Identify which of the following can exhibit t | vedclass

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(B) For a compound to exhibit keto-enol tautomerism,it must possess at least one $\alpha$-hydrogen atom attached to an $sp^3$ hybridized carbon atom a

Vedclass · Accepted Answer

$II$ only

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(B) For a compound to exhibit keto-enol tautomerism,it must possess at least one $\alpha$-hydrogen atom attached to an $sp^3$ hybridized carbon atom adjacent to the carbonyl group.In structure $(I)$,the $\alpha$-carbons are the bridgehead carbon and the carbon bearing two methyl groups. The bridgehead carbon has one hydrogen,but it is part of a fused ring system where the double bond formation (Bredt's rule) would be highly strained. The other $\alpha$-carbon is quaternary (no hydrogen).In structure $(II)$,the $\alpha$-carbons are the bridgehead carbon and the carbon adjacent to the carbonyl group. The bridgehead carbon has one hydrogen atom,which can be removed to form an enol.In structure $(III)$,both $\alpha$-carbons adjacent to the carbonyl groups are quaternary (substituted with methyl groups),meaning there are no $\alpha$-hydrogens available for tautomerization.Therefore,only structure $(II)$ can exhibit tautomerism.

Identify which of the following can exhibit tautomerism?

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