The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn. Concept introduction: Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place. Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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Answer 1

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Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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Answer 2

Question

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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Answer 3

Question

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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Answer 4

Question

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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Answer 5

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

Answer 6

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

Answer 7

Chapter 20, Problem 20.3YT

Interpretation Introduction

Interpretation:

The detailed mechanism for the reverse of the reaction in Equation 20-1 is to be drawn.

Concept introduction:

Transesterification reaction is the one in which one ester is converted to another. A typical reaction involves a nucleophile and a carboxylic acid derivative. It is called a nucleophilic addition–elimination mechanism, which describes the two steps that take place.

Step 1 is a nucleophilic addition in which a nucleophile attacks the electron poor carbonyl carbon. This forces the pair of electrons from the initial C=O to oxygen atom, which generates a negative charge in it. 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 as methoxide ion.

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 the reverse of the reaction in Equation 20-1.

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