Which of the following chemical system is non aromatic?
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Answer
(4) [figure]
Solution
A ring is aromatic when it is cyclic, planar, completely conjugated (every ring atom sp2) and has (4n+2) π electrons (Hückel's rule).
(1) Benzene ⇒ 6 π electrons (n = 1), fully conjugated ⇒ aromatic.
(2) Naphthalene ⇒ 10 π electrons (n = 2), fully conjugated ⇒ aromatic.
(3) Thiophene ⇒ 4 π electrons of the two C=C bonds + one lone pair of S in conjugation = 6 π electrons ⇒ aromatic.
(4) Cyclopenta-1,3-diene ⇒ the CH2 carbon is sp3, so cyclic conjugation is broken ⇒ non-aromatic.
Answer: (4)