Chapter 24, Problem 24.50AP

Interpretation Introduction

Interpretation:

The structure of compound X formed by the reaction of $\text{D-ribose-5-phosphate}$ with $\text{NaB}{\text{H}}_{\text{4}}$ and $\text{HI}{\text{O}}_{\text{4}}$ is to be stated.

Concept Introduction:

Sodium borohydride is a reducing agent which reduces carbonyl group to the alcohol group. Ribitol and Xylitol are both five carbon alditols. Periodic acid is a strong oxidizing agent which converts alcohol functional group to carbonyl functional group.

Answer:

The structure of X is shown below.

Explanation:

As X gives ribitol and xylitol on reduction with sodium borohydride, so, the oxidation of both alditols performed at carbon $-3$ will form the compound X. On performing oxidation of X with periodic acid two equivalents of formaldehyde are formed. The structure of X is shown below.

Figure 1

Conclusion:

The structure of compound X is shown in Figure 1.