Tertiary amines undergo reversible conjugate addition to a,b-unsaturated ketones (see Chapter 18). This process is the basis

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Tertiary amines undergo reversible conjugate addition to a,b-unsaturated ketones (see Chapter 18). 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. 

OH H. (CH;),N

(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)

(c)

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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