Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17, Problem 65P

(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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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?
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Chapter 17 Solutions

Organic Chemistry (8th Edition)

Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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