The synthesis of amobarbital, using diethyl malonate and urea as the starting material has to be proposed. Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen. The anion so formed is reacted with an alkyl halide . The anion abstracts the alkyl group from the alkyl halide. On heating, decarboxylation takes place which gives the desired carboxylic acid .

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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 17, Problem 90P

Interpretation Introduction

Interpretation: The synthesis of amobarbital, using diethyl malonate and urea as the starting material has to be proposed.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide. The anion abstracts the alkyl group from the alkyl halide. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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Barbiturates are prepared by treatment of diethyl malonate or a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate an urea. Barbital is prescribed under one of a dozen or more trade names. Propose a mechanism for This reaction The pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do you account for its acidity?

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 90P

Interpretation Introduction

Interpretation: The synthesis of amobarbital, using diethyl malonate and urea as the starting material has to be proposed.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide. The anion abstracts the alkyl group from the alkyl halide. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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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 90P

Interpretation Introduction

Interpretation: The synthesis of amobarbital, using diethyl malonate and urea as the starting material has to be proposed.

Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids of the desired length. The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide. The anion abstracts the alkyl group from the alkyl halide. On heating, decarboxylation takes place which gives the desired carboxylic acid.

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 17, Problem 90P

Interpretation Introduction