Unpaired electrons FIGURE 14-21 Energy diagram for the MOs of square cyclobutadiene (a) Four unhybridized p atomic orbitals on the C atoms of cyclobutadiene. (b) Energy diagram of the four T MOs of cyclobutadiene. The dashed line represents the energy of the unhybridized p AOs. AO energies Four p AOs Four T MOs (a) (b) HC CH HC. CH АO energies TT2 TT3 6 p AOs 6 п MOs (a) (b) (с) FIGURE 14-19 ↑ Energy

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.33P
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Draw the π MO energy diagram for [10]annulene, similar to those in Figures 14-19 and 14-21. Fill up the orbitals with the appropriate number of π electrons. Based on this diagram, should [10]annulene be aromatic or antiaromatic? Explain.

Unpaired electrons
FIGURE 14-21 Energy
diagram for the MOs of
square cyclobutadiene (a) Four
unhybridized p atomic orbitals on
the C atoms of cyclobutadiene.
(b) Energy diagram of the four
T MOs of cyclobutadiene. The
dashed line represents the energy
of the unhybridized p AOs.
AO energies
Four p AOs
Four T MOs
(a)
(b)
Transcribed Image Text:Unpaired electrons FIGURE 14-21 Energy diagram for the MOs of square cyclobutadiene (a) Four unhybridized p atomic orbitals on the C atoms of cyclobutadiene. (b) Energy diagram of the four T MOs of cyclobutadiene. The dashed line represents the energy of the unhybridized p AOs. AO energies Four p AOs Four T MOs (a) (b)
HC
CH
HC.
CH
АO energies
TT2
TT3
6 p AOs
6 п MOs
(a)
(b)
(с)
FIGURE 14-19
↑
Energy
Transcribed Image Text:HC CH HC. CH АO energies TT2 TT3 6 p AOs 6 п MOs (a) (b) (с) FIGURE 14-19 ↑ Energy
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