CH3 CH3 H3C N' Tetracaine Tetracaine can be synthesized from benzene. The synthesis involves the following steps: 1. Benzene + CH3CI, AICI3 to form product A; 2. A + HNO3, H2SO4 to form product B; 3. B + KMNO4, H20 to form product C; 4. C + SOCI2 to form product D; 5. D + HOCH2CH2N(CH3)2 to form product E; 6. E + H2, Pt to form product F; 7. F+ CH3CH2CH2CHO to form product G; 8. G + NABH3CN to form Tetracaine. Draw the structures of product A and product G.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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CH3
CH3
H3C
N.
H
Tetracaine
Tetracaine can be synthesized from benzene. The synthesis involves the following steps:
1. Benzene + CH3CI, AICI3 to form product A;
2. A + HNO3, H2SO4 to form product B;
3. B + KMNO4, H2O to form product C;
4. C + SOCI, to form product D;
5. D + HOCH2CH2N(CH3)2 to form product E;
6. E + H2, Pt to form product F;
7. F + CH3CH2CH2CHO to form product G;
8. G + NABH3CN to form Tetracaine.
Draw the structures of product A and product G.
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 one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Show the order of synthesis by drawing a reaction arrow between A and G, pointing toward the later-synthesized product.
Transcribed Image Text:CH3 CH3 H3C N. H Tetracaine Tetracaine can be synthesized from benzene. The synthesis involves the following steps: 1. Benzene + CH3CI, AICI3 to form product A; 2. A + HNO3, H2SO4 to form product B; 3. B + KMNO4, H2O to form product C; 4. C + SOCI, to form product D; 5. D + HOCH2CH2N(CH3)2 to form product E; 6. E + H2, Pt to form product F; 7. F + CH3CH2CH2CHO to form product G; 8. G + NABH3CN to form Tetracaine. Draw the structures of product A and product G. 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 one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Show the order of synthesis by drawing a reaction arrow between A and G, pointing toward the later-synthesized product.
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