Guide to Drawing Resonance Structures

1. Do not violate the octet rule!!! (DO NOT HAVE 5 BONDS TO CARBON!!!) 2. The overall charge of a molecule should not changeatoms may have charges, but the net charge of the entire molecule should not change. 3. Place resonance structures inside brackets ([ ]) and use to separate each structure 4. Do not break bonds! (e.g. do not break C-C, C-H, C-O, or C-N single bonds) 5. Carbon can have 6 or 8 electrons. Nitrogen will sometimes have 6 electrons, but this is very rare (e.g. in the minor resonance structure of the nitrosyl cation, NO+, nitrogen has six electrons). In general, however, nitrogen should have eight electrons around it. O, F, Cl, Br, and I must always have 8 electrons. Structures with a maximum number of octets are preferred. 6. Charges will be preferentially located on atoms of compatible electronegativity. For example, oxygen is more electronegative than carbon; therefore, a negative charge will preferentially be placed on oxygen rather than carbon in the dominant resonance structure. 7. Structures with a minimum of charge separation are preferred. This rule is derived from Coulombs law, which states that the separation of charges requires energy. Hence, neutral structures are better than dipolar ones. Minimize the number of charges you have in a resonance structure. 8. Unless starting with a radical, move electrons in pairs, using a double-headed arrow. 9. Do not jump lone pairs from one atom to another. Lone pairs can become bonds or bonds can become lone pairs. Bonds can migrate from one side of a carbon atom to another. Some Examples: (a) HN3

H N N N

H N N N

In the above resonance structures, note how the octet rule is satisfied for all 2nd period atoms (rule #1). No bonds were broken (rule #4), and rules #8 and #9 were applied. In addition, rule #2 was not violated.

(b) CH2O

H O H major

H O H minor

Rule #6 was applied in this example. Rules #1, #2, and #5 were also taken into account. The first structure is the major (dominant) structure, as none of atoms possess charges (rule #7) and the octet rule is satisfied for all 2nd period atoms.

(c) CH2NH2

H NH2 H minor

N H H major

Note how no atom has more than 8 electrons around it. While the nitrogen in the second structure is happier not having a positive charge (rule #6), the first structure is the major one, as all 2nd period atoms possess octets. In general, satisfying the octet rule (rule #1) takes precedence over other considerations.

(d) Ozone (O3)

(e) C5H7

C H

H C

C H

H C

H CH2 H H H

H H H H2C

H C

C H

H C

C H

This is an example illustrating rule #9. Notice how the lone pair of the anion does not jump to the central carbon; instead, the lone pair becomes the new bond in the second structure, and the electrons in the adjacent bond become the new lone pair.