It is to be shown how to synthesize hexan-1-one from acetoacetic ester. Concept introduction: In case of active methylene compounds, the protons on the α CH 2 group, which is flanked between the two electron-withdrawing groups, are significantly more acidic than normal ketones and esters. It is because the formed enolate conjugate base is stabilized by resonance as well as inductive effect. This negatively charged enolate anion is highly nucleophilic and reacts with electrophiles. This enolate anion reacts with an alkyl halide to produce the alkylated product via S N 2 reaction. An ester on acid or base-catalyzed hydrolysis produces corresponding carboxylic acid . β-Keto acid, on heating, undergoes decarboxylation reaction to produce corresponding keto compound and gaseous carbon dioxide ( CO 2 ) is liberated from the solution.

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Answer 1

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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 21, Problem 21.30P

Interpretation Introduction

Interpretation:

It is to be shown how to synthesize hexan-1-one from acetoacetic ester.

Concept introduction:

In case of active methylene compounds, the protons on the αCH2 group, which is flanked between the two electron-withdrawing groups, are significantly more acidic than normal ketones and esters. It is because the formed enolate conjugate base is stabilized by resonance as well as inductive effect. This negatively charged enolate anion is highly nucleophilic and reacts with electrophiles. This enolate anion reacts with an alkyl halide to produce the alkylated product via SN2 reaction. An ester on acid or base-catalyzed hydrolysis produces corresponding carboxylic acid. β-Keto acid, on heating, undergoes decarboxylation reaction to produce corresponding keto compound and gaseous carbon dioxide (CO2) is liberated from the solution.

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Answer 2

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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 21, Problem 21.30P

Interpretation Introduction

Interpretation:

It is to be shown how to synthesize hexan-1-one from acetoacetic ester.

Concept introduction:

In case of active methylene compounds, the protons on the αCH2 group, which is flanked between the two electron-withdrawing groups, are significantly more acidic than normal ketones and esters. It is because the formed enolate conjugate base is stabilized by resonance as well as inductive effect. This negatively charged enolate anion is highly nucleophilic and reacts with electrophiles. This enolate anion reacts with an alkyl halide to produce the alkylated product via SN2 reaction. An ester on acid or base-catalyzed hydrolysis produces corresponding carboxylic acid. β-Keto acid, on heating, undergoes decarboxylation reaction to produce corresponding keto compound and gaseous carbon dioxide (CO2) is liberated from the solution.

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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 21, Problem 21.30P

Interpretation Introduction

Interpretation:

It is to be shown how to synthesize hexan-1-one from acetoacetic ester.

Concept introduction:

In case of active methylene compounds, the protons on the αCH2 group, which is flanked between the two electron-withdrawing groups, are significantly more acidic than normal ketones and esters. It is because the formed enolate conjugate base is stabilized by resonance as well as inductive effect. This negatively charged enolate anion is highly nucleophilic and reacts with electrophiles. This enolate anion reacts with an alkyl halide to produce the alkylated product via SN2 reaction. An ester on acid or base-catalyzed hydrolysis produces corresponding carboxylic acid. β-Keto acid, on heating, undergoes decarboxylation reaction to produce corresponding keto compound and gaseous carbon dioxide (CO2) is liberated from the solution.

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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 21, Problem 21.30P

Interpretation Introduction