MCQMediumJEE 2025Aromatic Compounds & Benzene

JEE Chemistry 2025 Question with Solution

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

Eight cyclic compounds labeled (a) to (h), including charged rings and unsaturated rings, for classifying as aromatic or not aromatic.
  • A

    e, g aromatic and a, b, c, d, f, h 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

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

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: Compounds (a) to (h) are to be classified as aromatic or not aromatic.

Find: Which set of compounds is aromatic.

Use Huckel's rule for aromaticity:

  • cyclic molecule
  • planar molecule
  • fully conjugated π\pi system
  • contains (4n+2)(4n+2) π\pi electrons

A compound that fails planarity or full conjugation is not aromatic. A cyclic, planar, fully conjugated compound with 4n4n π\pi electrons is also taken here as not aromatic.

From the given solution:

  • (a) cyclic, planar, conjugated with 6π6\pi electrons, so it is aromatic.
  • (b) has 4π4\pi electrons, so it is not aromatic.
  • (c) cyclic, planar, conjugated with 6π6\pi electrons, so it is aromatic.
  • (d) cyclic, planar, conjugated with 6π6\pi electrons, so it is aromatic.
  • (e) cyclic, planar, conjugated with 6π6\pi electrons, so it is aromatic.
  • (f) is not planar, so it is not aromatic.
  • (g) has 4π4\pi electrons, so it is not aromatic.
  • (h) cyclic, planar, conjugated with 6π6\pi electrons according to the keyed result, so it is aromatic.

Therefore, the aromatic compounds are (a), (c), (d), (e), (h) and the not aromatic compounds are (b), (f), (g).

The correct option is D.

Step-by-step Classification

Given: The structures (a) to (h) shown in the figure.

Find: Which option correctly designates them as aromatic or not aromatic.

To determine aromaticity, check these conditions one by one:

  1. The molecule must be cyclic.
  2. The molecule must be planar.
  3. The molecule must be fully conjugated.
  4. The molecule must contain (4n+2)(4n+2) π\pi electrons.

The extracted solution states:

(a) Aromatic. It is cyclic, planar, conjugated, and has 6π6\pi electrons.

(b) Not aromatic. It has 4π4\pi electrons, so it does not satisfy Huckel's rule for aromaticity in this question's classification.

(c) Aromatic. It is cyclic, planar, conjugated, and has 6π6\pi electrons.

(d) Aromatic. It is cyclic, planar, conjugated, and has 6π6\pi electrons.

(e) Aromatic. It is cyclic, planar, conjugated, and has 6π6\pi electrons.

(f) Not aromatic. Its structure is not planar, so effective cyclic conjugation is prevented.

(g) Not aromatic. It has 4π4\pi electrons.

(h) Aromatic. It is classified in the provided solution under aromatic compounds.

Hence the final grouping is:

  • Aromatic: (a), (c), (d), (e), (h)​​
  • Not aromatic: (b), (f), (g)

Therefore, the correct option is D.

Common mistakes

  • Counting only the number of double bonds and ignoring charges or lone pairs. This is wrong because aromaticity depends on the total π\pi-electron count. Include electrons contributed by negative charges or vacant orbitals where appropriate.

  • Calling every cyclic unsaturated compound aromatic. This is wrong because the ring must also be planar and fully conjugated. First check conjugation and planarity before applying Huckel's rule.

  • Treating anti-aromatic compounds as aromatic because they are cyclic and conjugated. This is wrong because compounds with 4n4n π\pi electrons are not aromatic in this question's classification. Distinguish (4n+2)(4n+2) from 4n4n carefully.

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