TOPIC 5: Basic Concepts of Chemical Bonding
L24: Lewis Structures
- Octet Rule and Exceptions
-Resonance and multiple bonds
1
Lewis Dot Structures
• A molecular formula shows the number and identity of all the atoms in a compound,
but not how atoms are bonded to each other, eg NO -
3
• A Lewis dot structure shows the connectivity between atoms, as well as the
location of all bonding and nonbonding valence electrons.
HOW TO Draw the “best” Lewis Structure –Six (6) Steps
5
HOW TO Draw the “best” Lewis Structure –Using NO3- to illustrate
Step [1] Determine the total number of valence electrons in the molecule
N: 1s22s22p3
O: 1s22s22p4
Step [2] (i) Draw a skeleton for the molecule which connects all atoms using only
single bonds.
(ii) The least electronegative atom is placed at the centre.
(iii) The central atom should be the atom with the most available sites for
bonding
3
HOW TO Draw the “best” Lewis Structure –Using NO3- to illustrate
• Of the 24 valence electrons in NO3-, 6 are required for the single bonds.
Step [3] • The remaining 18 electrons are placed on the terminal O atoms to fulfil their
octets
Step [4] • Check to see if there are any remaining electrons. If so, place them on the
central metal. In this case there are none, all 24 are used up!
4
HOW TO Draw the “best” Lewis Structure –Using NO3- to illustrate
• Are the octets of all the atoms filled?
• If not, then fill the remaining octets by making multiple bonds
Step [5]
• Move a lone pair of electrons into a bonding pair of electrons that is shared with
the atom that is electron deficient.
5
HOW TO Draw the “best” Lewis Structure –Using NO3- to illustrate
Step [6]
• Formal Charge of 1st single bonded Oxygen
= 6 - 6 - ½(2) = -1
• Formal Charge of 2nd single bonded Oxygen
= 6 - 6 - ½(2) = -1
• Formal Charge of double bonded Oxygen
= 6 - 4 - ½(4) = 0
• Formal Charge of Nitrogen
= 5 - 0 - ½(8) = 1
• Total FC of the whole molecule = (-1) + (-1) + 0 + (+1) = -1 6
IMPORTANT
• No Lewis diagram is complete without formal charges
• It is best to have a formal charge of 0 for as many of the atoms in a structure as
possible. This becomes the most stable Lewis dot structure
• Also, the most stable Lewis dot structure of any polyatomic species is the one
in which the negative charge is on the most electronegative atoms
• Lewis dot structures are used to examine mechanisms of reactions, so knowing
which part/s of a molecule are electron deficient (+) and which are electron rich (-) is
very useful.
7
HoWo:
Draw Lewis structures for the following molecules:
(i) Nitric acid, HNO3 (iii) Thionyl chloride, SOCl2
(ii) Sulfur trioxide, SO3 (iv) Sulfuryl chloride, SO2Cl2
Nitric acid
Sulfur trioxide Sulfuryl chloride
H attached to
the atom which
is electron rich.
Refer to F.C. 8
TOPIC 5: Basic Concepts of Chemical Bonding
L5.1: Recarp on Chemical bonds
- Polarity of Bonds
L5.2: Lewis Structures
- Octet Rule and Exceptions
-Resonance and multiple bonds
9
Exceptions to the Octet Rule
• Most of the common elements generally obey the octet rule.
• H is a notable exception, because it needs only 2 e − in bonding.
• Elements in group 3A (13) do not have enough valence e − to form an octet in a
neutral molecule : B: [1s2 ] 2s2 2p1
Example; boron in BF3 is electron-deficient
10
HOW TO Draw the “best” Lewis Structure –Using NO3- to illustrate
Step [5] • Are the octets of all the atoms filled?
• If not, then fill the remaining octets by making multiple bonds
• Move a lone pair of electrons into a bonding pair of electrons that is shared with
the atom that is electron deficient.
11
Exceptions to the Octet Rule
• Most of the common elements generally obey the octet rule.
• H is a notable exception, because it needs only 2 e − in bonding.
• Elements in group 3A (13) do not have enough valence e − to form an octet in a
neutral molecule : B: [1s2 ] 2s2 2p1
Example; boron in BF3 is electron-deficient
12
IMPORTANT
• No Lewis diagram is complete without formal charges
• It is best to have a formal charge of 0 for as many of the atoms in a structure as
possible. This becomes the most stable Lewis dot structure
• Also, the most stable Lewis dot structure of any polyatomic species is the one
in which the negative charge is on the most electronegative atoms
• Lewis diagrams are used to examine mechanisms of reactions, so knowing which
part/s of a molecule are electron deficient (+) and which are electron rich (-) is very
useful.
13
Exceptions to the Octet Rule
• Most of the common elements generally obey the octet rule.
• H is a notable exception, because it needs only 2 e − in bonding.
• Elements in group 3A (13) do not have enough valence e − to form an octet in a
neutral molecule : B: [1s2 ] 2s2 2p1
Example; boron in BF3 is electron-deficient
14
Exceptions to the Octet Rule
• Most of the common elements generally obey the octet rule.
• H is a notable exception, because it needs only 2 e − in bonding.
• Elements in group 3A (13) do not have enough valence e − to form an octet in a
neutral molecule.
Example; boron in BF3 is electron-deficient
• Expanded octet: elements in the third row have empty d orbitals available to
accommodate more electron pairs.
• Thus, elements such as P and S may have more than 8 e− around them.
15
Lewis Dot Structures and Expanded Octet
Notice that in sulfur trioxide and sulfuryl chloride, the central S atom has more than 4 electron
pairs., ie it has more than an octet of electrons!
Sulfur trioxide Sulfuryl chloride
18
Exceptions to the Octet Rule
• Most of the common elements generally obey the octet rule.
• H is a notable exception, because it needs only 2 e − in bonding.
• Elements in group 3A (13) do not have enough valence e − to form an octet in a
neutral molecule.
Example; boron in BF3 is electron-deficient
• Expanded octet: elements in the third row have empty d orbitals available to
accommodate more electron pairs.
• Not true for all…..Only true IF that the Lewis dot structure is stable….
IMPORTANT! Let us consider AlCl3
19
Aluminium E.C.
Al: [1s2 2s2 2p6 ]3s2 3p1 4s0 (3d0)
Al: [Ne] 3s2 3p1 4S0 (3d0)
Let us consider AlCl3
IMPORTANT
• No Lewis diagram is complete without formal charges
• It is best to have a formal charge of 0 for as many of the atoms in a structure as
possible. This becomes the most stable Lewis dot structure
• Also, the most stable Lewis dot structure of any polyatomic species is the one
in which the negative charge is on the most electronegative atoms
• Lewis diagrams are used to examine mechanisms of reactions, so knowing which
part/s of a molecule are electron deficient (+) and which are electron rich (-) is very
useful.
23
TOPIC 5: Basic Concepts of Chemical Bonding
L5.1: Recarp on Chemical bonds
- Polarity of Bonds
L5.2: Lewis Structures
- Octet Rule and Exceptions
-Resonance and multiple bonds
25
Lewis Dot Structures: Resonance
Resonance structures are two Lewis dot structures having the same arrangement of atoms but a
different arrangement of electrons.
Consider Thionyl chloride Lewis dot structure
B
A
Thionyl chloride
Because S is able to expand its octet, one of the lone pairs on the oxygen atom moves to form
a bond with S resulting in double S=O bond and a total of 5 electron pairs around the central S
The two molecular forms (A and B) of thionyl chloride are referred to as resonance
forms/structures of thionyl chloride 26
Lewis Dot Structures: Resonance Structures
• The true structure is a hybrid of the resonance structures. Neither Lewis dot structure by
itself is the true structure of the molecule.
Thionyl chloride
• Resonance stabilizes a molecule by spreading out lone pairs in multiple bonds over a larger
region of space.
• A molecule or ion that has two or more resonance structures is said to be resonance-
stabilized.
27
Lewis Dot Structures: Expanded Octet and Resonance
Stability of the resonance structures;
Which of the two resonance structures is more stable than the other?
Thionyl chloride
A B
To answer that, we have to calculate the formal charges on each of the atoms in each one
of the molecules (A and B)
28
Lewis Dot Structures: Expanded Octet and Resonance
Thionyl chloride
A B
Formal charges:
S: 6 - 2 - (½ x 6) = +1 S: 6 - 2 - (½ x 8) = 0
O: 6 - 6 - ( ½ x 2) = -1 O: 6 – 4 - ( ½ x 4) = 0
Cl: 7- 6 - ( ½ x 2) = 0 Cl: 7- 6 - ( ½ x 2) = 0
29
Recarp: IMPORTANT
• No Lewis diagram is complete without formal charges
• It is best to have a formal charge of 0 for as many of the atoms in a structure as possible.
This is the most stable Lewis structure
• The most stable Lewis structure of any polyatomic species is the one in which the negative
charge is on the most electronegative atoms
• Lewis diagrams are used to examine mechanisms of reactions so knowing which parts of a
molecule are electron deficient (+) and which are electron rich (-) is very useful.
30
Lewis Dot Structures: Expanded Octet and Resonance
Thionyl chloride
A B
Formal charges:
S: 6 - 2 - (½ x 6) = +1 S: 6 - 2 - (½ x 8) = 0
O: 6 - 6 - ( ½ x 2) = -1 O: 6 – 4 - ( ½ x 4) = 0
Cl: 7- 6 - ( ½ x 2) = 0 Cl: 7- 6 - ( ½ x 2) = 0
The formal charges of structure B are all zeros, so it is the most stable resonance structure.
31
Resonance Structures of NO3-
Lewis Dot Structures: Multiple Bonds
Sometimes there is need for formation of a multiple bond in order for all the atoms to
have an octet.
Consider formation of oxygen molecule;
→
Each atom donates and Both atoms do not have
electron for sharing an octet
Two more electrons for
sharing Now both atoms have an
octet 33
HoWo: Consider formation of nitrogen molecule
HoWo
1. Draw the Lewis dot structures of the following molecules
(i) C2H4 (ii) IF2- (iii) SO42- (iv) N2
2. Where you have resonance structures, show which one
of the resonance structures will be the most stable.
11/3/2024 34
