MCQMediumJEE 2025Aromatic Compounds & Benzene

JEE Chemistry 2025 Question with Solution

The correct stability order of the following species/molecules is:

Three cyclic species labeled p, q and r are shown: p is cyclopropenyl anion, q is cyclopentadienyl anion, and r is cyclooctatetraene.
  • A

    q>r>pq > r > p

  • B

    r>q>pr > q > p

  • C

    q>p>rq > p > r

  • D

    p>q>rp > q > r

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: Species pp, qq and rr are to be compared for stability.

Find: The correct stability order.

The solution identifies stability using aromaticity, anti-aromaticity and resonance.

  1. Species pp is cyclopropenyl anion. It has 4π4\pi electrons, so it is anti-aromatic and therefore highly unstable.
  2. Species qq is cyclopentadienyl anion. It has 6π6\pi electrons, so it follows Hückel's rule (4n+2)π(4n+2)\pi and is aromatic, making it highly stable.
  3. Species rr is treated as more stable than the anti-aromatic species, but less stable than the aromatic species, due to relative resonance considerations.

Hence, the stability order is: q>r>pq > r > p Therefore, the correct option is A.

Aromaticity-Based Comparison

Given: The three species/molecules pp, qq and rr shown in the figure.

Find: Their decreasing order of stability.

Key idea: Aromatic compounds are especially stable because of cyclic conjugation and delocalized π\pi electrons satisfying Hückel's rule. Anti-aromatic compounds are destabilized, while non-aromatic compounds do not gain special aromatic stabilization.

From the extracted solution:

  • pp is anti-aromatic with 4π4\pi electrons.
  • qq is aromatic with 6π6\pi electrons.
  • rr is placed between qq and pp in stability.

So the final order is: q>r>pq > r > p Thus, the correct answer is A.

Common mistakes

  • Treating pp as stable only because it is cyclic is incorrect. Cyclic structure alone does not ensure stability; check the π\pi-electron count and aromatic character first.

  • Assuming every conjugated ring is aromatic is wrong. A species must satisfy Hückel's rule and maintain suitable cyclic conjugation; otherwise it may be anti-aromatic or non-aromatic.

  • Ignoring the role of charge in counting π\pi electrons leads to incorrect ordering. Include the electron contribution of the charged center before deciding whether a species is aromatic or anti-aromatic.

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