Why does cyclohex-2,5-dien-1,4-dione doesnt exhibit tautomerism?
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Tautomerism essentially requires the presence of α-hydrogen (the hydrogen atom present generally adjacent to the functional group, or the hydrogen atom present on the carbon which is adjacent to the carbon attached to the functional group).
Quinone has an α-hydrogen, however, its a vinylic hydrogen(hydrogen attached to a carbon atom which is sp2 hybridized), its very difficult to abstact such a hydrogen, and hence it becomes very less acidic. Therefore, no abstraction of α-hydrogen from it, by a base, hence, it does not show tautomerism
Quinone has an α-hydrogen, however, its a vinylic hydrogen(hydrogen attached to a carbon atom which is sp2 hybridized), its very difficult to abstact such a hydrogen, and hence it becomes very less acidic. Therefore, no abstraction of α-hydrogen from it, by a base, hence, it does not show tautomerism
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Step-by-step explanation:
Only those compounds which have atleast an alpha hydrogen show tautomerism. But that's not the only requirement, we need to see some more factors. In this case, although Quinone has an alpha hydrogen, but it is attached to a sp2 hybridised Carbon which makes it difficult to remove it, hence, effectively there is no such phenomenon called tautomerism.
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