Question

Both NaBH₄ and NaBD₄ are commercially available, and D₂O is common and inexpensive. Show how you would synthesize the following labelled compounds, starting with propanone.

Short answer

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

Step-by-step solution

Introduction

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

Reduction of ketone with NaBH4 or NaBD4  in presence of H2O or  D2O

Ketones on treatment with NaBD4 followed by hydrolysis with H20 yields a product in which the carbonyl group is reduced to hydroxyl group . Also, ketones on treatment with NaBD4 followed by hydrolysis with D20 yields a product in which the carbonyl group is reduced to hydroxyl group where D atom is present in place of H atom.

Synthesis of the given compounds from propanone (a ketone)