8.6: Resonance Structures: When One Lewis Structure Is Not Enough
8.6: Resonance Structures: When One Lewis Structure Is Not Enough
6: RESONANCE STRUCTURES
SKILLS TO DEVELOP
To understand the concept of resonance.
Resonance structures are a set of two or more Lewis Structures that collectively describe the electronic bonding a single polyatomic
species including fractional bonds and fractional charges. Resonance structure are capable of describing delocalized electrons that
cannot be expressed by a single Lewis formula with an integer number of covalent bonds.
OZONE (O ) 3
5. At this point, both terminal oxygen atoms have octets of electrons. We therefore place the last 2 electrons on the central atom:
6. The central oxygen has only 6 electrons. We must convert one lone pair on a terminal oxygen atom to a bonding pair of electrons—
but which one? Depending on which one we choose, we obtain either
Equivalent Lewis dot structures, such as those of ozone, are called resonance structures. The position of the atoms is the same in the
various resonance structures of a compound, but the position of the electrons is different. Double-headed arrows link the different
resonance structures of a compound:
The double-headed arrow indicates that the actual electronic structure is an average of those shown, not that the molecule oscillates
between the two structures.
When it is possible to write more than one equivalent resonance structure for a molecule
or ion, the actual structure is the average of the resonance structures.
THE CARBONATE (C O 2−
3
) ION
Like ozone, the electronic structure of the carbonate ion cannot be described by a single Lewis electron structure. Unlike O3, though,
the actual structure of CO32− is an average of three resonance structures.
1. Because carbon is the least electronegative element, we place it in the central position:
2. Carbon has 4 valence electrons, each oxygen has 6 valence electrons, and there are 2 more for the −2 charge. This gives
4 + (3 × 6) + 2 = 24 valence electrons.
3. Six electrons are used to form three bonding pairs between the oxygen atoms and the carbon:
4. We divide the remaining 18 electrons equally among the three oxygen atoms by placing three lone pairs on each and indicating the
−2 charge:
As with ozone, none of these structures describes the bonding exactly. Each predicts one carbon–oxygen double bond and two carbon–
oxygen single bonds, but experimentally all C–O bond lengths are identical. We can write resonance structures (in this case, three of
them) for the carbonate ion:
Note: We would expect that the bond lengths in the N O ion to be somewhat shorter than a single bond.
−
3
Strategy:
A. Draw a structure for benzene illustrating the bonded atoms. Then calculate the number of valence electrons used in this
drawing.
B. Subtract this number from the total number of valence electrons in benzene and then locate the remaining electrons such that
each atom in the structure reaches an octet.
C. Draw the resonance structures for benzene.
Solution:
A Each hydrogen atom contributes 1 valence electron, and each carbon atom contributes 4 valence electrons, for a total of
(6 × 1) + (6 × 4) = 30 valence electrons. If we place a single bonding electron pair between each pair of carbon atoms and between
each carbon and a hydrogen atom, we obtain the following:
Each carbon atom in this structure has only 6 electrons and has a formal charge of +1, but we have used only 24 of the 30 valence
electrons.
B If the 6 remaining electrons are uniformly distributed pairwise on alternate carbon atoms, we obtain the following:
Three carbon atoms now have an octet configuration and a formal charge of −1, while three carbon atoms have only 6 electrons
and a formal charge of +1. We can convert each lone pair to a bonding electron pair, which gives each atom an octet of electrons
and a formal charge of 0, by making three C=C double bonds.
Answer
SUMMARY
Some molecules have two or more chemically equivalent Lewis electron structures, called resonance structures. Resonance is a mental
exercise and method within the Valence Bond Theory of bonding that describes the delocalization of electrons within molecules. These
structures are written with a double-headed arrow between them, indicating that none of the Lewis structures accurately describes the
bonding but that the actual structure is an average of the individual resonance structures. Resonance structures are used when
one Lewis structure for a single molecule cannot fully describe the bonding that takes place between neighboring atoms relative to the
empirical data for the actual bond lengths between those atoms. The net sum of valid resonance structures is defined as a
resonance hybrid, which represents the overall delocalization of electrons within the molecule. A molecule that has several resonance
structures is more stable than one with fewer. Some resonance structures are more favorable than others.