joseph Le Bel added a third dimension to our
ideas about organic compounds. They proposed that the four bonds of carbon
are not oriented randomly but have specific spatial directions. Van’t Hoff went
even further and suggested that the four atoms to which carbon is bonded sit at
the corners of a regular tetrahedron, with carbon in the center.

A representation of a tetrahedral carbon atom is shown in Figure 4. Note the

conventions used to show three-dimensionality: solid lines represent bonds in the plane
of the page, the heavy wedged line represents a bond coming out of the page toward
the viewer, and the dashed line represents a bond receding back behind the page
away from the viewer. These representations will be used throughout this text.

The solid lines represent bonds in

the plane of the paper, the
heavy wedged line represents a
bond coming out of the plane
of the page, and the dashed
line represents a bond going
back behind the plane of the
page.
Figure 4: Representation of van’t hoff’s Tetrahedral carbon atom
➢ Nature of Chemical Bonds

1. COVALENT BONDS
➢ According to G.N. Lewis an atom is most stable if its outer shell is either filled or
contains eight electrons, and it has no electrons of higher energy.
➢ According to Lewis Theory an atom will give up, accept, or share electrons to
achieve a filled outer shell or an outer shell that contains eight electrons. This
theory has come to be called the octet rule (even though hydrogen needs only
two electrons to achieve a filled outer shell).

Losing or Gaining Electrons:

Lithium (Li) has a single electron in its
2s orbital. If it loses this electron, lithium ends
up with a filled outer shell—a stable
configuration. Lithium, therefore, loses an
electron relatively easily. Sodium (Na) has a
single electron in its 3s orbital; so, it, too,
Illustration 2: Based on the idea of Bruice, 2016
loses an electron easily. Because only valence
electrons are used in bonding, only valence electrons are shown in the following

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equations. (The symbol for the element represents the protons, neutrons, and core
electrons.) Each valence electron is shown as a dot. When the single valence electron
of lithium or sodium is removed, the species that is formed is called an ion because it
carries a charge.

Each of the elements in the first column

of the periodic table readily loses an electron
because each has a single electron in its
outermost shell. Fluorine has seven valence
electrons (Illustration 3). Therefore, it readily
acquires an electron to fill its outer shell.
Gaining the electron forms F-, a fluoride ion. Illustration 3: Based on the idea of Bruice, 2016

Elements in the same column of the

periodic table as fluorine (such as chlorine,
bromine, and iodine) also need only one
electron to have an outer shell of eight; so, they,
too, readily acquire an electron.
Illustration 4: Based on the idea of Bruice, 2016

Elements (such as fluorine and chlorine) that readily acquire an electron are said to be
electronegative.
A hydrogen atom has one valence
electron. Therefore, it can achieve
a completely empty shell by losing
an electron, or a filled outer shell
by gaining an electron.
Illustration 5: Based on the idea of Bruice, 2016

Loss of its sole electron results in a positively charged hydrogen ion. A positively
charged hydrogen ion is called a proton because when a hydrogen atom loses its
valence electron, only the hydrogen nucleus—which consists of a single proton—
remains. When a hydrogen atom gains an electron, a negatively charged hydrogen
ion—called a hydride ion—is formed.

Sharing Electrons:

Instead of giving up or acquiring electrons to achieve a filled outer shell, an atom

can achieve a filled outer shell by sharing a
pair of electrons. For example, two fluorine
atoms can each attain a filled second shell by
sharing their unpaired valence electrons. A
bond formed because of sharing electrons
between two nuclei is called a covalent
bond. A covalent bond is commonly shown
Illustration 6: Based on the idea of Bruice, 2016
by a solid line rather than by a pair of dots.

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Two hydrogen atoms can form a covalent bond
by sharing electrons. As a result of covalent
bonding, each hydrogen acquires a stable, filled
first shell.

Illustration 7: Based on the idea of Bruice, 2016

Similarly, hydrogen and chlorine can form a

covalent bond by sharing electrons. In doing so,
hydrogen fills its only shell, and chlorine achieves an
outer shell of eight electrons.

Illustration 8: Based on the idea of Bruice, 2016

Let’s now look at the bonds formed by

oxygen, nitrogen, and carbon. Oxygen has six
valence electrons, so it needs to form two
covalent bonds to achieve an outer shell of eight
electrons. Nitrogen, with five valence electrons,
must form three covalent bonds, and carbon,
with four valence electrons, must form four
covalent bonds. Notice that all the atoms in
water, ammonia, and methane have filled outer
shells.

Illustration 9: Based on the idea of Bruice, 2016

A simple way of indicating the covalent bonds in molecules is to use what are
called Lewis structures, or electron-dot structures, in which the valence shell electrons of
an atom are represented as dots. Thus, hydrogen has one dot representing its 1s electron,
carbon has four dots (2s2 2p2), oxygen has six dots (2s2 2p4), and so on. A stable molecule
results whenever a noble-gas
configuration is achieved for all
the atoms—eight dots (an octet)
for main-group atoms or two dots
for hydrogen. Simpler still is the
use of Kekulé structures, or line-
bond structures, in which a two-
electron covalent bond is
indicated as a line drawn
Illustration 10: Based on the idea of Mc Murry, 2011
between atoms.

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 The number of covalent bonds an atom forms depends on how many additional
valence electrons it needs to reach a noble gas configuration. Hydrogen has one
valence electron (1s) and needs one more to reach the helium configuration (1s2), so it
forms one bond. Carbon has four valence electrons (2s2 2p2) and needs four more to
reach the neon configuration (2s2 2p6), so it forms four bonds. Nitrogen has five valence
electrons (2s2 2p3), needs three more,
and forms three bonds; oxygen has six
valence electrons (2s2 2p4), needs two
more, and forms two bonds; and the
halogens have seven valence
electrons, need one more, and form
one bond. Illustration 11: Based on the idea of Mc Murry, 2011

Valence electrons that are not used for bonding

are called lone-pair electrons, or nonbonding
electrons. The nitrogen atom in ammonia (NH3),
for instance, shares six valence electrons in three
covalent bonds and has its Valence electrons
that are not used for bonding are called lone-
pair electrons, or nonbonding electrons. The nitrogen atom in ammonia (NH3), for
instance, shares six valence electrons in three covalent bonds and has its

Illustration 12: Based on the idea of Mc Murry, 2011

➢ Lewis Structures (A deep Discussion)

The chemical symbols we have been using, in which the valence electrons are
represented as dots or solid lines, are called Lewis structures. Lewis structures show us
which atoms are bonded together and tell us whether any atoms possess lone-pair
electrons or have a formal charge, two concepts described below. The Lewis structures
for H2O, H3O+, HO-, and H2O2 are shown here.

Note: Atoms in Lewis structures are always lined up linearly or at right angles

Lone Pair Electrons

When you draw a Lewis structure, make sure hydrogen atoms are surrounded by
two electrons and C, O, N, and halogen (F, Cl, Br, I) atoms are surrounded by eight

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electrons, in accordance with the octet rule. Valence electrons not used in bonding are
called nonbonding electrons, lone-pair electrons, or simply, lone pairs.

Formal Charge

Once the atoms and the electrons are in place, you must examine each atom to
see whether a formal charge should be assigned to it. A formal charge is the difference
between the number of valence electrons an atom has when it is not bonded to other
atoms and the number it “owns” when it is bonded. An atom “owns” all its lone-pair
electrons and half of its bonding (shared) electrons. (Notice that half the bonding
electrons is the same as the number of bonds.)

To apply the equation for formal charge to three of the oxygen containing
species. An oxygen atom has six valence electrons. In water (H2O), oxygen owns six
electrons – four lone pair electrons and half of the four bonding electrons. Because the
number of electrons it “owns” is equal to the number of valence electrons (6 – 6 = 0), the
oxygen atom in water does not have a formal charge.
The oxygen atom in the hydronium ion (H3O+) “owns” five electrons: two lone-pair
electrons plus three (half of six) bonding electrons. Because the number of electrons
oxygen “owns” is one less than the number of its valence electrons (6 - 5 = 1), its formal
charge is +1.
The oxygen atom in the hydroxide ion (HO-) “owns” seven electrons: six lone-pair
electrons plus one (half of two) bonding electron. Because oxygen “owns” one more
electron than the number of its valence electrons (6 - 7 = -1), its formal charge is -1.

Drawing Lewis Structures

➢ Nitrogen has five valence electrons. These are the appropriate formal charges of
nitrogen atoms in the following Lewis structures:

➢ Carbon has four valence electrons. The following are the Lewis structures and
have indicated formal charges.

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 A species containing a positively charged carbon is called a carbocation, and a
species containing a negatively charged carbon is called a carbanion. (Recall that a
cation is a positively charged ion and an anion is a negatively charged ion.) A species
containing an atom with a single unpaired electron is called a radical (often called a
free radical).

➢ Hydrogen has one valence electron, and each halogen (F, Cl, Br, I) has seven
valence electrons; so, the following species have the indicated formal charges:

When the atoms do not bear a formal charge or unpaired electron (neutral)
➢ Carbon always forms 4 covalent bonds and has no lone pairs
➢ Nitrogen always forms 3 covalent bonds and has 1 lone pair
➢ Oxygen always forms 1 covalent bond and has 2 lone pairs
➢ A halogen always forms 1covalent bond and has 3 lone pairs
➢ Hydrogen always forms 1 covalent bond and has no lone pairs

Each atom in the following Lewis structures has a filled outer shell. Notice that because
none of the molecules has a formal charge or an unpaired electron, H forms 1 bond, C
forms 4 bonds, N forms 3 bonds, O forms 2 bonds, and Br forms 1 bond. Notice, too, that
each N has 1 lone pair, each O has 2 lone pairs, and Br has 3 lone pairs.

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 ➢ Kekulé Structures (A deep Discussion)

Kekulé structures are like Lewis structures except that lone pairs are normally omitted

Condensed structures omit some of (or all) of the covalent bonds and list atoms bonded
to a particular carbon (or nitrogen or oxygen) next to it. Lone pairs are usually not shown
unless they are needed to draw attention to some chemical property of the molecule.

Below are the examples of Kekulé Structures and Condensed structures of the following
compound

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Table 5: Kekulé Structures and Condensed structures (Bruice, 2016)

Lesson 4.1 sp3 Hybrid Orbitals and the structure of Methane

In 1931, Linus Pauling proposed that an s orbital and three p orbitals can combine
or hybridize, to form four equivalent atomic orbitals with tetrahedral orientation. Shown
in Figure 5, these tetrahedrally oriented orbitals are called sp3 hybrids. Note that the
superscript 3 in the name sp3 tells how many of each type of atomic orbital combine to
form the hybrid, not how many electrons occupy it.

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 Figure 5: Four sp3 hybrid orbitals
(green), oriented to the corners of a
regular tetrahedron, are formed by
combination of an atomic s orbital (red)
and three atomic p orbitals (red/blue).
The sp3 hybrids have two lobes and are
unsymmetrical about the nucleus, giving
them a directionality and allowing them
to form strong bonds when they overlap
an orbital from another atom. (Mc
Murry, 2011)

The concept of hybridization explains how carbon forms four equivalent

tetrahedral bonds but not why it does so. The shape of the hybrid orbital suggests the
answer. When an s orbital hybridizes with three p orbitals, the resultant sp3 hybrid orbitals
are unsymmetrical about the nucleus. One of the two lobes is much larger than the other
(Figure 5) and can therefore overlap better with another orbital when it forms a bond. As
a result, sp3 hybrid orbitals form stronger bonds than do unhybridized s or p orbitals.

The asymmetry of sp3 orbitals arises because, the two lobes of a p orbital have
different algebraic signs, + and -. Thus, when a p orbital hybridizes with an s orbital, the
positive p lobe adds to the s orbital, but the negative p lobe subtracts from the s orbital.
The resultant hybrid orbital is therefore unsymmetrical about the nucleus and is strongly
oriented in one direction.

When each of the four

identical sp3 hybrid orbitals of a
carbon atom overlaps with the 1s
orbital of a hydrogen atom, four
identical C-H bonds are formed and
methane results. Each C-H bond in
methane has a strength of 439
kJ/mol (105 kcal/mol) and a length of 109 pm. Because the four bonds have a specific
geometry, we also can define a property called the bond angle. The angle formed by
each H-C-H is 109.5°, the so-called tetrahedral angle. Methane thus has the structure
shown in Figure 6.
Figure 6: The structure of methane, showing its 109.5° bond angles.

Lesson 4.2 sp3 Hybrid Orbitals and the structure of Ethane

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 The same kind of orbital
hybridization that accounts for the
methane structure also accounts for
the bonding together of carbon
atoms into chains and rings to make
possible many millions of organic
compounds. Ethane, C2H6, is the
simplest molecule containing a
carbon–carbon bond.

Illustration 13: Based on the idea of Mc Murry, 2011

We can picture the ethane molecule

by imagining that the two carbon
atoms bond to each other by overlap
of an sp3 hybrid orbital from each
(Figure 7). The remaining three sp3
hybrid orbitals of each carbon overlap
with the 1s orbitals of three hydrogens
to form the six C-H bonds. The C-H
bonds in ethane are like those in
methane, although a bit weaker—421
kJ/mol (101 kcal/mol) for ethane versus
439 kJ/mol for methane. The C-C bond
is 154 pm long and has a strength of
377 kJ/mol (90 kcal/mol). All the bond
angles of ethane are near, although
not exactly at, the tetrahedral value of 109.5°. Figure 7: The structure of ethane.
The carbon–carbon bond is formed by overlap of two
carbon sp3 hybrid orbitals. For clarity, the smaller
lobes of the hybrid orbitals are not shown.

Lesson 5: Non-Polar and Polar Covalent Bonds: Electronegativity

Covalent bonds are classified as nonpolar or polar depending on the difference

in the electronegativities of the atoms that share the electrons. Electronegativity is a
measure of the ability of an atom to pull electrons toward itself. The electronegativities of
some of the elements are shown in Table 5. Notice that electronegativity increases from
left to right across a row of the periodic table and from bottom to top in any of the
columns.

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 Table 6: The Electronegativities of Selected Elements (Bruice, 2016)

If the electronegativity difference between the bonded atoms is less than 0.5, then
the bond is a nonpolar covalent bond. That is, the atoms share the bonding electrons
equally—the electrons represented by the bond are symmetrically distributed around
each atom. Examples of nonpolar covalent bonds are shown below.

H—H F—F C—C C—H

If the electronegativity difference between the bonded atoms is between 0.5 and
about 1.9, then the bond is a polar covalent bond. The bonding electrons are
unsymmetrically distributed because the bonding atoms have sufficiently different
electronegativities; one end of a polar covalent bond has a partial negative charge (δ-
and one end has a partial positive charge (δ+). The negative end of the bond is the end
with the more electronegative atom. The greater the difference in electronegativity
between the bonded atoms, the more polar the bond.

The direction of bond polarity can be indicated with an arrow. By convention, chemists
draw the arrow in the direction the electrons are pulled. Thus, the head of the arrow is at
the negative end of the bond; a short perpendicular line near the tail of the arrow marks
the positive end of the bond. (Physicists draw the arrow in the opposite direction.)

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 If the electronegativity difference between the atoms is greater than 1.9, the
atoms do not share their electrons. One of the atoms transfers an electron to the other,
and the resulting ions (for example, Na+ and Cl-) are held together by electrostatic
attraction—an attractive force between opposite charges. Sodium chloride is an
example of an ionic compound (also known as a salt). Ionic compounds are formed
when an element on the left side of the periodic table transfers one or more electrons to
an element on the right side of the periodic table.

You can think of nonpolar covalent bonds—where the electrons are shared
equally—being at one end of the continuum of bond types and ionic compounds—
where no electrons are shared—at the other end. Polar covalent bonds fall somewhere
in between.

Illustration 14: Electronegativity Difference (Bruice,2016)

Lesson 6.1: Acids and Bases (Bronsted Lowry Definition)

A Brønsted–Lowry acid is a substance that donates a hydrogen ion (H+), and a

Brønsted–Lowry base is a substance that accepts a hydrogen ion. (The name proton is
often used as a synonym for H+ because loss of the valence electron from a neutral
hydrogen atom leaves only the hydrogen nucleus—a proton.) When hydrogen chloride
gas dissolves in water, for instance, HCl donates a proton and a water molecule accepts
the proton, yielding hydronium ion (H3O+) and chloride ion (Cl-). Chloride ion, the product
that results when the acid HCl loses a proton, is called the conjugate base of the acid,
and H3O+, the product that results when the base H2O gains a proton, is called the
conjugate acid of the base.

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 Acids differ in their ability to donate H_. Stronger acids, such as HCl, react almost
completely with water, whereas weaker acids, such as acetic acid (CH3CO2H), react
only slightly. The exact strength of a given acid HA in water solution can be expressed by
its acidity constant, Ka. Remember from general chemistry that the concentration of
solvent is ignored in the equilibrium expression and that brackets [] around a substance
refer to the concentration of the enclosed species in moles per liter.

Acid strengths are normally given using pKa values rather than Ka values, where the pKa
is the negative common logarithm of the Ka.

pKa = -- log Ka

A stronger acid (larger Ka) has a smaller pKa, and a weaker acid (smaller Ka) has a larger
pKa

Table 7: Relative Strengths of Some Common Acids and Their Conjugate Bases

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Notice that the pKa value shown in Table 7 for water is 15.74, which results from the
following calculation. Because water is both the acid and the solvent, the equilibrium
expression is

Another way to predict acid–base reactivity is to remember that the product conjugate
acid in an acid–base reaction must be weaker and less reactive than the starting acid
and that the product conjugate base must be weaker and less reactive than the starting
base. In the reaction of acetic acid with hydroxide ion, for example, the product
conjugate acid (H2O) is weaker than the starting acid (CH3CO2H) and the product
conjugate base (CH3CO2-) is weaker than the starting base (OH-).

Lesson 6.2: Acids and Bases (Lewis Definition)

A Lewis acid is a substance that accepts an electron pair, and a Lewis base is a
substance that donates an electron pair. The donated electron pair is shared between
the acid and the base in a covalent bond.

The fact that a Lewis acid can accept an electron pair means that it must have either a
vacant, low-energy orbital or a polar bond to hydrogen so that it can donate H_ (which

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has an empty 1s orbital). Thus, the Lewis definition of acidity includes many species in
addition to H+. For example, various metal cations, such as Mg2+, and metal compounds,
such as AlCl3, are Lewis’s acids because they have unfilled valence orbitals and can
accept electron pairs from Lewis bases.

The Lewis definition of a base—a compound with a pair of nonbonding electrons that it
can use in bonding to a Lewis acid—is like the Bronsted– Lowry definition. Thus, H2O, with
its two pairs of nonbonding electrons on oxygen, acts as a Lewis base by donating an
electron pair to an H+ in forming the hydronium ion, H3O+. Similarly, trimethylamine acts
as a Lewis base by donating an electron pair on its nitrogen atom to aluminum chloride.
In a more general sense, most oxygen- and nitrogen-containing organic compounds can
act as Lewis bases because they have lone pairs of electrons.

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Look closely at the two acid–base reactions just shown. In the first reaction, the Lewis
base water uses an electron pair to abstract H_ from the polar HCl molecule. In the
second reaction, the Lewis base trimethylamine donates an electron pair to a vacant
valence orbital of an aluminum atom. In both reactions, the direction of electron-pair
flow from the electron-rich Lewis base to the electron-poor Lewis acid is shown using
curved arrows. A curved arrow always means that a pair of electrons moves from the
atom at the tail of the arrow to the atom at the head of the arrow. We’ll use this curved-
arrow notation frequently in the remainder of this text to indicate electron flow during
reactions.

ELABORATE
v

Now it is your time to expand your horizon. Do the following activities.

1.Why are some compounds that contain carbon not considered as organic
compounds?

2. Why do atoms bond together, and how can bonds be described electronically?

3. How does electron sharing lead to bonding between atoms

4. Differentiate the idea of Bronsted-Lowry definition from Lewis’s definition

Congratulations! You are now done with lesson 1. Make sure to take notes of the
important details for your own reference.

EVALUATE

Lesson 2: Atomic Structure: Electron Configuration

Activity 1-Atomic number, Mass number, atomic mass, and Mass number:

a. Oxygen has three isotopes, 16O, 17O, and 18O. The atomic number of
oxygens is 8. How many protons and neutrons does each of the isotopes
have?
b. How many electrons does each have Na+, Ar, Cl- ?

c. Chlorine has two isotopes 35Cl and 37Cl; 75.77% of chlorine is 35Cl, and
24.23% is 37Cl. The atomic mass of 35Cl is 34.969 amu, and the atomic mass
of 37Cl is 36.966 amu. What is the atomic weight of chlorine?

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Activity 2-Atomic structure:
1. How many electrons does each of the following elements have in its
outermost electron shell (valence electron)?
a. Potassium b. Aluminum c. Calcium d. Fluorine
e. Chlorine f. Bromine g. Iodine
2. Give the ground state electron configuration of the following elements
a. Boron b. Phosphorous c. Oxygen d. Argon

Lesson 3: Chemical Bonding:

3. Find potassium (K) in the periodic table and predict how many valence
electrons it has.
4. Write both electron-dot and line-bond structures for the following
molecules, showing all nonbonded electrons:
a. CHCl3, chloroform b. H2S, hydrogen sulfide c. CH3NH2, methylamine
5. Why can’t an organic molecule have the formula C2H7?
6. Draw the Lewis structure for each of the following:
a. NO3 -- b. NO2+ c. NaOH d. +C2H5 e. HCO3 –
7. An atom with a formal charge does not necessarily have electron density
than the atoms in the molecule without formal charges. We can see this
by examining the potential maps for H2O, H3O+, and HO- (please see the
structures of these compounds above)
a. Which atoms bears the formal negative charge in the hydroxide ion?
b. Which atom has the greater electron density in the hydroxide ion?
c. Which atom bears the formal positive charge in the hydronium ion?
d. Which atom has the least electron density in the hydronium ion?
8. Draw the Lewis Structure of the following:
a. CH4O b. HNO2?

Lesson 4: sp3 Hybrid Orbitals

9. Draw a tetrahedral representation of tetrachloromethane, CCl4, using the
standard convention of solid, dashed, and wedged lines.
10. Draw a line-bond structure for propane, CH3CH2CH3.

Lesson 5: Non-polar and Polar Covalent Bonds: Electronegativity

11. Which element in each of the following pairs is more electronegative
a. Li or H b. Be or Br c. Cl or I
12. Order the bonds in the following compounds according to their increasing
ionic character: CCl4, MgCl2, TiCl3, Cl2O.

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 REFERENCES

Bruice, P. Y. (2016). Organic Chemistry (Eighth Edition). Santa Barbara, California: Pearson
Education, Inc.

March, M. B. (2007). March's Advanced Organic Chemistry (Sixth Edition). New Jersey, New
Jersey, USA: John Wiley & Sons, Inc.

Murry, J. M. (2011). Fundamentals of Organic Chemistry (Seventh Edition). Belmont, California:

Mary Finch.

Murry, J. M. (2012). Organic Chemistry (Eighth Edition). Belmont, California: Brrooks/Cole,

Cengage learning.

T.W. Graham Solomons, C. B. (2016). Organic Chemistry (Twelfth Edition). Chicago, USA: John
Wiley & Sons, Inc.

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 Appendix

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