Chapter 24, Problem 44P

Interpretation Introduction

Interpretation:

Given the structure of the substrate Compound A, the structural formula, including stereochemistry, of the product of oxidation with periodic acid, Compound B, ${\text{C}}_{\text{7}}{\text{H}}_{\text{12}}{\text{O}}_{\text{4}}$, is to be determined. The structural formula, including stereochemistry, of Compound C, ${\text{C}}_4{\text{H}}_8{\text{O}}_{\text{4}}$, formed on hydrolysis of Compound B is to be determined. The structural formula, including stereochemistry, of the product Compound D, ${\text{C}}_{\text{4}}{\text{H}}_{\text{6}}{\text{O}}_{\text{4}}$, obtained by the oxidation of C with bromine in water is to be determined.

Concept introduction:

Periodic acid oxidizes $\text{1, 2-difunctional}$ groups likevicinal diols, replacing the carbon-carbon bond with a hydroxyl group. If a hydroxyl group is already present on the oxidized carbon, the resulting geminal diol loses a molecule of water to form a carbonyl group.

Acid hydrolysis of cyclic acetals yields geminal diols, with the hydroxyl groups on the same side.

Bromine oxidizes the cyclic form of carbohydrates to a lactone ring.