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 $\text{α}$ carbon atom of ethyl acetoacetate.  Enolate ion is formed.  An aldol-like condensation reaction occurs. In second step, an $\text{α,}\text{β}$ 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 $\text{α}$ carbon atom of ethyl acetoacetate.  Enolate ion is formed. An aldol-like condensation reaction occurs.  In second step, an $\text{α,}\text{β}$ 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 $\text{α}$ carbon atom of ethyl acetoacetate.  Enolate ion is formed.  An aldol-like condensation reaction occurs.  In second step, an $\text{α,}\text{β}$  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 $\text{α}$ carbon atom of ethyl acetoacetate.  Enolate ion is formed.  An aldol-like condensation reaction occurs.  In second step, an $\text{α,}\text{β}$ 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.