The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained. Concept introduction: The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature. To explain: The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

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Answer 1

Question

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

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Answer 2

Question

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 5

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Answer 6

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Answer 7

Chapter 23.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.

Concept introduction:

The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.

To explain:

The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author explains the difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and

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