(a) Figure 11.16 is an electrostatic potential map of calicene, so named because its shape resembles a chalice (calix is the Latin word for “cup”). Both the electrostatic potential map and its calculated dipole moment (µ = 4.3 D) indicate that calicene is an unusually polar hydrocarbon. Which of the dipolar resonance forms, A or B, better corresponds to the electron distribution in the molecule? Why is this resonance form more important than the other?
(b) Which one of the following should be stabilized by resonance to a greater extent? (Hint: Consider the reasonableness of dipolar resonance forms.)
FIGURE 11.16
Electrostatic potential map of calicene
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