Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β − k e t o a c i d Concept introduction: Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below, If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation . Simple carboxylic acids do not decarboxylate readily. Decarboxylation of β − k e t o a c i d is shown below, The mechanism of thermal decarboxylation involves two processes, (i) Redistribution of electrons in a cyclic transition state. (ii) Cyclic transition state possesses keto-enol tautomerism.

Question

Predict the product formed when the compound shown below undergoes a reaction with MCPBA in CH2Cl2. MCPBA is meta-chloroperoxybenzoic 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 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

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Predict the product formed when the compound shown below undergoes a reaction with MCPBA in CH2Cl2. MCPBA is meta-chloroperoxybenzoic acid.

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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 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

Expert Solution & Answer

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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 17.41P

(a)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

The mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

(b)

Interpretation Introduction

Interpretation: Mechanism for the given type of decarboxylation reaction has to be proposed and it should be compared with the mechanism of decarboxylation of β−ketoacid

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

If carboxylic acid is heated to a very high temperature then of carbon dioxide will be eliminated from it this reaction is known as decarboxylation. Simple carboxylic acids do not decarboxylate readily.

Decarboxylation of β−ketoacid is shown below,

Simply the mechanism of thermal decarboxylation involves two processes,

(i) Redistribution of electrons in a cyclic transition state.

(ii) Cyclic transition state possesses keto-enol tautomerism.

Expert Solution & Answer

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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 17.41P

(a)

Interpretation Introduction