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?

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?

In the presence of an appropriate base, esters undergo self-condensation to afford the corresponding B-ketoesters as shown below. Explain in detail using reaction schemes (not mechanisms) why route C and not routes A and B would lead to the expected product. 2 x Ethyl acetate A: NaOH(aq) B: OMe- C: OEt- EtO CH3

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

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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

Trending nowThis is a popular solution!

See solution

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