a) Interpretation: The preparation of the compound shown using acetoacetic ester synthesis is to be given. Concept introduction: Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S N 2 attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation. To give: The preparation of the compound shown using acetoacetic ester synthesis.

Question

Indicate how the following compounds can be synthesized from cyclohexanone and any other necessary reagents:

Answer 1

Question

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

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Indicate how the following compounds can be synthesized from cyclohexanone and any other necessary reagents:

What reagents are needed to carry out the following syntheses?

Predict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+

Answer 2

Question

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

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Answer 3

Question

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

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Answer 4

Question

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

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Answer 5

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Answer 6

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Answer 7

Chapter 22.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Answer 8

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Answer 9

Interpretation Introduction

b)

Interpretation:

The preparation of the compound shown using acetoacetic ester synthesis is to be given.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To give:

The preparation of the compound shown using acetoacetic ester synthesis.

Answer 10

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Answer 21

Ch. 22.1 - Prob. 1P Ch. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3P Ch. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5P Ch. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7P Ch. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P

Solution Summary: The author explains how acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons.

Chapter 22 Solutions