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20. Carefully draw the structure of the enamine formed by the acid-catalyzed reaction of acetone with dimethylamine. v.1

20. Carefully draw the structure of the enamine formed by the acid-catalyzed reaction of acetone with dimethylamine. v.1

Chemistry
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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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20. Carefully draw the structure of the enamine formed by the acid-catalyzed reaction of acetone with dimethylamine. v.1
Transcribed Image Text:20. Carefully draw the structure of the enamine formed by the acid-catalyzed reaction of acetone with dimethylamine. v.1
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At first the carbonyl oxygen undergo protonation to give more electrophilic carbonyl system. Then nucleophilic attacks occurs by Me2NH to the protonated carbonyl carbon to give an tetrahedral intermediate which undergo condensation of water to give iminium ion. Then it undergo tataumerism to give ene+amine = enamine system. 

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