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Aromaticity

Mediumchemistry

For a planar cyclic molecule with a continuous ring of overlapping p orbitals, what number of delocalised pi electrons satisfies the Huckel criterion for aromaticity?

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About This Question

Subject
chemistry
Chapter
some basic principles of organic chemistry
Topic
aromaticity
Difficulty
Medium
Year
2025
Tags
aromaticityHuckel rule4n+2 electronsplanar conjugationdelocalised pi system

Solution

Correct Answer:

Aromaticity requires a cyclic, planar, fully conjugated system whose delocalised pi electrons number 4n + 2, where n is a non-negative integer; this is the Huckel rule. Testing the choices, six electrons correspond to n = 1, since 4(1) + 2 = 6, exactly satisfying the rule, which is why benzene with its six pi electrons is the archetypal aromatic molecule. Four pi electrons fit 4n with n = 1 and represent an antiaromatic count, the opposite of aromatic stabilisation, so that option is wrong. Eight pi electrons also equal 4n with n = 2, again antiaromatic rather than aromatic. Five pi electrons is an odd number that fits neither the aromatic nor a closed-shell pattern and cannot satisfy 4n + 2. Hence six delocalised pi electrons is the correct aromatic count, matching the NCERT description of benzene-like stability. Aromatic systems show enhanced thermodynamic stability, reduced reactivity toward addition, and a preference for substitution reactions that preserve the closed pi shell. The same 4n + 2 test extends to charged rings and heterocycles once their pi electrons, including relevant lone pairs, are counted correctly. Plausibility check: substituting n = 1 into 4n + 2 directly yields six, the smallest aromatic number beyond the trivial case, confirming the answer.

This medium difficulty chemistry question is from the chapter some basic principles of organic chemistry, covering the topic of aromaticity. It appeared in the 2025 exam.

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