ORGANIC CHEMISTRY 1

According to Carey, (2008), structure is the key to everything in

chemistry. The properties of a substance depend on how the atoms are
connected and bonded in a structure.

At the end of this unit, you will be able to:

 Differentiate saturated and unsaturated hydrocarbons.
 Name and draw chemical formulas of the different classes of organic compounds
 Explain the chemical reactions and methods of preparations of the other organic
functional groups of compounds

The next section is the content of this unit. Let us begin our study of organic chemistry
with a review of how the elements of C, H, O, and N combine by sharing electron pairs to form
bonds, and ultimately molecules.

Lewis Structures

Before we begin our study of the compounds of carbon we need to review some basic but
familiar ideas about the chemical elements and their structure.

● The compounds we encounter in chemistry are made up of

elements combined in different proportions.

● Elements are made up of atoms. An atom consists of a dense,

positively charged nucleus containing protons and neutrons and a
surrounding cloud of electrons.

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 2

Each proton of the nucleus bears one positive charge; electrons bear one negative
charge. Neutrons are electrically neutral; they bear no charge. Protons and neutrons have
nearly equal masses (approximately 1 atomic mass unit each) and are about 1800 times as
heavy as electrons. Most of the mass of an atom, therefore, comes from the mass of the
nucleus; the atomic mass contributed by the electrons is negligible. Most of the volume of an
atom, however, comes from the electrons; the volume of an atom occupied by the electrons is
about 10,000 times larger than that of the nucleus. The elements commonly found in organic
molecules are carbon, hydrogen, nitrogen, oxygen, phosphorus, and sulfur, as well as the
halogens: fluorine, chlorine, bromine, and iodine.

Each element is distinguished by its atomic number (Z), a number equal to the
number of protons in its nucleus. Because an atom is electrically neutral, the atomic
number also equals the number of electrons surrounding the nucleus.

Isotopes

Before we leave the subject of atomic structure and the periodic table, we need to
examine one other observation: the existence of atoms of the same element that have
different masses.

For example, the element carbon has six protons in its nucleus giving it an atomic
number of 6. Most carbon atoms also have six neutrons in their nuclei, and because each
proton and each neutron contributes one atomic mass unit (1 amu) to the mass of the atom,
carbon atoms of this kind have a mass number of 12 and are written as 12C.

● Although all the nuclei of all atoms of the same element will have the same number of protons,
some atoms of the same element may have different masses because they have different
numbers of neutrons. Such atoms are called isotopes.

For example, about 1% of the atoms of elemental carbon have nuclei containing 7
neutrons, and thus have a mass number of 13. Such atoms are written 13C. A tiny fraction of
carbon atoms have 8 neutrons in their nucleus and a mass number of 14. Unlike atoms of
carbon-12 and carbon-13, atoms of carbon-14 are radioactive. The 14C isotope is used in
carbon dating. The three forms of carbon, 12C, 13C, and 14C, are isotopes of one another.

Lewis structures

- Are used to show the outermost electrons of an atom. It was named after the American
chemist Gilbert N. Lewis (1875–1946) who devised this notation. A Lewis dot structure
shows the symbol of the element surrounded by a number of dots equal to the number
of electrons in the outer shell of an atom of that element. (Brown,et al. 2012, p.40)

Valence Electrons- are electrons found at the valence shell

Valence shell- is the outermost energy level occupied by valence electrons.

Table 3.1
Lewis Dot Structures for Elements 1-18

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 3

Adapted from “Organic Chemistry” (6th Ed.) (p.6) by Brown, et.al 2012, Brooks/Cole, Cengage Learning

Lewis Model of Bonding

Octet Rule is the name given wherein atoms react in ways to achieve eight valence
electrons on an outer shell. This is particularly common among second-row elements of Groups
1A–7A (the main-group elements)

Example: The ground state electron configuration of Na and Na + are:

Thus, Na+ has a complete octet of electrons in its valence shell and has the
same electron configuration as neon, the noble gas nearest it in atomic number.

Exceptions to the Octet Rule

The rule is applicable to the main- group elements, especially carbon, nitrogen, oxygen,
and the halogens, but also to metals such as sodium and magnesium. In carbon dioxide, for
example, each oxygen shares four electrons with the central carbon. These four electrons are
counted in both the carbon octet and the oxygen octet because they are shared.

C = 8 e- ; O2 = 8 e-

1. Most of the compounds of Groups 2A AND 3A, and H. They form incomplete octets.
(Mg Cl2, BF3, HCl)
2. Most compounds of Groups 5A,6A, and 7A in the third period where there are empty d
or f orbitals. They form “expanded” octets. (PCl5, SF6, ICl5).
3. Species containing an odd number of valence electrons like free radicals (CH3, OH,
NO2) The presence of odd electron species makes them paramagnetic.

Lewis structure of boron trifluoride. Each pair of dots

represents a pair of electrons. When placed between two atoms,
the electrons are in a bond. A bondcan be drawn as a line
between two atoms, which also indicates two electrons. Notice
that the central boron atom has only 6 electron in the final Lewis
Draft. Not Intended for Publication. For Classroom Use Only.
 ORGANIC CHEMISTRY 4

structure of this molecule

Formation of Chemical Bonds

An atom may become ionic, that is lose or gain enough electrons to acquire a completely
filled valence shell.

Anion is an atom that gains electrons while cation is an atom that loses electrons.
Wherein these ions attract with each other that leads to the formation of ionic crystals such as
sodium chloride. When atoms are held together primarily by attraction of oppositely charged
ions, we say that an ionic interaction exists between them. (This ionic interaction is often
referred to as an ionic bond.)

Covalent Bond is chemical bond formed between two atoms by sharing one or more
pairs of electrons. These bonds may be partially ionic and partially covalent that is called polar
covalent bonds.

Electronegativity and Chemical Bonds

Electronegativity is a measure of an atom’s attraction for electrons that it shares in a

chemical bond with another atom.

Table 3.2

Note: The most widely used scale of electronegativities (Table 2.2) was devised by Linus Pauling in the 1930s.
Adapted from “Organic Chemistry” (6th Ed.) (p.7) by Brown, et.al 2012, Brooks/Cole, Cengage Learning.

As you can see, the electronegativity values generally increase from left to right within a
period of the Periodic Table and generally decrease from top to bottom within a group. Values
increase from left to right because the increasing positive charge on the nucleus results in a
greater force of attraction for the atom’s valence electrons. Electronegativity decreases from top
to bottom because the increasing distance of the valence electrons from the nucleus results in a
lower attraction between the nucleus and these electrons.

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 5

Formation of Ions

Ions are formed by the transfer of electrons from the valence shell of an atom of lower
electronegativity to the valence shell of an atom of higher electronegativity. It will form if the
difference in electronegativity between interacting atoms is 1.9 or greater. In forming Na+F-, the
single 3s valence electron of sodium is transferred to the partially fi lled valence shell of fluorine:

Covalent Bonds

- Atoms that are held together by sharing electrons are joined by a covalent bond.
- A molecule is a neutral group of atoms joined together by covalent bonds.
- An oxygen molecule is an example of a diatomic molecule—a molecule that contains
two atoms.
- Molecules can also be made of atoms of different elements.
o A compound composed of molecules is called a molecular compound.
o Water is an example of a molecular compound.
- A molecular formula is the chemical formula of a molecular compound.
o A molecular formula shows how many atoms of each element
a substance contains.
o A molecular formula does not tell you about a molecule’s
structure.
o Molecular formulas also describe molecules consisting of
atoms of one element.
o The arrangement of atoms within a molecule is called its
molecular structure
- Atoms are arranged in different ways in space to form molecules
with different molecular structures.
- The representative unit of a molecular compound is a molecule. For an ionic
compound, the smallest representative unit is a formula unit.
- Molecular compounds tend to have relatively lower melting and boiling points than ionic
compounds.
- In covalent bonds, electron sharing usually occurs so that atoms attain the
electron configurations of noble gases.

Single Covalent Bonds

- Two atoms held together by sharing one pair of electrons are joined by a single
covalent bond.

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 6

- A pair of valence electrons that is not shared between atoms is called an unshared pair,
also known as a lone pair or a nonbinding pair.

Double and Triple Covalent Bonds

- Atoms form double or triple covalent bonds if they can attain a noble gas structure by
sharing two or three pairs of electrons.
- A double covalent bond is a bond that involves two shared pairs of electrons.
- Similarly, a bond formed by sharing three pairs of electrons is a triple covalent bond.

- The “octet” in the octet rule refers to eight of what?

o Each of the atoms joined by a covalent bond usually acquires eight electrons in
its valence shell. Most noble gases have eight valence electrons
- The octet rule cannot be satisfied in molecules whose total number of valence electrons
is an odd number. There are also molecules in which an atom has less, or more, than a
complete octet of valence electrons.

Important: The unequal sharing of electrons in a polar covalent bond is that the more
electronegative atom gains a greater fraction of the shared electrons and acquires a partial
negative charge, indicated by the symbol α _ . The less electronegative atom has a smaller
fraction of the shared electrons and acquires a partial positive charge, indicated by the symbol

3.1. Classify each bond as nonpolar covalent or polar covalent or state that
ions are formed.

a. S -H b. P-H c. C-F d. C-Cl

3.2. Using the symbols α+ and α-, indicate the direction of polarity in each
polar covalent bond.

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 7

- A large bond dissociation energy corresponds to a strong covalent bond.

- sigma bond (  bond): a bond formed when two atomic orbitals combine to form a
molecular orbital that is symmetrical around the axis connecting the two atomic nuclei
- pi bond ( bond): a covalent bond in which the bonding electrons are most likely to be
found in sausage-shaped regions above and below the bond axis of the bonded atoms

Bond Polarity

- The bonding pairs of electrons in covalent bonds are pulled between the nuclei of
the atoms sharing the electrons.
o When the atoms in the bond pull equally (as occurs when identical atoms are
bonded), the bonding electrons are
shared equally, and each bond formed
is a nonpolar covalent bond.
o When the atoms in the bond pull equally
(as occurs when identical atoms are
bonded), the bonding electrons are
shared equally, and each bond formed
is a nonpolar covalent bond.
o The more electronegative atom attracts
more strongly and gains a slightly
negative charge. The less
electronegative atom has a slightly
positive charge.
o The higher the electronegativity value, the greater the ability of an atom to attract
electrons to itself.
o The electronegativity difference between two atoms tells you what kind of
bond is likely to form.

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 8

- The electronegativity difference between two atoms is expressed as the absolute value.
So, you will never express the difference as a negative number.
- Molecules can be attracted to each other by a variety of different forces.
o Intermolecular attractions are weaker than either ionic or covalent bonds.

Van der Waals Forces

- The two weakest attractions between molecules are collectively called van der Waals
forces, named after the Dutch chemist Johannes van der Waals.
o Van der Waals forces consist of dipole interactions and dispersion forces.
o Dipole interactions occur when polar molecules are attracted to one another.
 The electrical attraction occurs between the oppositely charged regions of
polar molecules.
 Dipole interactions are similar to, but much weaker than, ionic bonds.

- Dispersion forces, the weakest of all molecular interactions, are caused by the motion
of electrons.

o They occur even between nonpolar molecules.

o The strength of dispersion forces generally increases as the number of electrons
in a molecule increases.

Hydrogen Bonds

- The dipole interactions in water produce an attraction

between water molecules. Hydrogen
bond
- The positive region of one water molecule attracts the negative
region of another water molecule.
- This relatively strong attraction, which is also found
in hydrogen-containing molecules other than water, is
called a hydrogen bond.
- Hydrogen bonds are attractive forces in which a hydrogen covalently bonded to a very
electronegative atom is also weakly bonded to an unshared electron pair of another
electronegative atom.

Why are hydrogen bonds important?

- Hydrogen bonds are the strongest of the intermolecular forces and are extremely
important in determining the properties of water and biological molecules such as
proteins.

Lewis Structures for Molecules and Polyatomic Ions

In writing Lewis structures for molecules and polyatomic ions, the following guidelines
will help you do this.
Draft. Not Intended for Publication. For Classroom Use Only.
 ORGANIC CHEMISTRY 9

 Determine the number of valence electrons in the molecule or ion.

Ex. H2O (H= 2; O=6) No. of valence electrons = 8

 Determine the connectivity (arrangement) of atoms in the molecule or ion.

Isomers are different compounds with the same molecular formula.

 Connect the atoms with single bonds. Then arrange the remaining electrons in
pairs so that each atom in the molecule or ion has a complete outer shell.
 Each pair of electrons (bonding electrons) shared between two atoms is shown
as a single line between the atoms. Each unshared pair of electrons (often called
a lone pair or nonbonding electrons) is shown as a pair of dots.
 If two atoms only share a single pair of electrons, they form a single bond and a
single line is drawn between them. If two pairs of electrons are shared between
two atoms, they form a double bond (two lines). If three pairs of electrons are
shared between two atoms, they form a triple bond (three lines).

Table 3.5 Lewis structures for some compounds

Note: Adapted from “Organic Chemistry” (6th Ed.) (p.11) by Brown, et.al 2012, Brooks/Cole,
Cengage Learning.

Structural Formulas of Organic Compounds

Draft. Not Intended for Publication. For Classroom Use Only.
ORGANIC CHEMISTRY 10

 Molecular Formula- gives the exact number of each type of

atoms present in a compound. It doesn’t
provide any information with regards to the bonding of molecules.

 Emperical Formula- provides the simplest possible ratio of the

different types of atom in a compound.

 Condensed structural Formula-is a formula that is written in a

form of text-based. Brackets are used to

designate molecule branching or , multiple similar groups.

However, there is an exemption
in cyclic compounds wherein the carbons are grouped.

 Displayed Formula/ Expanded Formula- shows all the atoms and

the bonds that are connected on each atom in a
molecule.These bonds are represented by lines
that indicates the strength of the bond in number.
Single and double bonds (2 lines) are common but
some molecules may also have triple bonds (3 lines).

 Structural Formula- is a formula that is similar to displayed

formula but not all bonds are displayed.
Atoms are indicated using subscript
numbers.The bonds between
carbon and hydrogen are simplified.

 Skeletal Formula- represents the carbon chain as zigzag line of which

at the end of line and vertices contains the carbon atoms.
Hydrogens are omitted unless displayed as part of
functional groups and atoms other that carbon and
hydrogen are also presented.

https://www.compoundchem.com/2014/04/11/a-brief-guide-to-types-of-organic-chemistry-formula/

Table 3.6. A Systematic Approach to Writing Lewis Structures

Steps Illustration
1. The molecular formula is determined Ethanol and dimethyl ether both have the
experimentally. molecular formula C2H6O.
2. Based on the molecular formula, In C2H6O, each hydrogen contributes 1
count the number of valence valence electron, each carbon contributes 4,
electrons. and oxygen contributes 6 for a total of 20.
3. Given the connectivity, connect Oxygen and the two carbons are connected
Draft. Not Intended for Publication. For Classroom Use Only.
ORGANIC CHEMISTRY 11

bonded atoms by a shared electron in the order CCO in ethanol and COC in
pair bond ( ) represented by a dash dimethyl ether. The connectivity and the fact
(O). that carbon normally has four bonds in
neutral molecules allow us to place the
hydrogens of ethanol and dimethyl ether.

4. Count the number of electrons in the The structural formulas in step 3 contain eight
bonds (twice the number of bonds), bonds, accounting for 16 electrons. Because
and subtract this from the total C2H6O contains 20 valence electrons, 4
number of valence electrons to give more are needed.
the number of electrons that remain to
be added.
5. Add electrons in pairs so that as many Both carbons already have complete octets in
atoms as possible have eight the structures illustrated in step 3. The
electrons. It is usually best to begin remaining four electrons are added to each
with the most electronegative atom. oxygen as two unshared pairs to complete its
(Hydrogen is limited to two electrons). octet. The Lewis structures are:
Under no circumstances can a
second-row element such as C, N, or
O have more than eight valence
electrons.

6. Calculate formal charges.

Formal Charge

Although we know how many valence electrons are present in a compound, it is harder
to determine around which atoms the electrons actually reside. To assist with this problem,
chemists often calculate the formal charge of each atom. The formal charge is the electric
charge an atom would have if all the electrons were shared equally.

The formal charge of an atom can be determined by the following formula:

V - the number of valence electrons of the atom in isolation,

N - the number of non-bonding valence electrons, and

B - the total number of electrons in covalent bonds with other atoms in the molecule.

Example: CO2 molecule

FC = 6 valence electrons – (4 non-bonding valence electrons + 4/2 electrons in covalent

bonds)

FC = 6 – 6 = 0

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 12

The oxygen atom in carbon dioxide has a formal charge of 0.

3.4 Calculate the formal charge on each nitrogen in the following

Lewis structure (azide ion) and the net charge on the species.

Resonance

According to the resonance concept, when two or more Lewis structures that differ
only in the distribution of electrons can be written for a molecule, no single Lewis structure is
sufficient to describe its true electron distribution. The true structure is said to be a resonance
hybrid of the various Lewis formulas, called contributing structures that can be written for the
molecule.

Rule Illustration
I. When can resonance be
considered?

1. The connectivity must be the same in The Lewis formulas A and B are not
all contributing structures; only the resonance forms of the same compound.
electron positions may vary among the They are isomers (different compounds with
various contributing structures. the same molecular formula).

The Lewis formulas A, C, and D are

resonance forms of a single compound.

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 13

2. Each contributing structure must have Structures A, C, and D (preceding example)

the same number of electrons and the all have 18 valence electrons and a net
same net charge. The formal charges charge of 0, even though they differ in
of individual atoms may vary among respect to formal charges on individual
the various Lewis structures. atoms. Structure E has 20 valence electrons
and a net charge of 2. It is not a resonance
structure of A, C, or D.

3. Each contributing structure must have

the same number of unpaired Structural formula F has the same atomic
electrons. positions and the same number of electrons
as A, C, and D, but is not a
resonance form of any of them.
F has two unpaired
electrons; all the electrons
in A, C, and D are paired.

4. Contributing structures in which the Lewis structures G and H are resonance

octet rule is exceeded for second-row contributors to the structure of nitric acid.
elements make no contribution. (The Structural formula I is not a permissible Lewis
octet rule may be exceeded for structure because it has ten electrons around
elements beyond the second-row.) nitrogen.

II. Which resonance form

contributes more?

5. As long as the octet rule is not Of the two Lewis structures for formaldehyde,
exceeded for second-row elements, the major contributor J has one more bond
the contributing structure with the than the minor contributor K.
greater number of covalent bonds
contributes more to the resonance
hybrid. Maximizing the number of
bonds and satisfying the octet rule
normally go hand in hand. This rule is
more important than rules 6 and 7.

The two structures L and M for nitrous acid

6. When two or more structures satisfy
have the same number of bonds, but L is the
Draft. Not Intended for Publication. For Classroom Use Only.
ORGANIC CHEMISTRY 14

the octet rule, the major contributor is major contributor because it lacks the
the one with the smallest separation separation of positive and negative charge
of oppositely charged atoms. that characterizes M.

7. Among structural formulas that The major contributing structure for cyanate
satisfy the octet rule and in which ion is N because the negative charge is on its
one or more atoms bears a formal oxygen.
charge, the major contributor is the
one in which the negative charge
resides on the most electronegative
atom.
In O the negative charge is on nitrogen.
Oxygen is more electronegative than nitrogen
and can better support a negative charge.

III. What is the effect of resonance?

8. Electron delocalization stabilizes a Structures P, Q, and R for carbonate ion are

molecule. Resonance is a way of equivalent and contribute equally to the
showing electron delocalization. electron distribution. The true structure of
Therefore, the true electron distribution carbonate ion is a hybrid of P, Q, and R and
is more stable than any of the is more stable than any of them.
contributing structures. The degree of
stabilization is greatest when the
contributing structures are of equal
stability.

Note: The rules of Resonance Structures. Adapted from Organic Chemistry (7th Ed.) (p. 27-28) by Carey, Francis A.,
McGraw-Hill

3.5. Write the resonance structures of the following:

a. SO2
b. CO32-

VSEPR Theory

Valence-shell elecetron pair repulsion theory focuses on pairs of electrons in the

valence shell. Electron pairs attain positions around the atom to minimize repulsions. This
results in the particular shapes for molecules.

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 15

The geometry of molecules is determined by the arrangement of bonding pairs and

lone pairs. The five common shapes of small molecules are linear, trigonal planar, tetrahedral,
trigonal bipyramid and octahedral. What determines the molecular shape or the molecular
geometry are the positions of the atomic nuclei.

Source: https://web.gccaz.edu/~chriy68124/VSEPR%20handout.pdf

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 16

Hybridization

 The combining of orbitals to form the same number of equivalent hybrid orbitals on a
single atom. It is a theoretical model used only to explain covalent bonding. The number
of hybrid orbitals generated is equal to the number of pure atomic orbitals that participate
in the hybridization process.
 Hybridization requires an input of energy; however, the system more than recovers this
energy during bond formation.
 Covalent bonds in polyatomic molecules and ions are formed by the overlap of hybrid
orbitals, or of hybrid orbitals with unhybridized ones. Therefore, the hybridization
bonding scheme is still within the framework of valence bond theory; electrons in a
molecule are assumed to occupy hybrid orbitals of the individual atoms.

sp3 Hybridization

Consider the CH4 molecule. Focusing only on the valence electrons, we can represent
the orbital diagram of C as
promote Hybridize

Because the new orbitals are formed from one s and three p orbitals, they are called sp3
hybrid orbitals.

We use hybridization to describe the bonding scheme only when the arrangement of
electron pairs has been predicted using VSEPR. If the VSEPR model predicts a tetrahedral
arrangement of electron pairs, then we assume that one s and three p orbitals are hybridized to
form four sp3 hybrid orbitals.

sp Hybridization

The beryllium chloride (BeCl2) molecule is predicted to be linear by VSEPR. The orbital
diagram for the valence electrons in Be is

First, we promote a 2s electron to a 2p orbital, resulting in

Now there are two Be orbitals available for bonding, the 2s However, if two Cl atoms were to
combine with Be in this excited state, one Cl atom would share a 2s electron and the other Cl
would share a 2p electron, making two nonequivalent BeCl

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 17

bonds. This scheme contradicts experimental evidence. In the actual BeCl2 molecule, the two
BeCl bonds are identical in every respect. Thus, the 2s and 2p orbitals must be mixed, or
hybridized, to form two equivalent sp hybrid orbitals:and 2p.

sp2 Hybridization

We will look at the BF3 (boron trifluoride) molecule, known to have a planar geometry.
Considering only the valence electrons, the orbital diagram of B is

First, we promote a 2s electron to an empty 2p orbital:

Mixing the 2s orbital with the two 2p orbitals generates three sp2
hybrid orbitals:

Pure Atomic Hybridization of Number Shape of Hybrid Examples

Orbitals of the Central of Orbitals
the Central Atom Hybrid
Atom Orbitals

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 18

Procedure for Hybridizing Atomic Orbitals

In essence, hybridization simply extends Lewis theory and the VSEPR model. To assign
a suitable state of hybridization to the central atom in a molecule, we must have some idea
about the geometry of the molecule. The steps are as follows:

1. Draw the Lewis structure of the molecule.

2. Predict the overall arrangement of the electron pairs (both bonding pairs and lone pairs) using
the VSEPR model (see Table 10.1).

3. Deduce the hybridization of the central atom by matching the arrangement of the electron
pairs with those of the hybrid orbitals shown in Table 3.8

For additional information, you may access the following links:

Structure and Bonding: https://www.youtube.com/watch?v=cpWHgKgKxGk
Covalent Bonding : https://www.youtube.com/watch?v=5I_1jRGSR9E
PolaR and Nonpolar Molecules: https://www.youtube.com/watch?v=PVL24HAesnc
Polarity, Resonance, Electron Pushing
https://www.youtube.com/watch?v=r83xGgfkxa8&list=RDCMUCX6b17PVsYBQ0ip5g
yeme-Q&index=17

Thank you for candidly reading the content and answering the
practice exercises. Now you had just learned the basic concepts of
structure and bonding of molecules, kindly proceed to the learning
activities. If you have questions regarding the activity, you may email
me at [email protected] or send me a message

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 19

Activity 1
Direction: Using the VSEPR Theory, draw a three-dimensional representation of the
compounds, then determine its total valence electrons, no. of bonded atoms no. of lone pairs,
molecular geometry, electron geometry , hybridization and formal charges. Write your answers
by completing the table below.

Draft. Not Intended for Publication. For Classroom Use Only.

Compound Lewis structure Total Formal No. of No. of lone Hybridization Molecular Electron
Valence charges bonded pairs geometry Geometry
Electrons Atoms
ORGANIC CHEMISTRY 20

1. N2H4

2. HOOH

3. CH2CL2

Draft. Not Intended for Publication. For Classroom Use Only.

 ORGANIC CHEMISTRY 21

4. C2H4

5. HONO

6. HCCCH3

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 22

Activity 2 Simulation

Direction: Explore the Model screen of the simulation using this link
https://phet.colorado.edu/sims/html/molecule-shapes/latest/molecule-shapes_en.html .
As you explore Model 1, answer the following questions.

1. How does adding an atom affect the position of existing atoms or lone pairs.

_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________

2. How is adding a lone pair affect the position of existing atoms and lone pairs?

_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________

3. Is the effect of adding bonded atoms and lone pairs to the central atom similar?
Explain why this could be the case.

_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________

4. How do the electrons in bonds (bonding domains differ from lone pairs? (non-
bonding domains)

_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________

5. How does the bonding of atoms affect the properties of organic compounds?

_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________
_________________________________________________________________________

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 23

Activity 3 Build a Molecular Model

Directions:

1. Gather at least 10 sources of organic compounds available at home or within your

locality. (Food (fruits or vegies, LPG for cooking, cosmetics, crops etc.)
2. Research and determine (1) simple organic compound present in each source.
3. Among the 10 organic compounds you identified, choose one and then create a
molecular model of your chosen compound using any indigenous materials.
In constructing a molecular model, consider the following;
a. Atoms. You should distinguish between different types of atoms in your molecule.
The sizes of the balls in your model should correspond to the relative sizes (covalent
radii) of the atoms. For example, if you have 3 H atoms and one N atom, the N
should be larger than the 3 H’s and the 3 H’s should all be of equal size. You may
also want to use different colors for different atoms.
4. Take a photo of yourself while constructing the model.
5. Include a description of the organic compound (model) you created. The description
must have the following:
a. Physical Properties
 Describe the physical state of a compound at room temperature (solid, liquid,
gas) and the melting point (°C). The other physical properties you choose will
depend on your compound (color, boiling point, solubility, etc.).
Chemical Formula:
b. Molecular Geometry
 Molecular Shape (e.g. trigonal planar). State the shape of your molecule. Use
the concepts behind VSEPR Theory to briefly explain why your molecule has
the specified shape. ♦ Bond Angles. State the bond angle(s) according to the
VSEPR Theory.
 Bond Angles. State the bond angle(s) according to the VSEPR Theory.
c. General Information.
 History. A brief history describing the data and circumstances of the
molecule’s discovery, who discovered it, the discovery date and other
pertinent information.
 Manufacturing/Extraction and Purification. A complete description of how the
molecule is extracted and/or manufactured. Also include a description of the
purifications method.
 Uses. Describe the different uses of the molecule. Include products in which
the product is found, and the effects the molecule has on humans and other
living organisms.
d. References
6. Make a compilation of this activity. Compilation must have the following:
a. Title of the Compilation (1st page)
b. Contents (2nd- 10th page)
c. Discussion (11th page)
On the discussion page or section you have to answer the following questions.
1. How do you feel while doing the activity?
2. What were the challenges you encountered while constructing a molecular model?
3. What are the implications of understanding common organic compounds in
agriculture?

Note: Create only one molecular model. For the remaining 9 sources, just a
photo of yourself while using it and the Lewis structure of the compound.
See attached Compilation Requirement sample.

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 24

I. Consider the structure of Vitamin E shown below, which is found most

abundantly in what germ oil, sunflower, and safflower oils:

a. Identify the various types of geometries present in each central atom using
VSEPR theory
b. Determine the various relative bond angles associated with each central
atom usig VSEPR theory.
c. Which is the most polar bond in Vitamin E?
d. Would you predict Vitamin E to be polar or nonpolar?

II. Lewis Structures

Direction: Propose skeletal structures for compounds that satisfy the following
molecular formulas. There is more than one possibility in each case.
(a) C5H12
(b) C2H7N
(c) C3H6O
(d) C4H9Cl

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 26

Carey, F. A. (2008). Organic Chemistry (7th ed.). McGraw-Hill Education.

Chang, R. (2010). Chemistry (10th ed.). McGraw-Hill Education.

Compound Interest. (2014, April 11). A Brief Guide to Types of Organic Chemistry Formulae
[Photograph]. Compoundchem.Com. https://www.compoundchem.com/2014/04/11/a-
brief-guide-to-types-of-organic-chemistry-formula/

Brown, T. E., LeMay, E. H., Bursten, B. E., Murphy, C., & Woodward, P. (2011). Chemistry: The
Central Science (12th Edition) (12th ed.). Prentice Hall.

Brown, W. H., Foote, C. S., Iverson, B. L., & Novak, B. M. (2012). Organic Chemistry (6th ed.).
Cengage Learning.

Edward J. Neth (University of Connecticut), Paul Flowers (University of North Carolina at

Pembroke), Klaus Theopold (University of Delaware), Richard Langley (Stephen F.
Austin State University), & Robinson, W. R. (2016). Chemistry: Atoms First by OpenStax
(hardcover version, full color) (1st ed.). XanEdu Publishing Inc.

Manager, L. (2020, October 9). Science Laboratory Safety Symbols and Hazard Signs,
Meanings. Lab Manager. https://www.labmanager.com/lab-health-and-safety/science-
laboratory-safety-and-hazard-signs-meanings-6644

McMurry, J. (2011). Organic Chemistry with Biological Applications 2e. Mary Finch.

McMurry, J. E. (2010). Fundamentals of Organic Chemistry, 7th Edition (7th ed.). Cengage
Learning.

Petrucci, R. H., Herring, G. F., Madura, J. D., & Bissonnette, C. (2010b). General Chemistry:
Principles and Modern Applications (10th Edition) (10th ed.). Pearson Prentice Hall.

Zumdahl, S. S., & Zumdahl, S. A. (21010). Chemistry (8th ed.). Charles Hartford.

Zumdahl, S. S., Zumdahl, S. L., & Decoste, D. J. (2007). World Of Chemistry (2nd ed.).
McDougal Littell.

3D Structure and Bonding: Crash Course Organic Chemistry #4. (2020, May 27). [Video].
YouTube. https://www.youtube.com/watch?v=cpWHgKgKxGk

GCSE Chemistry - Covalent Bonding #14. (2019, February 19). [Video]. YouTube.
https://www.youtube.com/watch?v=5I_1jRGSR9E

Polar & Non-Polar Molecules: Crash Course Chemistry #23. (2013, July 23). [Video]. YouTube.
https://www.youtube.com/watch?v=PVL24HAesnc

Polarity, Resonance, and Electron Pushing: Crash Course Organic Chemistry #10. (2020,
August 19). [Video]. YouTube.
https://www.youtube.com/watch?v=r83xGgfkxa8&list=RDCMUCX6b17PVsYBQ0ip5gye
me-Q&index=17

Draft. Not Intended for Publication. For Classroom Use Only.

ORGANIC CHEMISTRY 27

Draft. Not Intended for Publication. For Classroom Use Only.