The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed. Concept Introduction: Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Question

Describe the procedures on how will you prepare an ester.

Answer 1

Question

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Describe the procedures on how will you prepare an ester.

Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor products

Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)CH3CH2CH2CO2H(l)+CH2CH3OH(l)⟶H+CH3CH2CH2CO2CH2CH3(l)+H2O(l) A chemist ran the reaction and obtained 5.40 g of ethyl butyrate. What was the percent yield, The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.45g of butanoic acid and excess ethanol?

Answer 2

Question

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 3

Question

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 4

Question

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 5

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 6

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 7

Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 12

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Answer 23

Ch. 19.2 - Prob. 19.1P Ch. 19.2 - Prob. 19.2P Ch. 19.2 - Prob. 19.3P Ch. 19.3 - Prob. 19.4P Ch. 19.3 - Prob. 19.5P Ch. 19.3 - Prob. 19.6P Ch. 19.5 - Prob. 19.7P Ch. 19.5 - Prob. 19.8P Ch. 19.5 - Prob. 19.9P Ch. 19.6 - Prob. 19.10P

Solution Summary: The author explains that acetoacetic ester is a versatile starting material for the formation of new carbon-carbon bonds.

Chapter 19 Solutions