N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn. Concept introduction: The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

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Answer 1

Question

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

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Answer 2

Question

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

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Answer 3

Question

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

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Answer 4

Question

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

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Answer 5

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

Answer 6

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

Answer 7

Chapter 20, Problem 20.40P

Interpretation Introduction

Interpretation:

N, N-Diacylamides can be prepared by treating an acyl chloride with lithium nitride in a 3-to-1 ratio. A complete, detailed mechanism for the given reaction is to be drawn.

Concept introduction:

The nucleophilic addition-elimination mechanism has two steps. Step 1 is nucleophilic addition, in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O bond onto the O atom, which generates a negative charge on O. The product of that step is a tetrahedral intermediate, which, in Step 2, undergoes nucleophile elimination. A lone pair of electrons on the negatively charged O atom is used to regenerate the C=O double bond and the leaving group departs.

Answer 8

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Answer 11

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

Solution Summary: The author explains the nucleophilic addition-elimination mechanism for forming N, N-Diacylamides.

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