The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose. Concept introduction: The Wohl degradation : D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound. To find : open-chain form twoaldohexoses(a).

Question

Want to see the full answer?

Answer 1

Question

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Identify each chiral carbon as either R or S. Identify the overall carbohydrates as L or D

Ethers can be formed via acid-catalyzed acetal formation. Draw the mechanism for the molecule below and ethanol.

HOCH, H HO CH-OH OH H OH 11 CH₂OH F II OH H H 0 + H OH

Answer 2

Question

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Answer 6

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Answer 7

Chapter 24, Problem 64PP

Interpretation Introduction

Interpretation:

The open-chain form two aldohexoses should be identified which undergoes Wohl degradation to yield D-ribose.

Concept introduction:

The Wohl degradation: D-glucose is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded pentaacetyl glycononitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.

To find: open-chain form twoaldohexoses(a).

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 24.2 - Prob. 1CC Ch. 24.2 - Prob. 2CC Ch. 24.2 - Prob. 3CC Ch. 24.2 - Prob. 4CC Ch. 24.2 - Prob. 5CC Ch. 24.2 - Prob. 6CC Ch. 24.4 - Prob. 7CC Ch. 24.4 - Prob. 8CC Ch. 24.5 - Prob. 1LTS Ch. 24.5 - Prob. 9PTS

Want to see the full answer?

Chapter 24 Solutions