a) Interpretation: The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated. 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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation. To state: The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Question

Part II. count the expected number of signals in the 1H-NMR spectrum of these compounds HO 0 одев * Cl -cl "D"

Answer 1

Question

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

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Part II. count the expected number of signals in the 1H-NMR spectrum of these compounds HO 0 одев * Cl -cl "D"

Part I. Create a splitting tree diagram to predict the multiplet pattern of proton Hb in the compound below: 3 (Assume that "Jab >>> ³JbC) Ha Hb He он Ha NH2 Ha HC

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Answer 2

Question

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

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Answer 3

Question

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

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Answer 4

Question

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

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Answer 5

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

Answer 6

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Answer 7

Chapter 22.7, Problem 13P

Interpretation Introduction

a)

Interpretation:

The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps i) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.

Answer 8

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.

Answer 9

Interpretation Introduction

b)

Interpretation:

The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.

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 alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by 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

Chapter 22 Solutions