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.

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Answer 1

Question

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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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.

Which statement describes why aldol reactions with ketones are low yielding? A.Ketones do not have acidic protons. B.Ketones are too electron poor at the carbonyl carbon. C.Ketones can attack other ketones well but perform poorly in self-condensations. D.The product of a ketone addition to a ketone has considerable steric strain.

for the theroretical yield is the mol correct? also using the aldol condensation reaction in this portion are we using the aldol condensation reaction to synthesize acetophenone and para-methybenzaldehye. acetophenone 0.5 g, 4.2 mmol Para-methylbenzaldehyde 0.5 g, 4.2 mmol NaOH=0.18g = 4.5 mol Theroretical yield=0.93g =0.0519 mol Percent yield=76.8% Actual yield= 0.715 g Melting point observered= 93 degree Celsius Expected melting point =93-94.5 degree Celsius

Answer 2

Question

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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Answer 3

Question

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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Answer 4

Question

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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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

(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.

Answer 9

(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.

Answer 10

(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.

Answer 11

(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.

Answer 12

(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.

Answer 13

(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.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

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Chapter 17 Solutions