Republic of the Philippines

North Eastern Mindanao State University

Formerly Surigao del Sur State University
Cantilan Campus, Cantilan, Surigao del Sur 8317
Telefax No. 086-214-4221
[Link]

MODULE 1

LEYRA LYN U. MANILAG

Instructor
 I. Course Information

COURSE CODE: AdGE

COURSE TITLE: General Chemistry (Organic Chemistry)
COURSE CREDITS: Lecture: 2 units, Laboratory: 1unit
CONTACT HOURS: Lecture: 1 hr/unit, 2 hours every week for 18 weeks
Laboratory: 2 hrs/unit, 2 hours every week for 18 weeks
GRADING SYSTEM: Laboratory Subject
Class standing……………………………………………. 20%
• Attendance………………………………. 5%
• Quizzes…….... ………………………….10%
• Assignment……………………………….5%
Examinations……………………………………………….40%
Requirements………………………………………………40%
• Hands-on activities……………………… 30%
• Project…………………………………… 10%
_____
TOTAL 100%
COURSE DESCRIPTION:
This course covers the study of compounds of carbon, their properties, synthesis, reactions and decomposition. This will provide
the students a thorough and concise introduction to the most important and fundamental principles of Organic Chemistry. The students
are made to understand that functional groups are the basis for many organic syntheses. The wide scope of the subject provides an
understanding on the issues of energy, environment, health, industry, natural products, and food. It includes the study of common
elements with particular attention to application in criminal investigation, chemistry of carbons and carbon compounds and their principles,
and laboratory techniques used in the identification of metallic elements.
At the end of the semester, the students are expected to have skills in the nomenclature of both aliphatic and aromatic hydrocarbons,
know general properties of alkanes, alkenes, nomenclature of both aliphatic and aromatic alcohols, ethers, aldehydes, ketones,
monocarboxylic acids, aromatic acids and salts. An introduction to Biochemistry is also included in preparation for their Physiology
classes. Lastly, a brief introduction to structure determination using Mass Spectrometry and Infrared Spectroscopy is tackled.
COURSE LEARNING OUTCOMES:
At the end of the course, the students should be able to:
1. Determine the geometric structure of organic compounds using knowledge of atomic structure, hybridization, and covalent
bonding.
2. Employ the IUPAC nomenclature system to name organic compounds.
3. Draw structures from systematic names.
4. Solve and understand problems from various areas of organic chemistry, including reactivity patterns and mechanism of reactions.
5. Interpret infrared, mass, and nuclear magnetic resonance spectra in order to solve structure determination problems.
6. Employ appropriate and safe laboratory techniques to perform experiments, collaborating with partners.
7. Report the results of the laboratory experiments in a laboratory notebook, performing quantitative calculations, and interpreting
the results.
8. Value the importance of Organic Chemistry especially to everyday life.
9. Develop practical appreciation for the environmental implication of Organic Chemistry.
II. General Instruction
This module begins with an Introduction that encapsulates the topics or lessons that students of this course have to learn,
understand and value. This Module is composed of five parts of which the first part pertains to the Intended Learning Outcomes (ILOs).
The next part is the course direction where students are directed to focus their respective course works. The nitty-gritties of the course
are also placed in the lecture and discussion which is the third part of the module. Each student taking this course is also required to
answer all the assessment tasks to measure whether the student have learned from the lessons. For the students to grasp all the
essentials of the topics covered in a particular lesson, links, URLs, videos and other supplementary reading materials are provided in this
module.
III. Disclaimer
This module is a compilation of the works from internet sources, manuals, and books from different authors and will be used for
educational purpose only. Due recognition is given to the authors who are the sources of some parts found in this module. The
compiler/owner does not claim copyrights to any part taken from others sources.
IV. Academic Integrity
Academic honesty is required of all students. Plagiarism--to take and pass off as one’s own work, the work or ideas of another--is a
form of academic dishonesty. Penalties may be assigned for any form of academic dishonesty” (See Student Handbook/College
Manual). Sanctions for breaches in academic integrity may include receiving a grade of a “Failed” on a test or assignment. In addition,
the Director of Student Affairs may impose further administrative sanctions.
2|Page AdGE – Organic Chemistry
Lesson 1: Introduction to Organic Chemistry

Intended Learning Outcomes

At the end of the unit, the students will be able to:
1. Explain the fundamental principles of Organic Chemistry
2. Differentiate organic from inorganic chemistry
3. To determine the unique characteristics of carbon making it the center of organic chemistry

Organic chemistry is the study of the structures, properties, preparation, and reactions of a wide range of molecules known as
organic compounds. The term "organic" is widely used in ordinary English to denote "natural things." This is most likely due to early
scientists' belief that all organic molecules emanated from living systems and had a "vital force." Chemists discovered this was not the
case over 170 years ago. Organic compounds are important components of living systems, yet scientists can create many of them in the
laboratory using substances that have no direct biological relationship. A pure sample of an organic compound such as Vitamin C isolated
from natural sources such as an orange or other citrus fruits is chemically equivalent to a pure sample of Vitamin C prepared in a
laboratory. Because of the vast quantity of knowledge you will need to study and grasp, your trip through organic chemistry will be
challenging and will require focus and more attention.

1.1 DEVELOPMENT OF ORGANIC CHEMISTRY AS A SCIENCE

• In 1685, Organic Chemistry started when Nicholas Lemery studied the organic compounds that could be found in plants and
animals. These are fats and oil, that came from animals and plants respectively.
• In 1769, Scheele isolated the composition of chemical substances from plants and animals.
• In the 18th century, Antoinne Lavoisier was named the Father of Modern Chemistry. He performed the Combustion Experiment,
which is a process used to characterize chemical properties. This experiment is the reaction of organic substances to Oxygen and
it always gives out a product of Water and Carbon Dioxide.
• Finally, in 1828, Modern Organic Chemistry came into the world.

Organic Chemistry - is the study of carbon and its compounds or the study of the chemistry of life. All
organic compounds contain carbon in association with hydrogen, oxygen, nitrogen,
and other elements such as phosphorus.

1.2 MAJOR DIFFERENCES BETWEEN ORGANIC AND INORGANIC COMPOUNDS

In the early 19th century, scientists classified all known compounds into two categories: Organic compounds were derived from
living organisms (plants and animals), while inorganic compounds were derived from nonliving sources (minerals and gases). This
distinction was fueled by the observation that organic compounds seemed to possess different properties than inorganic compounds.
Organic compounds were often difficult to isolate and purify, and upon heating, they decomposed more readily than inorganic compounds.
To explain these curious observations, many scientists subscribed to a belief that compounds obtained from living sources possessed a
special “vital force” that inorganic compounds lacked. This notion, called vitalism, stipulated that it should be impossible to convert
inorganic compounds into organic compounds without the introduction of an outside vital force. Vitalism was dealt a serious blow in 1828
when German chemist Friedrich Wöhler demonstrated the conversion of ammonium cyanate (a known inorganic salt) into urea, a known
organic compound found in urine:
Over the decades that followed, other examples were found, and the concept
of vitalism was gradually rejected. The downfall of vitalism shattered the original
distinction between organic and inorganic compounds, and a new definition
emerged.
• Organic compounds - those compounds containing carbon atoms. The
defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms.

• Inorganic compounds - those compounds lacking carbon atoms. Carbonates (e.g. Sodium carbonate, Na2CO3), cyanides (e.g.
Ammonium cyanate, NH4OCN, potassium cyanide, KCN), and simple oxides like CO and CO2 are some carbon‑containing
compounds that are classified as inorganic.
1.3 THE UNIQUE CHARACTERISTICS OF CARBON
There are over 600 million compounds known today, but more than 90% of those compounds contain the element carbon, why? Carbon
is contained in most of these compounds because of its ability to form chains with itself, a property called catenation. Carbon shows to
maximum catenation property, it is a tetravalent element, that is, it is bonded to four other atoms in compounds.

1.4 IMPORTANCE AND OCCURRENCE OF ORGANIC COMPOUNDS

Organic chemistry occupies a central role in the world around us, as we are surrounded by organic compounds. The food that we
eat and the clothes that we wear are comprised of organic compounds. Our ability to smell odors or see colors results from the behavior
of organic compounds. Pharmaceuticals, soaps, perfumes, pesticides, paints, adhesives, and plastics are all made from organic
compounds. Our bodies are constructed mostly from organic compounds (DNA, RNA, proteins, etc.) whose behavior and function are
3|Page AdGE – Organic Chemistry
determined by the guiding principles of organic chemistry. The responses of our bodies to pharmaceuticals are the results of reactions
guided by the principles of organic chemistry. A deep understanding of those principles enables the design of new drugs that fight disease
and improve the overall quality of life and longevity. Accordingly, it is not surprising that organic chemistry is required knowledge for
anyone entering the health-related professions.

Lesson 2: Review on Atomic Structure and Chemical Bonding

Intended Learning Outcomes

At the end of the unit, the students will be able to:
1. To review the concept of atoms and the electronic configuration
2. To be able to identify and draw the structure of organic compounds
3. To apply the VSEPR theory in predicting the geometry of organic compounds
4. To determine the relationship between molecular geometry, bonds and hybridization.

This lesson reviews some relevant concepts from your general chemistry course that you should know. Specifically, we will focus
on the central role of electrons in forming bonds and influencing molecular properties. Throughout this lesson, we will learn how, when,
and why electrons flow during reactions. We will learn about the barriers that prevent electrons from flowing, and we will learn how to
overcome those barriers. In short, we will study the behavioral Patterns of electrons, enabling us to predict, and even control, the
outcomes of chemical reactions.
2.1 ELECTRONIC CONFIGURATION
• 1874, George Johnstone Stoney first proposed the existence of the electron and attempted to explain electrochemistry by
suggesting the existence of a particle bearing a unit of charge. Stoney coined the term electron to describe this particle.
• 1897, J. J. Thomson demonstrated evidence supporting the existence of Stoney’s mysterious electron and is credited with
discovering the electron.
• 1916, Gilbert Lewis defined a covalent bond as the result of two atoms sharing a pair of electrons.
Electron configuration - describes how electrons are distributed in an element’s atomic orbitals. While writing electron configurations,
a standardized notation is followed in which the energy level and the type of orbital are written first, followed by the number of electrons
present in the orbital written in superscript. However, the standard notation often yields lengthy electron configurations (especially for
elements having a relatively
large atomic number). In
such cases, an abbreviated
or condensed notation may
be used instead of the
standard notation. In the
abbreviated notation, the
sequence of completely
filled subshells that
correspond to the electronic
configuration of a noble gas
is replaced with the symbol
of that noble gas in square
brackets. This notation for
the distribution of electrons
in the atomic orbitals of
atoms came into practice
shortly after the Bohr model
of the atom was presented
by Ernest Rutherford and
Niels Bohr in the year 1913.
Electron Configurations are useful for:
❖ Determining the valency of an element.
❖ Predicting the properties of a group of elements (elements with similar electron configurations tend to exhibit similar properties).
❖ Interpreting atomic spectra.

4|Page AdGE – Organic Chemistry

Writing Electron Configurations
Shells: The maximum number of electrons that can be accommodated in a shell is
based on the principal quantum number (n). It is represented by the formula 2n 2,
where ‘n’ is the shell number. The shells, values of n, and the total number of
electrons that can be accommodated are tabulated on the right.
Subshells: The subshells into which electrons are distributed are based on the
azimuthal quantum number (denoted by ‘l’). This quantum number is dependent on
the value of the principal quantum number, n. Therefore, when n has a value of 4,
four different subshells are possible. When n=4,t the subshells correspond to l=0, l=1,
l=2, and l=3 and are named the s, p, d, and f subshells, respectively. The maximum
number of electrons that can be accommodated by a subshell is given by the formula
2*(2l + 1). Therefore, the s, p, d, and f subshells can accommodate a maximum of 2,
6, 10, and 14 electrons, respectively. All the possible subshells for values of n up to
4 are tabulated on the left.
Thus, it can be understood that the 1p, 2d, and 3f orbitals do not exist because the
value of the azimuthal quantum number is always less than that of the principal
quantum number.
Notation: The electron configuration of an atom is written with the help of subshell labels. These labels contain the shell number (given
by the principal quantum number), the subshell name (given by the azimuthal quantum number)
and the total number of electrons in the subshell in superscript. For example, if two electrons are
filled in the ‘s’ subshell of the first shell, the resulting notation is ‘1s2’. With the help of these
subshell labels, the electron configuration of magnesium (atomic number 12) can be written as
1s2 2s2 2p6 3s2.
Filling of Atomic Orbitals
Aufbau Principle - named after the German word ‘Aufbeen’ which means ‘build up’. This dictates
that electrons will occupy the orbitals having lower energies before occupying higher energy orbitals.
The energy of an orbital is calculated by the sum of the principal and the azimuthal quantum
numbers. According to this principle, electrons are filled in the following order: 1s, 2s, 2p, 3s, 3p,
4s, 3d, 4p, 5s, 4d, 5p, 6s, 4f, 5d, 6p, 7s, 5f, 6d, 7p… It is important to note that there exist many
exceptions to the Aufbau principle such as chromium and copper. These exceptions can
sometimes be explained by the stability provided by half-filled or completely filled subshells.
Pauli Exclusion Principle - states that a maximum of two electrons, each having opposite spins, can fit in an orbital. This principle can
also be stated as “no two electrons in the same atom have the same values for all four quantum numbers”. Therefore, if the principal,
azimuthal, and magnetic numbers are the same for two electrons, they must have opposite spins.
Hund’s Rule - describes the order in which electrons are filled in all
the orbitals belonging to a subshell. It states that every orbital in a
given subshell is singly occupied by electrons before a second
electron is filled in an orbital. In order to maximize the total spin, the
electrons in the orbitals that only contain one electron all have the
same spin (or the same values of the spin quantum number).
Representation of electronic Configuration of Atom
Hydrogen Electron Configuration Oxygen Electron Configuration Chlorine Electronic Configuration
The atomic number of hydrogen is The atomic number of oxygen is 8, Chlorine has an atomic number of 17.
1. Therefore, a hydrogen atom implying that an oxygen atom holds 8 Therefore, its 17 electrons are distributed
contains 1 electron, which will be electrons. Its electrons are filled in the in the following manner:
placed in the s subshell of the first following order: K shell – 2 electrons
shell/orbit. The electron K shell – 2 electrons L shell – 8 electrons
configuration of hydrogen is 1s1. L shell – 6 electrons M shell – 7 electrons
Therefore, the electron configuration of It can be written as 1s22s22p63s23p5 or as
oxygen is 1s2 2s2 2p4. [Ne]3s23p5

5|Page AdGE – Organic Chemistry

2.2 VALENCE ELECTRONS
❖ Valence electrons are the electrons in the outermost shell or energy level of an atom that can participate in interactions with other
atoms in a chemical reaction. Valence electrons are generally the electrons that are farthest from the nucleus. As a result, they may
be attracted as much or more by the nucleus of another atom than they are by their own nucleus.
❖ Since filled d or f subshells are seldom disturbed in a chemical reaction, we can define valence electrons as follows: The electrons
on an atom that are not present in the previous rare gas, ignoring filled d or f subshells. Gallium has the following electron
[Link]: [Ar] 4s2 3d10 4p1. The 4s and 4p electrons can be lost in a chemical reaction, but not the electrons in the filled 3d
subshell. Gallium therefore has three valence electrons.
❖ The number of valence electrons of an element can be determined by the periodic table group with the exception of the transition
metals.
❖ The number of valence electrons in atoms may cause them to be unreactive or highly
reactive. For those atoms that are reactive, the number of valence electrons also
determines whether they tend to give up or gain electrons in chemical reactions.
❖ An atom with a closed shell of valence electrons (corresponding to an electron
configuration s2p6) tends to be chemically inert. An atom with one or two valence
electrons more than a closed shell is highly reactive, because the extra valence electrons are easily removed to form a positive ion.
An atom with one or two valence electrons fewer than a closed shell is also highly reactive, because of a tendency either to gain
the missing valence electrons (thereby forming a negative ion), or to share valence electrons (thereby forming a covalent bond).
❖ Metals, which easily give up electrons, can conduct electricity. Nonmetals, which attract electrons, generally cannot. Metalloids such
as silicon and germanium can conduct electricity but not as well as metals.
2.3 OCTET RULE
❖ The octet rule refers to the tendency of atoms to prefer to have eight electrons in the valence shell. When atoms have fewer than
eight electrons, they tend to react and form more stable compounds. This octet can be made up by own electrons and some electrons
which are shared. Thus, an atom continues to form bonds until an octet of electrons is made. A complete octet is very stable because
all orbitals will be full.
❖ When discussing the octet rule, we do not consider d or f electrons. Only the s and p electrons are involved in the octet rule, making
it useful for the main group elements. The rule is especially applicable to carbon, nitrogen, oxygen, and the halogens, but also to
metals such as sodium or magnesium. Other rules exist for other elements, such as the duplet rule for hydrogen and helium, or the
18-electron rule for transition metals.
❖ The noble gases rarely form compounds. They have the most stable configuration (full octet, no charge), so they have no reason to
react and change their configuration. All other elements attempt to gain, lose, or share electrons to achieve a noble gas configuration.
❖ Atoms with greater stability have less energy, so a reaction that increases the stability of the atoms will release energy in the form of
heat or light
2.4 LEWIS STRUCTURE OF ORGANIC COMPOUNDS
Lewis Electron Dot Diagrams - diagrams of atoms that show only their valence
electrons. In this type of diagram, an element's chemical symbol is surrounded by dots that represent the valence electrons. Typically,
the dots are drawn as if there is a square surrounding the element symbol with up to two dots per side. An element never has more than
eight valence electrons, so there can’t be more than eight dots per atom.
The electrons shared by the two atoms in a covalent bond are counted twice, once for each atom. In carbon dioxide each oxygen shares
four electrons with the central carbon, two (shown in
red) from the oxygen itself and two (shown in black)
from the carbon. All four of these electrons are
counted in both the carbon octet and the oxygen
octet, so that both atoms are considered to obey the
octet rule.
2.5 VALENCE SHELL ELECTRON PAIR REPULSION (VSEPR) THEORY AND
MOLECULAR GEOMETRY
Molecular geometry - a method to determine the shape of a molecule based on the repulsion
occurring between bond electron pairs in the outermost (or valence) electron shell. It’s useful to
study molecular geometry to get information beyond that provided in a Lewis structure. Many
physical and chemical properties are affected by the shape of molecules.
VSEPR - a molecular geometry model that helps predict the general shape of a molecule but
doesn’t provide information about the length or type of bonds. The VSEPR theory assumes that
each atom in a molecule will achieve a geometry that minimizes the repulsion between electrons
in the valence shell of that atom. The two primary founders of the VSEPR theory are Ronald
Nyholm and Ronald Gillespie. VSEPR is often explained to beginners as simpler postulates:
1. In polyatomic molecules (i.e. molecules made up of three or more atoms), one of the
constituent atoms is identified as the central atom to which all other atoms belonging to the

6|Page AdGE – Organic Chemistry

 molecule are linked. The least electronegative atom must be selected as the central atom (since this atom has the highest ability to
share its electrons with the other atoms belonging to the molecule).
2. Molecular shape can be determined by the number of electron pairs present.
3. Electron pairs tend to repel one another.
4. Electron pairs arrange themselves to minimize the electron-electron repulsion between them and maximize the distance between
them.
5. The valence or outermost electron shell is assumed to be spherical.
6. Multiple bonds are accounted as single electron pairs, and bonded electron pairs as a single pair.
7. Lone pair electrons have the
maximum repulsion, and bond
pair electrons the minimum.
8. All electron pairs assume
positions of least repulsion.
9. Repulsive interaction of
electron pairs is greatest
between lone pairs and least
between bond pairs: bond pair
– bond pair < lone pair – bond
pair < lone pair – lone pair.
To use a VSEPR table, first determine the coordination
number or number of electron pairs.
1. Count the valence electrons of the central atom.
2. Add an electron for each bonding atom.
3. Subtract an electron if the central atom has a positive
charge; and add an electron for a central atom with
negative charge.
4. Halve your count to get the total electron pairs.
Finally, look up your molecule on the chart by coordination
number and number of atoms. Alternatively, you can count
the lone electron pairs, which are also indicated on the chart.
Example: Once you know PCl5 has five electron pairs, you
can identify it on a VSEPR chart as a molecule with a trigonal
bipyramidal molecular geometry. Its bond angles are 90 °
and 120 °, where the equatorial-equatorial bonds are 120 °
apart from one another, and all other angles are 90 °.
2.6 VALENCE BOND THEORY
The Valence Bond Theory states that covalent (shared electron) bonds form between the electrons in the valence orbitals of an atom
by overlapping those orbitals with the valence orbitals of another atom. When the bonds form, it increases the probability of finding the
electrons in the space between the two nuclei.
There are two different types of overlaps that occur:
Sigma (σ) Bonds form between the two nuclei with the
majority of the electron density forming in a straight line
between the two nuclei. It is often referred to as a "head-
to-head" bond.
Pi (π) Bonds form when two un-hybridized p-orbitals
overlap. It is often referred to as a "side-by-side" bond.

2.7 HYBRIDIZATION
Hybridization is the idea that atomic orbitals fuse to form newly hybridized orbitals, which in turn, influences molecular geometry and
bonding properties.
• Atomic orbitals with equal energies undergo hybridization.
• The number of hybrid orbitals formed is equal to the number of atomic orbitals mixing.
• It is not necessary that all the half-filled orbitals must participate in hybridization. Even completely filled orbitals with slightly
different energies can also participate.
• Hybridization happens only during the bond formation and not in an isolated gaseous atom.
• The shape of the molecule can be predicted if the hybridization of the molecule is known.
• The bigger lobe of the hybrid orbital always has a positive sign, while the smaller lobe on the opposite side has a negative sign.

7|Page AdGE – Organic Chemistry

Knowledge of the number and types of overlaps an atom makes allows us to determine the degree of hybridization it has. In other
words, you only have to count the number of bonds or lone pairs of electrons around a central atom to determine its hybridization. The
following rules give the hybridization of the central atom:
➢ 2 bonds to another atom or lone pairs = sp
➢ 3 bonds to another atom or lone pairs = sp2
➢ 4 bonds to another atom or lone pairs = sp3
➢ 5 bonds to another atom or lone pairs = sp3d
➢ 6 bonds to another atom or lone pairs = sp3d2
Based on the types of orbitals involved in mixing, the
hybridization can be classified as sp3, sp2, sp, sp3d, sp3d2, sp3d3.
Carbon atoms have the ability to bond to themselves and to
other atoms with sp, sp2, and sp3 hybrid orbitals
Carbon Atoms Using sp Hybrid Orbitals
• This type of hybridization involves the mixing of one ‘s’ orbital and one ‘p’ orbital of equal energy to
give a new hybrid orbital known as an sp hybridized orbital.
• It forms linear molecules with an angle of 180°
• sp hybridization is also called diagonal hybridization.
• Each sp hybridized orbital has an equal amount of s and p character – 50% s and 50% p character.
Examples of sp2 Hybridization
• All compounds of beryllium like BeF2, BeH2, BeCl2
• All compounds of carbon-containing triple bond like C2H2.
When sp hybrid orbitals are used for sigma bond, the two sigma
bonds around the carbon are linear. Two other p orbitals are
available for pi bonding, and a typical compound is the
acetylene or ethyne HC≡CH. The three sigma and two pi bonds
are shown below.
Note that molecules H−C≡C−H, H−C≡N, and C≡O have the
same number of electrons. Bonding in these molecules can be
explained by the same theory, and thus their formation is no
surprise. The O=C=O molecule is linear, and the carbon atom
in this molecule also involves the sp hybrid orbitals. Two pi
bonds are also present in this simple molecule. As an exercise,
draw a picture to show the two sigma and two pi bonds for this
molecule.
Carbon Atoms Using sp2 Hybrid Orbitals
• sp2 hybridization is also called trigonal hybridization.
• It involves mixing of one ‘s’ orbital and two ‘p’ orbitals of equal energy to give a new hybrid orbital
known as sp2.
• A mixture of s and p orbital formed in trigonal symmetry and is maintained at 120 0.
• All the three hybrid orbitals remain in one plane and make an angle of 120° with one another.
Each of the hybrid orbitals formed has a 33.33% ‘s’ character and 66.66% ‘p’ character.
• The molecules in which the central atom is linked to 3 atoms and is sp 2 hybridized
have a triangular planar shape.
Examples of sp2 Hybridization
• All the compounds of Boron i.e. BF3, BH3
• All the compoun;ds of carbon-containing a carbon-carbon double bond, Ethylene
(C2H4)
When carbon atoms make use of sp2 hybrid orbitals for sigma bonding, the three bonds lie
on the same plane. One such compound is ethene, in which both carbon atoms make use
of sp2 hybrid orbitals. One of the remaining p orbitals for each carbon overlap to form a pi
bond. A pi bond consists of two parts where bonding electrons are supposed to be located.
A picture depicting the sigma and pi bonds in ethene from the same source as the previous
picture is shown on the right.
Carbon atoms make use
of sp2 hybrid orbitals not
only in ethene, but also
in many other types of
compounds. The
following are some of
these compounds:

8|Page AdGE – Organic Chemistry

Carbon Atoms Using sp3 Hybrid Orbital
• When one ‘s’ orbital and 3 ‘p’ orbitals belonging to the same shell of an atom mix together to form four new equivalent orbital
• the type of hybridization is called a tetrahedral hybridization or sp3. The new orbitals formed are called sp3 hybrid orbitals.
• These are directed towards the four corners of a regular tetrahedron and make an angle of 109°28’ with one another.
• The angle between the sp3 hybrid orbitals is 109.280
• Each sp3 hybrid orbital has 25% s character and 75% p character.
• Example of sp3 hybridization: ethane (C2H6), methane.
In ethane, the carbon atoms use sp3 hybrid orbitals for the formation of sigma bonds. The four bonds
around each C atom point toward the vertices of a regular tetrahedron, and the ideal bond angles are
109.5°. The simplest compound is methane, CH4, which is the first member of the alkane family. The
next few members are ethane, CH3CH3, propane, CH3CH2CH3, butane, CH3CH2CH2CH3, etc.
Prediction of sp, sp2, sp3 Hybridization state
We know that hybridization is nothing but the mixing of orbitals in different ratio to form some newly
synthesized orbitals called hybrid orbitals. The mixing pattern is as follows: s + p (1:1) - sp hybrid orbital; s + p (1:2) - sp2 hybrid orbital;
s + p (1:3) - sp3 hybrid orbital
Formula used for the determination of sp, sp2 and sp3 hybridization state:
Power on the Hybridization state of the central atom = (Total no of σ bonds around each central atom -1)
All single (-) bonds are σ bond, in double bond (=) there is one σ and 1π, in triple bond (≡) there is one σ and 2π. In addition to these
each lone pair (LP) and Co-ordinate bond can be treated as one σ bond subsequently.
Example:
a. In NH3: central atom N is surrounded by three N-H single bonds i.e. three sigma (σ) bonds and one lone pair (LP) i.e. one additional
σ bond. So, in NH3 there is a total of four σ bonds [3 bond pairs (BPs) + 1 lone pair (LP)] around central atom N. Therefore, in this
case power of the hybridization state of N = 4-1 = 3 i.e. hybridization state = sp3.
b. In H2O: central atom O is surrounded by two O-H single bonds i.e. two sigma (σ) bonds and two lone pairs i.e. two additional σ
bonds. So, altogether in H2O there are four σ bonds (2 bond pairs + 2 lone pairs) around central atom O, So, in this case power of
the hybridization state of O = 4-1 =3 i.e. hybridization state of O in H2O = sp3.
c. In H3BO3:- B has 3σ bonds (3BPs but no LPs) and oxygen has 4σ bonds (2BPs & 2LPs) so, in this case power of the hybridization
state of B = 3-1 = 2 i.e. B is sp2 hybridized in H3BO3. On the other hand, power of the hybridization state of O = 4-1= 3 i.e.
hybridization state of O in H3BO3 is sp3.
d. In I-Cl: I and Cl both have 4σ bonds and 3LPs, so, in this case power of the hybridization state of both I and Cl = 4 - 1 = 3 i.e.
hybridization state of I and Cl both are sp3.
e. In CH2=CH2: each carbon is attached with 2 C-H single bonds (2 σ bonds) and one C=C bond (1σ bond), so, altogether there are
3 sigma bonds. So, in this case, power of the hybridization state of both C = 3-1 = 2 i.e. hybridization state of both C’s are sp2.
References
Offline
1. McMurry, J., Organic Chemistry. 8th ed., Thomson Brooks–Cole, 2011
2. Brown, W.H., Introduction to Organic Chemistry, 1998
3. Clapp, L.B., Organic Chemistry. Microsoft® Student 2009. Redmond, WA: Microsoft Corporation, 2008
4. Carrey, F.A., Organic Chemistry. 4rth ed., North America: The McGraw-Hill Companies, Inc., 2003
5. Bettelheim, F., Brown, W. and March, J., Introduction to Organic and Biochemistry. 5th ed., Singapore: Brooks/Cole, 2004
6. Atkins, Robert and Carey Francis, Organic Chemistry A Brief Course. 3rd ed., New York: The McGraw Hill Companies, Inc., 2004
7. Mohrig, Jerry R., Hammond, Schatz P., and Merill, T., Modern Projects and Experiments in Organic Chemistry. 2nd ed., New
York: Freeman and Company, 2003
Online
1. Morley, R., Alcohols, Phenols, and Ethers, Available: [Link] 2 September 2005
2. Coletti, J., Alcohol Models, Available: [Link] 2
September 2005
3. Perottet, J., Identifying Electrophile and Nucleophile, Available: [Link]
2 September 2005
4. [Link]
5. Valence electrons and open valences. (2019, June 6). [Link]
6. [Link]
ms-ps/
7. Gillespie RJ. 1992. Electron densities and the VSEPR model of molecular geometry. Can. J. Chem.. 70(3):742-
750. [Link]
8. [Link]

9|Page AdGE – Organic Chemistry

INSTRUCTOR INFORMATION

Name : Leyra Lyn U. Manilag

E-mail Address : llumanilag@[Link]
Consultation Hours : MWF 10:00 – 11:00 am
Mode of Teaching/
Learning Delivery : Flexible Learning
Tools/Platforms : Printed Modules; Messenger; Google Classroom, Google Meet

10 | P a g e AdGE – Organic Chemistry