In 3-Methyl-2-cyclohexenone,which hydrogen ca | vedclass

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(B) Deuterium exchange in ketones occurs via the formation of an enolate ion,which requires the presence of $\alpha$-hydrogens.In $3-Methyl-2-cyclohex

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$H_4$

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(B) Deuterium exchange in ketones occurs via the formation of an enolate ion,which requires the presence of $\alpha$-hydrogens.In $3-Methyl-2-cyclohexenone$,the hydrogens at positions $H_1, H_3, H_5$ are $\alpha$-hydrogens relative to the carbonyl group or the double bond,making them acidic enough to be removed by a base.$H_2$ is part of the methyl group attached to the $sp^2$ hybridized carbon,and these hydrogens are also exchangeable due to the conjugation of the resulting enolate.$H_4$ is a $\beta$-hydrogen relative to the carbonyl group and is attached to an $sp^3$ hybridized carbon that is not adjacent to the carbonyl group,making it non-acidic and unable to form a stable enolate.Therefore,$H_4$ cannot undergo deuterium exchange.

In $3-Methyl-2-cyclohexenone$,which hydrogen cannot undergo deuterium exchange when it reacts with $CH_3O^{-} / CH_3OD$?

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