The total number of aromatic compounds/species from the following is [figure]
- 6
- 4
- 3
- 5
Answer
(2) 4
Solution
Aromatic species: cyclic, planar, completely conjugated ring with (4n + 2) π electrons; a compound containing such a ring (e.g. a benzene ring) is an aromatic compound.
(i) p-Benzoquinone: both C=O groups lie outside the ring, so there is no cyclic π-sextet ⇒ non-aromatic.
(ii) Tropylium cation: 7 sp2 carbons, 6π electrons (n = 1) ⇒ aromatic.
(iii) Phenanthrene: 14π electrons (n = 3), three fused benzenoid rings ⇒ aromatic.
(iv) 1,2-Dihydronaphthalene: contains a benzene ring (6π) ⇒ aromatic compound.
(v) Cyclobutadienyl dication: 4 sp2 carbons, 2π electrons (n = 0) ⇒ aromatic.
(vi) Cyclohexadienyl anion shown: one ring carbon is sp3 (CH2) ⇒ cyclic conjugation broken ⇒ non-aromatic.
∴ Aromatic compounds/species = (ii), (iii), (iv) and (v) = 4
Answer: (2)