(a) Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted. Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C 2 of a product.

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Answer 1

Question

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

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What aldoses are formed when the following aldoses are subjected to the Kiliani-Fischer synthesis: (a) D-threose; (b) D-ribose; (c) D-galactose?

(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?

A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?

Answer 2

Question

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

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Answer 3

Question

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

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Answer 4

Question

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

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Answer 5

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 6

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 7

Chapter 28, Problem 28.25P

Interpretation Introduction

(a)

Interpretation: The aldoses formed when D-threose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 8

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 9

Interpretation Introduction

(b)

Interpretation: The aldoses formed when D-ribose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 10

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 11

Interpretation Introduction

(c)

Interpretation: The aldoses formed when D-galactose is subjected to the Kiliani–Fischer synthesis are to be predicted.

Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at C2 of a product.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

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