Chapter 21.6, Problem 18P

Interpretation Introduction

Problem 21.18

The $\text{p}{K}_{\text{a}}\text{'}\text{s}$ of ethyl acetoacetate and diethyl malonate are $11$ and $13$, respectively. Write a structural formula for the most stable enolate of each using resonance to show the electron delocalization in each enolate.

Interpretation:

The structural formulas for the most stable enolate of ethyl acetoacetate and diethyl malonate is to be drawn and by considering the resonance the delocalization of electrons in each enolate is to be shown.

Concept Introduction:

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Enol refers to an intermediate structure that consists of an alkene group connected with a hydroxyl group at one end of its double bond. The removal of an alpha hydrogen atom from aldehyde or ketone forms enolate ion.

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Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.