To describe how the given compound can be prepared starting from ethyl acetoacetate Concept introduction: Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below, Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis) Steps involved in acetoacetic ester synthesis are, Deprotonation of α carbon in acetoacetic ester Alkylation of enolate Hydrolysis of ester using aqueous acid Decarboxylation at high temperature

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Answer 1

Question

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

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Answer 2

Question

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

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Answer 3

Question

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Expert Solution & Answer

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See solution

Answer 4

Question

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

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Answer 5

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 6

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 7

Chapter 21, Problem 69PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 8

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 9

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 10

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 11

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared starting from ethyl acetoacetate

Concept introduction:

Acetoacetic ester synthesis is a process in which a halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyl dihalide is used for acetoacetic ester synthesis a cyclic product is expected. (Intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

Deprotonation of α carbon in acetoacetic ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

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Answer 15

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions