Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials. Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

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Answer 1

Question

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

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Answer 2

Question

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

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Answer 3

Question

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

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Answer 4

Question

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

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Answer 5

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 6

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 7

Chapter 18, Problem 85P

(a)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 8

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 9

(b)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 10

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 11

(c)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 12

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 13

(d)

Interpretation Introduction

Interpretation: Hagemann’s ester is to be prepared by the use of a mixture of ethyl acetoacetate and formaldehyde as starting materials.

Concept introduction: The reaction of preparation of Hagemann’s ester follows a series of steps. In first step, a base abstracts a proton from the α carbon atom of ethyl acetoacetate. Enolate ion is formed. An aldol-like condensation reaction occurs. In second step, an α, β unsaturated compound undergoes a Michael addition reaction with ethyl acetoacetate. In third step, the product of Michael addition reaction undergoes intramolecular aldol addition reaction. In last step, the cyclic aldol addition product undergoes dehydration and a hydrolysis followed by decarboxylation to form the Hagemann’s ester.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 18.1 - Prob. 1P Ch. 18.1 - Prob. 2P Ch. 18.1 - Prob. 3P Ch. 18.1 - Prob. 4P Ch. 18.1 - PROBLEM 5♦ List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8P Ch. 18.4 - Prob. 9P Ch. 18.4 - Prob. 10P

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