Which of the following compounds does not und | vedclass

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(D) Base-catalyzed exchange of $\alpha$-hydrogen with $D_2O$ requires the formation of an enolate intermediate. The enolate must be able to achieve a

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Both $(b)$ and $(c)$

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(D) Base-catalyzed exchange of $\alpha$-hydrogen with $D_2O$ requires the formation of an enolate intermediate. The enolate must be able to achieve a planar geometry at the $\alpha$-carbon to stabilize the negative charge through resonance with the carbonyl group. In bicyclic systems like bicyclo[$2.2$.$1$]heptan$-2-$one and camphor,the $\alpha$-hydrogens at the bridgehead position or those constrained by the rigid bicyclic framework cannot form a stable,planar enolate due to Bredt's rule,which prohibits the formation of a double bond at a bridgehead position in small bicyclic systems. Therefore,these compounds do not undergo base-catalyzed exchange.

Which of the following compounds does not undergo base-catalyzed exchange in $D_2O$ even though it has an $\alpha$-hydrogen?

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