, ..

Resonance
. . . Structures
 Two valid Lewis structures can be drawn
for the ion, CH2COCH3- H
. . .
..O.. - H . O. H
.. ..
H O
H .
C C - .. C C C H
H H C C
H C
H H H H

resonance structures ..

FC = 6
 Resonance structures: -6
 Lewis structures that differ
-1/2(2) only in the
placement of electrons.
-1
 Resonance Structures
 CH2COCH3- exists as a resonance hybrid
 a substance that requires 2 or more
,
resonance structures to adequately ..
represent it
. . .

 properties of the substance are a blend of

all possible resonance structures
H
. . . ..
..O.. - H . O. H H O
H .
C C - .. C C C H
H H C C
H C
H H H H
 Resonance Structures
 The negative charge on CH2COCH3- is
delocalized over both the carbon and
oxygen.
 spread out over two or more atoms by
resonance
, ..
 Charge delocalization makes CH 2COCH3
-
. . .
more stable.
 It is resonance stabilized because the
charge can be spread out over 2 or more H
. .. - .. O.. H . .
atoms. H
.O..
H H . O.
- .. C C C H
C C H H C C
H C
H H
H H
 Drawing Resonance Structures
 Rules for drawing resonance structures:
 All resonance structures must be valid
Lewis structures
, ,
 Only electrons can be.. moved
.. around
 nuclei cannot be moved
-
 Resonance stabilization
- is most important
when it helps delocalize a charge over two
or more atoms H H
. . . . . . . .
H . O. H
H . O. H H . O. H
H . O. H
H C C
H CC HC C H H C CH CC HC C H
H H
H H H H
. . ..
.
Are these resonance structures?
. ..
 Resonance Structures
 To convert from one resonance structure
to another:
 move nonbonding electrons or pi electrons
towards either:
 a positive charge
 an adjacent pi bond
 a more electronegative atom

 Remember, the electrons move.

 The charge is delocalized (and moves to a
new atom) as a result of the electrons
moving.
 Resonance Structures
,

 Curved .arrows
. . are commonly used to show
the movement of electrons when
converting from one resonance structure
to another.
 Arrow begins at the electron pair that is
moving.
. .. . .
.O . - .
H O. H
H .
C C H
- .. C C C H
H C
H H H H
 .. .
.
.O . H O H ..O.. H
H . H .
- ..
CResonance Structures
- .. C
C C C C CH C
H H
H C H H
H C H
Example: Draw
H H all possible
major resonance
H H
structures for the following.
+
CH2
H CH3 FC = 6 H CH3 FC = 6
- .. -6 + -6
H C C C H -1/2(2) H C C C H -1/2(2)
.
..O.. HHO H -1
H H . -1
- ..
C C C C C H
H
H .. - C H H
CH2 +
H H CH2

O ..O..
.
..O.. .. H O H
H . CH .
FC.O=.-6..
H . H O H
C +C H 3 C C C H - .. +
H -6 C C C H
H C C C C H C H
 Resonance Structures
 The resonance structures for a particular
substance sometimes have different energy
and stability.
 Major contributor:
 the more stable resonance structure
– lower energy
 has the greatest influence on the properties
and behavior of the resonance hybrid

 Minor contributor
 the less stable resonance structure
– higher energy
 Resonance Structures
 A resonance hybrid most strongly
resembles the lowest energy resonance
structure (major contributor).

 Lewis structure of the major contributor

is characterized by:
 as many octets as possible
 as many bonds as possible
 negative charge on the most
electronegative atom
 as little charge separation as possible
 Resonance Structures
Example: Consider the following two
resonance structures for CH3OCH2+. Which
one is the major contributor?

H H
H C O C H H C O C H
H H H H
 3-Dimensional Drawings
 VSEPR can be used to determine the
electron domain and molecular geometries
around any main group atom.
 Draw the Lewis structure.
 Count the number of electron domains.
 Assign the geometry.

 2 e.d. =
 3 e.d. =
 4 e.d. =
 A A
3-Dimensional Drawings
 You must
C also be able to draw an
C
appropriate 3-dimensional structure for
A E
organic molecules.
B A E
D B
B D
B In the plane of
B
the slide Going back and
A B A away from you
B B A
B B B
B Coming out
B toward you
Trigonal planar

tetrahedral
 3-Dimensional Drawings
Example: Draw a 3-dimensional drawing of
acrylic acid, H2C=CHCO2H
 3-Dimensional Drawings
Example: Draw a 3-dimensional structure
for acetone.
 Condensed Structural Formulas
 Condensed structural formula
 each central atom is shown with the atoms
that are bonded to it
 atoms bonded to the central atom are
usually listed after the central atom
– Put substituents in parentheses
– two or more identical groups are shown
in parentheses with a subscript to
indicate quantity
 the bonds between atoms are usually not
shown
 exception: double and triple bonds
between two carbons should be shown
 Condensed Structural Formulas
H O
Examples: H HC OC H
H H H H H
H H H H H CH C H
C C
HH C CC C H
C C H H C H
HH HHH H H CH3CH(OH)CH2CH(CH3)2
H
CH3CHO
CH
CH33CH
CH22CH
CH33
H2C CHCH3 CH3CHO
H O
H O H HO H
H Br H H H
H C C C C C H
H
H C C C C H H H H H
H Br H H H C H
H
CH3C(Br)2CH2CH3
CH3CH(OH)CH
OH 2
CH(CH3)2
 Line Angle Drawings
 Line-angle formula or drawing
 bonds are represented by lines
 carbon atoms are present:
 where a line begins or ends (if no other atom
is shown at the end of the line)
 where two lines meet
 Heteroatoms like N, O, S and halogen atoms
are always shown.
 Aldehyde hydrogens are always shown.
 Other hydrogens are shown only if attached
to an atom that has been drawn using its
elemental symbol.
 H O Line HAngle
O
Drawings
CH CH(OH)CH CH(CH ) 3 2 3 2
H H H
H C C HH C
Examples: C C O C C
H
H
H O H H
H H H H HC H
H O H C C O C C H
H HH O H HH H H
H C C H CH3CH2CO2CH2CH3
CH3CHO H C C C C C H
H CH3CH2CO2CH
O 2CH3
O CH3CH(OH)CH2CH(CH3)2 H H H H
HH H O O
H C H
H
CH3CHO H HH H O
H C O C
C H C C HH H
O HH C O C H
H O H H HH C C C
H O H OH H
H H C C C C C H H O HH

H H H H
H C H
-CO2R where R = alkyl
-COgroup
R where R = alkyl group
H 2
 H H
H C C H
C O C
Line Angle Drawings
H HH H
O HH O HH
H H O
H Line CangleC drawings
H H areC intended
HH toC show
H
C O H
C C H H C H
3-d structure. C O C C O C
H H H
H H H
 Common errors:

incorrect correct
incorrect correct

Alkynes are linear, not

Substituents on a
tetrahedral or trigonal
tetrahedral C are
planar.
~109.5o apart, not 180o
as this drawing shows.
 Chemical Formulas
Example: Draw the condensed structural
formula and the line angle drawing for:

OH H O
H C C C OH
C C H
H H
H

CH3 O H

H C C C C C H
CH3 H
 H C C H
HH C O C
O
H
H
C Chemical
C
H
HH Formulas
H
C O C
Example:
H Draw H
the condensed structural
formula for

H
O
Br
O HH N
H H
H C Br
C H
C O C

H H