Polarity, Formal
Charge, and
Resonance
Flash Review
CHEM 371 Polarity
H
H
δ+
δ-
δ+
δ-
δ+
δ-
H
S
H
O
H
F
Covalent Bond
Polar Covalent Bond
Increasing Electronegativity Difference
Tetrahedral
Trigonal
Pyramid
Bent
Methane
Ammonia
Water
Non-Polar
Polar
Polar Non-Polar
Polar
Bond dipoles are equivalent and
cancel out
Bond dipoles are inequivalent
and do not cancel out
2
Linear
Linear
Trigonal
Planar
Trigonal
Planar
3
4
Tetrahedral
Tetrahedral
Trigonal
Bipyramidal
Trigonal
Bipyramidal
Octahedral
Octahedral
5
6 Polarity
Number of Lone Pairs
0
Non-Polar
2
Polar
Linear
1
Trigonal
Planar
Bent
2
Tetrahedral
Trigonal
Pyramid
Bent
3
Trigonal
Bipyramidal
Seesaw
T-Shaped
Linear
4
Octahedral
Square
Pyramidal
Square
Planar
T-Shaped
Linear
Steric Number
3
4
5
6 Calculating Formal Charge
# of electrons
in free atom
Formal Charge =
# of electrons
# of electrons
=
assigned in molecule from lone pairs
–
# of electrons
assigned in molecule
+ ½
# of electrons
shared in bonds
F.C. (O) = 6 – (6 + ½ (2))
F.C. (O) = -1
2 electrons
shared in bonds
6 electrons
from lone pairs
F.C. (S) = 6 – (0 + ½ (8))
F.C. (S) = +2
8 electrons
shared in bonds
0 electrons
from lone pairs
-1
-1
+2
-1
Sum of formal charges agrees with
overall charge
Large Absolute Formal Charge
-1 Calculating Formal Charge
# of electrons
in free atom
Formal Charge =
# of electrons
# of electrons
=
assigned in molecule from lone pairs
–
# of electrons
assigned in molecule
+ ½
# of electrons
shared in bonds
4 electrons
from lone pairs
2 electrons
shared in bonds
F.C. (O1) = 6 – (6 + ½ (2))
F.C. (O1) = -1
F.C. (O2) = 6 – (4 + ½ (4))
1
4 electrons
shared in bonds
F.C. (O2) = 0
2
4 electrons
from lone pairs
F.C. (S) = 6 – (0 + ½ (12))
F.C. (S) = 0
12 electrons
shared in bonds
0 electrons
from lone pairs
0
-1
0
-1
Sum of formal charges agrees with
overall charge
Reduced Formal Charge
0 Examples of Formal Charge
N = 5 – (2 + ½(6))
N=0
N = 5 – (2 + ½(6))
N=0
C = 4 – (2 + ½(6))
N = -1
N = 5 – (2 + ½(6))
N=0
C = 4 – (2 + ½(6))
N = -1
O = 6 – (2 + ½(6))
N = +1
O = 6 – (2 + ½(6))
N = +1
0
N
N
No Net
Dipole
C
0
-1
-1
N
C
0
Dipole
Towards C
O
0
N
+1
Dipole
Towards C
O
+1
Dipole
Towards N Resonance
Resonance Hybrids result from two or more Resonance Contributors.
Please note, electrons are not shifting back and forth, this is
importantly not an interconverting equilibrium.
2 Bonds
1 Bond
1 1/2 Bonds
-
-½
-½
Resonance Hybrid
Resonance Contributors
Nitrite
Ion
-
1 Bond
2 Bonds
-
1 1/3 Bonds
-2/3
-
-2/3
-
-
Carbonate
Ion
-2/3
-
2 Bonds
1 1/2 Bonds
1 Bond
Benzene