The use of periodic acid as a distinguishing reagent between an aldohexose and a ketohexose. Further, the product formed with each of the compounds and the respective number of molar equivalents of HIO 4 consumed is also to be determined. Concept Introduction: ▸ The aldose or ketose carbon sugars that have six membered carbon atoms are referred to as aldohexoses and ketohexoses, respectively. Glucose is an example of aldohexose and fructose is an example of ketohexose. The structures of each have been described below: ▸ Furthermore, both the aldohexoses and ketohexoses undergo periodate oxidation, in order to yield different products, as a result of the cleavage of the C − C bonds.

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Chapter 22, Problem 10PP

Interpretation Introduction

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The use of periodic acid as a distinguishing reagent between an aldohexose and a ketohexose. Further, the product formed with each of the compounds and the respective number of molar equivalents of HIO4 consumed is also to be determined.

Concept Introduction:

▸ The aldose or ketose carbon sugars that have six membered carbon atoms are referred to as aldohexoses and ketohexoses, respectively. Glucose is an example of aldohexose and fructose is an example of ketohexose. The structures of each have been described below:

▸ Furthermore, both the aldohexoses and ketohexoses undergo periodate oxidation, in order to yield different products, as a result of the cleavage of the C−C bonds.

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a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D.