Molecules that are considered aromatic have 'special' stability.Which of the following (I - V) DO NOT satisfy the requirements for aromaticity?

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Let’s break down what it means for a molecule to be aromatic: a cyclic, planar system with continuous p-orbital overlap (full conjugation) and a total number of π electrons that fits Huckel’s rule (4n + 2, where n is a nonnegative integer).

Option I: This structure does not meet one or more of the aromaticity criteria. In particular, it lacks complete conjugation around the ring (there’s an interruption in the continuous overlap of p-orbitals), so it cannot be considered cyclic and planar with a continuous π-electron cloud. Therefore, it does not satisfy aromaticity.

Option II: Similar to I, this configuration fails to provide a fully conjugated loop around the ring system. Without uninterrupted p-orbital overlap around the entire ring, the system cannot sustain a delocalized π-electron cloud required for aromatic stability. Hence, II does not satisfy aromaticity.

Option III: This is a monocyclic ring with a continuous set of conjugated double bonds and the ring is planar, giving a delocalized π-electron cloud. The total number of π electrons fits the 4n + 2 rule for an appropriate n (n = 1 for a six-electron system, as in benzene-like rings). Thus, III is aromatic.

Option IV: This structure also presents a fully conjugated, cyclic system in which all atoms along the ring contribute p-orbitals and the electrons are delocalized around the loop. If the electron count matches 4n + 2 (e.g., six or ten π electrons depending on the exact ring fusion pattern), it will be aromatic. Therefore, IV satisfies aromaticity.

Option V: Likewise, this fused or extended ring system provides a continuous conjugated framework and, given the typical electron count for such fused aromatics (commonly 10 π electrons for naphthalene-type systems), it adheres to Huckel’s rule. Consequently, V is aromatic.

In summary, I and II fail to meet the necessary criteria for aromaticity due to interrupted conjugation, while III, IV, and V possess fully conjugated cyclic systems with the proper π-electron counts, satisfying the aromaticity requirements.

Molecules that are considered aromatic have 'special' stability.Which of the following (I - V) DO NOT satisfy the requirements for aromaticity?

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