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The following scheme is an abbreviated version of the mechanism of an organic reaction called the Mannich reaction. Add all the lone pairs and/or formal charges that are necessary. CH3 H H. CH3 IN-CH3 N-CH3 CH3 `H H H. N-CH3 H H./ CH3 N-CH3 CH3 С -N H CH3 CH3 H CH3 CH3 H CH3

The following scheme is an abbreviated version of the mechanism of an organic reaction called the Mannich reaction. Add all the lone pairs and/or formal charges that are necessary. CH3 H H. CH3 IN-CH3 N-CH3 CH3 `H H H. N-CH3 H H./ CH3 N-CH3 CH3 С -N H CH3 CH3 H CH3 CH3 H CH3

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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The following scheme illustrates an abbreviated version of the mechanism for an organic reaction known as the Mannich reaction. The diagram consists of several stages, indicated by double-headed and single-headed arrows, showing the transformation of reactants to products with lone pairs and charges where necessary. 1. **Initial Reaction:** - A carbonyl compound (\[H_2C=O\] with an additional hydrogen bonding to carbon) reacts with a secondary amine (\[(CH_3)_2NH\]). - An arrow points from the carbonyl oxygen's lone pair to a hydrogen on the secondary amine nitrogen, indicating proton transfer. - This leads to an equilibrium state where a protonated amine and an alkoxide ion form. 2. **Formation of an Imine:** - The alkoxide ion pushes a pair of electrons back to reform the carbonyl, driving out water and forming an iminium ion (\[CH_2=NH^+\]) stabilized by resonance with the nitrogen lone pair. - Arrow representations show electron movement between different functional groups, maintaining charge balance. 3. **Enamine Intermediate and Final Product:** - An enolate ion now attacks the iminium ion, facilitated by electron pair movement shown by arrows. - The formation of a C-N bond occurs after a series of equilibria, resulting in the final Mannich base with a new C-C bond formation. **Overall Explanation:** In this reaction mechanism, electron movement is indicated by curved arrows. Positive and negative charges are clearly marked, revealing how the reaction progresses from reactants to the final Mannich base. The role of each functional group and the changes they undergo reflect fundamental principles of organic chemistry mechanisms, like nucleophilic attack and resonance stabilization.
Transcribed Image Text:The following scheme illustrates an abbreviated version of the mechanism for an organic reaction known as the Mannich reaction. The diagram consists of several stages, indicated by double-headed and single-headed arrows, showing the transformation of reactants to products with lone pairs and charges where necessary. 1. **Initial Reaction:** - A carbonyl compound (\[H_2C=O\] with an additional hydrogen bonding to carbon) reacts with a secondary amine (\[(CH_3)_2NH\]). - An arrow points from the carbonyl oxygen's lone pair to a hydrogen on the secondary amine nitrogen, indicating proton transfer. - This leads to an equilibrium state where a protonated amine and an alkoxide ion form. 2. **Formation of an Imine:** - The alkoxide ion pushes a pair of electrons back to reform the carbonyl, driving out water and forming an iminium ion (\[CH_2=NH^+\]) stabilized by resonance with the nitrogen lone pair. - Arrow representations show electron movement between different functional groups, maintaining charge balance. 3. **Enamine Intermediate and Final Product:** - An enolate ion now attacks the iminium ion, facilitated by electron pair movement shown by arrows. - The formation of a C-N bond occurs after a series of equilibria, resulting in the final Mannich base with a new C-C bond formation. **Overall Explanation:** In this reaction mechanism, electron movement is indicated by curved arrows. Positive and negative charges are clearly marked, revealing how the reaction progresses from reactants to the final Mannich base. The role of each functional group and the changes they undergo reflect fundamental principles of organic chemistry mechanisms, like nucleophilic attack and resonance stabilization.
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