Republic of the Philippines

ISABELA STATE UNIVERSITY

Echague, Isabela

COLLEGE OF ARTS AND SCIENCES

Second Semester, School Year 2024-2025

Module 4
1. Title : Structure of Organic Compounds
2. Introduction
Covalent bonds hold atoms together by sharing of electrons. By this process, two atoms can mutually
complete their valence shells to become more stable. A molecule is a collection of atoms held together by
covalent bonds. For example, two hydrogen atoms, each with a single electron, can share their electrons to form
a covalent bond and create the diatomic hydrogen molecule. In this molecular state, both individual hydrogen
atoms attain the noble gas configuration of Helium.
3. Learning Outcome
At the end of the chapter the students are expected to:
a) draw Lewis structuresof organic compounds
b) write expanded, condensed and line-angle formulas of given molecules
c) determine the formal charge of a given the structure

4. Learning Content
Structure of Organic Compounds
Topic 1. Rules In Drawing Lewis Structural Formula
1. Use every atom in the molecular formula
2. Satisfy the valence (the no of covalent bond formed) of each atom:

X- halogens - F, Cl, Br, I

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3. Write each atom showing its valence e-s. Assign a valence to each.
4. Bond together continuously with single bonds all atoms with a valence greater than 1. In bonding 2 atoms in
a single bond, use 1 e- from each.
5. Attach the monovalent atoms to the polyvalent atom until all valences are satisfied.
6. If there are insufficient monovalent atoms, insert double or triple bonds between polyvalent atoms until all
valences are satisfied. Making cyclic structures may also be helpful.
Example:
Draw Lewis structure for the ff molecules

1. C3H8 2. C3H6

H H H

H- C- C=C-H

H
Carbon with double bond cyclic structure
Topic 2. Formal Charge
• Defined as the charge of the elements in a compound that is determined by its structure and the
distribution of the e-s
Formal Charge = [# valence electrons on neutral atom] – [(# lone electron pairs) + (no. Of bonds attached to the atom)]

▪ Valence electrons = corresponds to the group number of the element in the periodic table (for Group A
or representative elements).
▪ Lone Pairs = lone electrons sitting on the atom. A pair counts as two.

Formal Charge Calculation Shortcut

Formal Charge = Should – Has

Valence e-s - ( lone pairs and no. of bonds attached)

Example:
Calculate the formal charge of the ff
1.Hydroxide ion

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Let’s apply the shortcut:

Hydrogen should have 1 valence electron Hydrogen has one attached

electron H= 1–1=0

Neutral oxygen should have 6 valence electrons

Oxygen has 7 attached electrons as shown in red
Should – Has = 6 – 7 = -1
Hydroxide has a negative formal charge on the oxygen atom.
Net charge= total charges present in the structure

Net charge = 0 -1 = -1

What about Nitrate?

Due to resonance we would show three structures for nitrate. However we’ll just look at one

Now for formal charge

Nitrogen:

Should – Has = 5 – 4 = +1

Neutral nitrogen should have 5 valence electrons but our drawing only shows 4 attached.

Next we’ll look at the double bond oxygen.

Should – has = 6 – 6 = 0

The double bound oxygen is happy, stable, and has a net neutral charge.

Finally we have 2 single bound oxygen atoms with 3 lone pairs each. Since they are identical we have to
calculate just one to get the answer for both.
Should – Has = 6 – 7 = -1
Oxygen should have 6 valence electrons, each of the remaining oxygen atoms have 7 attached electrons for a net
negative charge.
Net Charge = +1 – 2 = - 1

Ex. 3. Try one more simple yet tricky example. Carbon monoxide.

Tricky because carbon monoxide is neutral, but don’t let this fool you. Many a hemoglobin has been fooled by
CO making it such a deadly poison.

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There are 2 types of molecules with a net zero charge
1. molecules with no formal charge
2. molecules with formal charge that cancel out for a net zero formal charge.

CO Lewis Structure and Formal Charge

Carbon should have 4, has 5 attached, formal charge = -1

Oxygen should have 6, has 5 attached, formal charge = +1
+1 and -1 cancel for a net formal charge of zero

Net charge = - 1 + 1 = 0

Topic 3. Resonance Structure

➢ Resonance structure is a symbolic nonexistent structure, differing only in position of e-s which
are used to describe an actual molecule or ion
➢ Shows how delocalization of pi (𝜋) e-s in the double bond can stabilize the molecule

Delocalization

➢ Defined as the movement of e-s within a molecule

➢ The greater the no of resonance structures the more stable is the molecule
➢ The “average” of the resonance forms used to describe a molecule or ion that cannot be
described by a single structure is called “resonance hybrid”

Resonance structures that are more important and have greater contribution are called major
contributor. The less important structures that also have less contribution are called minor contributor

Simple Rule In Determining And Interpreting Resonance Structures

1. Individual resonance forms are imaginary, not real. The real structure is a resonance hybrid, a composite of
the different resonance structures.
2. Resonance structures differ only in the placement of their pi and non-bonding electrons. When drawing
resonance structure, only pi electrons or unshared pairs may be shifted. They may only be shifted to adjacent
atoms or bond positions.
3. Different resonance structures of a substance don’t have to be equivalent. When 2 resonance structures are
non-equivalent, the actual structure of the resonance hybrid is closer to the more stable form than the less stable
form.
4. Resonance structures must be valid Lewis structures and obey rules of valency. Resonance structures that
carry more than an octet of electron are not contributor to the real structure.
5. The more important resonance structures have a acomplete octet for each atom with as little charge
separations as possible.
6. The resonance hybrid is more stable than any individual resonance structure.

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Example: O3

The double-headed arrow indicates that the actual electronic structure is an average of those shown, not that the
molecule oscillates between the two structures.

The Nitrate (NO3−) ion

Topic 4. Formula of Organic compounds

1. Molecular formula indicates the atomic composition of the compound ex C4H10
2. Structural formula shows the arrangement of atoms and bonds

Structural Formula
1. Expanded or Complete Structural Formula
• a structural formula that shows all valences and the bonds between atoms.

• For example: C4H10

2. Condensed Structural Formula

➢ the abbreviated or condensed forms of structural formula, which shows only specific bonds, other
bonds are left out as implied.
➢ For example: butane, C4H10
CH3-CH2-CH2-CH3
➢ Further condensation
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 CH3CH2CH2CH3
➢ Large structures with repeated structural subunits can be represented by grouping subunits within
parenthesis:
Ex. CH3-CH2-CH2-CH3

can be written as
CH3(CH2)2CH3

In cases where there is branching:

This structure may be written as:

CH3C(CH3)2CH2(CH2)2CH3

3. Line angle or Bond-Line Structures

Rules for drawing Line angle or bond-line structures:
a. Carbon atoms are not shown unless needed for special emphasis or clarity.
b. A carbon atom is assumed to be located at the end of each line segment or at intersection of two or more
lines with multiple lines.
c. Multiple bonds are shown with multiple lines.
d. Hydrogen atoms on other atoms such as oxygen and nitrogen are explicitly stated.
Example:

CH3(CH2)2CH3 is presented as

Each numbered corner represents the carbon

atom

Is represented as

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Example 1: Give the condensed and line angle formula for the following compound

Condensed structure: CH3CH2CH2CH3

Line angle structure:

Example 2.

Example 3
Give the complete structure structure for

(CH3)2CHCH(CH3)(CH2)3CH3 -

or

5. Teaching and Learning Activities

1. Draw Lewis structure for the following hydrocarbons

a. C7H16 b. C7H14

2. Draw the line-angle structure for the following compounds:

a. (CH3)2CHCH2CH2CH3 b. CH3CH(CH3)CH2(CH2)4CH3.

3. Write the condensed formula for each structure.

a.

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 b.

4. Calculate the formal charge of each element in the structure. What is the net charge of the structure.

.
a. b. c.

6. Recommended learning materials and resources for supplementary reading.

Formal Charges and Resonance | Chemistry for Majors
https://courses.lumenlearning.com/chemistryformajors/chapter/formal-char

7. Flexible Teaching Learning Modality (FTLM) adopted

1. Google meet, Google classroom
2. module, student activity

8. Assessment Task
Quiz/recitation

9. References (at least 3 references preferably copyrighted within the last 5 years, alphabetically
arranged)
1. John Olmsted, Gregory M. Williams Chemistry: The Molecular Science Jones & Bartlett Publishers
1996. 366-371
2. Francis A. Carey Advanced Organic Chemistry Springer 2001. 4-6
3. L. G. Wade, Jr. Whitman College Organic Chemistry Fifth Edition 2003

ISUE - CAS-DSM-016
Revision: 1
Effectivity: August 1, 2020

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