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

27. Heterocycles

Directing Effects in Substituted Pyrroles, Furans, and Thiophenes

Organic Chemistry

27. Heterocycles

Directing Effects in Substituted Pyrroles, Furans, and Thiophenes

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Multiple Choice

Predict the product of the following EAS reaction.

structure of product

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Verified step by step guidance

Identify the type of reaction: The reaction involves bromination of a heteroaromatic compound, specifically a pyrrole derivative, which is an example of Electrophilic Aromatic Substitution (EAS).

Analyze the structure: The starting compound is a pyrrole ring with a methyl group and a hydroxyl group attached. The pyrrole nitrogen is protonated, making the ring more electron-rich and reactive towards electrophiles.

Determine the directing effects: The hydroxyl group is an activating, ortho/para-directing group, while the methyl group is also an ortho/para-directing group. However, the pyrrole ring itself is highly reactive and typically undergoes substitution at the 2-position (adjacent to the nitrogen) due to its electron-rich nature.

Consider the reaction conditions: The reaction is carried out with Br2 at 0°C, which suggests a controlled bromination, likely leading to monosubstitution rather than polysubstitution.

Predict the product: Given the high reactivity of the pyrrole ring and the directing effects of the substituents, the bromine is most likely to substitute at the 2-position of the pyrrole ring, adjacent to the nitrogen atom.