Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 18, Problem 62P

(a)

Interpretation Introduction

Interpretation: The product of Perkin condensation has to be written

Concept introduction: For the given condensation reactions,

In first case, acetic anhydride is treated with a base and a proton is abstracted.  The enolate ion thus formed attacks carbonyl carbon of benzaldehyde.  Loss of water molecule results in the formation of the product of Perkin condensation.

In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.

In third case, diethyl malonate is treated with a base and enolate ion is formed.  Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species.  Loss of a water molecule results in the formation of the product of Knoevenagel reaction.

In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.

(b)

Interpretation Introduction

Interpretation: The compound formed after addition of water to the product of Perkin condensation has to be written.

Concept introduction: For the given condensation reactions,

In first case, acetic anhydride is treated with a base and a proton is abstracted.  The enolate ion thus formed attacks carbonyl carbon of benzaldehyde.  Loss of water molecule results in the formation of the product of Perkin condensation.

In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.

In third case, diethyl malonate is treated with a base and enolate ion is formed.  Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species.  Loss of a water molecule results in the formation of the product of Knoevenagel reaction.

In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.

(c)

Interpretation Introduction

Interpretation: The product of Knoevenagal condensation has to be written

Concept introduction: For the given condensation reactions,

In first case, acetic anhydride is treated with a base and a proton is abstracted.  The enolate ion thus formed attacks carbonyl carbon of benzaldehyde.  Loss of water molecule results in the formation of the product of Perkin condensation.

In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.

In third case, diethyl malonate is treated with a base and enolate ion is formed.  Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species.  Loss of a water molecule results in the formation of the product of Knoevenagel reaction.

In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.

(d)

Interpretation Introduction

Interpretation: A compound formed after product of Perkin condensation is heated in an acidic medium has to be written

Concept introduction: For the given condensation reactions,

In first case, acetic anhydride is treated with a base and a proton is abstracted.  The enolate ion thus formed attacks carbonyl carbon of benzaldehyde.  Loss of water molecule results in the formation of the product of Perkin condensation.

In second case, water is added to the product of Perkin condensation and it causes hydrolysis of the ester to form an acid.

In third case, diethyl malonate is treated with a base and enolate ion is formed.  Enolate ion attacks a molecule of benzaldehyde and forms an intermediate species.  Loss of a water molecule results in the formation of the product of Knoevenagel reaction.

In fourth case, the product of Knoevenagel reaction on acidic hydrolysis gives carboxylic acid and on heating undergoes decarboxylation.

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Students have asked these similar questions
There are other condensation reactions similar to the aldol and Claisen condensations:a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkincondensation: b. What compound is formed if water is added to the product of a Perkin condensation?c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no a-hydrogens and a compound such as diethyl malonatethat has an a-carbon flanked by two electron-withdrawing groups. Draw the product obtained from the following Knoevenagel condensation: d. What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?
There are other condensation reactions similar to the aldol and Claisen condensations: a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation
The Knoevenagel condensation reaction is a variant of the aldol reaction. A major drawback of the aldol reaction is self-aldehyde condensation. Identify the starting material in the Knoevenagel reaction that suppresses self-condensation and explainyour choice.

Chapter 18 Solutions

Organic Chemistry

Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
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