JEE Main · 2024 · Shift-ImediumGOC-505

Which of the following are aromatic?

General Organic Chemistry (GOC) · Class 11 · JEE Main Previous Year Question

Question

Which of the following are aromatic? image

Options
  1. a

    B and D only

  2. b

    A and C only

  3. c

    A and B only

  4. d

    C and D only

Correct Answera

B and D only

Detailed Solution

Hückel’s rule predicts that annulenes will be aromatic if their molecules have (4n + 2) π\pi electrons and have a planar carbon skeleton. Consider the [14], [16], [18], [20], [22], and [24]annulenes as examples. Of these, as Hückel’s rule predicts, the [14], [18], and [22] annulenes (4n + 2 when n = 3, 4, 5, respectively) have been found to be aromatic. The [16] annulene and the [24] annulene are not aromatic; they are antiaromatic. They are 4n compounds, not 4n + 2 compounds. image Examples of [10] and [12] annulenes have also been synthesized and none is aromatic. We would not expect [12]annulenes to be aromatic since they have 12 π\pi electrons and do not obey Hückel’s rule. The following [10]annulenes would be expected to be aromatic on the basis of electron count, but their rings are not planar. image The [10]annulene I has two trans double bonds. Its bond angles are approximately 120 o^o; therefore, it has no appreciable angle strain. The carbon atoms of its ring, however, are prevented from becoming coplanar because the two hydrogen atoms in the center of the ring interfere with each other. Because the ring is not planar, the p orbitals of the carbon atoms are not parallel and, therefore, cannot overlap effectively around the ring to form the p molecular orbitals of an aromatic system. image

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