CHEM 109A

CLAS
Determining Formal Charge - KEY

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
(a decent assumption in organic chemistry).
Procedure
1. Draw Lewis structure(s)
2. Count the number of electrons around each atom (all lone pairs and the bonding
electrons) in thklmnlnne structure.
3. Subtract the number of electrons around each atom in the structure from the
number of valence electrons.
For example
1. Determine the FC on each atom in the following compounds
a. water

Hs

# valence e-

e- in structure

6
(2 lone pair + the bonding e-)

FC
0
There is no FC on any atom in the molecule

b. hydronium ion

, so should look like

Hs

# valence e-

e- in structure

5
(1 lone pair + the bonding e-)

+1

FC
FC of +1 on O atom
c. borohydride ion

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CHEM 109A

CLAS
Determining Formal Charge - KEY

, so should look like

Hs

# valence e-

e- in structure

4
( the bonding e-)

-1

FC
FC of -1 on B atom

d. formic acid (HCOOH)

Structure A

Hs

O1

O2

# valence e-

e- in structure

FC

Structure B

Hs

O1

O2

# valence e-

e- in structure

FC

0
0
-1
+1
Structure A has no FC & therefore is the more stable resonance
contributor.
FCs of Structure B balance each other out, so there is no net charge on
the molecule. The total (net) FC must be the same for all resonance
contributors.
e. nitrobenzene

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CHEM 109A

CLAS
Determining Formal Charge - KEY

Structure A

Hs

Cs

O1

O2

# valence e-

e- in
structure

FC

+1

-1

Structure B

Hs

Cs

O1

O2

# valence e-

e- in
structure

FC

0
0
+1
-1
0
FCs balance each other out, so there is no net charge on the molecule.
Both resonance contributors have the same amount of FC on the same
atoms so they contribute equally to the resonance hybrid (see Drawing
Resonance Structures Handout).

OR (instead of performing steps 2 & 3 above) you can learn to identify some
common bonding patterns and the associated FC.
Bonding Patterns & FC reproduced from an Aue handout. Most common patterns
are in bold font.
FC
on

Carbon
4 bonds
CH4

Nitrogen
3
bonds
1 lp

NH3

Oxygen
2
bonds
2 lp

H2O

Fluorine
1 bond
3 lp

HF

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CHEM 109A

CLAS
Determining Formal Charge - KEY

H2CO
formaldehy
de

N2H2

CH2CH2

CHCH

N2
3 lp

2 bonds
1 lone
pair (lp)

1 bond
2 lp
carbene

3 bonds

+1

(sextet = very
unstable, but can
be stabilized by
hyperconjugation
)

3
bonds
1 lp
4
bonds
NH4+
ammoniu
m ion

2 bonds
1 lp

5 bonds
CH5+

nitrene
(sextet = very
unstable)

(sextet = very
unstable)

CH3+
methyl
cation

(sextet = very
unstable)

2
bonds
H2F+
+
H3O
2 lp fluoroniu
hydroiuniu
m ion
m ion

3 lp

NH2

(sextet = very
unstable)

(sextet = very
unstable)

(exceeds octet =
very unstable)

+2

F+
fluoreniu
m ion

2 bonds
1 lp
OH2+2
(sextet = very
unstable)

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CHEM 109A

CLAS
Determining Formal Charge - KEY

-1

3 bonds
1 lp

CH3methyl
anion

2 bonds
2 lp

1 bond
3 lp
NH2-

HOhydroxide
ion

4 lp

Ffluoride
ion

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