CH3 NH Coniine Conine, C,H,„N, is the toxic principle of the poison hemlock drunk by Socrates. It can be synthesized from acrylonitrile (H,C=CHCN) and ethyl 3-oxohexanoste. The synthesis pro follows: 1. Deprotonation of ethyl 3-0xohexanoate to form enolate anion 1; 2. Michael addition to acrylonitrile to form intermediate 2: 3. Protonation to form Michael adduct 3; 4. Ester hydrolysis and decarboxylation to form oxonitrile 4; 5. Reduction to form oxoamine 5: 6. Cyclization to form imine 6. 1. Catalytic hydrogenation to form Coniine. Draw the structures of enolate anion 1 and imine 6.

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CH3
NH
Coniine
Coniine, CH N. i the toxic principle of the poison hemlock drunk by Socrates. It can be synthesized from acrylonitrile (H,C=CHCN) and ethyl 3-oxohexanozte. The synthesis proceeds as
follows
1. Deprotonation of ethyl 3-oxohexanoate to form enolate anion 1;
2. Michzel addition to acrylonitrile to form intermediate 2;
3. Protonation to form Michzel adduct 3;
4. Ester hydrolysis and decarboxylation to form oxonitrile 4;
5. Reduction to form oxoamine 5;
6. Cyclization to form imine 6:
7. Catalytic hydrogenation to form Conine.
Draw the structures of enolate anion 1 and imine 6.
• 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
• Draw enolate anions in their carbanion form
• Drzw one structure per sketcher. Add zdditional sketchers using the drop-down menu in the bottom right corner.
• Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthesized compound.
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Transcribed Image Text:CH3 NH Coniine Coniine, CH N. i the toxic principle of the poison hemlock drunk by Socrates. It can be synthesized from acrylonitrile (H,C=CHCN) and ethyl 3-oxohexanozte. The synthesis proceeds as follows 1. Deprotonation of ethyl 3-oxohexanoate to form enolate anion 1; 2. Michzel addition to acrylonitrile to form intermediate 2; 3. Protonation to form Michzel adduct 3; 4. Ester hydrolysis and decarboxylation to form oxonitrile 4; 5. Reduction to form oxoamine 5; 6. Cyclization to form imine 6: 7. Catalytic hydrogenation to form Conine. Draw the structures of enolate anion 1 and imine 6. • 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 • Draw enolate anions in their carbanion form • Drzw one structure per sketcher. Add zdditional sketchers using the drop-down menu in the bottom right corner. • Show the correct order of synthesis by drawing a reaction arrow between the two compounds, pointing from the earlier towards the later synthesized compound. ChemDoodle >
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