Problem

The cyclopentadienide ion has the formula The ion consists of a regular pentagon of C a...

The cyclopentadienide ion has the formula The ion consists of a regular pentagon of C atoms, each bonded to two C neighbors, with a hydrogen atom bonded to each C atom. All the atoms lie in the same plane (a) Draw a Lewis structure for the ion. According to your structure, do all five C atoms have the same hybridization? Explain. (b) Chemists generally view this ion as having sp2 hybridization at each C atom. Is that view consistent with your answer to part (a)? (c) Your Lewis structure should show one nonbonding pair of electrons. Under the assumption of part (b), in what type of orbital must this nonbonding pair reside? (d) Are there resonance structures equivalent to the Lewis structure you drew in part (a)? If so, how many? (e) The ion is often drawn as a pentagon enclosing a circle. Is this representation consistent with your answer to part (d)? Explain. (f) Both benzene and the cyclopentadienide ion are often described as systems containing six π electrons. What do you think is meant by this description?

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