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Use the narrative of the mechanism, steps 1. through 6. below, to diagram/draw the mechanism of the following reaction. Show each step described in the narrative. N(CH3)2 carbonyl compound--ketone 1. Nucleophilic addition of HN(CH3)2 to form a tetrahedral intermediate that contains both an ammonium ion and an oxide. enamine 2. the oxide removes one of the hydrogens from the ammonium to form an aminol intermediate. This compound is not stable--compounds with sp³ hybridized carbons bound to two or more non-halogen heteroatom substituents tend to be unstable. 3. The hydroxyl oxygen takes a proton from the trace amount of acid H₂O* in the reaction mixture to form an oxonium intermediate. 4. The amine lone pair forms a pi bond with the former carbonyl carbon and forces water to leave; giving rise to an imminum ion/ammoniumion. 5. A free molecule of the secondary amine (or a molecule of the solvent, or water from the trace acid solution) removes a hydrogen from a carbon that was alpha to the former carbonyl carbon. 6. The carbanion lonepair becomes a pi bond between the former calphha carbon and the former carbonyl carbon; concurrently, the pi bond between the nitrogen and the former carbonyl carbon becomes a nitrogen lonepair. accessibility: Investigate

Use the narrative of the mechanism, steps 1. through 6. below, to diagram/draw the mechanism of the following reaction. Show each step described in the narrative. N(CH3)2 carbonyl compound--ketone 1. Nucleophilic addition of HN(CH3)2 to form a tetrahedral intermediate that contains both an ammonium ion and an oxide. enamine 2. the oxide removes one of the hydrogens from the ammonium to form an aminol intermediate. This compound is not stable--compounds with sp³ hybridized carbons bound to two or more non-halogen heteroatom substituents tend to be unstable. 3. The hydroxyl oxygen takes a proton from the trace amount of acid H₂O* in the reaction mixture to form an oxonium intermediate. 4. The amine lone pair forms a pi bond with the former carbonyl carbon and forces water to leave; giving rise to an imminum ion/ammoniumion. 5. A free molecule of the secondary amine (or a molecule of the solvent, or water from the trace acid solution) removes a hydrogen from a carbon that was alpha to the former carbonyl carbon. 6. The carbanion lonepair becomes a pi bond between the former calphha carbon and the former carbonyl carbon; concurrently, the pi bond between the nitrogen and the former carbonyl carbon becomes a nitrogen lonepair. accessibility: Investigate

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
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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Use the narrative of the mechanism, steps 1. through 6. below, to diagram/draw the mechanism of the following reaction. Show each step described in the narrative. N(CH3)2 carbonyl compound--ketone 1. Nucleophilic addition of HN(CH3)2 to form a tetrahedral intermediate that contains both an ammonium ion and an oxide. enamine 2. the oxide removes one of the hydrogens from the ammonium to form an aminol intermediate. This compound is not stable--compounds with sp³ hybridized carbons bound to two or more non-halogen heteroatom substituents tend to be unstable. 3. The hydroxyl oxygen takes a proton from the trace amount of acid H₂O* in the reaction mixture to form an oxonium intermediate. 4. The amine lone pair forms a pi bond with the former carbonyl carbon and forces water to leave; giving rise to an imminum ion/ammoniumion. 5. A free molecule of the secondary amine (or a molecule of the solvent, or water from the trace acid solution) removes a hydrogen from a carbon that was alpha to the former carbonyl carbon. 6. The carbanion lonepair becomes a pi bond between the former calphha carbon and the former carbonyl carbon; concurrently, the pi bond between the nitrogen and the former carbonyl carbon becomes a nitrogen lonepair. Accessibility: Investigate
Transcribed Image Text:Use the narrative of the mechanism, steps 1. through 6. below, to diagram/draw the mechanism of the following reaction. Show each step described in the narrative. N(CH3)2 carbonyl compound--ketone 1. Nucleophilic addition of HN(CH3)2 to form a tetrahedral intermediate that contains both an ammonium ion and an oxide. enamine 2. the oxide removes one of the hydrogens from the ammonium to form an aminol intermediate. This compound is not stable--compounds with sp³ hybridized carbons bound to two or more non-halogen heteroatom substituents tend to be unstable. 3. The hydroxyl oxygen takes a proton from the trace amount of acid H₂O* in the reaction mixture to form an oxonium intermediate. 4. The amine lone pair forms a pi bond with the former carbonyl carbon and forces water to leave; giving rise to an imminum ion/ammoniumion. 5. A free molecule of the secondary amine (or a molecule of the solvent, or water from the trace acid solution) removes a hydrogen from a carbon that was alpha to the former carbonyl carbon. 6. The carbanion lonepair becomes a pi bond between the former calphha carbon and the former carbonyl carbon; concurrently, the pi bond between the nitrogen and the former carbonyl carbon becomes a nitrogen lonepair. Accessibility: Investigate
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