The one equivalent of the malonic ester reacted with one equivalent of 1 , 5 − dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid . Concept introduction: In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1 , 5 − dibromopentane . The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1 , 5 − dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed. In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1 , 5 − dibromopentane . The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

Question

Use the malonic ester synthesis to prepare each carboxylic acid.

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 17, Problem 71P

(a)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

(b)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

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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 17, Problem 71P

(a)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

(b)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

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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 17, Problem 71P

(a)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

(b)

Interpretation Introduction

Interpretation:

The one equivalent of the malonic ester reacted with one equivalent of 1,5−dibromopentane and two equivalents of base has to be predicted formed the unknown carboxylic acid.

Concept introduction:

In first case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the intermediate compound and a nucleophilic center is generated. The nucleophilic carbon attacks another end of 1,5−dibromopentane and a cyclic compound is formed. On hydrolysis and heating, the carboxylic acid is formed.

In second case, base initiates the reaction by abstraction of a proton from the malonic ester. Enolate anion is formed which attacks 1,5−dibromopentane. The second equivalent of base abstracts a proton from the second equivalent of malonic ester and a nucleophilic center is generated. The nucleophilic carbon attacks the previously formed compound. On hydrolysis and heating, the carboxylic acid is formed.

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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 17, Problem 71P

(a)

Interpretation Introduction