Organic Chemistry

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270 CHAPTER 7 Electron Delocalization and Resonance• More About Molecular Orbital Theory

δ+

resonance contributors

resonance hybrid

resonance contributors

resonance hybrid

CH 3 CH CHCH 3

CHCH 3

CH CH CHCH 3

+
CH 3 CH

+

resonance contributors

CH 3 CH CH
resonance hybrid

resonance contributors

resonance hybrid

CH 2

resonance contributors

CH 3 CH CH CH CH CH 2

+

+

+

+

+

resonance contributors

δ+ δδ++

δ+

resonance hybrid

CH 3 CH CH
resonance hybrid

CH CH

δ+

δδ++

δδ++ δδ++

δδ++

δδ++ δδ++

CH 2 CH 2 CH 2 CH 2

+
CH 2

CH 3 CH CH 2

CH 2

CH CH CH 3 CH

++
CH CH CH CH CH 2

Figure 7.2
Resonance contributors are
obtained by moving electrons
toward a positive charge.

p

resonance hybrid

resonance contributors

CH 2 CH
resonance hybrid

CH CH 2

CH 2 CH 2

− + + −
CH

resonance contributors

CH H 2 CCH

resonance contributors

resonance hybrid

CH CH 2 CH 2 CH CH CH 2

resonance hybrid

resonance contributors

resonance contributors

resonance hybrid

Figure 7.3N
Resonance contributors are
obtained by moving electrons
toward a bond. (In the
second example, the red arrows
lead to the resonance
contributor on the right, and
the blue arrows lead to the
resonance contributor on the
left.)

p

p

The electrons can be moved in one of the following ways:


  1. Move electrons toward a positive charge or toward a bond (Figures 7.2
    and 7.3).

  2. Move lone-pair electrons toward a bond (Figure 7.4).

  3. Move a single nonbonding electron toward a bond (Figure 7.5).p


p

p p

BRUI07-263_297r4 21-03-2003 11:31 AM Page 270

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