Resonance
A resonance structure is one of two or more Lewis structures for a
single molecule that cannot be represented accurately by only one
Lewis structure.
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What are the resonance structures of the carbonate (CO32-) ion?
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Curved Arrows
• Curved arrows used for drawing resonance structures do not represent the
motion of electrons—they are simply tools that allow us to draw resonance
structures with ease. These tools treat the electrons as if they were moving,
even though the electrons are actually not moving at all.
• The tail shows where the electrons are coming from, and the head shows where
the electrons are going (remember, the electrons aren’t really going anywhere,
but we treat them as if they were for the purpose of drawing the resonance
structures).
• There are two rules that must be followed when drawing curved arrows for
resonance structures:
1. Avoid breaking a single bond.
2. Never exceed an octet for second-row elements.
The curved arrows indicate that we should draw a resonance
structure in which a lone pair has been pushed to become a pi-bond,
and the pi=bond has been pushed to become a lone pair. We then
complete the resonance structure by assigning any formal charges.
Notice that both resonance structures have zero net charge:
One curved arrow shows the carbon-carbon pi-bond being
pushed up, and the other curved arrow shows the carbon-
oxygen pi-bond becoming a lone pair:
In summary,
We developed the concept of resonance using the allyl
cation as an example, and we saw that the positive charge of
an allyl cation is spread out over two locations. This
spreading of charge, called delocalization, is a stabilizing
factor. That is, the delocalization of either a positive charge
or a negative charge stabilizes a molecule. This stabilization
is often referred to as resonance stabilization, and the allyl
cation is said to be resonance stabilized. Resonance
stabilization plays a major role in the outcome of many
reactions.
