PROBLEMS:

(Formal Charges)
4.1 Assign formal charges to each atom in the following structures. Show your work.

C = -1 C=0 H=0 C=0

O = +1 H=0 C=0 O = -1
N=0 O = +1
H=0
Solution:
Atom Formal Charge = no. of valence e - – (no. of non-bonding e - + ½ of no. of bonding e -)
a. Carbon Formal Charge = 4 – [ 2 + ½ (6)] = -1
Oxygen Formal Charge = 6 – [ 2 + ½ (6)] = +1
b. Carbon Formal Charge = 4 – [ 0 + ½ (8)] = 0
Hydrogen Formal Charge = 1 – [0 + ½ (2)] = 0
c. Hydrogen Formal Charge = 1 – [ 0 + ½ (2)] = 0
Carbon Formal Charge = 4 – [ 0 + ½ (8)] = 0
Nitrogen Formal Charge = 5 – [ 2 + ½ (6)] = 0
d. Carbon Formal Charge = 4 – [0 + ½ (8)] = 0
Oxygen (Single Bond) Formal Charge = 6 – [ 6 + ½ (2)] = -1
Oxygen (Double Bond) Formal Charge = 6 – [ 2 + ½ (6)] = +1
Hydrogen Formal Charge = 1 – [ 0 + ½ (2)] = 0
4.2 Choose the best structure based on formal charges. Show your work and explain it.

First Structure: Second Structure:

Carbon FC = 4 – [0 + ½ (8)] = 0
Oxygen (Single Bond) FC = 6– [6+½ (2)] = -1
Oxygen (Double Bond) FC =6– [2+½ (6)] = +1
(4)] = 0
Hydrogen FC = 1 – [ 0 + ½ (2)] = 0
Carbon FC = 4 – [0 + ½ (8)] = 0
Oxygen (Double Bond) FC =6– [4+½ (4)] = 0
Oxygen (Single Bond) FC =6– [4+½
Hydrogen FC = 1 – [ 0 + ½ (2)] = 0
 The second structure is the best resonance structure for the carboxyl group (COOH).
Even though both structures have a net formal charge of zero, the formal charges of both
oxygen of each structure are different. In which in the first structure, its oxygen with a
single bond has a formal charge of -1 and its other oxygen with a double bond has formal
charge of +1. While in the second structure, both oxygen atoms with single and double
bond has zero formal charge.

First Structure: Second Structure:

First Oxygen FC = 6 – [4 + ½ (4)] = 0 First Oxygen FC = 6 – [2 + ½ (6)] = +1
Second Oxygen FC = 6 – [4 + ½ (4)] = 0 Second Oxygen FC = 6 – [4 + ½ (6)] = -1
Hydrogen FC = 1 – [0 + ½ (2)] = 0 Hydrogen FC = 1 – [0 + ½ (2)] = 0

The first structure is the best resonance structure for hydrogen peroxide (H2O2). Among
the two resonance structures shown above, the first structure has the greatest number of
full octets. In the first structure, its two oxygen atoms have full octets. While in the
second structure, one oxygen atom has ten valence electrons whereas its other oxygen
atom has six valence electrons. And another reason is that in the first structure, all of
atoms’ formal charges are zero. While in the second structure, its two oxygen atoms have
a formal charge of +1 and -1, respectively.

First Structure: Second Structure:

Carbon (Single Bond) FC = 4– [0 + ½ (8)] = 0
Carbon (Double Bond) FC = 4– [0+½ (8)] = 0
Nitrogen FC = 5 – [2 + ½ (6)] = 0
Oxygen (Double Bond) FC =6– [4+½ (4)] = 0
Hydrogen FC = 1 – [ 0 + ½ (2)] = 0
Carbon (Single Bond) FC = 4– [0 + ½ (8)] = 0
Carbon (Double Bond) FC = 4– [0+½ (8)] = 0
Nitrogen FC = 5 – [0 + ½ (8)] = -3
Oxygen (Single Bond) FC =6– [6+½ (2)] = +1
Hydrogen FC = 1 – [ 0 + ½ (2)] = 0

The first structure is the best resonance structure for acetaldoxime acetamide
aminoacetaldehyde (C2H5NO). All of the atoms in the first structure are neutral. While in
the second structure, two of its atoms has a formal charge. In which its nitrogen atom has
a formal charge of -3 and its oxygen atom has +1 for its formal charge.
(Resonance Structures)
4.3 Write the required equivalent resonance structures for the following molecules and ions:
                  (a) O3:
O O O and O O O
   (b) CO3-2:
O O O

O C O , O C O and O C O

4.4 For each, draw the possible resonance structures that the molecule can have. Assign formal
charges in each and circle the most plausible structure for the molecule.
(a) OCN-:
O C N , O C N , O C N
(b) N2O: 
N N O , N N O , N N O

(c) SO42-:
O O O

O S O , O S O , O S O

O O O

O O O

O S O , O S O , O S O

O O O

O S O * I did not choose one most plausible resonance structure

 O but six resonance structures. Since they are all identical in
charge and there is no change in electronegativity
between

the two oxygen atoms.