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JEE MainChemistryGeneral Organic Chemistry

Consider the following two compounds: (I) [10]-annulene (II) 1,6-methano[10]annulene Which of the following statements correctly describes their aromatic character?

Options

  1. A(I) is non-aromatic, while (II) is aromatic.
  2. BBoth (I) and (II) are aromatic.
  3. C(I) is aromatic, while (II) is non-aromatic.
  4. DBoth (I) and (II) are non-aromatic.

Correct answer

A. (I) is non-aromatic, while (II) is aromatic.

Step-by-step solution

Compound (I), [10]-annulene, possesses 10 electrons which satisfies the Hückel (4n+2) rule for n=2 . However, due to severe steric repulsion between the internal hydrogen atoms, the ring cannot maintain planarity. Consequently, it lacks a continuous cyclic electron delocalisation and is non-aromatic. Compound (II), 1,6-methano[10]annulene, has the internal hydrogens replaced by a - CH ₂- bridge. This structural modification ties the ring back and removes the trans-annular steric hindrance, allowing the 10 perimeter

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