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Question: Designate whether each of the following compounds is aromatic or not aromatic....

Designate whether each of the following compounds is aromatic or not aromatic.

A

a, c, d, e, h aromatic and b, f, g not aromatic

B

b, e, f, g aromatic and a, c, d, h not aromatic

C

a, b, c, d aromatic and e, f, g, h not aromatic

D

e, g aromatic and a, b, c, d, f, h not aromatic

Answer

a, c, d, e, h aromatic and b, f, g not aromatic

Explanation

Solution

Aromaticity is determined by planarity, cyclic conjugation, and Hückel’s rule (4n+24n+2 π electrons).

  • (a) Cyclopentadienyl anion: 6 π electrons → aromatic.
  • (b) Cyclopentadienyl cation: 4 π electrons → antiaromatic → not aromatic.
  • (c) Cyclobutadiene dication (2 π electrons): meets Hückel’s 4n+24n+2 with n=0n=0aromatic.
  • (d) Cyclobutadiene dianion (6 π electrons): planar 4‑membered with two lone pairs → aromatic.
  • (e) Cyclooctatetraenyl cation: 6 π electrons → aromatic.
  • (f) Neutral cyclooctatetraene: 8 π electrons, adopts nonplanar tub conformation → not aromatic.
  • (g) Cyclobutane: saturated ring, no continuous π system → not aromatic.
  • (h) Cyclopropenyl cation: 2 π electrons → aromatic.