To describe how the given compound can be prepared using acetoacetic ester synthesis Concept introduction: Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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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Record the amounts measured and calculate the percent yield for Part 2 in the table below. Dicyclopentadiene measured in volume Cyclopentadiene measured in grams 0 Measured Calculated Mol Yield Mass (g) or Volume (mL) Mass (g) or Volume (ml) 0.6 2.955 Part 2 Measurements and Results Record the amounts measured and calculate the percent yield for Part 2 in the table below. 0.588 0.0044 2.868 0.0434 N/A Table view List view Measured Calculated Mol $ Yield Melting Point (C) Mass (g) or Volume (ml) Mass (g) or Volume (ml.) Cyclopentadiene 0.1 0.08 0.001189 measured in volume Maleic Anhydride 0.196 N/A cis-norbornene-5,6-endo- dicarboxylic anhydride 0.041 0.0002467 N/A N/A N/A 0.002 N/A N/A 128

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Answer 2

Question

Chapter 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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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See solution

Answer 3

Question

Chapter 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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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Check out a sample textbook solution

See solution

Answer 5

Chapter 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 21.5, Problem 33PTS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 13

(d)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an 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 alkyldihalide 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 14

Expert Solution & Answer

Answer 15

Expert Solution & Answer

Answer 16

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Answer 17

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 - APPLY the skill As with aldehydes and ketones, the...Ch. 21.1 - Draw the enolate ion that is formed when each of...Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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