Chem 335 - Winter 2000
Organic Chemistry II
Dr. Carl C. Wamser

Chapter 18 Skills

Knowledge - Level 1

know the terminology:

aldol condensation, crossed aldol, directed aldol
Claisen condensation
kinetic vs. thermodynamic control
enamine
alkylation, acylation
acetoacetic ester, malonic ester
Michael reaction, conjugate addition
Robinson annelation
acetyl Co-A

Concepts - Level 2

recognize the reasons for kinetic vs. thermodynamic control of a reaction

recognize the nucleophilicity of carbonyl alpha-anions

recognize the special reactivity of conjugated enones towards nucleophilicity
(conjugate or Michael addition)

Applications - Level 3

predict products of aldol ractions or Claisen condensations,
including cases of intramolecular or crossed reactions

predict products from enamine alkylations or acylations

predict products from Michael additions

predict products from malonic ester or acetoacetic ester syntheses

illustrate or identify the Robinson annelation reaction sequence

Analytical Skills - Level 4

write mechanisms for acid- or base-catalyzed aldol reactions

write mechanisms for base-catalyzed Claisen condensations

Synthetic Skills - Level 5

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