Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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6:49 minutes

Problem 101a

Textbook Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

a. How can tyramine be prepared from b-phenylethylamine?

Verified step by step guidance

Step 1: Analyze the structures of tyramine and β-phenylethylamine. Tyramine has a hydroxyl (-OH) group attached to the benzene ring, while β-phenylethylamine lacks this functional group. The goal is to introduce the hydroxyl group onto the benzene ring of β-phenylethylamine.

Step 2: Select an appropriate reaction to introduce the hydroxyl group. A common method is electrophilic aromatic substitution, where a hydroxyl group can be added to the benzene ring. This can be achieved using phenol synthesis methods, such as hydroxylation with reagents like dilute sulfuric acid and sodium nitrite.

Step 3: Protect the amine group (-NH2) of β-phenylethylamine to prevent unwanted side reactions during the hydroxylation process. This can be done by converting the amine into a protecting group, such as an amide, using acylation (e.g., reaction with acetic anhydride).

Step 4: Perform the hydroxylation reaction on the benzene ring of the protected β-phenylethylamine. This introduces the hydroxyl group at the desired position on the aromatic ring.

Step 5: Remove the protecting group from the amine to regenerate the free amine group, yielding tyramine. This can be achieved by hydrolysis of the amide under acidic or basic conditions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Tyramine Synthesis

Tyramine can be synthesized from b-phenylethylamine through a process called hydroxylation, where a hydroxyl group (-OH) is added to the aromatic ring. This reaction typically involves the use of enzymes or chemical reagents that facilitate the introduction of the hydroxyl group, resulting in the formation of tyramine, which is a phenolic compound.

b-Phenylethylamine Structure

b-Phenylethylamine is an organic compound with a structure that includes a phenyl group attached to an ethylamine chain. Its structure is crucial for understanding its reactivity and how it can be transformed into other compounds, such as tyramine, through specific chemical reactions that modify the amine or aromatic functionalities.

Hydroxylation Reactions

Hydroxylation reactions are chemical processes that introduce hydroxyl groups into organic molecules. In the context of synthesizing tyramine from b-phenylethylamine, hydroxylation is essential as it alters the compound's properties and reactivity, allowing for the formation of biologically active compounds like tyramine, which plays a role in neurotransmission.