Organic Chemistry C02 Engr. Esmael O.

Larubis, MCHEM
Determining Formal Charge and Resonance Structures

Formal Charge (FC) is a method used to estimate the electron density at an atom in a
molecule. Using this method assumes that all bonds are covalent which means all
electrons are shared equally .

Procedure
1. Draw Lewis structure(s)
2. Determine the valence electrons of an atom (V)
3. Count the number of Non-bonding electrons in an atom. Each lone pair has two
non-bonding electrons. (N)
4. Count the number of Bonding electrons in an atom. Each line has two electrons.
(B)
5. Solve for the Formal Charge, FC

Example:

Part I. Determine the FC on each atom in the following compounds

a. water

H O
Valence
1 …. (Group IA) 6….. (Group VIA)
electrons, V
Nonbonding
0 …..(no lone pairs) 4…… (has 2 lone pairs)
electron, N
Bonding
2 …..(because of one bond) 4…….(because of two bonds)
electrons, B
Formal
FC= 1- 0 - (2/2) = 0 FC= 6 – 4 – (4/2) = 0
Charge, FC
Total FC 0

There is no FC on any atom in the molecule

Page 1 of 4
Organic Chemistry C02 Engr. Esmael O. Larubis, MCHEM
Determining Formal Charge and Resonance Structures

b. hydronium ion

Each H O
Valence
1 …. (Group IA) 6….. (Group VIA)
electrons, V
F
Nonbonding
C 0 …..(no lone pairs) 2…… (has 1 lone pairs)
electron, N
Bonding
o 2 …..(because of one bond) 6…….(because of three bonds)
electrons, B
f
Formal
FC= 1- 0 - (2/2) = 0 FC= 6 – 2 – (6/2) = +1
Charge, FC
+ FC
Total +1
1

The O atom has a +1 FC, thus the overall structure will carry a +1 FC.

c. borohydride ion

Each H B
Valence
1 …. (Group IA) 3….. (Group IIIA)
electrons, V
Nonbonding
0 …..(no lone pairs) 0…… (has no lone pairs)
electron, N
Bonding
2 …..(because of one bond) 8…….(because of four bonds)
electrons, B
Formal
d. f FC FC= 1- 0 - (2/2) = 0 FC= 3– 0 – (8/2) = -1
Charge,
o
Total FC -1
r

Page 2 of 4
 Organic Chemistry C02 Engr. Esmael O. Larubis, MCHEM
Determining Formal Charge and Resonance Structures

d. Formic acid (HCOOH)

For Structure A

Each H O1 O2
Valence
1 …. (Group IA) 6….. (Group VIA) 6….. (Group VIA)
electrons, V
Nonbonding 0 …..(no lone
4…… (has 2 lone pairs) 4…… (has 2 lone pairs)
electron, N pairs)
Bonding 2 …..(because of 4….(because of double
4….(because of 2 bonds)
electrons, B one bond) bond)
Formal FC= 1- 0 - (2/2) =
FC= 6 – 4 – (4/2) = 0 FC= 6 – 4 – (4/2) = 0
Charge, FC 0
Total FC 0

For Structure B

Each H O1 O2
Valence
1 …. (Group IA) 6….. (Group VIA) 6….. (Group VIA)
electrons, V
Nonbonding 0 …..(no lone
6…… (has 3 lone pairs) 2…… (has 1 lone pairs)
electron, N pairs)
Bonding 2 …..(because of
2….(because of one bond) 6….(because of 3 bonds)
electrons, B one bond)
Formal FC= 1- 0 - (2/2) =
FC= 6 – 6 – (2/2) = -1 FC= 6 – 2 – (6/2) = +1
Charge, FC 0
Total FC 0

Structures A and B are resonance structures, which is caused by the

delocalization of electrons from the double bond (pi-electrons). The best structure among
all resonance structures is the one with zero formal charges in all component atoms.

Page 3 of 4
Organic Chemistry C02 Engr. Esmael O. Larubis, MCHEM
Determining Formal Charge and Resonance Structures
Here are the basis of selection of the best representative example, usually called as
plausible structure:

Rank 1: Has zero formal charges in all component atoms.

Rank 2: Has the least magnitude of formal charges in component atoms, with the + sign
in an electropositive atom and a – sign in an electronegative atom.

Rank 3: Has large magnitude of formal charges in component atoms, with the + sign in
an electropositive atom and a – sign in an electronegative atom.

Rank 4: Has negative charge in an electropositive atom or has a positive charge in an

electronegative atom.

Thus, in the problem above, the best representative chemical structure of formic acid is
Structure A.

Part II. Given the following resonance structures of SO3, which is the MOST
PLAUSIBLE or ACCEPTABLE.

Based from the ranking above, from the least to the most plausible, the order is:

Structure A < Structure B < Structure C < Structure D

Structure D is the MOST plausible because it has zero formal charge in every component
atom. Structure C follows because it has lesser magnitude of charges than the other two
structures. The S in Structure C carries 1+ formal charge while Structure B and A carry
2+ and 3+, respectively.

Page 4 of 4