Organic Chemistry III

Professor Carl C. Wamser

Chem 336 - Spring 2007

Chapter 21 Skills

Ester Enolates

Knowledge - Level 1

know the terminology:

Claisen condensation
Dieckmann condensation
acetoacetic ester, malonic ester
barbiturates
alkylation, acylation
LDA


Concepts - Level 2

recognize the acidity of beta-dicarbonyl compounds and their enolates as nucleophiles


Applications - Level 3

predict products of Claisen condensations, including cases of intramolecular or mixed condensations

predict products from malonic ester or acetoacetic ester syntheses


Analytical Skills - Level 4

write mechanisms for base-catalyzed Claisen condensations


Synthetic Skills - Level 5

create a synthetic sequence to prepare a given target molecule
especially using Claisen condensations or the malonic or acetoacetic ester syntheses