What are the rules for drawing resonance structures?
The rules for drawing resonance structures are:
- You can never move atoms.
- You can move only π electrons or lone pairs that are in
#p# orbitals. - All resonance structures must have the same number of valence electrons.
You can never move atoms
If atoms move, we have isomers, not resonance contributors.
The structures above are resonance contributors, because only electrons have moved. All atoms are in the same position in each structure.
You can move only π electrons or lone pairs that are in
#p# orbitalsThe moving electrons must be on a "donor atom." The "acceptor atom" must be next to the donor atom.
The acceptor atom must have a positive charge or be able to accept an electron pair.
Electrons move towards a positive charge or to a more electronegative atom.
In the first example above, a lone pair of electrons on
#"O"# moves toward a positive charge. It forms a π bond between#"O"# and the adjacent atom.In the second example, a pair of π electrons on
#"C"# moves toward a positive charge. It forms a π bond on the other side of the#"C"# atom.In the third example, a pair of π electrons moves onto the more electronegative
#"O"# atom. This results in the formation of formal charges.All resonance structures must have the same number of valence electrons.
Electrons are not created or destroyed. You must have as many electrons in the structures that you create as there were in the starting structure.
The rule is violated above because structure E has 12 valence electrons and structure F has 14 valence electrons. So E and F are not resonance structures (F also violates the octet rule).
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The rules for drawing resonance structures are as follows:
- Ensure that the overall charge and the number of valence electrons remain the same.
- Only electrons involved in π (pi) bonds and lone pairs on atoms can be moved.
- Avoid violating the octet rule for second-row elements (C, N, O, and F) unless it's necessary for resonance.
- Avoid creating formal charges greater than necessary.
- Minimize the separation of formal charges.
- Resonance structures should represent valid Lewis structures of the molecule.
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When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
- Do full valence shells always result in a formal charge of zero?
- How many resonance structures can be drawn for #"PO"_4^(3-)#?
- Why carboxylic acids act neither like aldehydes nor like ketones based on resonance?
- Does the cyanide ion only have one dominant resonance structure? Why?
- When are resonance structures more stable?

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