Lewis Structures, Formal Charge, and Resonance Structures

Lewis Structures Resonance Structures Assessing the Relative Importance of Resonance Structures

Lewis symbols are represented by putting the valence electrons around the atom as dots. Some molecules can be represented with more than one Lewis structure. Follow these rules to determine which resonance structure is more stable/important, i.e. it
Remember, Valence electrons are the ones in the outermost energy level. For example: contributes more to the resonance hybrid:
The number of valence electrons corresponds to the group number of the element. Rule 1. Atoms, in general, "don't like" charges, so having no charge is better:
O O H H
For example, Na: 1, Mg: 2, B: 3, C: 4, N: 5.
C C
Lewis structures are electron dot representations for molecules. H3C C O H3C
C
O H2C NH H2C NH
NH
O O NH
H2C C H2C C
Follow these steps to draw Lewis structures: C C C CH3 C CH3
These structures are called resonance structures or resonance forms. They are separated by a H3C CH3 H3C CH3
H H
1. Write the correct skeletal structure for the molecule double-headed arrow (two arrows are used for equilibrium). better better

* Hydrogen atoms are always terminal (only one bond) Only the arrangement of electrons is different in Resonance structures - atoms have the same
What if both resonance strucutres have a charge?
connectivity.
* Put more electronegative elements in terminal positions
Rule 2. More atoms with complete octet make the resonance structure more stable.
2. Sum the valence electrons from all the atoms The accurate representation of a molecule or ion is given by the resonance hybrid where the
3. Use a pair of electrons to form a bond between each pair of bound atoms. charge is shared between the atoms: H H
O O
4. Add the remaining electrons to satisfy the octet for more electronegative atom first. C C CH3 H3C N N H3C N N
H3C CH3 H3C
O O O
5. If any atoms lack an octet, make a double or triple bond to give them an octet. Resonance hybrid better better
H3C C O H3C
C
H3C C O
no octet no octet
O
Example: Draw the Lewis structure of carbon dioxide.
Rule 2.1a. If it is a negative charge, choose the one where the charge is on a more
Step 1 Step 2 Step 3 Step 4 Step 5 To show the movement of the electrons, Curved Arrow notation is used. electronegative atom.
C: 1 × 4 e– = 4 e– O:C:O O:C:O O:C:O
OCO Curved arrow has a Tail and a Head. The tail starts from the middle of a lone pair or a bond and

Increasing Size
O: 2 × 6 e– = 12 e– 16-4 = 12e– left O O
No octet-4 e– the head stops on a specific atom or middle of a bond: C C Increasing Electronegativity
16 e– total O :: C :: O H3C CH2 H3C CH2
or better
Formal Charge O C O H H oxygen is more electronegative
C C New bond formed
Tail Head H2C 2 NH H2C 2 NH
1 3 1
Formal charges are assigned to individual atom(s) in the molecule. 3
The trends for stabilizing a negative charge are the same as for the acidity (ARIO).
The formal charge is the difference between the valence electrons of an atom and how many Adjacent electronegative atoms also stabilize the negative charge.
In this case, the first arrow makes a new bond between carbon 1 and 2.
electrons it "owns". Formal charge can be calculated with this formula: FC = V - (N +B)
Cl H Cl H
V - number of valence electrons, N - number of non-bonding electrons, B - number of bonds The second arrow breaks the bond between carbon 2 and 3 and puts the lone pair on the nitrogen.
C C C C
Cl C CH3 Cl C CH3
Learning the standard valency, lone pairs and charges patterns for drawing correct Lewis structures Remember: Curved arrows show movement of electrons - do not start them from a positive H H
better
will help you a lot in drawing Lewis structures and recognizing any formal charges to be added. charge or a plain atom. Starting from a negative charge is also acceptable. Cl's stabilize the negative charge by induction

Rule 2.1b. If it is a negative charge, and you are comparing elements from different
Curved arrows in Resonance structures:
rows in periodic table, choose the one where the charge is on the bigger atom.
1) Do not exceed the octet on 2nd row elements.
O O NH NH
H C C C
O H3C S H3C S H3C S C
O CH3 C CH3 H3C S
H3C C H2C N C CH
CH3 H3C 3 better better
H2 H3C CH3
sulfur is larger and more polarizable
exceeds the octet for the atom
Rule 3. For carbocations, the resonance structure with the charge on the more
2) Do not break single bonds (atoms must have the same placement in resonance structures).
substituted carbon is more stable - major contributor:
CH3 CH3
O C O + H H
H3C C CH3 H3C CH CH3
H 2o carbocation H3C C C C CH3 H3C
C
C
C
CH3 3o carbocation - better

Wrong - breaking a single bond and making new species is not drawing resonance structures. CH3 H CH3 H
H
Examples: Identify any formal charges in the following molecule: H C O Rule 4. Aromaticity also brings additional stability, so a resonance structure with
H One good pattern to remember is that resonance structures involve a bond, one way or the
the restored aromatic system is a major contributor (Organic II):
other. It is either making a bond or breaking a bond or both.
Identify any element(s) that does not follow its valency according to the table.
You can only move electrons in writing resonance structures, not changing the way atoms are
In this case, it is the oxygen, as it only has one bond. H
connected. So, one way of drawing a resonance structure above would be starting the arrow from O O
H C O (Oxygen with one bond - "odd")
H the lone pair and then break the bond:

So, the formal charge of the oxygen will be: FC (O) = 6 – (6 + 1) = -1 CH3 CH3
better - aromatic better - aromatic
Therefore, put a negative charge on the oxygen: O C O C
H H3C C CH3 H3C C CH3
H C O H H
H
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