OH O R' Н DABCO

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction.

OH O
R'
Н
DABCO
Transcribed Image Text:OH O R' Н DABCO
Expert Solution
Step 1

Catalyst DABCO is 1,4-diazabicyclo[2,2,2]-octanee. The sturecture of DABCO is shown below;

Chemistry homework question answer, step 1, image 1

Step 2

In the first step DABCO combines with a, b-unsaturated carbonyl compound to form in-situ nucleophile.

Chemistry homework question answer, step 2, image 1

In the second step, the nucleophilic species adds a molecule of aldehyde and DABCO acts as a base and abstracts a proton.

Chemistry homework question answer, step 2, image 2

 

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