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CHEM 201
Wize Chemistry
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Welcome
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Lewis Structures &

Resonance Structures
01 The Periodic Table & Properties
The Periodic Table of Elements
The periodic table is something we are going to see a lot of in chemistry! It organizes the elements
by their atomic number (Z) and is organized into groups (columns) and periods (rows).

Elements in the same group have very similar reactivity which we will talk about more when we
learn about things like valence electrons, bonding, and Lewis structures.

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You should be familiar with each of the following labels:

● Groups
● Periods
● Alkali Metals
● Alkaline Earth Metals
● Transition Metals
● Nitrogen group (aka Pnictogens)
● Oxygen group (aka Chalcogens)
● Halogens
● Noble (Inert) Gases
● Metals
● Non-metals
● Metalloids
● Lanthanides and Actinides (aka Rare Earth Metals)

Practice Questions
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02 How to Draw Lewis Structures

Drawing Lewis Structures
Drawing the "best" Lewis structure for a molecule is a great skill to have for your chemistry class!
This concept will come in handy in the upcoming chapters as well. We will follow the steps below
each time.

WIZ E T IP

Steps for Drawing Lewis Structures:

1) Calculate the total number of valence electrons for the molecule.

2) Write out all atoms, with the least electronegative atom in the middle (but H is never in
the middle)

3) Connect all atoms with single bonds.

4) Put lone pairs on atoms, except H, until you run out of electrons. Put extra lone pairs on
the central atom.

5) Shift lone pairs to make double or triple bonds to satisfy the Octet Rule and get the
best formal charges.

Octet Rule: atoms need to have 8 electrons in the valence shell

Examples: C, N, O, F all need 8 electrons in their valence shell to have the "best" Lewis structure

Example: CF 4 → the C atom has 8 valence electrons and each F atom has 8 valence electrons in
the Lewis Structure

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Exceptions to the Octet Rule

Some elements are octet deficient (require less than 8 electrons in their valence shell)

Examples:
H and He can only have 2 electrons

Be can only have 4 electrons

In group 13, Al and B can only have 6 electrons

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Some elements have an expanded octet (can have more than 8 electrons in their valence shell)

Examples:
Non-metals in period 3 and onwards can have expanded octet.
P can have 10 electrons

S can have 12 electrons

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Some molecules like radicals have an odd number of electrons (these are rare!)

Example: NO
First let’s count the number of valence electrons (VE) in both atoms.

● N →5 VEs
● O → 6 VEs
○ So in total there are 11 VEs which is an odd number. We would be left with a molecule that
looks like this:

Note: There is an unpaired electron on the N. This is called a radical molecule and is highly
reactive so it is very short-lived.

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Formal Charges

The last thing we need to check to ensure we have the BEST Lewis Structure is to count formal
charges.

WIZ E CO NCEPT

The best formal charge for an atom is zero.

If the formal charges for a molecule can't be 0 the best Lewis Structure for that molecule
will have the lowest possible formal charges.

If formal charge is not zero, consider assigning negative formal charge to more
electronegative elements and positive formal charges to less electronegative elements, if
possible.

FC = V E − bonds connected to the atom - lone pair electrons on the atom

FC is the formal charge of an atom

VE are the valence electrons the atom has

Example:
OF 2

Example Problem

Example: Lewis Structures

Draw Lewis structures of the following molecules.

a) PCl3

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b) NH4 +

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c) SeF 4

Example Problem

Example: Lewis Structure

Draw the Lewis Structure for SO4 2-

Practice Questions
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03 Strength of Acids and Bases

How to Determine the Stronger Acid by Looking at Conjugate
Bases

We just learned that the stronger an acid, the (stronger/weaker) its conjugate base.
For a strong acid, the conjugate base is so weak that it has no basic properties!

Weak conjugate bases (want to/don't want to) react.

Therefore, it makes sense that weak conjugate bases are (more/less) stable.

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WIZ E CO NCEPT

Stronger acids will always have the more stable conjugate base!

Example #1: If we consider HF vs HI, which of these is the stronger acid?

We can compare their conjugate bases:

Now which of the conjugate bases is more stable?

Both conjugate bases have a negative charge, so do you think the more stable conjugate base
would be the one with the negative charge spread over a smaller or larger distance?

Therefore, the more stable conjugate base is ( Atomic Radius) and the stronger
acid is !

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Example #2: Order the following acids in order of increasing acidity:

HI, PhOH, and H2 SO4

So first, let's consider the conjugate bases:

Again all of the conjugate bases have a negative charge, so the most stable conjugate base will be
the one that stabilizes that charge the most

● If we want our negative charge to be stabilized, do we want the charge to be spread over a
large distance, or concentrated over a small distance?

● If we want our negative charge to be stabilized, would we want a more EN atom to have the
charge or a less EN atom to have the charge?

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Now let's draw out the conjugate bases to see what their structures look like:
I-, PhO-, and HSO4 -

Do any of the structures have resonance?

If they do, which ones have resonance? (draw out resonance if they have it!)

Would resonance make the conjugate more or less stable?

Therefore, our least stable conjugate base is: . This means that is the
acid.

Now, out of the conjugate bases with resonance, what element has the charge initially?
Do you think this is more or less stable than having the negative charge on C?

If you consider the resonance structures, does the charge always stay on O? Yes or no and
for which conjugate base?

Therefore, in order of increasing acidity (in order of least stable conjugate base to most
stable conjugate base):

Do you think if we had more resonance that would make the conjugate base more or less stable?

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Summary

1) Resonance is the most important factor in determining conjugate base stability

More resonance present=more stable conjugate base

2) Having the negative charge on the most electronegative element is next most important.
Also pay attention to which atoms carry the negative charge in resonance structures.
The more stable conjugate base will have the negative charge on more electronegative elements.

3) Having other electronegative atoms present also help to stabilize the charge in the conjugate
base (inductive effect)

4) When comparing atoms with negative charges, the larger the atomic radius, the more stable
the conjugate base.

Acidity of Oxyacids
Oxyacid: an acid made up of a non-metal element and an acidic -OH group

Examples:

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The strength of an oxyacid depends on two things:

1) The Number of O atoms

Think about the conjugate base of the acid.

● If we deprotonate the acid and there are many Os, those Os are quite electronegative and
can help spread the negative charge so it is not concentrated in one area, thus stabilizing
the conjugate base.

● An oxyacid with more Os is a stronger acid than an oxoacid with less Os

Example: Which one is more acidic? Carboxylic acid or sulphuric acid?

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2) The EN of the central non-metal atom

If we are trying to determine the stronger oxyacid, consider their conjugate bases.

● The conjugate base that has a central non-metal atom that is more electronegative will be
able to spread the charge on the conjugate base, stabilizing it.

● Therefore, the oxoacid with the more electronegative central atom will be the stronger
acid (if we are dealing with 2 oxoacids with the same # of Os)

Example: Which is the stronger acid? Sulphuric acid or phosphoric acid?

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Summary

In general, for oxyacids with the same # of O atoms, we have increasing acid strength with
(increasing/decreasing) EN of central non-metal atom

And for oxyacids with a different # of O atoms, the stronger oxyacid will be the one with (more/less)
O atoms

04 Resonance
Resonance Structures
Resonance structures: are used to describe molecules with delocalized electrons which cannot
be described by a single Lewis structure

Resonance structures follow the same rules as Lewis structures and the same features that make a
good Lewis structure also make good resonance structures.

WIZ E CO NCEPT

The atoms will be connected in the exact same way for each resonance structure (no single
bonds can change).

The only thing that moves are the multiple bonds and lone pairs

WIZ E T IP

How to Draw Resonance Structures:

1. If it is not provided draw a Lewis structure.

2. Move lone pairs and double bond around to spread out charge.

3. If you move a lone pair into a multiple bond, make sure your new structure doesn’t break
the octet rule

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Example: Resonance structures for CO3 2-

Resonance structures are not discrete molecules which exist individually, but rather the
molecule exists as an average of all of its resonance structures.

Resonance hybrid: The "average" of all of a molecule's resonance structures (see below)

Average C-O bond order: 1 1/3

Average Charge on oxygen: -2/3

Equivalent Vs Non-Equivalent Resonance Structures

If there is more than one relatively good Lewis structure for a molecule, the molecule exhibits
resonance.

Equivalent Resonance Structures

All resonance structures are equally stable.

Example:

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In reality, the molecular structure will be the average (hybrid) of each resonance form:

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Non-Equivalent Resonance Structures

One resonance structure is better than the other.

WIZ E T IP

The major contributor (aka the more stable resonance structure) is the one where the
negative charge resides on the most electronegative atom!
The major contributor will also have the smallest charges (charges more spread out).

You could be asked to identify the most stable resonance structure on an exam.

Example:

Out of these two non-equivalent resonance structures, which is the more stable one? The one on
the left or right?

Example Problem

Example: Draw the Resonance Structures

Draw all the reasonable resonance structures for SO3 F - . Are these equivalent or non-equivalent
resonance structures?

Example Problem

Example: Resonance Structures and Stability

Draw all reasonable resonance structures for the following compounds.
Are they equivalent or non-equivalent resonance structures?
If one resonance structure is more stable than the other(s), indicate which one is most stable.

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a) N3 -

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b) PO4 3-

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