Among the following, the aromatic compounds are: (A) (see structure) (B) (see structure) (C) (see structure) (D) (see structure) Choose the correct answer from the following options:ABCD
(A)(B), (C) and (D) only
(B)(A) and (B) only
(C)(A), (B) and (C) only
(D)(B) and (C) only✓ Correct
Answer: (D)
Solution
A ring is aromatic when it is planar, cyclic, completely conjugated and holds (4n+2)π electrons. Benzene has six π electrons spread over six sp2 carbons and meets every condition. The cyclopentadienyl anion puts the carbanion lone pair into a p orbital that joins the two double bonds, so six π electrons circulate over five sp2 carbons and Huckel's rule is again satisfied. The cyclopentadienyl cation has an empty p orbital and only four π electrons in the cyclic conjugation, which makes it antiaromatic. In 5-methylenecyclohexa-1,3-diene the third double bond points out of the ring and one ring carbon remains sp3, so the conjugation around the ring is broken and the compound is non-aromatic. The aromatic compounds are benzene and the cyclopentadienyl anion.
JEE Main · 2021 · 16 Mar 2021 · Shift 1 · Single correct option