The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an electron to the pentadienyl radical to give the pentadienyl anion. Which carbon atoms share the negativecharge? Does this picture agree with the resonance picture?
The pentadienyl radical, H2C“CH¬CH“CH¬CH2
#
, has its unpaired electron delocalized over three carbon atoms.
(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.
(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?
(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?
(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)
762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).
(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpaired
electron onto three carbon atoms.
(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atoms
share the positive charge? Does this picture agree with the resonance picture?
(h) Add an electron to the pentadienyl radical to give the pentadienyl anion. Which carbon atoms share the negative
charge? Does this picture agree with the resonance picture?
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