A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided. Concept introduction: By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O . Under these acidic conditions, no strong base should appear.

Question

Want to see the full answer?

Answer 1

Question

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Propose a mechanism for the following reaction and develop it.

When a 1,5-diketone is treated with acid, a 2,6-dialkyl pyran is produced, as shown here. Propose a mechanism for this reaction.

The treatment of a nitrile with cyanide yields an a- aminomalononitrile, as shown here in the reaction. Provide a detailed mechanism for this reaction. CN NaCN EN HCN -NH2 ČN An a-aminomalononitrile

Answer 2

Question

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Answer 6

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

Answer 7

Chapter 18, Problem 18.86P

Interpretation Introduction

Interpretation:

A detailed mechanism for the reaction, in which, treatment of a nitrile with base followed by acid hydrolysis yields a β-keto nitrile as shown, is to be provided.

Concept introduction:

By counting the carbons, we can see that two molecules of the nitrile are joined by an Aldol-type reaction. α-Carbon of one nitrile is attached to the terminal C1 of the other nitrile molecule. In the mechanism, ethoxide removes an α- proton from the nitrile to make a carbanion nucleophile. The carbanion nucleophile attacks another molecule of nitrile. Under these basic conditions, no strong acid should appear. Upon addition of acid, a C=N group is formed, which is hydrolysed to make C=O. Under these acidic conditions, no strong base should appear.

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. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains how a detailed mechanism for formation of -keto nitrile is provided with the help of Aldol type reaction and acid hydrolysis.

Concept explainers

Videos

Want to see the full answer?

Chapter 18 Solutions