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:
- Move electrons toward a positive charge or toward a bond (Figures 7.2
and 7.3). - Move lone-pair electrons toward a bond (Figure 7.4).
- 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