CH 2 Resonance

Electron resonance
&
Drawing chemical
structure
1
Resonance Forms
• Some molecules are have structures that cannot
be shown with a single representation.
• The real structure is a hybrid of the different
resonance forms.
• Arrows connecting resonance forms are double
headed.
• In a resonance form, only the electrons are
moved.
2
• For example, benzene (C6H6) has two
resonance forms with alternating double and
single bonds.
• All its C-C bonds equivalent, midway between
double and single.
3
Resonance Forms
Resonance Forms can be compared using
the following criteria, beginning with the
most important:
– Has as many octets as possible.
– Has as many bonds as possible.
– Has the negative charge on the most
electronegative atom.
– Has as little charge separation as possible.
4
Major and Minor Contributors
• The major contributor is the one in which
all the atoms have a complete octet of
electrons.
O O
C C
H H H H
MAJOR MINOR
The carbon atom does

not have a complete
octet of electrons.
5
Major and Minor Contributors
(Continued)
• When both resonance forms obey the octet
rule, the major contributor is the one with
the negative charge on the most
electronegative atom.
N C O N C O
MAJOR MINOR
The oxygen is more electronegative,

so it should have the negative
charge.
6
Non-Equivalent Resonance
• Opposite charges should be on adjacent
atoms.
CH3 O N O CH3 O N O
MAJOR MINOR
The most stable one is the one with the smallest

separation of oppositely charged atoms.
7
Solved Problem 2
Draw the important resonance forms for [CH3OCH2]+. Indicate which structure is major and minor
contributor or whether they would have the same energy.
Solution
The first (minor) structure has a carbon atom with only six electrons around it. The second (major)
structure has octets on all atoms and an additional bond.
8
Solved Problem 3
Draw the resonance structure the compound below. Indicate which structure is major and minor
contributor or whether they would have the same energy.
Solution
Both of these structures have octets on oxygen and both carbon atoms, and they have the same number
of bonds. The first structure has the negative charge on carbon; the second has it on oxygen. Oxygen is
the more electronegative element, so the second structure is the major contributor.
9
Resonance Forms
• The structure of some compounds are not adequately represented

by a single Lewis structure.
• Resonance forms are Lewis structures that can be interconverted by
moving electrons only.
• The true structure will be a hybrid between the contributing
resonance forms.
10
Resonance Forms for the
Acetate Ion
• When acetic acid loses a proton, the resulting acetate

ion has a negative charge delocalized over both of the
oxygen atoms.
• Each oxygen atom bears half of the negative charge,
and this delocalization stabilizes the ion.
• Each of the carbon–oxygen bonds is halfway between a
single bond and a double bond, and they are said to
have a bond order of 1½.
11
Type of Formula
• Three types of chemical formula:
 Empirical formula
 Tell us the types of atoms and their numerical ratio in a molecule or
the simplest ratio of atoms in a molecule
 If u are given the empirical formula CH2, its molecular formula could
be C2H4, C3H6 or any multiple CH2.
 Molecular formula
 Tell us the actual number of each type of atom in a molecule
 The molecular formula of ethane is C2H6.
 Structural formula
 Show the structure of a molecule, that is the order of attachment of
the atoms.
12
Structures and Formulas
• Condensed structures: C-H and C-C and single bonds
are not shown but understood.
• If C has 3 H’s bonded to it, write CH3; and so on.
Condensed
H H
1 2
H C C H
CH3CH3
H H
H H H H
1 2 3 4
H C C C C H CH3CH2CH2CH3
H H H H
13
• Horizontal bonds between carbon are not shown in
condensed structures, but vertical bonds are added for
clarity.
Condensed
H H Br H
1 2 3 4 Br
H C C C C H
H H H H
CH3CH2CHCH3
H H O H O
1 2 3 4
H C C C C H HOCH2CH2CCH3
OH H H
14
Skeletal structures
• C’s not shown, assumed to be at each

intersection of two lines (bonds) and at the end
of each line.
• H’s bonded to C’s are not shown – whatever
number is needed will be there.
• All atoms other than C and H are shown.
15
Skeletal Structures
H H H H
1 2 3 4 C C
H C C C C H C C
H H H H
H H H H H O 1 2 3 4 5 6
1 2
H C C C C C C
3 4 5 6 O
H H H H H H
H
16
17
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CH 2 Resonance

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CH 2 Resonance

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Electron resonance

The carbon atom does

The oxygen is more electronegative,

The most stable one is the one with the smallest

• The structure of some compounds are not adequately represented

• When acetic acid loses a proton, the resulting acetate

• C’s not shown, assumed to be at each

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