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
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
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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.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
opy aste
O=
Transcribed Image Text: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. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. opy aste O=
Draw the structure(s) of the organic product(s) of the Claisen condensation reaction between ethyl acetate and ethyl benzoate.
• You do not have to consider stereochemistry.
• Draw only the condensation product, including the self-condensation product if applicable. Do not draw the structure of the leaving group.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
• Separate multiple products using the + sign from the drop-down menu.
ору
aste
ChemDoodle®
||
Transcribed Image Text:Draw the structure(s) of the organic product(s) of the Claisen condensation reaction between ethyl acetate and ethyl benzoate. • You do not have to consider stereochemistry. • Draw only the condensation product, including the self-condensation product if applicable. Do not draw the structure of the leaving group. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. ору aste ChemDoodle® ||
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