The structures for compound A and B are to be predicted. Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C 1 - C 2 bond.

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Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two Daldohexoses, 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?

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

Treatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.

Answer 2

Question

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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Answer 3

Question

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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Answer 4

Question

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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Answer 5

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

Answer 6

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

Answer 7

Chapter 28, Problem 28.27P

Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

Answer 8

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Answer 11

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

The structures for compound A and B are to be predicted. Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C 1 - C 2 bond.

Solution Summary: The author explains that the structures of D-aldopentose A and D - aldotetroses B are to be predicted.

Concept explainers

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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Chapter 28 Solutions

The structures for compound A and B are to be predicted. Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C 1 - C 2 bond.

Solution Summary: The author explains that the structures of D-aldopentose A and D - aldotetroses B are to be predicted.

Concept explainers

Interpretation: The structures for compound A and B are to be predicted. Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

Want to see the full answer?

Chapter 28 Solutions

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.