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

Nucleophilic Aromatic Substitution

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Nucleophilic Aromatic Substitution

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Multiple Choice

Provide the structure of the product formed from the reaction of 1-bromo-2,4,6- trinitrobenzene with one equivalent of sodium methoxide.

Product structure of nucleophilic aromatic substitution with sodium methoxide.

Structure of 1-bromo-2,4,6-trinitrobenzene.

Product structure after nucleophilic substitution with sodium methoxide.

Structure of 1-bromo-2,4-dinitrobenzene.

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Verified step by step guidance

Identify the reactants: 1-bromo-2,4,6-trinitrobenzene and sodium methoxide (NaOCH3). The structure of 1-bromo-2,4,6-trinitrobenzene includes a benzene ring with a bromine atom and three nitro groups (NO2) at the 2, 4, and 6 positions.

Understand the reaction type: This is a nucleophilic aromatic substitution (S_NAr) reaction. The presence of electron-withdrawing nitro groups on the benzene ring makes it susceptible to nucleophilic attack.

Determine the nucleophile: Sodium methoxide (NaOCH3) dissociates in solution to form methoxide ion (OCH3^-), which acts as the nucleophile.

Predict the site of nucleophilic attack: The methoxide ion will attack the carbon atom bonded to the bromine atom, as the bromine is a good leaving group and the adjacent nitro groups stabilize the negative charge through resonance.

Outline the reaction mechanism: The methoxide ion attacks the carbon atom bonded to the bromine, displacing the bromine and forming a new carbon-oxygen bond. The product is 2,4,6-trinitroanisole, where the methoxy group (OCH3) replaces the bromine atom on the benzene ring.