Question

What compound is formed when a dilute solution of cyclohexanone is shaken with NaOD in${\mathbf{D}}_2\mathbf{O}$ for several hours?

Short answer

The compound formed when a dilute solution of cyclohexanone is treated with NaOD in ${\mathrm{D}}_2\mathrm{O}$is as follows.

Step-by-step solution

Step-by-Step SolutionStep 1: Use of strong base to remove α hydrogens

A strong base is needed for removing hydrogens as it abstracts protons present at $\mathbf{\alpha }$ carbons of carbonyl compounds. For example, NaOD is a catalytic sodium deuteroxide. This base removes all the hydrogens present at$\alpha$ carbon and replaces them with a deuterium atom.

Step 2: Cyclohexanone, when shaken with NaOD in D2O

When a dilute cyclohexanone solution is treated with catalytic sodium deuteroxide (NaOD) in ${\text{D}}_{\text{2}}\text{O}$, the ${}^{\text{-}}\text{OD}$acts as a base that removes all the $\alpha$hydrogen present in the cyclohexanone ring and replace it with a deuterium atom, there are two $\mathrm{\alpha }$carbons of the carbonyl group present, one is on the left side, and the other is on the right side. The reaction is as follows.

Cyclohexanone, when shaken with NaOD in${\text{D}}_{\text{2}}\text{O}$