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

3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ

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 18, Problem 79P

(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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ

2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O

4. For the reactions below, draw the expected product. Be sure to indicate relevant stereochemistry or formal charges in the product structure. a) CI, H e b) H lux ligh Br 'H

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 18, Problem 79P

(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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 18, Problem 79P

(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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 18, Problem 79P

(a)

Interpretation Introduction