Chapter 3, Problem 33P

Interpretation Introduction

Interpretation:

The syntheses of the given organic compounds from the unlabeled compounds are to be determined.

Concept Introduction:

Labeling is used to identify particular hydrogen atom. The isotopes of hydrogen, deuterium and tritium with atomic mass 2 and 3 amu respectively, are usually used.

Acetanide is synthesized by reacting with strong base sodamide. The acetylene proton is highly acidic and is deprotonated in presence of sodamide, to give corresponding sodium salt of phenylacetylene which is a strong base. This in turn is treated with ${\text{T}}_2\text{O}$ which acts as a strong base to give the tritium labeled product.

Sodium hydride is used to synthesize the strong base alkoxide which reacts with ${\text{D}}_2\text{O}$ to give deuterated alcohol. Sodium hydride reacts with 2-propanol and undergoes electrophilic substitution of the proton with sodium. Sodium isopropoxide reacts with deuterium oxide and forms isopropyl alcohol with deuterium.

Sodium hydride is used to synthesize the strong base alkoxide which reacts with ${\text{D}}_{\text{2}}\text{O}$ to give deuterated alcohol