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20 August, 22:21

Draw all the plausible resonance structures of thiophene,

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  1. 21 August, 01:14
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    Here's what I find.

    Explanation:

    I get the five resonance contributors shown below.

    Except for the bottom structure, the S atom always has a + charge and the C atoms have a negative charge.

    The resonance hybrid has six π electrons, so thiophene is aromatic.

    Note that only one of the lone pairs on S is involved in the resonance system.

    The other lone pair is in an sp² orbital, which is in the plane of the ring and therefore cannot participate in resonance.
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