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NCERT Exemplar · Q18

Q.Examine the four structures given as the options below and select the one(s) that are aromatic. (More than one option may be correct.)

(i) Cyclopropenyl cation, C3H3(+): a three-membered carbon ring containing one C=C double bond, with a positive charge (empty p-orbital) on the third carbon.
(ii) Cyclobutadiene: a four-membered carbon ring containing two C=C double bonds (drawn in a bent, non-planar shape).
(iii) Biphenyl, C6H5-C6H5: two benzene rings joined to each other by a single carbon-carbon bond.
(iv) Cyclopropenyl anion, C3H3(-): a three-membered carbon ring containing one C=C double bond, with a lone pair and a negative charge on the third carbon.
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Aromaticity is decided by Huckel's rule: a cyclic, planar, fully conjugated ring is aromatic only when it contains (4n+2) pi electrons. Counting pi electrons, the cyclopropenyl cation has 2 and biphenyl's rings have 6 each, so both are aromatic; cyclobutadiene and the cyclopropenyl anion each have 4 pi electrons (a 4n count) and are antiaromatic, i.e. not aromatic.

Concept - Huckel's rule

A species is aromatic when it is (1) cyclic, (2) planar, (3) has every ring atom carrying an unhybridised p-orbital so the pi cloud is continuous, and (4) contains (4n+2) pi electrons where n = 0, 1, 2, ... A conjugated, planar ring that instead holds 4n pi electrons is antiaromatic and is actually destabilised.

Counting pi electrons in each structure

  1. Cyclopropenyl cation, C3H3(+): the three-membered ring has one C=C double bond (2 pi electrons) and an empty p-orbital on the positively charged carbon. Total = 2 pi electrons = 4n+2 with n = 0 -> aromatic.
  2. Cyclobutadiene: the four-membered ring has two C=C double bonds = 4 pi electrons = 4n with n = 1 -> antiaromatic -> not aromatic. …

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