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

Lewis Structure, Hybridization & Molecular Geometry a) Draw the Lewis Structure of the molecules; Label the hybridization of each carbon atom; Predict the approximate molecular geometry around each carbon atom. CH3CHO CH3CN b) Draw the Lewis Structure of Nitromethane; Predict the approximate molecular geometry around the nitrogen atom. CH3NO2 c) Draw the Lewis Structure; Label the hybridization of the boron atom; Predict the approximate molecular geometry. BF3 BF4

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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Lewis Structure, Hybridization & Molecular Geometry a) Draw the Lewis Structure of the molecules; Label the hybridization of each carbon atom; Predict the approximate molecular geometry around each carbon atom. CH3CHO CH3CN b) Draw the Lewis Structure of Nitromethane; Predict the approximate molecular geometry around the nitrogen atom. CH3NO2 c) Draw the Lewis Structure; Label the hybridization of the boron atom; Predict the approximate molecular geometry. BF3 BF4

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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