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Topic: para benzoquinone doesnot show tautomerism  (Read 4595 times)

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Offline sapta

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para benzoquinone doesnot show tautomerism
« on: May 08, 2006, 02:23:07 AM »
Why doesnot para benzoquinone show tautomerism despite having alpha-H atoms?One book says it's because its alpha -H atoms are attached to sp2 hybridised C atoms.But the same book says 4-pyridone shows tautomerism which has also alpha-H atoms attached to sp2 C atoms.
« Last Edit: May 08, 2006, 02:28:26 AM by sapta »
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Offline AWK

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Re: para benzoquinone doesnot show tautomerism
« Reply #1 on: May 08, 2006, 02:36:29 AM »
In benzoquinone H atom is at carbon, in pyridone at nitrogen - this is a big difference.
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Offline lemonoman

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Re: para benzoquinone doesnot show tautomerism
« Reply #2 on: May 08, 2006, 07:34:05 AM »
The tautomerized (enol) structure of pyridone is aromatic too, giving it extra stability.  This can't happen in benzoquinone.
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