The mechanism for the elimination step in the Wohl degradation is to be drawn. Concept Introduction: In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Question

Want to see the full answer?

Answer 1

Question

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw the mechanism for the dehydration step in the Wohl degredation.

Draw the product formed when attached compound is treated with two equivalents of CH3CH2CH2CH2MgBr followed by H2O.

Draw the organic products formed in attached reaction, and indicate the stereochemistry of products that contain stereogenic centers.

Answer 2

Question

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Answer 6

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

Answer 7

Chapter 20, Problem 67P

Interpretation Introduction

Interpretation:

The mechanism for the elimination step in the Wohl degradation is to be drawn.

Concept Introduction:

In Wohl degradation, the first step is aldose carbonyl group is converted to the oxime. Then oxime is dehydrated by an acetic anhydride to give the nitrile (a cyanohydrin). The formation of cyanohydrin is reversible in nature. It undergoes a basic hydrolysis to give aldose with one less carbon with a loss of HCN molecule.

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. 20.1 - Prob. 1P Ch. 20.2 - Prob. 2P Ch. 20.2 - Prob. 3P Ch. 20.3 - Prob. 4P Ch. 20.3 - Prob. 5P Ch. 20.3 - Prob. 6P Ch. 20.4 - Prob. 7P Ch. 20.4 - Prob. 8P Ch. 20.5 - Prob. 9P Ch. 20.5 - Prob. 10P

Solution Summary: The author explains the mechanism for the elimination step in the Wohl degradation.

Concept explainers

Want to see the full answer?

Chapter 20 Solutions