Question:

Which compound amongst the following is not an aromatic compound?

Updated On: May 2, 2025
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The Correct Option is D

Solution and Explanation

To determine which compound is not aromatic, we need to check for the following criteria commonly associated with aromaticity:

  • Planarity: The molecule must be flat, allowing delocalized π-electrons to exist over the entire ring.
  • Cyclic Structure: The compound must be a closed ring of atoms.
  • Complete Conjugation: The π-electrons must form a conjugated system, indicating overlap of p-orbitals continuously around the ring.
  • Hückel's Rule: The compound must have (4n+2) π-electrons, where n is a non-negative integer (0, 1, 2, ...).

Examining the provided compound options, one of them does not meet these criteria:

The last compound, represented by the image, is not aromatic. Upon analysis:

  1. Planarity: This compound has structural elements that may prevent planarity, disrupting potential delocalization of π-electrons.
  2. Cyclic Structure: It may form a ring; however, structural irregularities lead to a loss in conjugation.
  3. Conjugation and Hückel's Rule: The disruption in planarity and incomplete overlap of p-orbitals result in the inability to satisfy the (4n+2) π-electron rule for aromatic stability.

Thus, it fails the aforementioned criteria, categorizing it as a non-aromatic compound.

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Concepts Used:

Aromatic hydrocarbon

Aromatic hydrocarbons, sometimes known as arenes, are aromatic organic molecules made up entirely of carbon and hydrogen. In aromatic compounds a benzene ring which is named after the simple aromatic chemical benzene, or a phenyl group when part of a larger structure, is the configuration of six carbon atoms.

Read More: Aromaticity

Reactions of Aromatic Hydrocarbons:

1. Aromatic Substitution Reactions

This reaction involves the replacement of one substituent on the ring of an aromatic hydrocarbon, commonly a hydrogen atom, by a different substituent group.

The common types of aromatic substitution reactions are:

  • Nucleophilic aromatic substitution reactions
  • Electrophilic aromatic substitution reactions
  • Radical nucleophilic aromatic substitution reactions

2. Coupling Reactions

In these types of reactions, the coupling of two fragments that have a radical nature is achieved with the help of a metal catalyst