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Lewis Structures Handout

1. The document discusses Lewis structures, resonance theory, and how to draw resonance structures for organic molecules. 2. It explains that Lewis structures show bonding and lone pairs but one formula can have multiple structures, and resonance theory is needed when one structure does not fully describe the bonding. 3. Resonance structures differ by electron placement, not atoms, and the actual structure is a resonance hybrid between the extremes represented by different structures.

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208 views

Lewis Structures Handout

1. The document discusses Lewis structures, resonance theory, and how to draw resonance structures for organic molecules. 2. It explains that Lewis structures show bonding and lone pairs but one formula can have multiple structures, and resonance theory is needed when one structure does not fully describe the bonding. 3. Resonance structures differ by electron placement, not atoms, and the actual structure is a resonance hybrid between the extremes represented by different structures.

Uploaded by

baleah
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Lewis Structures and

Resonance
UCI Chem 51A
Dr. Link
Goals
After this lesson you should be able to:

1. Explain why Lewis structures are integral to organic chemistry.

2. Draw valid Lewis structures.

3. Count formal charge.

4. Explain the need for resonance theory.

5. Explain what is a resonance structure and what is not.

6. Draw valid resonance structures.

7. Properly use curved arrow notation.

8. Identify major and minor resonance contributors.

9. Draw the resonance hybrid for a structure.


Lewis Structures: Quick
Review

Lewis structures are representations of


molecules that depict bonds and lone pairs.

Why are structures needed?

In gchem, you used mainly formulas.


One Formula, Many
Structures
C2H6O

ethanol dimethyl ether

1 formula can = multiple structures!


How to Draw Lewis
Structures:
1. Count valence electrons. (As you become more comfortable
drawing structures you can sometimes skip this step, but
occasionally double-check!)

2. Arrange atoms. Organic formulas will usually give you an


idea of how.

3. Draw in single bonds. Distribute lone pairs. Count your


electrons.

4. Check for octets. IF NEEDED add double or triple bonds.


(Don’t get double-bond-happy!)

5. Maximize octets, minimize formal charge. (More on this


later.)
Lewis Structure
Examples

H 2O CH3CO2H
8 e- 24 e -
Electron Accounting
Methods: Formal Charge
Formal charge lets us know if an atom is electron-rich or electron-poor!
(Important for reactions later!)

Counting formal charge is different than counting for octet rule! Be


careful!

Counting rules:

1. Count formal charge for individual atoms in a structure.

2. Non-bonding pairs count as 2 electrons. Bonds count as 1 electron.

3. Compare number of electrons in structure to NORMAL number of


valence electrons.

Extra electrons in structure? (-) charge

Fewer electrons in structure? (+) charge


Formal Charge Examples

SO42-
When 1 Structure Doesn’t
Show the Full Picture...

Our ability to represent the true bonding


nature of molecules is limited by the way our
brains work and how we draw things!

We can draw multiple structures that differ


only by placement of electrons.

What does this mean?


Rules for Drawing
Resonance Structures
1. Move electrons ONLY, not atoms.

2. Don’t split up electron pairs. If electrons


are paired, move both together.

3. Follow Lewis structure general rules.

Note: Expanded octet or non-octets are


possible.
Resonance Structure
Examples
-1
-1 -1

-1 +2 -1 +1

-1

-1 -1 -1 -1

+1
The Curved-Arrow
Formalism
Organic chemists use curved arrows to show movement of electrons.

Rules for “arrow pushing”:

1. Arrows show movement of ELECTRONS ONLY!

2. Arrows begin at electrons, so you have two options:

A. Non-bonding (lone) pairs

B. Existing bonds

3. Arrows end where the electrons are going, so you have two options:

A. An atom (to form a new non-bonding pair)

B. An existing bond (to form a double or triple bond)

THESE RULES ARE VERY IMPORTANT!!! YOU WILL USE THEM IN ALL
OCHEM CLASSES!!!
Resonance Structure and
Curved Arrow Practice
NOT Resonance
Structure Examples
Don’t
move
atoms!

rotation =
resonance
too many
e- on C!!!
Resonance Theory

Resonance structures are NOT REAL.

Resonance structures are NOT IN


EQUILIBRIUM. (Note the arrow type.)

Resonance structure are NOT ISOMERS.

So what are they?!


Resonance Hybrids

Resonance structures we draw are the -1


extremes of a spectrum.
-1
The “real” structure of the molecule is
called a resonance hybrid and is
-1
somewhere between the extremes.
-1 -1 -1
How do we know that?
Evidence that Lewis
Structures Fail
-1 -1

-1 -1 -1
-1

All C-O bonds equal!


Bond Length
C-O 143 pm
C=O 122 pm
carbonate 129 pm
More on Resonance
Hybrids

+ =

Fictitious Fictitious Real!


Not All Resonance Structures
are Created Equally!

Maximize bonds and octets.

Minimize formal charge.

When formal charge is necessary, (-) on


more electronegative atoms, (+) on less
electronegative atoms.

Major contributors vs. minor contributors.


Major and Minor
Contributors
-1 -1

-1 +1
-1

-1 -1

+1 +1
Wrapping Up
Practice drawing Lewis structures, including formal
charge.

Practice drawing resonance structures, including


formal charge.

Practice using the curved arrow notation.

Practice determining whether a resonance structure


would be a major or minor contributor to the
resonance hybrid.

Practice drawing the resonance hybrid.

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