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
- A(I) is non-aromatic, while (II) is aromatic.
- BBoth (I) and (II) are aromatic.
- C(I) is aromatic, while (II) is non-aromatic.
- 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