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.

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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.

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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.

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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.

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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.

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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

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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.

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