a) Interpretation: How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown. 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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms. Both reactions involve the same steps such as i) enolate ion formation ii) S N 2 attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation. To show How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Question

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Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

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Students have asked these similar questions

ion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐

Decide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑

Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions ΔΗ is (pick one) A This reaction is faster above 103. °C than below. AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous only above -9. °C. AS is (pick one) ΔΗ is (pick one) C The reverse of this reaction is always spontaneous. AS is (pick one) 18 Ar

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

Answer 6

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Answer 7

Chapter 22.SE, Problem 46AP

Interpretation Introduction

a)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Answer 8

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The compound shown is a derivative of carboxylic acid. Hence it can be prepared using malonic ester synthesis. The acid has two methyl groups attached to the carbon adjacent to ester groups. It can be prepared by replacing the two hydrogens on the active methylene group of malonic ester by two methyl groups. This is achieved by treating the ester with two equivalents of sodium ethoxide and two equivalents of methyl bromide.

Answer 13

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 3

Answer 14

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Answer 15

Interpretation Introduction

b)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Answer 16

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 5

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

: The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,6- dibromohexane displaces the bromide ion to produce a Î±- substituted acetoacetic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield methyl cycloheptyl ketone.

Answer 21

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 6

Answer 22

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Answer 23

Interpretation Introduction

c)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Answer 24

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 8

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The compound shown is a carboxylic acid. Hence it can be prepared using malonic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of malonic ester to yield the enolate anion. The nucleophilic attack of the anion on 1,3- dibromopropane displaces the bromide ion to produce a Î±- substituted malonic ester. The second acidic hydrogen of the ester is then removed by another ethoxide ion which is followed by the nucleophilic attack of the anion on the other carbon bearing bromine to produce a cyclic diester. Upon treating with aqueous acids the ester groups get hydrolyzed to give a dicarboxylic acid. The dicarboxylic acid eliminates a CO₂ molecule on heating to yield cyclobutylcarboxylic acid.

Answer 29

Conclusion

The compound shown can be prepared by using malonic ester synthesis.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 9

Answer 30

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.

Conclusion

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 12

Answer 31

Interpretation Introduction

d)

Interpretation:

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis is to be shown.

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. Malonic ester synthesis converts an alkyl halide to a carboxylic acid having two more carbon atoms.

Both reactions involve the same steps such as i) enolate ion formation ii) S_N² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To show

How to prepare the compound shown using either an acetoacetic ester synthesis or malonic ester synthesis.

Answer 32

Expert Solution

Answer to Problem 46AP

The compound shown can be prepared by using an acetoacetic ester synthesis as shown below.

Organic Chemistry, Chapter 22.SE, Problem 46AP , additional homework tip 11

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The compound is a methyl ketone. Hence it can be prepared using aceto acetic ester synthesis. The base ethoxide ion abstracts a proton from the active methylene group of acetoacetic ester to yield the enolate anion. The nucleophilic attack of the anion on allyl bromide displaces the bromide ion to produce Î±- allylsubstituted acetoacetic ester. Upon treating with aqueous acids the ester group gets hydrolyzed to give a Î²- ketocarboxylic acid. The ketocarboxylic acid eliminates a CO₂ molecule on heating to yield hex-5-ene-2-one.