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 23, Problem 44P

(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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Students have asked these similar questions

Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?

1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH

Answer 2

Question

Chapter 23, Problem 44P

(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 23, Problem 44P

(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 23, Problem 44P

(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 23, Problem 44P

(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 23, Problem 44P

(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 23, Problem 44P

(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. 23.2 - Compare each of the mechanisms listed here with...Ch. 23.2 - Prob. 3P Ch. 23.2 - Prob. 4P Ch. 23.3 - a. Draw the mechanism for the following reaction...Ch. 23.5 - Prob. 7P Ch. 23.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 23.6 - Prob. 9P Ch. 23.7 - Prob. 10P Ch. 23.7 - Prob. 12P Ch. 23.7 - 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 23 Solutions