Question

Consider the following reaction scheme How many deuterium are present in the compound D?

Answer 1

3

Answer 2

The reaction sequence converts vinylcyclohexane to cyclohexyl methyl ketone (C). The final step involves the reaction of cyclohexyl methyl ketone with NaOD/D₂O (excess). The hydrogens on the methyl group alpha to the carbonyl are acidic and undergo exchange with deuterium from D₂O. Thus, all three hydrogens of the methyl group are replaced by deuterium, forming cyclohexyl trideuteromethyl ketone (D) with the structure C₆H₁₁-CO-CD₃. Therefore, there are 3 deuterium atoms in compound D.