Question

a. If the biosynthesis of palmitic acid were carried out with ${\mathbf{CD}}_3\mathbf{COSR}$ and nondeuterated malonyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

b. If the biosynthesis of palmitic acid were carried out with ${}^{-}{\mathbf{OOCCD}}_3\mathbf{COSR}$ and nondeuterated acetyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

Short answer

1. Three deuterium
2. Seven deuterium

Step-by-step solution

Step-by-Step SolutionStep 1: Palmitic acid

The molecular formula for the palmitic acid is ${\mathbf{C}}_{16}{\mathbf{H}}_{32}{\mathbf{O}}_2$ . It is a saturated fatty acid generally found in the human body. It can also be provided by diet or carbohydrates and amino acids.

Palmitic acid is used in the preparation of soaps and cosmetics.

Deuterium atoms to be incorporated

(a)

In this process, three deuteriums to be incorporated into palmitic acid because only one ${\text{CD}}_{\text{3}}\text{COSR}$is used in the synthesis.

(b)

Seven deuteriums are to be incorporated into palmitic acid because seven ${\text{OOCCD}}_{\text{2}}\text{COSR}$ are used in the synthesis and each ${}^{-}{\text{OOCCD}}_{\text{2}}\text{COSR}$loses one deuterium in the dehydration step.