Monosaccharides - Ruff Degradation - Online Tutor, Practice Problems & Exam Prep

Show that the Ruff degradation of either D-allose or D-altrose results in the formation of the same product, D-ribose.

Determine the final product when L-glucose reacts with Br₂, H₂O, then H₂O₂ and Fe₂(SO₄)_3.

The degradation of D-gulose produces D-xylose, an aldopentose. What is the furanose structure of D-xylose?

Ruff degradation of D-mannose produces D-arabinose. Ruff degradation of D-arabinose produces D-erythrose. What are the Fischer structures of D-arabinose and D-erythrose?

Ruff degradation of D-talose produces the same product as the Ruff degradation of D-galactose. D-galactose is an aldohexose and C4 epimer of glucose. What is the structure of D-talose?

Show the product that will be obtained from the reaction shown below:

(i) Draw the following reaction: The Ruff degradation of L-ribose produces L-erythrose. The Kiliani-Fischer synthesis of L-erythrose produces a mixture of L-arabinose and L-ribose.

(ii) What is the structure of L-arabinose?

A D-aldohexose sugar A undergoes oxidation with HNO₃ and an optically inactive aldaric acid is formed. When A undergoes Ruff degradation, followed by the oxidation of the resulting aldopentose, the aldaric acid formed is also optically inactive. Provide the structure of A.

In 1891, Emil Fischer used simple chemical reactions and clever reasoning about stereochemistry and symmetry to determine the structures of glucose and the seven other D-aldohexoses. He was awarded the Nobel Prize for this work in 1902. Fischer determined that D-glucose is an aldohexose and used Ruff degradations to convert it to (+)-glyceraldehyde. 

When D-galactose and D-talose undergo Ruff degradation, they produce the same aldopentose product, D-lyxose. When oxidized with nitric acid, D-lyxose produces an optically active aldaric acid. Provide the two possible structures for D-lyxose.

Identify whether the following observation is inconsistent with the concept that optically inactive reactants cannot produce optically active products:

When D-galactose oxidizes with HNO₃, an optically inactive aldaric acid is formed. When it undergoes Ruff degradation and the pentose formed also undergoes oxidation, an optically active aldaric acid is produced.

D-talose undergoes two cycles of Ruff degradation to form an aldotetrose. Draw the structure of the aldotetrose formed. Will the oxidation of the aldotetrose with HNO₃ form an optically active aldaric acid?

In 1891, Emil Fischer used simple chemical reactions and clever reasoning about stereochemistry and symmetry to determine the structures of glucose and the seven other D-aldohexoses. He was awarded the Nobel Prize for this work in 1902. Fischer determined that D-glucose is an aldohexose and used Ruff degradations to convert it to (+)-glyceraldehyde. 

When D-xylose undergoes Ruff degradation, it produces the aldopentose D-threose. When oxidized with nitric acid, D-threose produces an optically active aldaric acid. Give the structure for D-threose.