Question

Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wolf degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?

Short answer

Answer

Step-by-step solution

Aldopentose

A monosaccharide consisting of an aldehyde and five carbon atoms is termed aldopentose. A few examples of aldopentoses are arabinose and xylose.

Aldotetrose

A monosaccharide possessing four carbon atoms and an aldehyde is termed aldotetrose. Several aldotetroses are present, and one among them is the erythrose.

Identification of D-aldopentose and D-aldotetrose

Optically active aldaric acids are acquired due to the oxidation of two D-aldopentoses (A’ and A’’). The structure of the aldaric acids are given as:

Structure of the aldaric acidsCompound A’’ gets subjected to Wohl degradation forming an aldotetrose. This gets oxidized to an optically active aldaric acid. The structure of D-aldopentose is A’’. The structure can be given as:

Structure of D-aldopentoseThe structure of the aldotetrose can be given as:

Structure of aldotetrose