Recognize the Patterns

Common resonance patterns we will explore:

  1. 𝜋 Bond Between Atoms of Differing Electronegativity:


    A 𝜋 bond is between two atoms with different electronegativities (e.g., C=O, C=NR).

    The more electronegative atom pulls the 𝜋 electrons towards itself, forming a lone pair and a negative charge.
    The other atom, now lacking the electrons, develops a positive charge.

  2. Lone Pair Next to a Positive Charge:

    This is the reverse of pattern 1 (𝜋 Bond Between Atoms of Differing Electronegativity)
    A lone pair on an atom is adjacent to a positively charged carbon atom.

    The lone pair shifts to form a new 𝜋 bond with the positively charged carbon, neutralizing the charge on the carbon.
    This results in a new resonance structure with a positive charge on the atom that donated the lone pair.

  3. Allylic Carbocation:


    A positively charged carbon atom is next to a carbon-carbon double bond (𝜋 bond).

    The 𝜋 electrons shift to form a new 𝜋 bond with the positively charged carbon, neutralizing the charge on the carbon.
    This results in a new resonance structure with a positive charge on the adjacent carbon.

  4. Lone Pair Next to a 𝜋 Bond (Allylic Lone Pair):


    A lone pair on an atom is located next to a carbon-carbon double bond (𝜋 bond).

    The lone pair can shift to form a new 𝜋 bond, pushing the existing 𝜋 bond electrons onto the adjacent carbon atom.
    This results in a new resonance structure with the lone pair on the adjacent carbon.

  5. Conjugated 𝜋 Bonds in a Ring:


    Alternating double and single bonds within a ring structure (conjugated system).
    Example: Benzene (C6H6).

    𝜋 electrons can shift around the ring, creating multiple equivalent resonance structures.