To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents Concept introduction: Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis) Steps involved in malonic ester synthesis are, Deprotonation of α carbon in malonic acid ester Alkylation of enolate Hydrolysis of ester using aqueous acid Decarboxylation at high temperature The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents, Ester=carboxylic acid + alcohol Alchol=reduction of carboxylic acid Amide=Reaction with ammonia To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

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 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

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Name the molecules & Identify any chiral center CH3CH2CH2CHCH₂CH₂CH₂CH₂ OH CH₂CHCH2CH3 Br CH3 CH3CHCH2CHCH2CH3 CH3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).

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 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

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 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 6

Chapter 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 7

Chapter 22.5, Problem 36ATS

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 10

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 11

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using malonic ester synthesis starting from diethyl malonate and other reagents

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic 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 malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

The formed carboxylic acid can be converted into carboxylic acid derivatives by reaction with respective reagents,

Ester=carboxylic acid + alcohol

Alchol=reduction of carboxylic acid

Amide=Reaction with ammonia

To describe : To describe how the given compound can be synthesized using diethyl malonate and other reagent.

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

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Check out a sample textbook solution

See solution

Answer 15

Ch. 22.1 - Prob. 1CC Ch. 22.1 - Prob. 2CC Ch. 22.1 - Prob. 3CC Ch. 22.1 - Prob. 1LTS Ch. 22.1 - Prob. 4PTS Ch. 22.1 - Prob. 5ATS Ch. 22.1 - Prob. 6CC Ch. 22.1 - Prob. 7CC Ch. 22.1 - Prob. 8CC Ch. 22.2 - Prob. 9CC

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Chapter 22 Solutions