The given substituted acetic acid has to be prepared using malonic ester synthesis. Concept Introduction: Malonic 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

Provide an explanation (in detail) on how base catalysts speed up nucleophilic reactions of carbonyl compounds.

Answer 1

Question

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 2

Question

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic 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 malonic ester is a versatile starting material for the formation of new carbon-carbon bonds.

Chapter 19 Solutions