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Summary: CHM 2220 Organic Chemistry 2220 Winter Term 2009
Problem Set #4 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
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1) Tertiary amines undergo reversible conjugate addition to ,-unsaturated ketones. This process
is the basis for the Baylis-Hillman reaction, which is catalyzed by tertiary amines, that resembles
a crossed Aldol reaction. An example is shown below. 4 PTS
CHO
O OH O
+
Me3N
(a) Formulate a mechanism for this process. Begin with conjugate addition of the amine to the
enone.
Give the products of each of the following Baylis-Hillman reactions:
(b) H
O O
Me3N
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