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 17, Problem 89P

(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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What is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones? a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water. b. The rate of reaction in base catalyzed process is slower than acid catalyzed process. c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound. d. Only 1 and 3 are correct.

9. What type of product results when an aldehyde undergoes an aldol reaction with heat? a. conjugated diene b. B-hydroxy aldehyde c. a,ß-unsaturated aldehyde d. B-ketoester

1. Give the synthetic route.

Answer 2

Question

Chapter 17, Problem 89P

(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 17, Problem 89P

(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 17, Problem 89P

(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 17, Problem 89P

(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 17, Problem 89P

(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 17, Problem 89P

(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. 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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