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

When heated, carboxylic salts in which there is a good leaving group on the carbon beta to the carboxylate group undergo decarboxylation/elimination to give an alkene.Propose a mechanism for this type of decarboxylation/elimination. Compare the mechanism of the decarboxylations with the mechanism for decarboxylation of b-ketoacids. In what way(s) are the mechanisms similar?

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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When heated, carboxylic salts in which there is a good leaving group on the carbon beta to the carboxylate group undergo decarboxylation/elimination to give an alkene.Propose a mechanism for this type of decarboxylation/elimination. Compare the mechanism of the decarboxylations with the mechanism for decarboxylation of b-ketoacids. In what way(s) are the mechanisms similar?

H₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br за

Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. CH3 CH3 CH3 НО, НО, H,SO, + H,O HO HO Only this glycol This glycol is is formed. not formed. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?

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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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 17, Problem 17.41P

(a)

Interpretation Introduction