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Pi-molecular orbital diagram of Benzene. Predict whetherthe aromaticity of the followingi) Thiopheneii) Cyclobutadieneiii) Furan

Question

Pi-molecular orbital diagram of Benzene.

Predict whether the aromaticity of the following:

i) Thiophene
ii) Cyclobutadiene
iii) Furan

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Solution

i) Thiophene: Thiophene is an aromatic compound. It has a five-membered ring with four carbon atoms and one sulfur atom. The sulfur atom contributes one electron to the pi system, and the four carbon atoms contribute one electron each from their p-orbitals. This gives a total of 5 pi electrons, which satisfies Hückel's rule (4n+2, where n=1) for aromaticity.

ii) Cyclobutadiene: Cyclobutadiene is not aromatic. It has a four-membered ring with four carbon atoms, each contributing one electron to the pi system. This gives a total of 4 pi electrons, which does not satisfy Hückel's rule for aromaticity.

iii) Furan: Furan is an aromatic compound. It has a five-membered ring with four carbon atoms and one oxygen atom. The oxygen atom contributes one electron to the pi system, and the four carbon atoms contribute one electron each from their p-orbitals. This gives a total of 6 pi electrons, which satisfies Hückel's rule (4n+2, where n=1) for aromaticity.

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