(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 28.26P

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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Treatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.

Which aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) D-lyxose; (c) D-galactose?

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

Answer 2

Question

Chapter 28, Problem 28.26P

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 28.26P

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 28.26P

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 28.26P

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 28.26P

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 28.26P

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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