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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What is the [OH⁻] of a 1.80 M solution of pyridine (C₅H₅N, Kb = 1.70 × 10⁻⁹)?

What is the percent ionization in a 0.260 M solution of formic acid (HCOOH) (Ka = 1.78 × 10⁻⁴)?

Determine the pH of solution of HC3H5O2 By constructing an ICE table writing the equilibrium constant expression, and using this information to determine the pH. The Ka of HC3H5O2 is 1.3 x 10-5

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

Want to see the full answer?

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

Want to see the full answer?

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

Want to see the full answer?

Check out a sample textbook solution

See solution

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

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. 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

Want to see the full answer?

Chapter 23 Solutions