NHCH3 cat. H* .CH3 CH3CH2CHO + NH2CH3 The Mannich reaction is one of the few three-component reactions in organic chemistry. In this reaction, a ketone, an aldehyde and an amine react together under acid catalyzed form the final product. The mechanism involves the following steps: 1. Following initial protonation of the carbonyl oxygen, nucleophilic attack by the amine forms a protonated carbinolamine 1; 2. Proton transfer and elimination of water forms iminium ion 2; 3. The enol form of the ketone attacks the iminium ion to form adduct 3; 4. Deprotonation of adduct 3 leads to the final product. Write out the mechanism on a separate sheet of paper and then draw the structure of adduct 3.
NHCH3 cat. H* .CH3 CH3CH2CHO + NH2CH3 The Mannich reaction is one of the few three-component reactions in organic chemistry. In this reaction, a ketone, an aldehyde and an amine react together under acid catalyzed form the final product. The mechanism involves the following steps: 1. Following initial protonation of the carbonyl oxygen, nucleophilic attack by the amine forms a protonated carbinolamine 1; 2. Proton transfer and elimination of water forms iminium ion 2; 3. The enol form of the ketone attacks the iminium ion to form adduct 3; 4. Deprotonation of adduct 3 leads to the final product. Write out the mechanism on a separate sheet of paper and then draw the structure of adduct 3.
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 2E
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