Given that the third and fourth steps in the synthesis of Hagemann’s ester from ethyl acetoacetate are intramolecular aldol cyclization to yield a substituted cyclohexenone and a decarboxylation reaction. Both reactions are to be shown and products of each step are to be shown. Concept introduction: In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic enone as the products. The reaction occurs in three steps i) Abstraction of α-hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon in the same molecule iii) Protonation of the alkoxide intermediate. A β-ketoacid normally eliminates CO 2 on heating. To show: The third and fourth steps in the synthesis of Hagemann’s ester from ethyl acetoacetate, the intramolecular aldol cyclization to yield a substituted cyclohexenone and a decarboxylation reaction and further to show the products of these reactions.

Question

> Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? esc ? A O O •If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. olo 18 Ar Explanation Check BB Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibility

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Question

Chapter 23.SE, Problem 72AP

Interpretation Introduction

Interpretation:

Given that the third and fourth steps in the synthesis of Hagemann’s ester from ethyl acetoacetate are intramolecular aldol cyclization to yield a substituted cyclohexenone and a decarboxylation reaction. Both reactions are to be shown and products of each step are to be shown.

Concept introduction:

In intramolecular aldol reactions dicarbonyl compounds such as diketones react with a base to yield a cyclic enone as the products. The reaction occurs in three steps i) Abstraction of α-hydrogen by a base to yield an enolate anion ii) Attack of the anion on the carbonyl carbon in the same molecule iii) Protonation of the alkoxide intermediate.

A β-ketoacid normally eliminates CO₂ on heating.

To show:

The third and fourth steps in the synthesis of Hagemann’s ester from ethyl acetoacetate, the intramolecular aldol cyclization to yield a substituted cyclohexenone and a decarboxylation reaction and further to show the products of these reactions.

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> Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? esc ? A O O •If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. olo 18 Ar Explanation Check BB Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibility

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> For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Substrate B Faster Rate X CI (Choose one) (Choose one) CI Br Explanation Check Br (Choose one) C 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy A F10