JEE Main · 2021 · 16 Mar 2021 · Shift 1 · Hydrocarbons

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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:
Structure A
A
Structure B
B
Structure C
C
Structure D
D
  1. (A)(B), (C) and (D) only
  2. (B)(A) and (B) only
  3. (C)(A), (B) and (C) only
  4. (D)(B) and (C) only✓ Correct

Answer: (D)

Solution

A ring is aromatic when it is planar, cyclic, completely conjugated and holds electrons.
Benzene has six electrons spread over six carbons and meets every condition.
The cyclopentadienyl anion puts the carbanion lone pair into a orbital that joins the two double bonds, so six electrons circulate over five carbons and Huckel's rule is again satisfied.
The cyclopentadienyl cation has an empty orbital and only four 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 , 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

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