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Determining Formal Charge - KEY
Determining Formal Charge - KEY
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).
Procedureuuu
1. Draw Lewis structure(s)
2. Count the number of electrons around each atom (all lone pairs and the bonding
electrons) in the structure.
3. Subtract the number of electipiiiiiiiiuurons 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
O
6
6
e- in
1
(2 lone pair + the
structure
bonding e-)
FC
0
0
There is no FC on any atom in the molecule
# valence e-
Hs
1
b. hydronium ion
O
# valence e6
5
e- in
1
(1 lone pair + the
structure
bonding e-)
FC
0
+1
FC of +1 on O atom
c. borohydride ion
Page 1 of 4
CHEM 109A
CLAS
Determining Formal Charge - KEY
Hs
1
B
# valence e3
e- in
4
1
structure
( the bonding e-)
FC
0
-1
FC of -1 on B atom
d. formic acid (HCOOH)
Structure A
Hs
C
O1
O2
# valence e1
4
6
6
e- in
1
4
6
6
structure
FC
0
0
0
0
Structure B
Hs
C
O1
O2
# valence e1
4
6
6
e- in
1
4
7
6
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
Page 2 of 4
CHEM 109A
CLAS
Determining Formal Charge - KEY
Structure A
Hs
Cs
N
O1
O2
# valence e1
4
5
6
6
e- in
1
4
4
6
7
structure
FC
0
0
+1
0
-1
Structure B
Hs
Cs
N
O1
O2
# valence e1
4
5
6
6
e- in
1
4
4
7
6
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
Nitrogen
CH4
2 bonds
1 lone
pair (lp)
NH3
3 bonds
1 lp
4 bonds
0
Oxygen
CH2CH2
N2H2
CHCH
N2
carbene
(sextet = very
unstable)
1 bond
2 lp
2 bonds
2 lp
H2O
Fluorine
1 bond
3 lp
HF
H2CO
formaldehyde
3 lp
nitrene
(sextet = very
unstable)
(sextet = very
unstable)
Page 3 of 4
CHEM 109A
CLAS
Determining Formal Charge - KEY
3 bonds
CH3+
methyl cation
4 bonds
(sextet = very
unstable, but can be
stabilized by
hyperconjugation)
+1
5 bonds
CH5+
2 bonds
1 lp
NH4
ammonium
ion
3 bonds
1 lp
H3O
hydroiunium
ion
2 bonds
2 lp
3 lp
NH2+
(sextet = very
unstable)
F+
fluorenium
ion
(sextet = very
unstable)
2 bonds
1 lp
+2
H2F+
fluoronium
ion
OH2+2
(sextet = very
unstable)
-1
3 bonds
1 lp
CH3methyl anion
2 bonds
2 lp
1 bond
3 lp
NH2
4 lp
Ffluoride ion
HOhydroxide ion
Page 4 of 4