LEWIS STRUCTURE

A Lewis Structure is a very simplified representation of the valence shell electrons in a molecule. It is
used to show how the electrons are arranged around individual atoms in a molecule. Electrons are
shown as "dots" or for bonding electrons as a line between the two atoms. The goal is to obtain the
"best" electron configuration, i.e. the octet rule and formal charges need to be satisfied.

Lewis structure does NOT attempt to explain the geometry of molecules, how the bonds form, or how
the electrons are shared between the atoms. It is the simplest and most limited theory on electronic
structure.

We will consider only the valence electrons when were dealing with Lewis structure. The numbers in
the periodic table are the valence electrons of that element. Observe the pattern with respect to its
arrangement in the periodic table. Elements in the same family (or column) has the same valence
electrons.

Valence electrons can be drawn as shown below.

Step 1: Find the Total Number of Valence Electrons

In this step, add up the total number of valence electrons from all the atoms in the molecule.This
should be the total number of electrons present in the molecule.

Example: CH2O (subscript indicates no. of atom of that element)

No. of atoms: No. of valence electrons per atom
C = 1 atom C = 4 electrons
H = 2 atoms H = 1 electron
O = 1 atom O = 6 electrons
Total No. of valence electrons
C = 1 atom x 4 electrons = 4
H = 2 atoms x 1 electron = 2
O = 1 atom x 6 electrons = 6
Total 12 electrons should be present in the molecule of CH2O

Step 2: Find the Number of Electrons Needed to Make the Atoms "Happy"
An atom is considered "happy" when its outer electron shell is filled. Elements up to period (or row)
four on the periodic table need eight electrons to fill their outer electron shell. This property is often
known as the "octet rule" (8 electrons). H and He only needs 2 electrons and does not follow the octet
rule.

Example: CH2O
No. of electrons per atom needed for it to be “happy”:
C = 8 electrons
H = 2 electrons
O = 8 electrons

Total No. of electrons needed to make atoms “happy”

C = 1 atom x 8 electrons = 8
H = 2 atoms x 2 electron = 4
O = 1 atom x 8 electrons = 8
Total 20 electrons

Step 3: Determine the Number of Bonds in the Molecule

Covalent bonds are formed when one electron from each atom forms an electron pair. (Covalent
bonds - sharing of electrons). Step 2 tells how many electrons are needed and Step 1 is how many
electrons you have. Subtracting the number in Step 1 from the number in Step 2 gives you the number
of electrons needed to complete the octets. Each bond formed requires two electrons, so the number
of bonds is half the number of electrons needed, or:
(Step 2 - Step 1) divide by 2

Example: CH2O
Step 2 = 20 electrons
Step 1 = 12 electrons
Difference is 8 electrons. Since a bond requires 2 electrons, we divide 8 electrons by 2 to give us 4
bonds. The molecule CH2O has 4 bonds.

(Step 2 only tells us how many are needed by the molecule for it to be “happy” and since the electrons from Step 1
are not enough to reach the amount of electrons in step 2, covalent bond or sharing of electrons are formed
between atoms to be “happy.” Step 3 tells us how many bonds could be formed for all atoms to be “happy.”)

Step 4: Choose a Central Atom

The central atom of a molecule is usually the least electronegative atom or the atom with the highest
valence. To find electronegativity, either rely on periodic table trends or consult a table that lists
electronegativity values. Electronegativity decreases moving down a group on the periodic table and
increases moving from left to right across a period. Hydrogen and halogen (F, Cl, Br family) atoms tend
to appear on the outside of the molecule and are rarely the central atom.

Example: CH2O, Carbon is the central atom. In our example we can assume the structure of the
molecule as shown below
H
C O
H

(Organic molecules mostly have C as central atom).

Step 5: Draw a Skeletal Structure
Connect the atoms to the central atom with a straight line representing a bond between the two atoms.
The central atom can have up to four other atoms connected to it.

Example: CH2O
H
C O
H

Each bond contains 2 electrons, so far we have placed 6 electrons in the molecule (3 bonds x 2
electrons). In step 1, the total number of electrons contributed by each atom is 12 electrons. 6
electrons are not yet accounted in the structure.

Step 6: Place Electrons Around Outside Atoms

Complete the octets around each of the outer atoms. If there are not enough electrons to complete the
octets, the skeletal structure from Step 5 is incorrect. Try a different arrangement. Initially, this may
require some trial and error. As you gain experience, it will become easier to predict skeletal
structures.

Example: CH2O
H
C O
H

Let us count the number of electrons around each atom.

C - 3 bonds are present around the atom. 3 bonds x 2 electrons = 6 electrons (does not follow octet
rule, it still needs 2 electrons for it to be happy)
H - 1 bond present per H atom. 1 bond x 2 electrons = 2 electrons. (since the maximum for H is 2
electrons, it is now happy)
O - 1 bond present. 1 bonds x 2 electrons = 2 electrons (does not follow octet rule, it still needs 6
electrons for it to be happy)

From Step 5, 6 electrons are not yet accounted in the molecule and O needs 6 more electrons for it to
follow the octet rule. We can put 6 electrons around O. Since these electrons are not involved in a
bond, we place them as LONE PAIRS.

Let us count again the number of electrons around each atom.

C - 3 bonds are present around the atom. 3 bonds x 2 electrons = 6 electrons (does not follow octet
rule, it still needs 2 electrons for it to be happy)
H - 1 bond present. 1 bond x 2 electrons = 2 electrons. (since the maximum for H is 2 electrons, it is
now happy)
O - 1 bond present. 1 bond x 2 electrons = 2 electrons
3 lone pairs. 3 lone pairs x 2 electrons = 6 electrons
Total of 8 electrons around O (follows octet rule, it is now happy)
Step 7: Place Remaining Electrons Around the Central Atom
Complete the octet for the central atom with the remaining electrons. If there are any bonds left over
from Step 3, create double bonds with lone pairs on outside atoms. A double bond is represented by
two solid lines drawn between a pair of atoms. If there are more than eight electrons on the central
atom and the atom is not one of the exceptions to the octet rule, the number of valence atoms in Step 1
may have been counted incorrectly. This will complete the Lewis dot structure for the molecule.

Example: CH2O
Since C has not yet followed the octet rule, we can convert one of the lone pairs from the O and
convert it to a bond so the electrons can be shared by C and O. And recall from Step 3 that we have
computed 4 bonds for this molecule.

Let us check our Lewis structure

Let us count again the number of electrons around each atom.
C - 4 bonds are present around the atom. 4 bonds x 2 electrons = 8 electrons (follows octet rule, it is
now happy)
H - 1 bond present. 1 bond x 2 electrons = 2 electrons. (since the maximum for H is 2 electrons, it is
now happy).
O - 1 bond present. 2 bonds x 2 electrons = 4 electrons
2 lone pairs. 2 lone pairs x 2 electrons = 4 electrons
Total of 8 electrons around O (follows octet rule, it is now happy)

From step 1, the molecule can only have 12 electrons

Bonding/shared electrons = 4 bonds x 2 electrons = 8 electrons
Lone pairs = 2 lone pairs x 2 electrons = 4 electrons
Total of 12 electrons

This is the correct Lewis structure for CH2O or formaldehyde.

Another example
ClNO

Step 1
No. of atoms: No. of valence electrons per atom
Cl = 1 atom Cl = 7 electrons
N = 1 atom N = 5 electrons
O = 1 atom O = 6 electrons

Total No. of valence electrons

Cl = 1 atom x 7 electrons = 7
N = 1 atom x 5 electrons = 5
O = 1 atom x 6 electrons = 6
Total 18 electrons should be present in the molecule of ClNO

Step 2
No. of electrons per atom needed for it to be “happy”:
Cl = 8 electrons
N = 8 electrons
O = 8 electrons

Total No. of electrons needed to make atoms “happy”

C = 1 atom x 8 electrons = 8
H = 1 atom x 8 electrons = 8
O = 1 atom x 8 electrons = 8
Total 24 electrons
Step 3
From Step 2 = 24 electrons
From Step 1 = 18 electrons
Difference is 6 electrons or 3 bonds.

Step 4
Central atom is N since it is the least electronegative. (Cl cannot be a central atom because it can only
form 1 bond. The valence electrons of Cl is 7, it only needs 1 more electron to follow the octet rule. Cl
can only form 1 bond. N is less electronegative than O)

Step 5
Cl N O

Step 6 (Put lone pairs on outside atoms to follow the octet rule)

Let us count the number of electrons around each atom.

Cl - 1 bond x 2 electrons = 2 electrons
3 lone pairs x 2 electrons = 6 electrons
Total = 8 electrons
O - 1 bond x 2 electrons = 2 electrons
3 lone pairs x 2 electrons = 6 electrons
Total = 8 electrons

Step 7
Before we proceed to the central atom, let us first count how many electrons are present in our
structure

Bonding/shared electrons = 2 bonds x 2 electrons = 4 electrons

Lone pairs = 6 lone pairs x 2 electrons = 12 electrons
Total of 16 electrons, the total number of electrons for this molecule is 18 electrons (from step 1). 2
electrons not yet accounted in the structure.

Let us count the electrons in our central atom

N = 2 bonds x 2 electrons = 4 electrons (needs 4 more electrons to follow the octet rule)
Step 3, we can form 3 bonds. Then one of the lone pairs in O can be shared between N and O. Cl
cannot have more than one bond
2 electrons that we have not yet accounted will be drawn as lone pair for N.

Let us check our Lewis structure

Let us count again the number of electrons around each atom.
Cl - 1 bond x 2 electrons = 2 electrons
3 lone pairs x 2 electrons = 6 electrons
Total = 8 electrons (follows octet rule)
N - 3 bonds x 2 electrons = 6 electrons
1 lone pair x 2 electrons = 2 electrons
Total = 8 electrons (follows octet rule)
O - 1 bond x 2 electrons = 2 electrons
3 lone pairs x 2 electrons = 6 electrons
Total = 8 electrons (follows octet rule)
From step 1, the molecule can only have 18 electrons
Bonding/shared electrons = 3 bonds x 2 electrons = 6 electrons
Lone pairs = 6 lone pairs x 2 electrons = 12 electrons
Total of 18 electrons

This is the correct Lewis structure for ClNO.

Common Bonding Patterns for Atoms in Organic Compounds

Practice the following problems. (from the link I have previously shared in our gc)

ELECTRONEGATIVITY
 Electronegativity is an atom's tendency to attract electrons to itself in a chemical bond.
 The greater the difference between atom electronegativity values, the more polar the chemical
bond formed between them.

Which atoms are more electronegative? (look at the arrows in the periodic table)
F vs O Ans F
C vs N Ans N
Cl vs Br Ans Cl
P vs N Ans N
O vs P Ans O
B vs C Ans C

Top electronegative elements are nitrogen, oxygen, and fluorine or N, O, F

Fluorine is the most electronegative element
Francium is the least electronegative element
BOND LENGTH
Bond length is defined as the distance between the centers of two covalently bonded atoms.
Generally, the length of the bond between two atoms is approximately the sum of the covalent radii of
the two atoms. The smaller the atoms, the shorter the bond length. Bond length increases in the
following order: triple bond < double bond < single bond.

(Atomic radius and electronegativity trend in the periodic table is inversely proportional)

Which has longer bond length

Single bonds:
H-F vs H-Cl Ans. H-Cl (Cl is larger than F)
C-Br vs C-I Ans C-I (I is larger than Br)
C-N vs C-O Ans C-N (N is larger than O)
H-H vs C-H Ans C-H (C is larger than H)

For multiple bonds:

C=C vs C-C Ans C-C (single bond is longer than double bond)
C=C vs C=C Ans C=C (double bond is longer than triple bond)

BOND STRENGTH
Stable molecules exist because covalent bonds hold the atoms together. We measure the strength of a
covalent bond by the energy required to break it, that is, the energy necessary to separate the bonded
atoms. Separating any pair of bonded atoms requires energy. The stronger a bond, the greater the
energy required to break it.

Bond Length is inversely related to Bond Strength

Which has stronger bond

Single bonds:
H-F vs H-Cl Ans. H-F
C-Br vs C-I Ans C-Br
C-N vs C-O Ans C-O
H-H vs C-H Ans H-H

For multiple bonds:

C=C vs C-C Ans C=C
C=C vs C=C Ans C=C
BOND ANGLE and GEOMETRY

Valence-shell electron-pair repulsion (VSEPR) model (pronounced “vesper”), which can be used to
predict the shapes of many molecules and polyatomic ions. The premise of the VSEPR theory is that
electron pairs located in bonds and lone pairs repel each other and will therefore adopt the geometry
that places electron pairs as far apart from each other as possible.

Let’s take for example methane or CH4, we usually draw methane as shown below where the angles
between the 2 H are 90o

H C H

But when we look at the 3D structure of this molecule, it is actually

where the geometry is tetrahedral and the angles between 2 H is 109.5o. The electrons in the H will
repel the electrons in the other H. This then results to the H maximizing the space around C just to stay
away from the other H. It is important that we view the molecules on how it actually is in a 3D
perspective. Since it is difficult to draw a 3D molecule in a piece of paper, we use the wedge and
broken lines to show bonds coming forward out of the paper and bonds going backward out of the
paper, respectively. The lines show bonds that are along the plane of the paper.

DRAWING ORGANIC STRUCTURE

A. LINE BOND STRUCTURE
(refer to page 8 in the module)

Because organic molecules often contain many atoms, we need shorthand methods to simplify their
structures. The two main types of shorthand representations used for organic compounds are
condensed structures and skeletal structures.

B. CONDENSED STRUCTURE
(refer to page 7 in the module for the instructions on how to convert to condensed structure)

We first look at the groups/substituents attached to C

1st C from the left, it is attached to 3 H and to 2nd C.
So we write that as CH3
2nd C, attached to 2 H, 1st C and 3rd C
So we write that as CH2
3rd C, attached to 2 H, 3rd C and 4th C.
So we write that as CH2
4th C, attached to 3H and 3rd C.
So we write that as CH3

we then connect the carbon atoms

1st C (CH3) is attached to 2nd C (CH2).
So we write that as CH3CH2
2nd C is attached to 3rd C (CH2).
So we write that as CH3CH2CH2
3rd C is attached to 4th C (CH3).
So we write that as CH3CH2CH2CH3

The condensed structure may be further simplified by using parentheses around like groups. Two
CH2 groups bonded together become (CH2)2. Two CH3 groups bonded to the same carbon become
(CH3)2C

You can only simplify if they are the same set of atoms and attached to the same C
Example a both have the same set of atoms (1 C, 3H) and attached to the same C. This may be
simplified to (CH3)2, which shows there are 2 CH3 attached to the same C. If they are not on the
same C, you cannot simplify them.

You can also simplify if they are the same set of atoms and located next to each other
Example b both have CH2 on 2nd and 3rd C. Since they are next to each other, this can be
simplified to (CH2)2, which means there are 2 CH2 between 1st and 4th C.

C. SKELETAL STRUCTURE
Skeletal structures are used for organic compounds containing both rings and chains of atoms. Three
important rules are used in drawing them.
1. Assume there is a carbon atom at the junction of any two lines or at the end of any line. The lines
are the bonds between 2 atoms. Carbon atoms are not shown in a skeletal structure. The lines in the
example below are bonds between 2 C atoms.

C
a) has C atoms and can be viewed as C C
b) has C atoms and can be viewed as C C
2. Assume there are enough hydrogens around each carbon to give it four bonds. Hydrogen attached
to carbon will not be shown in the skeletal structure.

We will use the same set of example in No. 1 and convert it to its line bond structure (tandaan: apat
dapat sa Carbon)

C
a) or C C

The 1st C (blue circle) has one line, which means it has one bond. C should have 4 bonds around it, so
the number of H attached to the 1st C should be 3.
The 2nd C (orange rectangle) has two lines, which means it has 2 bonds. C should have 4 bonds
around it, so the number of H attached to the 2nd C should be 2.
The 3rd C (green triangle) has one line, which means it has one bond. C should have 4 bonds around it,
so the number of H attached to the 3rd C should be 3.
H H H
H C C C H

The line bond structure for the molecule is H H H

b) or C C

The 1st C has one line, which means it has one bond so the number of H attached to the 1st C should
be 3.
The 2nd C has one line, which means it has one bond so the number of H attached to the 2nd C should
also be 3.
H H
H C C H

The line bond structure for the molecule is H H

3. Draw in all heteroatoms (N, O, F, Cl, etc) and the hydrogens directly bonded to them.

Example:
Convert the molecule to its skeletal structure:

1) Ans

2) Ans
Sample conversion of line bond structure to its condensed and skeletal structure.

Isomers
(will get back on this topic in chapter 4 when we discuss stereochemistry)

Index of hydrogen deficiency or degree of unsaturation

(will get back on this topic when we discuss alkenes)
Answers to Sample Problem in Lewis Structure

This lecture notes were copied/compiled from the following references:

https0://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_Modules_(Phys
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https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_202_-_General_Chemistry_II/Unit_4%3A_
Lewis_Structures/4.2%3A_Lewis_Structures/4.2%3A_Lewis_Structures_(Problems)

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https://opentextbc.ca/chemistry/chapter/7-5-strengths-of-ionic-and-covalent-bonds/#:~:text=Generally%2C%20as%20the%20b
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https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_202_-_General_Chemistry_II/Unit_4%3A_Lewis_Structures/4.2%3A_Lewis_Structur
es/4.2%3A_Lewis_Structures_(Problems)

https://www.google.com/search?q=electronegativity+periodic+table+trend&safe=strict&sxsrf=ALeKk03sb6gMaNXKnKOjw70ZBRdGg0r0jA:1602946054006&tbm=isch&so
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hUkJaYKHe_2DSkQ9QF6BAgJEFM&biw=1366&bih=635#imgrc=yAdZnPEjP35exM

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ch&source=iu&ictx=1&fir=L9Y-OqFv5qNXIM%252CWKnS4_u5z7a_RM%252C_&vet=1&usg=AI4_-kTOQ4M2lw1hsvxneHg86PpVrRpXyg&sa=X&ved=2ahUKEwiC9ay09
LvsAhXGGKYKHcDODM4Q9QF6BAgREEU#imgrc=mjNY99CxkaCC1M

https://pressbooks.bccampus.ca/chem1114langaracollege/chapter/9-1-condensed-structure-and-line-structure-cw/

(Due to limitation in time, this lecture note was not reviewed and typographical error may be present)