The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed. Concept introduction: Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction. Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton. Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton. Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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Answer 1

Question

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO

b. H3C CH3 H3O+ ✓ H OH

2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3

Answer 2

Question

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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Answer 3

Question

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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Answer 4

Question

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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Answer 5

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

Answer 6

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

Answer 7

Chapter 22, Problem 43P

(a)

Interpretation Introduction

Interpretation:

The mechanism of decarboxylation of α-keto acids in presence of 3-amino-2-oxindole has to be proposed.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The possibility of 3-aminoindole over 3-amino-2-oxindole as effective catalyst has to be predicted.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton.

Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removing a proton.

Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3P Ch. 22.2 - Prob. 4P Ch. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7P Ch. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9P Ch. 22.7 - Prob. 10P Ch. 22.7 - Prob. 12P Ch. 22.7 - Prob. 13P

Solution Summary: The author explains the mechanism of decarboxylation of -keto acids in presence of 3-amino-2-oxindole.

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Chapter 22 Solutions